Debbie Millman:
How does something come from nothing? How do creators actually create? These are the questions Adam Moss has long been asking. They also happen to be some of the questions that I try to investigate with every guest on every episode of this podcast. How did you become you and how did you make that? Adam Moss is the former editor of New York Magazine, and before that, he was the editor of the New York Times magazine. He has left an indelible mark on those magazines and on the many others he’s worked on. Adam Moss is also an artist. He came late to the fine arts and he’s a little reluctant to call himself an artist. We’re going to talk all about that and how he wrote and created his brand new book, The Work of Art: How Something Comes From Nothing. Adam Moss, welcome to Design Matters.

Adam Moss:
Thank you, Debbie. Glad to be here.

Debbie Millman:
Adam, I understand you have really tiny handwriting.

Adam Moss:
Yes, I do. Do you want to see it?

Debbie Millman:
Was it always really tiny, or did that evolve from your work as an editor?

Adam Moss:
Oh no. It was always that way. I don’t know, can you really change your handwriting?

Debbie Millman:
It’s interesting. I look back at my handwriting when I was younger. It was much neater than it is now. Now I scribble more. But I’ve also noticed that my mother’s handwriting has never changed, ever. From the time I remember first seeing it till now.

Adam Moss:
I don’t think my handwriting has changed. My signature did after I spent a good deal of time trying to perfect it and make it look lovely.

Debbie Millman:
And why did you do that?

Adam Moss:
Because I’m vain and because I hoped one day that somebody would want my signature on something other than a check.

Debbie Millman:
Oh yeah, an autograph maybe.

Adam Moss:
Yes.

Debbie Millman:
You were born in Brooklyn.

Adam Moss:
That’s true.

Debbie Millman:
But your family moved to Hewlett, Long Island when you were a little boy, when you were a junior in high school. I understand you were a bit of a theater geek.

Adam Moss:
Oh my God. Where did you get that information? Yes, but actually it was earlier.

Debbie Millman:
Even earlier.

Adam Moss:
Yeah, it was my geek-itude. Theater geek-itude was exhausted by the time I was a junior, largely because I didn’t really have the aptitude that I had fantasized having as a younger person. I was actually a pretty good actor when I was 11, and then I hit puberty and it really just all just vanished.

Debbie Millman:
Were you more of a dramatic actor or a musical actor?

Adam Moss:
I aspired to be a musical actor. I aspired to be at chorus boy, that’s what I wanted more than anything.

Debbie Millman:
The reason I was mentioning junior high was because I understand that when you were in junior high every year in your school, a student got to direct the annual play and you wanted that job. You wanted-

Adam Moss:
You have such excellent researchers. Yes, that is true.

Debbie Millman:
Because of your experience at the time and your passion for theater, you thought there was no one else even remotely qualified to get the job of director of this play. I’m wondering if you can share what happened next.

Adam Moss:
I did look around and I was an actor. Also, I had been in the school play over and over, and I had done a million parts. I must have played every part in You’re a Good Man, Charlie Brown in camp. I loved it. Yeah, I thought it was just my turn and it wasn’t. There was one day when they were supposed to tell you whether you… There were three finalists and I was one of the finalists, and I invited two of my friends to be with me when I got the big phone call, and they did a very cruel thing, which is that they made the person who did get the job call the person who didn’t get the job. So I got that phone call from this lovely girl who did a great job to tell me that I had failed to get this job, which was crushing.

Debbie Millman:
Oh, I can understand. I was also a theater geek in high school, and remember when I didn’t get parts that I so desperately wanted.

Adam Moss:
Yeah. But they gave me as a consolation prize, they were doing Fiddler on the Roof and they gave me, I was Motel that year. So that was fine. I got to sing Wonder of Wonder, Miracle of Miracles, and all was fine.

Debbie Millman:
I don’t know if you’re going to want to talk about this and we can always edit it out, but I understand that when you didn’t get the part-

Adam Moss:
Oh. My mother ran into the principal’s office. Is that what you want to talk about?

Debbie Millman:
Not so much that part.

Adam Moss:
It was an amazing thing because my mother did not have a history of standing up for me this way.

Debbie Millman:
That’s why I was going to ask you about it.

Adam Moss:
But she was horrified and moved, I think, by my terrible sorrow. Yeah, went to the principal and said, “Why didn’t he get this job?” Or whatever you want to call it, this assignment. And the principal said, “He’s not a leader. He does not have the ability to get other people to rally around something,” which I don’t know if it was true at the time, but it certainly in retrospect was a very helpful thing to me, even though it was cruel and crushing because it spurred me to be the person he didn’t think I was.

Debbie Millman:
You have written about how you thought that maybe it was the beginning of your real ambition.

Adam Moss:
Yeah. [inaudible 00:05:39] always had a ambivalent feeling about ambition. I think I was always ambitious. In fact, the signs of my ambition are very, very clear if I do a retrospective look at my life. But I came of age in the 60s and ambition a dirty word, even though ambition just really took different forms. But the notion of ambition was somehow tied to capitalism, even though that was not at all what I wanted, but I was afraid of wanting something too much. So I struggled with that as a way to identify myself, and then at some point I had to concede that I was a very ambitious person.

Debbie Millman:
I don’t want to go too far into the future, but I do want to ask you this question about when you left New York Magazine because you stated that your plan for the future was to try living with less ambition.

Adam Moss:
That’s true, and I think I have succeeded. It took a little while to get used to that, but ambition is exhausting. I had just had it as a habit for so long and I was kind of wiped out. I did try for the first months after I left the job to try to live a life of simpler pleasures, not needing the dopamine of the things that ambition gets you. I started to paint and I started to paint just for myself, which was a kind of ambition, but also not a public ambition. Then it really wasn’t until I wrote this book and even this book that I wrote, I wrote it for myself. I did not write it in order for it to be a bestseller or something. I wrote it to just satisfy a curiosity that I had and actually a kind of obsession that I had that was not an ambitious obsession. It was more of a personal obsession. So I think that I do live with less ambition now and I’m happier for it.

Debbie Millman:
Your book is very much a deconstruction of how people are artists and how people make art, and it occurred to me when I was thinking about the role of ambition in your life, the role of ambition in my life. I was wondering if there was any type of common denominator that you began to understand in the artists that you spoke with about the role ambition plays in their lives?

Adam Moss:
I think ambition is very important in an artist’s life, particularly an artist of the kind that I talked to for this book, this dataset of 43 of them, because ambition is one of the things that fuels drive and that you need a kind of superhuman drive to accomplish what these people have accomplished, but also the creative life is just full of obstacles. There are just bits of self-sabotage, landmines everywhere you step and in order to persevere through them, you need fuel. And that fuel can be a lot of things. It could be outrage, it could be sorrow, it could be loneliness, but it is often propelled by ambition. Now, that’s not mean necessarily ambition to sell a million dollar painting, although that comes into it. It’s the ambition to make something, but then we can talk later even about that because it’s really more the ambition to make rather than the ambition to make something.

Debbie Millman:
The one thing that you said about that experience that I thought was really compelling was you telling yourself, “Fuck this, I am strong enough. I can do this.” And it made me wonder if the very seed of ambition is about proving something to oneself.

Adam Moss:
I think that’s absolutely true. Even if it’s the kind of ambition that requires validation, the reason you require that validation is that there’s something that’s missing in you and that you’re trying to fill.

Debbie Millman:
Going back to some of your-

Adam Moss:
Long Island?

Debbie Millman:
Origin story. Yes. As you were growing up, you discovered what you’ve described as your own piece of library paradise in the stacks of magazines at your local library where you perused old periodicals from World War II. That really surprised me. You described these as stimulants for your imagination. What interested you in that particular time period?

Adam Moss:
It was really just the availability of it, but also the magazines of the 40s are wonderful and the advertisements of the 40s are wonderful, and I would spend as much time perusing those as I would reading stories. But I suppose if I was going to be in a shrinks chair, it was also my parents’ era, so I was interested in the life that they lived. It’s a kind of just way to live history, to rediscover history, but also I got very entranced with the magazine form, which was complemented by a kind of simultaneous worship of the magazines that came through the mail slot in my house, and that I would read at other people’s houses.

My parents were charter subscribers of New York Magazine, which opened up the world of New York City, which was enormously appealing, especially considering how uncomfortable I was in the suburban life that they had put me in. So this was a kind of a exit door, exit door of the imagination, but it was an exit door. And also magazines in like 1966, ’67, ’68, ’69, ’70, ’71 were fabulous laboratories of storytelling experimentation, in addition to being very exciting because the times were very exciting. So the dual action of visiting magazines of history and visiting magazines of the present or then present, just really excited me. I was just into magazines as early as I can remember.

Debbie Millman:
Was it just magazines or was it also newspapers? Long Island Newsday was quite good in the 70s.

Adam Moss:
Yeah, I wasn’t actually into newspapers. In fact, later I would get a job through strange circumstances as a copy boy at the New York Times, a job that any person who aspires to be a newspaper reporter or editor… Well, no one aspires to be an editor, but reporter would love, and I was blasé about it. It was interesting. I found it interesting, but it wasn’t actually what I wanted to do because I didn’t find the newspaper itself as a form to be as compelling to me as what was going on in the more subjective and visually enthralling world of magazines.

Debbie Millman:
You said that you got the job as a copy boy or a copy… Copy-

Adam Moss:
Copy boy, that’s what it was called, yeah.

Debbie Millman:
Under Strange Circumstances. And I’m wondering what those were because I couldn’t find out. I really searched for the way in which you entered the world of the New York Times. I know you went to Oberlin College, and I know you had an internship at The Village Voice, but I could not find out how you got to the New York Times.

Adam Moss:
Well, I’ll tell you.

Debbie Millman:
Okay. Yay.

Adam Moss:
I graduated from college. I had worked at The Village Voice the summer before. I didn’t know what I wanted to do with my life though I was, as I say, very excited about the prospect of journalism. No more magazine journalism, the newspaper journalism. And my father has a friend, still alive, who was dating a Swedish woman, and that Swedish woman was very interested in marrying my father’s friend. And that Swedish woman, having never met me, vouched for me to her friend, her other Swedish friend who happened to be married to Sydney Gruson, who was the vice chairman of the New York Times. And so without inviting this call, I got a call one day from Sydney Gruson’s office and said, “He would like to meet you and would you come up and see him?” So I did, and I got stoned before I went, but that was-

Debbie Millman:
As one did at that time.

Adam Moss:
As one did at that time. But that was the kind of level of it didn’t matter to me really. He had two children, one child who went to Oberlin, and the other child who went to Harvard, and I had had a short stint at Harvard as well. He was very interested in the establishment, non-establishment, duality of his children’s experience, but also of my own life. We got along great, and I walked out of there with a job.

Debbie Millman:
Did the Swedish woman marry your father’s friend?

Adam Moss:
She did not.

Debbie Millman:
Oh.

Adam Moss:
Sad story.

Debbie Millman:
Yes.

Adam Moss:
But anyway, I did meet her at one point and she was a lovely person. And I’m very grateful to her for that, even though it was a bit of a surprise, but I should probably say… Do you know what a copy boy was? It’s a great old vestigial job. It was back before computers, of course. A newspaper had editors and writers, and when the copy had to go from editor to writer, the writer or the editor would raise their hand and yell, “Copy,” and you would run and grab the piece of paper and run to the other, the reporter or the editor, and run back and run back and run back and run back. It was a crazy fun job that just vanished like so many others.

Debbie Millman:
Yeah, it sounds like the ball boy or girl at a tennis.

Adam Moss:
Yeah. It’s similar. It’s similar, yeah. But during this time… So I worked there at night and I worked at Rolling Stone during the daytime because that was a magazine and they were starting a new magazine for college students. So I really, I had a life of working one job, then working another job and never sleeping and was wonderful time.

Debbie Millman:
You worked at Rolling Stone putting together a magazine called The Rolling Stone College Papers, and then from there I believe you were simultaneously at the New York Times, but then went on to Esquire–

Adam Moss:
That’s correct.

Debbie Millman:
To work on their annual college publication. But that magazine was killed the day after you arrived at Esquire?

Adam Moss:
I believe it was the day I arrived.

Debbie Millman:
Oh, the day of.

Adam Moss:
But in any case, it was too late. They had me. They had hired me as a pipsqueak editor, and it was a wonderful time to be at Esquire because Philip Moffitt and Chris Whittle, who had bought the place were somewhat insecure about their abilities to edit a big city magazine. They had come from Tennessee having done a very successful startup thing there, which gave them the money to buy Esquire. And they had brought back the great editors. One of, I talked about the New York Magazine, but one of the other, of course fantastic magazines of the 60s was Esquire, probably the best run of a magazine ever. That was really my dream job. So there I was, and they had brought back all these editors and the editors weren’t much interested in working, and they were very happy to have a young editor to do their jobs for them.

Debbie Millman:
So before you were 30 years old, you worked for The Village Voice, Rolling Stone, the New York Times, and Esquire?

Adam Moss:
That’s true.

Debbie Millman:
What did you make of that trajectory?

Adam Moss:
I didn’t think about it. The only thing I realized was that I was the only one of my college friends working, and because you just didn’t do it in those days. You would go through Europe with a backpack or-

Debbie Millman:
Peace Corps.

Adam Moss:
Yeah, Peace Corps and work on a farm. And I had a very unusual career trajectory. And it never felt like it was any decision I made. It was just the way things happen. Of course, in retrospect, you see all the decisions you actually did make to make it happen, but it was not how I experienced it.

Debbie Millman:
In 1987, Leonard Stern, the owner of The Village Voice, was looking to start another and invited you among many others to pitch ideas. I read that Leonard didn’t have a strong sense of what he wanted to publish other than he wanted to create a magazine that was, in his words, less pinko. Allison Stern, Leonard Stern’s wife, was particularly interested in what you pitched, although it seemed when you were pitching that Leonard was not as interested. Can you talk about what you pitched and how you developed the original idea for the pitch?

Adam Moss:
At Esquire, I had been working on this other magazine, I think it was called Manhattan. It was-

Debbie Millman:
Manhattan. Yeah, Jay [inaudible 00:18:26].

Adam Moss:
It was nothing.

Debbie Millman:
I just have to interrupt you for a second.

Adam Moss:
Yeah.

Debbie Millman:
It wasn’t nothing at the time.

Adam Moss:
Where it went was something, but my pitch, you asked me what my pitch was. My pitch was like… It was really… I thought there was a place in the market between The Village Voice and New York Magazine, and I had this half-assed idea of what that could be. And I had presented it to a consultant, a guy named Jack Berkowitz, great guy. And he told me my idea was terrible and that it would never make any money because he was looking at it from that perspective. But he was also the consultant on this project, and he had said to me, “Hey, just pitch it. They’re having a bake-off. Just pitch your idea.” And I pitched, and I really don’t think the idea had much merit at all. But I think my own eagerness was probably winning.
And yeah, it was 10 o’clock at night in skyscraper, in 50s I think, in Manhattan, and I pitched the thing, and there was utter silence. Allison had just injured the room. I think mine was the only idea that she’d heard, and I think she thought the whole thing seemed fun. Really out of shame because the silence was so awful, I went to the bathroom. This is the story you’re looking for, I’m sure. At the urinal, I was doing my business and Leonard came in to do his business and he said, “Yeah, we’ll do your magazine.”
And then I got a bunch of people together and hired, well, I think a bunch of children, which was all I could afford, and thank God for it because there was just a kind of youthful passion and somewhat organically Seven Days emerged, which was basically a function of our own naivete about what a magazine should feel like and look like. But it became this kind of conversational collage that reflected the week. It was different and probably fresh. We got a lot of incredible talent work for it. Yeah, it was all wonderful.

Debbie Millman:
It was a wonderful sliver of time in the world of magazines at that time.

Adam Moss:
You have to remember that that was a period when there was a lot of optimism [inaudible 00:21:03] magazines and there were starting up all over the place.

Debbie Millman:
Yeah. New York Woman, Egg-

Adam Moss:
Spy.

Debbie Millman:
Spy, of course. I remember very vividly Seven Days, and not just Seven Days, but also this sense that Adam Moss had arrived. And he was now-

Adam Moss:
Oh, You’re nice.

Debbie Millman:
No, no. I don’t want to fawn. That’s not what I want to do. But because it was such an important moment in my life as well. Living in New York surrounded by magazines, I was working at a number of different magazines. Nowhere as near in the stratosphere is the ones that you were working on, but it was still a great, great passion. I had a friend that worked at Manhattan, inc. and a friend that worked at New York Woman and a friend that worked at Spy. So I was very immersed in this world. And for our listeners, when Seven Days came out, it really did change quite a lot of the way in which you thought about and considered a magazine. And it’s interesting you said that you think the entire history of Seven Days is the history of people who didn’t know any better doing all the things that their elders had dismissed, because most of the time it didn’t work. But it did work for a while.

Adam Moss:
I still believe that.

Debbie Millman:
I still that it did work for a while.

Adam Moss:
Yeah, and it worked. It was a kind of accidental explosion of naiveté that yes, somehow worked. And prefigured a lot of storytelling forms that would emerge later around the internet in particular. But that kind of conversational, very subjective, personal expression, filter of experience of news experience, but also personal experience that was related to exactly that moment in time, that was what animated the magazine. And yeah, I look back on it, some parts of it I cringe at, but for the most part I’m just as excited. But it’s very much of its time so that somebody might chance upon it in a library, just the way I did those magazines of the 40s. And they will instantly know what the world was like in 1989 in New York City for a certain demographic.

Debbie Millman:
Despite only lasting two years. Two weeks after the magazine closed, Seven Days won the National Magazine Award for General Excellence, which is a highly competitive accolade. And this propelled you to begin working at the New York Times where you were brought in to quote, “Decalcify the place,” unquote. And you’ve said that in doing so at the time, you got a lot of grief. They didn’t want to be decalcified?

Adam Moss:
No, they certainly did not want. The rank and file did not. The rank and file, they were very invested in the establishment traditions of the New York Times. That’s why they worked there, and they were very important. But there were some leaders of the Times, Joe Lelyveld, the man who hired me in particular, who thought it needed some breaking down. Not entirely, didn’t want to change it. Tremendous reverence for the institution, but felt that it had some cobwebs. And so he assigned me this absolutely preposterous assignment, which is to go in there and make trouble. I was 30, and I learned very quickly to ignore my brief. Anyone who wanted to bend the place a little bit, I was there to help them do that. And there were some interesting projects. They were all pretty small.

But the one piece of the institution that I wanted to participate in, because it’s the only one that I had an idea about was the magazine. And the editor at the time was not interested in my being there for excellent reason. And eventually there was, this guy named Jack Rosenthal, and he asked me to come on first in this wrecker role, and then eventually as his partner, editorial director, and then I became editor of the magazine afterwards.

Debbie Millman:
How did you feel as a wrecker? Did you feel courageous at the time? Were you tentative nervous, ballsy?

Adam Moss:
Foolhardy. Naive. Naiveté is really, it’s a theme in my life. I think it maybe still is. I just didn’t realize how many traditions I was trampling on. But on the other hand, I also knew what I didn’t know. I was not particularly cocky. I was more like a child in a room of adults, and I acted like a child, and I played as a child, and that had benefits and that had a lot of problems. But I grew up fast there and they taught me a lot. And in fact, I feel very much formed by what I learned at the New York Times and very grateful for that education. I really became a journalist there. And before that, I was faking it.

Debbie Millman:
The magazine still has a lot of your imprint in it now, all these years later. It’s still very much influenced by how you reimagined it. Could be. It’s a magazine, it’s not an insert.

Adam Moss:
Yeah, I’d like to take full credit for that. But that was really… Like many of these things, that was really a confluence of a lot of things happening at once, largely economics. The Times was really making a national push into national distribution, but also a business model of national advertising. A lot of that advertising was magazine-like advertising. So there was a desire for the magazine to be a gatherer of that kind of advertising. And so there was a kind of… I don’t want to call it an open check because it really was not that large, but there was permission given to detach it from its history as a supplement and to turn it into a freestanding magazine that happened to be distributed in the New York Times and that had the New York Times DNA, which was a really interesting brief, and one that Jack and I worked on. And then later I worked on with the staff as the editor.

Debbie Millman:
You left the Times in the early aughts, but not after more accolades awards and increase in readership, a whole different way of really assessing the magazine. And you went on to New York Magazine as editor, and you were brought in again to remake it by then, owner Bruce Wasserstein. I read that you approached it as a kind of restoration project as opposed to a re-imagination, and you wanted to bring back some of the values of the original co-founders, Clay Felker and Milton Glaser while still pointing it to the future. What were the values you deemed most important to restore?

Adam Moss:
One of them was both Clay and Milton had a perspective that what the magazine was really about was not New York City, but a New York City way of looking at the world. And that there was a filter that could be applied to Washington, could be applied to Hollywood, could be applied overseas to London, other places, that it was really a magazine of the cosmopolitan world. New York Magazine inspired a lot of city magazines, but it actually never was a city magazine. And the owners of the magazine before Bruce took it over, very much remade it themselves in the mold of the magazines that were imitators of New York. So I was trying to go back to that original idea, which I thought was bigger and more interesting and more adventurous, and to remake the magazine in 2004 to feel like it was a magazine of 2004, but it had the values that animated its founding.

Debbie Millman:
Adam, we could do a whole series, a whole series on Design Matters about the relaunch of New York Magazine. But I do want to get to your glorious new book. Suffice it to say that since the redesign and relaunch in 2004, New York Magazine has won more national magazine awards than any other publication, including the award for General Excellence in 2006, ‘7, 2010, 2011, 2014, 2016, as well as the Society of Publication Designers Award for 2013 Magazine of the Year. Most recently, the magazine won a George Polk Award in Magazine Reporting for the Bill Cosby rape investigation. And it’s also been awarded several Pulitzer prizes.

Adam Moss:
Many after I left, I just should say.

Debbie Millman:
Okay, but still-

Adam Moss:
But yes, yes, yes, yes, yes, yes, yes. Thank you.

Debbie Millman:
So congratulations.

Adam Moss:
Thank you.

Debbie Millman:
You not only re-imagined the print magazine, you also embraced the magazine killer called the internet and knew digital-only brands, five of which Vulture, the Cut, Intelligencer, The Strategist, and Grub Street are now considered heavyweights in modern online editorial. And New York Magazine is now as much of a digital company as it is a print company.

Adam Moss:
Absolutely. Yeah.

Debbie Millman:
When so many editors couldn’t or wouldn’t adapt their publications to the digital world, what gave you the sense that this was going to be the game changer it ended up becoming?

Adam Moss:
It wasn’t that I thought it was a game changer, it was that I thought that it was interesting. And I had come from the New York Times just recently, which had… They were making a few mistakes, but basically they were getting it right about how to create a digital newspaper. And I found that very exciting. And there were several experiments, even at the very early NewYorkTimes.com that I did with the magazine that were exciting to me. I wanted to bring that spirit. I just wasn’t scared of it.

And also, the owners of New York Magazine were not scared of the internet for reasons that really, I’ve told this story too many times and it’s boring, but they were making money on their own digital site for arcane reasons, but they were. That became a business imperative too. I just keep saying this, not because I’m an economist, but you need the right conditions on the ground to do anything creative really. And in all these instances, the right conditions, the right economic conditions enabled the creative things that we were able to do.

But I was just crazy interested in it, and each experiment we did trying to build out a sort of satellite, not a satellite, but a constellation really of digital magazines, was interesting to me and interesting to my colleagues. It spurred us on to do more and more and more. We started with this thing called Grub Street, and then… [inaudible 00:31:54] food. And then we realized, “Okay, if these things were vertical as opposed to horizontal,” which is to say about one subject, “That could be wonderful. And maybe the voice should be the same voice as the print magazine, but sped up for digital purposes.”

And gave a lot of license to the early writers who helped create the voice. Grub Street became Intelligencer, which eventually became Vulture, on culture and entertainment. And Intelligencer went through several iterations, but eventually became a news site. And then The Cut, which was a kind of women’s magazine, but a very different kind of women’s magazine than it had ever been made before. And lo and behold, we had this fleet of magazines that were built for the internet and had the DNA of New York in them. And that proved to really work.

Debbie Millman:
In 2019 after 15 years of nonstop growth and innovation, you decided to leave New York Magazine. At that point, you had also somewhat secretly taken to painting. Did your new fine arts pursuit influence your departure?

Adam Moss:
No, I don’t think so. I had always loved the visual parts of magazine making, and I have a house in Cape Cod that used to be an art school just by coincidence. And there is just a feeling of being there that you can see the ladies with their bonnets painting en plein air on the dune. And I found that interesting. And then one summer I just decided to try to do a painting a day without any… I had no experience, I mean like zero experience doing this, and I just started to experiment, started painting at three and ended at five, whatever it was it was. And that was crazy fun to me. And then when I got back to New York, someone made a gift of giving me an art teacher, and that was the first time I got a teacher, but I was still working in New York at the time, and…

No, I left New York because I felt that I could only edit the magazine for myself and that I was no longer the reader. I had seen the ways in which an editor who didn’t have themselves as a compass could screw up a magazine and how it could become contagious. I just didn’t want to do that, so I had to get out of the way. So I left without any sense of what I’d want to do, except as you’ve mentioned before, to try to do something with less ambition. It was more like, “Okay, let’s see what happens” without any true sense.

But I did enjoy painting enough that I thought, “Maybe I should paint full time. And I had a problem, which is that I actually was kind of good at the beginning. My first six months, I would say painting, I was a much more successful painter than I ever was again.

Debbie Millman:
Why?

Adam Moss:
Because I was looser, because I was naive. I didn’t know better. Really, it’s really, I can’t believe how thematically consistent this all is. And then as soon as I did know more, as soon as I took more classes and that kind of thing, my work started to just stiffen up and fall off a cliff. So that was deeply, deeply upsetting to me, and though I enjoyed it, it scared me.

Debbie Millman:
Why?

Adam Moss:
Because I really wanted it and I didn’t know how to get there, and I didn’t have any roadmap whatsoever to get there. I could acquire skills, but I was already, I think, aware that skills training wasn’t the problem. I did lack skills, but you can always get skills. I really felt that there was a way of thinking as an artist and a degree of courage and risk-taking that I did not have in solo activity. I’d had it in a group because the group is safe, and the group eggs you on and making something together in a group is really still the greatest thing in the world to me. But here I was alone and not making enough progress.

So that’s really when I realized that I just wanted to talk to people who were successful in making art. By art, I mean any kind of art. Novels and poems and visual art. And then I was afraid that they wouldn’t be truthful with me. They wouldn’t know how to be truthful with me because so much of the process of making art is secretive and people are afraid of jinxing the muse. So they develop a kind of set spiel, and that’s how they talk about their art, and it’s about the project and all of that stuff, but that’s not what I wanted to know. I really wanted to know how something is made and what goes through a person’s mind when they’re making it, and what goes through a person’s emotional makeup, what kind of person is successful at this?

So that’s when I devised this idea of concentrating on a single work from each of these people and asking them to trace the evolution in as many different layers as they could, both practically what they did, but also very much their kind of emotional journey. And then also part as a go to help them remember truthfully, and also just because I love this stuff, to accompany it with a gallery of the artifacts of the making of the thing, the notes and the sketches and the doodles that were their tools making the work. Then I looked at all that and I kind of had a book, or I had a structure of a book, or I knew what the book was.

Debbie Millman:
Before we talk about the book, I want to ask you another question about your own journey as a painter. Was it hard for you to suddenly not be good at something when you’d been so good at so many things for so long?

Adam Moss:
I think so. I had actually taken up piano earlier in my life, and in part because you have to listen to yourself play the piano, and I was really a bad piano player. I gave that up, and my thinking at the time was that I couldn’t tolerate not being good at something. It was just too painful to me. And I realized how many things over my life I had discarded that I wasn’t good at. I’m not good at most things. And because I’d had this one moment when I thought, “I maybe could paint,” it wasn’t the same thing. It wasn’t something I was just going to throw over.

And also because I really physically enjoyed making art, I enjoyed the physical sensation of it in a way that was new to me and was exciting to me. And so I didn’t want to give it up, but I think it was more vexing to me because in a kind of group… There’s a chapter in the book on David Simon where somebody observes that he needed the bounce, this great phrase, the bounce to make television, to make the wire, which is what we were talking about. And I recognized in that that was really how I had worked my whole life, is that I had thrived in the bounce. The ricochet between creative people was really… That was the environment in which I was successful, and here I was just by myself, and it was an environment that I was not being successful, and I was trying to capture the inner dialogue. I knew what the group dialogue sounded like, and here I was trying to capture the inner one.

Debbie Millman:
So the struggles to understand your own voice as an artist is what led you to… That was a driving force behind-

Adam Moss:
Yeah. My voice, how you endure through failure and frustration, a very, very big part of it. How you… Some simple things, really actually not at all simple things, but simple to describe, where to start, where to end. What gives you the faith that you can do this. These were all questions that were questions of temperament and personality. And so in some ways, I don’t really usually describe it this way, but I was trying to understand the artistic personality.

Debbie Millman:
One of the things that first attracted me to this effort was the title, the Work of Art, which I think is one of the great book titles of all time, I have to say. This subtitle is How Something Comes from Nothing. But is it true that the original title of the book was Editing?

Adam Moss:
Yeah. Well, originally-

Debbie Millman:
It’s so different.

Adam Moss:
I know, it’s so different. Although the original idea of it was to try to claim for editing a much wider sense than we usually have for it. So I wanted to talk about editing as what I’m doing right now and choosing this word instead of that word or how we dress, or basically how we make artistic decisions, make decisions, and that was what the book was going to be, and it was going to be as applied to creative people and blah-blah-blah-blah-blah. Eventually that just became too limited because the editing, which is kind of this mid-zone, I think, between the imagining and the shaping, there’s a kind of judging aspect, which is similar to the function of editing. Editing just seemed too limited a term. But in some ways, the book is still about editing. It’s just not editing the way I think anybody thinks of what the word means.

Debbie Millman:
Yeah, in many ways, editing is about choice-making.

Adam Moss:
Absolutely.

Debbie Millman:
And this is a book about how you made choices to create this thing that you created.

Adam Moss:
Yeah, absolutely. That’s exactly true. Yeah.

Debbie Millman:
I read that you hate writing and that you think you’ve been a terrible writer for most of your life. How is that even remotely possible, Adam? I can’t even come up with the right kind of question to ask you about this.

Adam Moss:
Just think of it. If you’ve been an editor all your life, you have a very keen sensitivity to what is off, and that applies to your own work as well. I was super self-conscious, and I had this overly wound up editing scrutiny of my own work, and it got me nowhere. I had to really teach myself to write for the book, and that was a wonderful process actually. Although agonizing. I wrote the book really in a voice that was just completely not me. It was a voice that I just made up, is what I thought a book should sound like. It was really pretentious. And everything was an overreach. And then I-

Debbie Millman:
Did you decide that, or did an editor decide that?

Adam Moss:
No, I decided that it was just, I had this wrong-headed idea about what… “Okay, I’m an author now, how should I sound?” Terrible. A good enough editor recognized how bad it was, and then I went back and rewrote the whole book once I actually did find my voice. I think why I hated writing so much is because I just hated what I was writing.

Debbie Millman:
You wrote that you decided to create a book deliberately in a way that would be writer-proof.

Adam Moss:
Writer proof, yes.

Debbie Millman:
And that the writing would be the least important part.

Adam Moss:
Yes.

Debbie Millman:
But I don’t think that that is the result at all. I think that part of… Some of my favorite parts of the book are your musings and candor in looking at what you were looking at and coming to the decisions that you did. My favorite parts are the parts that you actually wrote,

Adam Moss:
And you know what? Those were all the parts that I added at the end. So at the beginning, it was very much the artist’s voices were the driving force of the book, and I had a conversation with a wonderful editor friend of mine named Susie [inaudible 00:43:57], I’ll give her a moment here. And she said, “Where are you in this book?” I had to reluctantly concede that she was right, and she had the idea that the footnotes were a particularly good way to impose myself on the book in a sort of Talmudic way. But I also rewrote into the book. At that point, the book opened up. It really became a different book and a much better one, I think.

Debbie Millman:
You were invited by Frank Rich, a writer from the New York Times and New York Magazine, and also an executive producer of the television program Veep to visit the show. And that became a real impetus for writing this book, and I’m wondering if you can talk about how that happened.

Adam Moss:
Sure. I went to the set of Veep and I sat with the writers who all sit in little director’s chairs behind David Mandel, who was the showrunner of the show at the time. And I watched them do a scene that probably didn’t last more than five minutes all afternoon or a good deal of the afternoon. And there was one joke in there that landed on a Jewish holiday, and Dave Mandel did not think it worked exactly. So he had summoned the group to come up with what are called alts, which was alternatives to the joke to calibrate the joke and fine-tune it and make it funnier. One after another that he just barked an alternative out. He changed, he just kept changing the holiday. It was like Hanukkah, and then it was like Purim and Simchat Torah.

Debbie Millman:
[inaudible 00:45:32].

Adam Moss:
Simchat Torah because it’s the funniest. And Purim. And the group would laugh or they wouldn’t laugh. And finally he came up with the thing that he liked best. I can’t even remember what that was. He can’t even remember what that was. And I left just in awe of the kind of rigor that they brought to a joke that would be an absolute throwaway moment in a television show that nobody would notice. It was just like it’s wallpaper. I love that. I’ve always been a Calvinist. I’ve always been an admirer of work, and I’ve always really been an admirer of creative work. I walked out of there. It wasn’t at that moment that I decided to do the book, but it was one of the seeds that spurred the book on.

Debbie Millman:
One of the things that I like so much about the book is how the process, so to speak, and I hate the word process-

Adam Moss:
Me too.

Debbie Millman:
But the magic of creating art is revealed, and so many times, because great works of art, whether they be great jokes or great puzzles or great sandcastles or great paintings or poems feel effortless. It takes so much work to get to that loose.

Adam Moss:
Absolutely. Effortless. So much effort to make the effortless, yes.

Debbie Millman:
Yeah. And that example of trying out the different jokes… I also learned a lot. I had no idea that that’s how jokes-

Adam Moss:
Yeah, me neither.

Debbie Millman:
Can be constructed, that you try all these things out. It just seems like they’re so effortless that they’re just fully formed. And that’s not the case in the 43 case studies in this book. Just to give our listeners a sense of this opus, it features interviews, sketches, scripts, drawings, drafted pages in journals, song lyrics, story outlines, and all sorts of intriguing never-seen-before ideas in the making of some of the most preeminent artists of our time. They span genres and mediums. They include filmmakers, songwriters, painters, playwrights, composers, poets, chefs, a puzzle maker, a sandcastle maker, a cartoonist, a newspaper editor and designer, and even a radio pioneer. And you interview more than 40 people. You ask them to take you through the process of making one specific work and drawing on what you call process artifacts to chronicle their thinking. How much fun was this project?

Adam Moss:
Enormous fun. Two parts of it were really fun. The first part of it was the conversations with the artists themselves. I loved that. I am intrinsically a worshiper of creative people. I just really admire it. And so that I just love that and I learned so much. And then I also loved the physical construction of the book. I worked with-

Debbie Millman:
Like Hayman.

Adam Moss:
Luke Hayman and his colleagues at Pentagram, and he was very generous in letting me play with him and his colleagues to make a book that we both wanted to be a book that didn’t look or feel like other books. So I really enjoyed that part too. Now, we had talked earlier about the part that I didn’t like, which was sitting in a room and writing the damned book. I just found that to be agony.

Debbie Millman:
You write about Elizabeth Gilbert and how in her TED talk on the subject, Elizabeth Gilbert speaks about how in Ancient Greece and Rome people believed that creativity was this divine attendant spirit that came to human beings from some distant and unknowable source for distant and unknowable reasons. And it reminds me of something Rick Rubin wrote in his book, The Creative Act. He stated that, “If you have an idea you’re excited about and you don’t bring it to life, it’s not uncommon for the idea to find its voice through another maker.” And this isn’t because the other artists stole your idea, but because the idea’s time has come. And I’m wondering, speaking to so many people about the way in which they approach their work, do you feel that that muse is sort of out there for an artist through hard work and sitting in the chair every day will come to them, or is it something that they conjure? I really struggle with the idea about whether ideas come through the artist or from the artist.

Adam Moss:
It’s got to be both, don’t you think? That’s when it really works, is that if the artist brings what they have inside them to the table, or those that feel that it’s otherworldly, if they’re struck at that moment by some otherworldly inspiration. It must meet the moment. There’s really many, many instances in this book of work that I don’t think could have been made if it had been made at a different time. That’s true of historical circumstances or economic circumstances. But it’s also true of just the artist’s experience. The artist gets to a point where he or she can make the thing. And before that, it would’ve been impossible. Or a medium has changed. I mentioned David Simon. David Simon could not have made The Wire if HBO hadn’t existed. So there are all sorts of things that create opportunities and the opportunity meets the internal churning of the artist, and that’s when the greatness happens.

Debbie Millman:
You mentioned earlier in our conversation that artists can sometimes be secretive about their process, and I’m wondering, is it really being secretive or is it being unaware and not necessarily being able to admit that?

Adam Moss:
I think both. I think that’s very true what you say. A lot of them are secretive, A lot of them are superstitious. There’s a tremendous amount of superstition involved with this because people fear that it’s fragile. Whatever their connection is to however they identify the muse, it’s tenuous and easily broken. And if they look at it too hard, the whole thing will just dissolve in front of them. So it took a certain kind of brave person or a foolhardy person, or just a really introspective kind of person to want to participate in this project. And there were a lot of people who said no, and it was a sorting of the sort of like, “This sounds interesting to me,” because to your point, I never think of this before, and now you’ve just made me interested in where these ideas come from. Tony Kushner, who’s a very introspective person, said, “As I’m writing something, if something good comes out, it’s like, where did that come from?” It is a question that they don’t necessarily know the answer to. So a lot of these artists felt that our conversations were akin to therapy.

Debbie Millman:
You write that in your view, there are three stages of making art. The first is imagining, and the final one is shaping, which are somewhat self-explanatory, but the one in the middle and the one most interesting to me is judging. Can you talk a little bit about what that is?

Adam Moss:
We’ve talked a lot about judging in this conversation, so that the judging is what someone else might call editing, it’s bringing intelligence to bear on part one, which is what has the imagination brought, which generally is a kind of big mess that happens if you think of a first draft of a story or you think of a first pass of a painting. It’s kind of just a this and that kind of jumble, but under there, somewhere there is something worth working on. And it’s not the latter part, the shaping, that’s as you said self-explanatory, I think that’s true, which is the technique, the whittling, et cetera. It’s really, what is this and what could it be? It’s more of a thinking process. It’s the engagement of the brain. It’s not necessarily a conscious engagement of the brain, but it is something that the brain is doing to try to make sense of what they have in front of them and what it might turn into.

Debbie Millman:
As I was thinking about this, it felt like this was the manifestation of an idea, and that to me seemed like the most interesting part of the work. The imagination part, you get the spark, you don’t. You get the idea, you don’t. But the making part is the most fun.

Adam Moss:
I think so. I think it’s the most important stage, and it’s a stage that no one gives a whole lot of thought to. Technique is fun and there’s all sorts of wonderful pleasures in making anything physically. But the really crucial moment is the evaluation and the strategy, which is what this middle part is about.

Debbie Millman:
Many artists in the book also talk about getting into a flow state, which I often compare to an athlete getting in the zone. That period you describe as one of utter absorption where all the distractions in life disappear. Time even seems to evaporate. Did any of the artists in the book have tips for igniting or expediting or extending that state?

Adam Moss:
No, unfortunately they did not, but they all, almost to a one, talked about it in terms of exaltation. It’s the reward. I thought of it very much akin to almost a hallucinogenic experience, and it has that same kind of body high to be in it.

Debbie Millman:
Yeah, it’s magic. At the beginning of the Art of Work, you state that you’re a painter, but you feel ridiculous saying that.

Adam Moss:
Yeah.

Debbie Millman:
You feel ridiculous saying that. After all these interviews and this deep examination of what it means to be an artist, do you still feel ridiculous?

Adam Moss:
I still don’t know that I would call myself a painter. I don’t feel ridiculous painting. There’s something that actually I heard on your podcast that was really very helpful to me, and it was Lynda Barry was on. And she talked about how nobody, when they get on a bicycle… Do you remember this? How nobody when they get on a bicycle thinks that they can win the Tour de France. They ride a bicycle because A, they’re trying to get somewhere, or B, they’re just trying to have a good time. And why do we think differently about art?

There was something at the end of this project about people’s insistence that the piece, the work, the physical object that they were making, whether it’s a book or a poem or a painting or joke, was not actually the most important thing to them. In fact, they were largely indifferent to it. They were proud of it. It was good. It was nice. It was the end. They weren’t dismissive of it typically, although sometimes they were. But they did feel that it was not the point. That the point was the, what I like to think of as the verb, was the making.

And once I got that, I had a different attitude about my painting. That sense of critical punishment I was inflicting on myself disappeared, and I felt the pleasures… Whether they were flow state pleasures or not, I felt the pleasures of the making, and that gave me delight. And now I actually really do love painting. I know it sounds pat, but it is true that it gave me back my love of painting. I’m painting obsessively again, but I’m not painting obsessively to make good stuff. It’d be nice if good stuff happened. I have no problem with that, and I am getting a little closer to maybe showing my painting-

Debbie Millman:
That was my next question. I know that the only two people that have… Well, I think… Did you show it to one interviewer?

Adam Moss:
Yeah. I let Ari Shapiro from NPR. He wanted a scene, and I understood that as a magazine editor. And I thought, “It’s radio. I can let you into this room and no one will ever see what you saw. So okay, you’ll see it. And you’re lovely, generous guy. And I’m sure you’ll think it was fine. But the audience won’t see it.” So I did let him in, yes.

Debbie Millman:
So he’s one of three. Your husband, your art teacher, and now-

Adam Moss:
Although someone else reminded me that they’re number four, because it’s someone that I had been sharing the studio with for a while and I kind of forgot that he worked within. When I wasn’t there, he worked within the world of my work.

Debbie Millman:
Well, I hope the world gets to see it at some point. My last question isn’t really a question. It’s really more of a quote. I want to quote something that you said. You were asked about finishing the book and being out in the world, and if you have a better understanding of the mystery of making art, and you said this, “I’ve gotten one part of the answer, which is that the work of art is the work. It’s the most banal observation, but that it’s not about the thing you make, it’s about the making. It took me three years to figure out that that was actually true.” And let me tell you, it has changed my life.

Adam Moss:
Yeah.

Debbie Millman:
Adam, I just want to say thank you. Thank you for making so much work that has mattered for so much of my life, my adult life, and thank you so much for joining me today on Design Matters.

Adam Moss:
Oh, thank you, Debbie. I’ve really enjoyed this conversation. Thank you so much.

Debbie Millman:
Adam Moss’s latest book is titled The Work of Art: How Something Comes From Nothing. This is the 19th year we’ve been podcasting Design Matters, and I’d like to thank you for listening. And remember, we can talk about making a difference, we can make a difference or we can do both. I’m Debbie Millman, and I look forward to talking with you again soon.

Debbie Millman:
David, I understand that you are planning to title the last book you ever write Basically Fine?

David Remnick:
No, I think I’m going to title it Home By 10.

Debbie Millman:
Well, tell us the story of Basically Fine.

David Remnick:
I have no idea what basically fine is.

Debbie Millman:
Oh, it was when you interviewed Kenzaburō Ōe and you sent the article to-

David Remnick:
Oh, my God. How do you remember these things? I’m going to confess to you, and this is going to be a problem for you. If I wasn’t married to the woman I married to, I would not remember any of my life. The nature-

Debbie Millman:
Fortunately, I know your wife.

David Remnick:
Yes. Anything before my wife, I have no idea. So we’ll struggle here for the next some minutes, but I’m not kidding around. Kenzaburō Ōe, like a lot of stories for journalists, is somebody that … Kenzaburō Ōe won the Nobel Prize, Japanese author, I think just died very recently. I was assigned to write a profile of Kenzaburō Ōe when I was a writer for The New Yorker and Tina Brown was the editor. I really struggled with this piece. His English was about, it’s better than my Japanese, but it was not great. I came home and I did not have what I like best in this world other than my friends and family and peace and love and understanding, which is a full notebook. A half-filled notebook is hell on Earth, and yet I wrote the piece anyway because that’s what one does. I went into my editor, Jeff Frank’s office, and I saw the note from Tina Brown and it said, “Jeff, I guess Remnick’s piece is basically fine.” Let me just say in the annals of editor reaction, basically fine sucks.

Debbie Millman:
You might not remember anything.

David Remnick:
It sucks really bad. I tried to put it out of my mind, but you thankfully now have reinserted it.

Debbie Millman:
Just to prepare you, that might be happening a few more times. You were born in New Jersey in what you-

David Remnick:
I was, deepest, darkest.

Debbie Millman:
No, I’m going to be bringing up a lot of things that you’ve said before.

David Remnick:
That’s all right.

Debbie Millman:
I need you to know right now that you can trust me that the sources are good. You’ve described your upbringing as an East Coast version of what is seen in the film, American Graffiti, marching bands, football teams, and very middle class in a blue collar Springsteenian way.

David Remnick:
That’s right. No ocean.

Debbie Millman:
You went to kindergarten in a yeshiva. That doesn’t feel particularly Springsteenian.

David Remnick:
Well, from where I come from it is. My parents sent me to a religious school for a year because I was large and impatient and I missed the cutoff date. Do they still have cutoff dates for kids? So I missed the cut-off date, so I was a little on the old side to be waiting yet another year. So they sent me to a yeshiva in Patterson, New Jersey and it was called Yavne. I had my mouth washed out with soap by Mrs. Wool.

Debbie Millman:
Why?

David Remnick:
She should rot in hell. I think I-

Debbie Millman:
Very yeshiva-like.

David Remnick:
By the way, not just any soap. You know that lava soap, which is combination soap and a stone?

Debbie Millman:
Yeah.

David Remnick:
It was that. I think I said a bad word of some kind like tuchus. That would get you to skip a grade now. Got my mouth washed out with soap.

Debbie Millman:
You were a newspaper junkie as a child and began reading The Village Voice at your neighborhood 7-Eleven.

David Remnick:
I did.

Debbie Millman:
I didn’t even know 7-Eleven sold The Village Voice.

David Remnick:
Well, I didn’t, strictly speaking, buy it either. I would sit on the floor of the 7-Eleven and read it cover to cover and that’s what I thought I’d do with my life. I thought even as I got older, I think The Village Voice really had two big moments. When it was first invented, it was invented as a product of the ’60s, obviously. In fact, it’s a new book about … The Village Voice is said to be very, very good. I haven’t read it yet.

Debbie Millman:
It’s covered on today’s New Yorker website.

David Remnick:
I don’t read it. I hear The New Yorker website is excellent, and the magazine is said to be good too.

Debbie Millman:
It’s pretty good.

David Remnick:
Funny cartoons and whatnot. No photographs on the cover though.

Debbie Millman:
Caption contest.

David Remnick:
They have that too. I should subscribe.

Debbie Millman:
I’m really actually hoping you’re going to give me some tips.

David Remnick:
Unsubscribing? Oh, I’ve got a lot of tips on that.

Debbie Millman:
No, no, no, on how to get to the top three in the caption contest. That’s a bucket list item for me.

David Remnick:
Okay. Can I just digress from The Village Voice for a second? Occasionally, I’m invited to a fancy thing, and not very often and once in a while I’ll go because curiosity killed the cat. So I went to this thing and I was introduced to then Mayor Michael Bloomberg and he says, “Hello. Hello.” I was very polite, well brought up in New Jersey and whatnot. He said, “I’ve tried to win the cartoon caption contest dozens and dozens of times and I’ve never won.” Now prior to this conversation, I had had what my dearly departed mother would call a big drink. So I said, “Wait a minute, you’re the mayor of New York. You are the richest person in New York and you want to win the fucking caption contest too?” He just didn’t find this funny at all and he said, “Yes, yes.”

Debbie Millman:
We take it very seriously.

David Remnick:
I think he take himself very seriously. So anyway, I worshiped The Village Voice because it was … The New York Times is the weather and it was the establishment word and all that, and The Voice was this other thing and filled with writers who wrote about themselves. There were different spots in politics and there was feminism. What was that? There was all this stuff about race, although there were very few Black writers, God knows a condition not limited to just The Village Voice at that time. Even in North Jersey, you don’t feel like you’re sitting here in Williamsburg or Manhattan or whatever. It feels a million miles away. So to listen to WBAI or WNEW FM for music or the Caribbean station or this, that, and the other thing, radio is a big part of this imagining another life.

Debbie Millman:
Well, you were a child insomniac and you’ve described yourself as an adolescent, no sleeper, all night listener, and eyes wide open, ceiling-staring dreamer.

David Remnick:
That wasn’t cocaine at work. It was just a sense of wanting to be elsewhere and knowing that there was this world across the river. Now, a person with a real imagination, someone like John Updike or name your favorite writer-

Debbie Millman:
Roxane Gay.

David Remnick:
Yeah, would certainly have had the imagination to know that Hillsdale, New Jersey had its own emotional depths and interests as Updike made of his Pennsylvania. I did not. I did not. New York City was where I wanted to be from the time I began going with my parents to visit my grandparents in Brooklyn and great grandmother in Coney Island and in Trump houses, by the way.

Debbie Millman:
Wow. Are you still an insomniac?

David Remnick:
Pardon me?

Debbie Millman:
Are you still an insomniac?

David Remnick:
Oh, no. I sleep like a rock because I live here. Mission accomplished.

Debbie Millman:
You started writing for your high school newspaper-

David Remnick:
I did.

Debbie Millman:
… The Smoke Signal when you were 13. From what I understand, none of your classmates were interested in contributing to the paper.

David Remnick:
No.

Debbie Millman:
So you wrote and edited the entire paper by yourself. Is it true you made up different bylines so it wouldn’t seem as if you were writing it on your own?

David Remnick:
I still do. Are you a fan of Rachel Aviv?

Debbie Millman:
Mm-hmm.

David Remnick:
That’s me. She’s good, isn’t she? She’s really good.

Debbie Millman:
She’s my favorite.

David Remnick:
Patrick Radden Keefe? Me too. Me too.

Debbie Millman:
Now, you put this together yourself via old-school layout and paste-up techniques on your kitchen table. How was it printed? Was it mimeographed?

David Remnick:
Well, let me tell you how paper was. You printed it out and you cut it and used scissors and glue. It was a big [inaudible 00:09:20] It was a big deal and it was a terrible … First of all, beginning with the title. It was called The Smoke Signal because we were the Pascack Valley Indians. They aren’t anymore. I think they’re like the Warriors or something, and The Smoke Signal became the I don’t know what else, but that came-

Debbie Millman:
The Signal, right?

David Remnick:
… 30 years later, not The Signal. That would be the CIA newspaper. I didn’t do it completely by myself, but nobody was really terribly interested in this. That could have been the first signal that the newspaper business was in trouble.

Debbie Millman:
You also got a job for what you’ve described as, quote, “writing stupid little articles for one of the community giveaway papers-“

David Remnick:
I did.

Debbie Millman:
“… featuring information about school board meetings,” but you also described it, and I love this, as the most romantic thing ever.

David Remnick:
Well, I left my house and I asked people impertinent questions and they answered them. In other words, I think reporters discover this very early on or anybody that has a medium that they can put between themselves and the world, a canvas, a notebook. It’s a form of permission. It’s a form of permission, and to have that permission at a preposterously young age and to have what seemed like ancient important people like 40-year-old school board members answer your questions, it was very suggestive of something exhilarating.

Debbie Millman:
You also started to play guitar around that time.

David Remnick:
I did.

Debbie Millman:
I believe your first instrument was something you called a gazinta guitar.

David Remnick:
A gazinta guitar would mean a bigger healthy guitar. No, I had a crap guitar, but remember, what was the guitar? The guitar was like a notebook. The guitar is a way to be a part of this thing that was happening that you wanted to be a part of. I wouldn’t have picked up a flute, well, unless you wanted to be Jethro Tull.

Debbie Millman:
I was going to say Ian Anderson.

David Remnick:
Yeah, Jethro and Ian Anderson, but I just desperately wanted to … Look, I grew up in very, in all seriousness, what struck me as a very dull, conventional, hemmed in environment with a mother who was quite ill, who had very serious MS, and how she managed to this day I don’t know, and a father who soon would be quite ill and not be able to work when he hit about in his 50s. There was a certain desire to be another, to enter the big world however deceptive that might be. That certainly was the animating spirit of everything I did.

I learned about that other world through various mediums. One of them was very early bumping into the obvious music, most particularly Bob Dylan, and then you’d listen to that and then that would throw you to reading Allen Ginsberg or, or, or, or, and it happens to a lot of people. I’m sure a lot of people in this room at a certain age, something sparks you, whether you read or listen or you have a friend that leads you in some way. So all these things were very important to me.

Debbie Millman:
How did your parents’ illnesses impact your ambition?

David Remnick:
Well, it suggested that at a very peculiar age early on, and I know I’m not alone in this and I’m far from in the global sense or even in the metropolitan sense, the most disadvantaged, but it suggested that the future would require me to help them. I was the older of two kids. My father struggled on for a while, but he was a dentist and he had very, very small dental practice. At a certain point when he was, I don’t know … I think he lied about it for years because he had a tremor in his hand. His wife is sick, he has two kids to support and he’s screwed in the conventional making-a-living sense. I think he lied about it for a while, but patients, I think you all know as dental patients, we all have an identity as dental patients, that a dentist who comes at you with a shaking hand is not a good prospect for future business. It’s like a bad Buster Keaton movie.

So by the time I came back from Moscow in my late 20s or 30, whatever I was, they were all in debt and things collapsed. Again, I’m not weeping about this except I think back at them and they were much younger than me and they were probably terrified, but in my egomaniacal teenage imagination, I knew that I had to make a living.

Debbie Millman:
How did that impact the choices that you were making about what you wanted to-

David Remnick:
I couldn’t be a novelist. I couldn’t say, “You know what? My parents are going to stake me a little bit and I’m going to move into a tiny apartment with a roommate. I’m going to be the next pick your favorite novelist.” ‘That was not … I needed a job.

Debbie Millman:
What gave the sense that journalism would be a more secure option?

David Remnick:
Let’s just let that sit in the rest of my-

Debbie Millman:
I love that people laugh at my jokes, but that wasn’t really a joke.

David Remnick:
Well, first of all, the journalism business, even though I didn’t know it at the time, was fat and happy in those days. I’m sensing that there are some people here in the audience who are in a state of, when they think about the journalism business or the podcasting business, what’s the word we now use constantly, precarity, which I think became a word three years ago, I’m not sure before.

Debbie Millman:
Along with unprecedented.

David Remnick:
Exactly. As somebody who now is ostensibly in charge of a lot of people, I’m thinking about this all the time. In other words, I’m 65 years old, but I’m working with a lot of people who are 27 and 34, and they want to have an exciting, interesting, engaged life. That’s why they got into journalism and didn’t go work for Goldman Sachs. It wasn’t for the dough. They deserve to make a living, but the whole business model has exploded.

Back to your question, I was so lucky that right out of college, having had internships at Newsday and the Washington Post, I stuck around at the Washington Post. There aint many Washington Posts left anymore. A lot of my friends went to the Miami Herald, which was this terrific, flawed but terrific place to learn and to write and maybe spend your whole career there. There’s barely a Miami Herald.

Debbie Millman:
Do you feel that choosing journalism over becoming a novelist or a poet, I know you also wrote poetry, was a compromise?

David Remnick:
That would’ve really filled the coffers for my parents. They collected elegies.

Debbie Millman:
You could really raise a family on that income. Do you feel like it was a compromise?

David Remnick:
I did at the time. The self-proclaiming of oneself as a novelist, just, first of all, there was no fiction around. It’s not as if I had written anything. I always hear all the time people who say, “I’ve always wanted to write. I want to write,” and I would never answer this way because there’s a certain cruelty in it but, “Then write.” If you’re going to do that, you will find a way. You have to find a way. There are all kinds of writer biographies about how people found a way. Graham Greene was a night copy editor at a newspaper, I presume not making a hell of a lot of money, but enough to eat and house himself. He got up early and he pushed himself and he wrote novels and got started and he was good at it. There is no law that at any given moment there are going to be the world is going to treat you the way you want to be treated. That’s the fact. I needed a job.

Debbie Millman:
You went to Princeton University, which you said getting in was a miracle.

David Remnick:
To this day, I don’t understand it. If I presented the SAT scores that I did have now, there’s no way, and the high school I went to, nobody went to these places. Again, I don’t get it. There must have been some mistake.

Debbie Millman:
You studied-

David Remnick:
I’m not kidding around. I really don’t, I don’t get it. I was top of my class. There were other people at the top of the class and I don’t get it.

Debbie Millman:
They never reached out to you and asked you to come back?

David Remnick:
You know what? I had some stupid nervous interview with a Thai and I don’t know.

Debbie Millman:
You studied Russian and French, majored in comparative literature. Your parents thought that majoring in comparative literature was weird.

David Remnick:
My father asked me, “What are you comparing?”

Debbie Millman:
What are you comparing?

David Remnick:
Good question. Smart guy. I was comparing it to dentistry as it happens and Tolstoy won. Concerning how I made my life later in the Russia biz a bit, here were the grades that I got in Russian, C plus and D, and then I got out of the Russian business. What happened was I had had some in high school. The only interesting course that my high school offered was Russian. I think some-

Debbie Millman:
Really?

David Remnick:
I don’t know. We this wonderful man named Frank Falk. I don’t know how he washed up at this high school, but he was teaching Russian. I thought, “Wow, cool.” I took it for four years, and when I got out after four years, I could say those boys are crossing these bridges or something like that and that was it. So I thought third year at least, right? I took the test they sometimes give you, the aptitude test, and Veronika Dolinko said to me, she’s the teacher, she said, “David, I think you should start from beginning.” I said, “Well, surely. Second year then,” and she said, “It is your funeral,” and so it was, and so it was, but I started all over again years later.

Debbie Millman:
I actually minored in Russian literature in English translation.

David Remnick:
There you go.

Debbie Millman:
Just to avoid that whole scenario.

David Remnick:
That’s fine.

Debbie Millman:
While at Princeton, you joined the University Press Club, in 1979, you co-founded the student newspaper, the Nassau Weekly.

David Remnick:
Still exists.

Debbie Millman:
I know. It’s incredible.

David Remnick:
It is amazing.

Debbie Millman:
You also became a stringer for the New Brunswick Home News, the Asbury Park Press- … and interned at the Washington Post and Long Island News Day. Overachiever much?

David Remnick:
Yeah, I guess. I have one quality that I will fess to. I have what my grandparents would call zitsfleysh. I put in front of a task, I will complete it. If I have to write a long piece in three days, I won’t move from the chair. It might not be all that good, but I will complete it.

Debbie Millman:
How are you able to write that fast?

David Remnick:
I don’t know. It’s like … Again, I will fess up to that. The quality somebody else will have to fess up to, I don’t know. It’s like asking how does a seal know how to balance a ball on his or her nose. It’s just that that thing that I learned how to do. I think part of it is that I didn’t learn how to be a reporter by blogging at home, which is another generational thing, and I’ve nothing against that, different qualities come out of it, but I had this traditionalist training of covering police at night and having to do things very quickly. I was a sports reporter for two years at the Washington Post, and you would have to cover ball games at night and write an account of the game in 20 minutes. So you build muscles. Why does a dancer jump higher than we do? Because they spend all day long training. They just do training early on.

Debbie Millman:
You interned at the Washington Post and then stayed there after graduation until they told you to go away for a year.

David Remnick:
I did, and I taught in Japan knowing no Japanese at a Catholic university. So they had this Jewish kid from Jersey at a Jesuit school in Tokyo. The day I landed, the three priests greeted me and they said that I may not date any students. Of course, I’m a really good boy and I said, “Okay.” So I had a rather monastic Japanese existence and I read like a book or two a day. I couldn’t speak any language. I think they wanted me to stay for two years and I stayed six months and I traveled around all over Southeast Asia on $5 a day and all the hashish you could pocket and came back and started a job at the Washington Post for real.

Debbie Millman:
Well, actually, you made a stop in Paris.

David Remnick:
I did.

Debbie Millman:
Clad in a Leon Russell T-shirt and $9 Converse sneakers.

David Remnick:
Yeah, those were good.

Debbie Millman:
You made money singing Bob Dylan songs in the subway.

David Remnick:
It’s the earlier time, but yes, I was a busker. So next time you’re on the subway and somebody … I don’t know. What are the most common songs you hear on the subway being sung to you? Give the person a little dough because they need it, but I had a great time. It was really fun.

Debbie Millman:
You made enough money to survive doing the busking.

David Remnick:
Oh, if you stay in a hotel for $4 a night, it doesn’t take long to make that much money.

Debbie Millman:
You returned after you’re a year away where you worked at the Washington Post for the next 10 years. You worked with the legendary Ben Bradley who was the editor of the Post during that time, and you said that you and most-

David Remnick:
And legendary podcaster, Malcolm Gladwell as well.

Debbie Millman:
Yes, I’m going to mention that a little bit. You said that you and most of your young colleagues saw Bradley the way one might see a great orca in a fish tank.

David Remnick:
Right. So they had glass. It was the beginning of the glass office period. He was in his post-Watergate period, so he was already a celebrity and he was incredibly handsome in an old wasp way.

Debbie Millman:
Yes. Jason Robards.

David Remnick:
Oh, my. Jason Robards didn’t come close to looking as good as Ben Bradley and all the presidents men. I’m sorry. He got the voice. He got the great voice and the whole thing and the cursing in fluent French. He had it all going on, but he was also in this late mannerist period. His accomplishments, the big accomplishments were a little behind. He was coasting a little bit, I’d say. He was enjoying it. He was enjoying life, but I was terrified of this guy and I had almost no contact with him. Even when half the hierarchy of the Washington Post came to Moscow, when I was there to interview Mikhail Gorbachev, Bradley just stayed home. He wanted no part of it. I think the jet lag was too much.

Debbie Millman:
What was the biggest thing you learned from him?

David Remnick:
Fearlessness in an editor is essential. If we can be serious for a moment, and I’ve been at this for a while now, and The New Yorker is many things, I hope. I hope it’s funny. I hope it has literary depth, but one thing it has to do is put pressure on power. It has to ask hard questions. It has to not pander to its audience in any way. It has to do hard work, and that’s not always … You don’t always sleep well. We have a lot of safeguards. Beyond the talent and the efforts of the writers, we also have an extraordinary checking department of really devoted people going over every, not just spellings and when So-and-So was born, but really beating the hell out of these pieces to make sure they’re right, but they also have to be fair.

We live in a world that is unbelievably confusing and difficult and contentious and polarized and mysterious, and it’s a high order to get things right. Bradley is among those journalists who knew that like in life, you wake up every day and you make one mistake after another and you have to proceed fearlessly. Otherwise, you’re just not going to have any value to the reader of the greater world.

Debbie Millman:
Given the state of politics in the US right now and the potential futures that may unfold, how worried-

David Remnick:
Again.

Debbie Millman:
Again. How worried are you about the validity of the news being questioned?

David Remnick:
I think it should be questioned.

Debbie Millman:
Well, in terms of what-

David Remnick:
You mean us being questioned?

Debbie Millman:
Yeah, us being questioned as fake news, the whole way in which the news has been in many ways seen as false, lies, untruths.

David Remnick:
I think there’s one thing that we need to, at this late date, recognize, concede and deal with is that it’s not so much that Donald Trump is a, because that’s what you’re talking about, not only, but part of it, that Donald Trump is not just an autocrat and a demagogue, he’s also very talented demagogue and very … I’m not sure how talented an autocrat he is, but certainly a talented demagogue that other people trying the same stunts, we’ve seen them in American history and they haven’t been as successful. Our history is filled with demagogues and would-be autocrats and worse, racists, misogynists, and so on, but his ability to lock in to a certain base, psychology and comedy and a sense of arousal at a visceral level is astonishingly effective, maybe not in this room, I’m assuming not in this room.

Debbie Millman:
I’m hoping.

David Remnick:
I’m assuming fairly unanimously, but in the greater world, it is an astonishing thing that you have a president of the United States you can object to whatever particular issue you might have, whether it’s the Middle East or economics or immigration, whatever it is, but to compare one to the other and know that they are in a tie is I think that’s another thing that’s very, very hard for our writers and our readers to make sense of and understand is, how this could possibly be? How it is that we live in the same country that elected Barack Obama in 2008 and 2012 and, in fact, many of the same voters then voted to elect Donald Trump president? That is an astonishingly complicated piece of business to understand. I think that we do our best and fail all the time and then have to wake up and try again.

Debbie Millman:
You were in Russia during the Gorbachev-Yeltsin years. You returned to the US in 1992. You wrote your first book, Lenin’s Tomb: The Last Days of the Soviet Empire. You received both the Pulitzer Prize for nonfiction and the George Polk Award. After writing over 150 major stories on everything from the Soviet dissident, Anatoly Shcharansky to the Indianapolis 500, you left the Post to become a staff writer at The New Yorker, and you were hired by then editor Tina Brown. This was not your first attempt to work there. Can you tell us about the queer letter you sent editor William Shawn when you were still in college?

David Remnick:
This was really ballsy. So William Shawn … The New Yorker was a very, from the outside at least, a very insular special institution. I should say the one advantage of being a dentist’s son is that dentists have waiting rooms and waiting rooms at least then were filled with magazines. On Saturdays after my father closed up shop, I’d go in and read all the magazines. One magazine that I was not especially interested in was The New Yorker. It seemed not for me. It seemed not of the ’70s. I was interested in Rolling Stone, which now seems like of another time.

Debbie Millman:
No. Then it was a Bible.

David Remnick:
The invention of the insight of Rolling Stone was that it discovered that the counterculture was the culture. That’s a profound insight. Think of everything else, what you will or Jann Wenner, whatever, but that was an insight. It was a business, but it was exciting, certainly to a 16-year-old imagination and sitting in New Jersey. So I wasn’t interested in The New Yorker. Then I got to college. I had this teacher, a writing teacher named John McPhee, who, by the way, wrote about stuff that didn’t innately excite me, geology. Then I got into it and it was magnificent. It was like discovering Renaissance painting or something. I just, “Oh, how did I miss this all my life?”

Also, he was a writer as a teacher. He wasn’t a scholar of literature. He was an actual practicing writer. This was enormously influential to me and exciting. That’s what I wanted to do. So The New Yorker became more enticing. I wrote a query letter to William Shawn, who was a gnomic, genius, odd, distant figure. It was like writing a letter to Buddha, and you expected about the same result.

Debbie Millman:
Dear Buddha.

David Remnick:
Dear Buddha. “Dear Mr. Shawn, I’d like to write a profile of this guy Tom Page, who was a squash champion, who grew up in Dayton, Ohio, first family of Dayton Ohio, weirdly rich but had a squash court in his backyard. When he broke his right arm, his strong arm, he played with his left arm and he beat everybody anyway. He took an enormous amount of drugs, and it turned out he’s also quite disturbed and died very young, but he seemed like the profile of a deeply eccentric, interesting person.” I got back the following letter, “Dear Mr. Remnick, Mr. wind covers racket sports for us.” I loved the Mr. Wind part.

Debbie Millman:
love the racket sports part.

David Remnick:
I’m like, “Who the fuck is Mr. Wind?” and then it says, “Sincerely yours, William Shawn,” and that I don’t have this letter kills me to this day. Mr. Wind turned out to be Herbert Warren Wind, who wrote very, very, very, very long pieces about golf tournaments. The structure of the piece would be we came to the first hole.

Debbie Millman:
Go on.

David Remnick:
There would be many columns, which brought us to the second hole, which was a dogleg left of 343 yards, par four. People ask me, “Why are the pieces in The new Yorker so long?” and I say, “You should have seen it back when.” We used to do four-part series on literally on grains. Of course, there were four part series that were brilliant, Janet Malcolm or whatever, McPhee, but there’s a sociology to this too. So why are Dostoevsky and Dickens’ novels so long? There’s so long because in the 19th century, literary magazines were middle-class entertainment and Crime and Punishment being published in the Bell [inaudible 00:34:20] or Dickens being published in Blackstones. This was entertainment for the ascending middle-class audience that was going to read a novel, and they were entertaining and they were episodic and they were realist, and they went on. There’s a sociology to the art question.

William Shawn’s, one of his biggest challenges as an editor, and all editors have peculiar challenges to the time, one of his biggest challenges is, “I need to have enough editorial matter to go next to the gazillion ads I am publishing.” I don’t have that problem. I have a different kind of business.

Debbie Millman:
Well, when you took over in 1998, the magazine had lost an estimated $170 million since the Newhouse family had bought it in 1985. This was not the only precarious time in its history. I believe you are in possession of a letter from co-founder Raoul Fleischmann to a colleague stating that they needed to shut the magazine down in May of 1925, just three months after the debut issue.

David Remnick:
That was before the word precarity was around, but there it was.

Debbie Millman:
It took three years, but the magazine has actually been profitable since 2001.

David Remnick:
Look, I will say this, our business changed a lot. The old style of all magazines was subscriptions were very cheap so that it would get in a lot of hands, and so advertisers would reach as many people as possible of a certain kind of audience depending on what the magazine was or newspaper or television network or whatever it might be. The nature of advertising has changed, and it’s completely and utterly dominated by Google and Facebook. I don’t know what the real numbers are, but something like 75% of the ad market is to that and the rest is scraps. The result has been, in addition to other factors like Craigslist and so on, has been the decimation of mid-level newspapers.

There’s really only a few exceptions to this and magazines, and it’s tragic. It’s tragic. Not that every publication that’s been lost or diminished is perfect, but the changed landscape is deeply, deeply, deeply worrying for all kinds of reasons that we can talk about. The only other alternative that I know of at the moment is subscriptions, the same thing that television’s discovered. Luckily enough, fairly early, we changed our emphasis and we basically said to you, readers of the New Yorker, without saying it, that, “I can’t give this away anymore. You have to pay more than a cup of coffee a week to have this extraordinary thing in your hands or on your phone or whoever you choose to read it.”

The New Yorker, in fact, gives you a great deal more per day, per week than when Mr. Shawn was editing it, but the subscription model, now that we’ve had a lot of success with it for a while, now the subscription model is facing challenges too because you’ve all had this discovery. You’ve all woken up and go, “Wait a minute, I have Netflix, I have Paramount+, I have …” and then there are even apps now to get rid of or shave down your subscriptions.

Debbie Millman:
Yeah, which was the original cable system.

David Remnick:
Exactly. So we’re in a time of real flux, and editors spend a lot more time thinking about business than they probably, if they’re being honest with themselves, would like to. They want to be thinking about writing and graphic design and all kinds of things, but if you don’t have your eye on business, and this goes with public radio or look at what’s happening in the podcast business. We have The New Yorker Radio Hour with my colleague David Crass now. We have a terrific time doing this. We’re thinking about how to develop it, make it better all the time, but we also have to pay attention to economics. Otherwise, you wake up and something terrible has happened, and I’m determined.

We’re going to celebrate 100th anniversary next year, The New Yorker. I don’t want that to be an occasion for us to show off at a museum of ourselves. There’ll be some of that to be sure, but I want people in this room and their children to be reading The New Yorker that is a lot better than the one that we have now in the future. So I think about that kind of thing all the time.

Debbie Millman:
When you first made the announcement of your expansion into podcasts, you stated, “While I readily admit to the gall of it, we come to this project with a deep respect for the history and creative range of the medium.” Why did you feel it was galling to expand into the podcast world?

David Remnick:
Because it’s like … I’m not saying we’re Michael Jordan, but when Michael Jordan left the Chicago Bulls to go play baseball, that was, one could argue it was both galling and a little stupid and like, “Why are you doing that?”

Debbie Millman:
I think it was actually interesting.

David Remnick:
I once said, “Maybe I’ll write a novel.” He said, “Stay in your lane. Stay in your lane.” I don’t believe in necessarily staying in your lane, but there is that instinct toward, “Okay. You know how to do this. You know how to make hamburgers. Make hamburgers.” Sometimes places that expand and suddenly start serving something else fail. I just think it’s enormous fun, and I also think it reaches other people.

Debbie Millman:
Is there an underlying principle or philosophy that is guiding the continued expansion into podcast?

David Remnick:
That’d be good, and they have to make their own way. The latest one, two things have started of late. There’s a culture podcast with Alex Schwartz and Vincent Cunningham and Naomi Fry, which is extremely fun and funny and smart. We purchased a podcast that you probably know called In the Dark, and In the Dark was being run out of, I think, Minnesota Public Radio for a while, and they stayed in Minnesota. This is a reporting and narrative podcast, more like in the mode of serial, say, and it’s really hard to do, and they work a long time on their reporting. They’re working on their third season and they’ve been around for some years. These are serious reporters. I felt that they were kindred souls and so did the head of Condé Nast. So we don’t see them a hell of a lot.

There’s an editor at the new Yorker named Will Davidson who works with them, and Chris Bannon, who heads podcasts and audio in general. Condé Nast isn’t in deep contact with them, but they’re really ambitious. They’re shooting for the moon. They also had a mini season that took a New Yorker piece by Heidi Blake called The Runaway Princesses. I thought it was terrific.

Look, I just listened to a lot of audio. It’s always meant a lot to me, podcasts and radio, and I just thought it was an experiment worth trying. We’ve had failed experiments too. In video, we did a thing with Amazon that I think if we’re being honest, it was a noble failure. It wasn’t embarrassing, but it didn’t take off. It didn’t garner the attention. It didn’t quite work.

Debbie Millman:
How long do you give something before you make that decision?

David Remnick:
Well, sometimes economics will dictate that. Economics might tell you. Quite frankly, audio is less expensive to do, although In The Dark, because it’s so intensively reported, like serial, like any number of other things, that’s more expensive to do.

Debbie Millman:
In a recent episode of The New Yorker Radio Hour, you interviewed a meme mixologist. I’ve never heard that job title before.

David Remnick:
God knows I hadn’t either.

Debbie Millman:
Can you share what that actually is for the audience?

David Remnick:
No, I can’t, no. Have you ever had the feeling, and maybe you’re having it right now, that you were interviewing something and the producers have said, “We’re going to interview a meme mixologist,” and you say, “Okay, that that’s fine,” and you get through the interview as if in a haze, and at the end you say, “I really don’t know what that is.”

Debbie Millman:
Fair enough, but no, I’m not experiencing that, thankfully. The last thing I want to talk to you about is music. In your latest book, Holding the Note: Profiles and Popular Music, you state that there’s no one who has meant more to you than Bob Dylan. The passion first-

David Remnick:
I don’t think I’m alone in that.

Debbie Millman:
Anybody here?

David Remnick:
Okay. Well, older crowd perhaps.

Debbie Millman:
This passion was first ignited in 1966 when you first heard the song I Want You.

David Remnick:
That’s right. So weird experience. Again, I don’t remember much. Look, the story I’m about to tell you may be completely false in the sense that it was a novelist named Harold Brodke, and he wrote a novel called The Runaway Soul. The novel opens with his own birth and Harold claimed that he really remembered it, and it was important to him this self-mythologizing at some level because there’s no earthly way that he remembered his birth. I do think this is true. So I want to be honest because-

Debbie Millman:
Well, it could be a memory of a memory.

David Remnick:
Exactly. Because I’m a journalist, just when I read memoirs, I read them in this spirit, all of them, including Bob Dylan’s memoir, by the way.

Debbie Millman:
We’ll get to that in a minute.

David Remnick:
When I was seven, something like that, my mother got sick. She had the first serious attack of multiple sclerosis. My father and my brother at that time must have been four, my father was not able to go to the hospital. I guess I was past the limit. My father took me to the hospital and it was very scary seeing your mother in the hospital bed. Seeing your parents doing anything other than being in the kitchen is scary.

The primal scene, let’s not even think about that, but sick is really, that I really do remember. As I recall, I heard this … We played the radio. My father liked music too and he had good taste, R&B, jazz, classical. Someone was on the radio singing with a voice like this was not Paul Revere & the Raiders. This was not your average pop music. This was not Chad and Jeremy. This was, “The guilty undertaker sighs. The lonesome organ grinder cries,” and what the fuck was he singing about? I was seven years old and it was thrilling.

I was not yet at the age where I was allowed to buy albums. There was this store called E. J. Korvette, a department store, not a high-level one. It was out on, I don’t know, Route 17 or Route 4, somewhere in Jersey.

Debbie Millman:
Korvette with a K.

David Remnick:
There you go. I bought this album because kids can’t decide, that Beatles album or that. So I bought something called Best of ’66, always hedging my bets, and it was okay. Then there was that song. It was $1.99, I think, the album. So I bought other Bob Dylan albums going backwards. So that would’ve been the time of Blonde on Blonde and then Highway 61 Revisited and going backwards and backwards until he was nothing but an acoustic guitar and harmonica.

That was a revelatory thing at a very young. I knew what the Beatles were. Even in the minivan taking us to yeshiva, kids wore Beatles wigs with a yarmulke on top. It’s a great look. It’s a great look, but this was something completely mysterious. To this day, I think the last time I saw Bob Dylan was four months ago with one of my children who’s now 32. They’ve all, well, certainly, Alex Noah have gone with me any number of times. I don’t know whether they’re indulging me or not. I can never quite tell.

Debbie Millman:
In 2004, you were hoping to get an exclusive excerpt of his recently published memoir in The New Yorker. You almost had it in the bag.

David Remnick:
I got screwed with my pants on.

Debbie Millman:
Dylan wanted the cover. Dylan wanted the cover of The New Yorker.

David Remnick:
Let’s just say that Bob Dylan has remained unmoved by and unimpressed by my hero worship. It doesn’t keep him up nights. Apparently, I’m not alone. So what happened was I had heard that he was writing a memoir and that it was good and that it wasn’t like Tarantula, which is, I don’t know, a surrealist experiment. I was summoned. I said, “Well, send the manuscript to the publisher.” I said, “I can’t send the manuscript. It would be like sending the Dead Sea Scrolls to my apartment.” So I went to the Dylan office, I won’t even tell you where it is, but you have to press a button that says, I don’t know, AB Cube Carpets. It’s like a CIA thing. You go up there and it’s just Dylan everything, Dylan tote bags and Dylan albums and Dylan this and Dylan that. If I had gone when I was 16, my head would’ve exploded into a thousand pieces.

They sit me in a little room with a bare table and a manuscript and a glass of water. I sat there and read the book straight through, Chronicles, anyone, and it was terrific. I said to the publisher and the Dylan guy, nice people, “I’m in. Don’t call Rolling Stone. That’s not your audience anymore,” I don’t know, whatever bullshit I told them. I was trying to get it for The New Yorker. I’m a competitive person. We made an agreement and we made a handshake agreement, and it still pisses me off.

Debbie Millman:
I know.

David Remnick:
This many years ago, it looked like John Kerry was running for president. Half the people here weren’t born yet, and it really pisses me off this thing. It got to the summer and they call and they said, “Okay. We’re about to publish it,” and I said, “Great. 7,000 words, the New York bit in the beginning, we’re all set and we’ll try to figure out what to do about fact checking and copy editing. Bob doesn’t necessarily have to be completely involved,” and so on and so forth, whatever shit I was slinging. I just thought everything’s going to be great.

Then they said, “Bob wants a cover.” I said, “Bob wants a cover? We have dogs on the cover or bowl of fruit or a joke or Barry Blitt making fun of whatever … We don’t do that. We don’t have photographs in the cover.” I thought I’d changed their mind, and there was a pause and they said, “Bob wants a cover.”

It was like talking to your parents at your worst, “Bob wants a cover.” I said, “I can’t do it.” I said, “I’m sure we can find some way to work this out.” “Bob wants a cover,” and that was it. They went to Newsweek. By that time, Bob looked like Vincent Price with a little mustache and a cowboy hat. I thought, “They’re never going to put Bob Dylan on the cover. It’s the middle of a presidential race.”

Debbie Millman:
It’s election year.

David Remnick:
They put him on the cover and they ran this excerpt. Apparently, Bob Dylan survived the experience of not being published in The New Yorker. Then another thing happened. I saw that he had these paintings. He’s a painter. He also makes whiskey and iron gates, a man of parts.

Debbie Millman:
He’s got range.

David Remnick:
He’s got range. These paintings, some of them are kind of good. There was one, a painting of Katz’s Delicatessen, the pastrami capital of the world, and it’s pretty good, and it’s a good New Yorker cover. It’s a New York scene. I make an arrangement. We’re all set to go. Two weeks out, I get a phone call, “Bob doesn’t want to do it.” So I feel our relationship is not on an equal level somehow.

Debbie Millman:
You think?

David Remnick:
Yeah.

Debbie Millman:
Malcolm Gladwell is here today to receive the 2024 Audio Van Gogh Award. You worked together at the Washington Post.

David Remnick:
Did I come in second? I’m just asking.

Debbie Millman:
Maybe next year. You worked together at the Washington Post, and he said this about you. “At the Washington Post, there was one day when David Remnick had three stories on the front page which I don’t think has ever been repeated. He was in a league by himself. So the idea that he would have a second act where he would outperform his first act is kind of unbelievable.”

David Remnick:
Have I ever mentioned publicly how much I love Malcolm Gladwell? Look, that happened, the front page thing, because I was blessed. I was sent to Moscow at a time where American interest and what was going on was singular, and the news and the interest and the varied topics of what were going on every day were so fascinating and, thankfully, so fascinating to our readers at the Washington Post that I think it was the journalistic equivalent of holding out a bucket in a rainstorm and it just filled up with stories. I could go to my mailbox in the morning, my mailbox, and come up with a story just by reading my mail.

Debbie Millman:
Well, you could. I don’t know that-

David Remnick:
Any idiot could. No, no, no, I mean it. At that time, every single day in a newspaper, in a literary journal, something was being published that had never happened before. They’re publishing Anna Akhmatova or Solzhenitsyn or Nabokov or Orwell or, “Oh, my God, there’s the first report we’ve ever seen on the war in Afghanistan.” We forget, now that things are so dreadful in Russia and not only Russia, how dreadful they are, how incredibly promising it was to be alive in Moscow in 1989 or 1990 and, by the way, in the world.

Part of what shaped me is when I was a young reporter, the world was very promising, but it’s always filled with misery. We are half-conscious, crazy people doing the best we can and the worst we can all the time, but there was this moment of promise in the Middle East, in Eastern Europe, in Central Europe, in South America, democratic promise. I’m not saying heaven on earth, but promise.

For all kinds of reasons that we could spend many, many hours discussing, so much of this was squandered that it’s very hard not to view current times through that prison for somebody of my vintage. I don’t want to die like that. I don’t want to go to my rest thinking that this country has given up on its democratic promise no matter how flawed we are even at our best or these other parts of the world. It wasn’t just the fact that I was 32 years old and you’re innately, although I don’t know that that’s the case now with people who are 32 years old, but there was some sense that the world could turn a corner for the better, not perfect by any stretch of the imagination, but the idea that history could go backward so profoundly is instructive about the precarity of human arrangements and behavior and foolishness. That’s why I’m in this business not just because it’s so immensely fun and satisfying, but because I hope it helps somehow lead the other way.

Debbie Millman:
Well, what I can say is that with you at the helm of The New Yorker, it gives all of us hope that that’s possible.

David Remnick:
That’s immensely generous. Thank you so much. Thanks for having me.

Debbie Millman:
David Remnick, thank you so much.

Debbie Millman:
As longtime listeners know, I do a lot of research for this podcast. I go deep on internet searches. I read, listen, and transcribe other interviews. I try and unearth forgotten early work. I don’t call my guests’ friends or parents or former teachers. But by the time I interview someone, I feel like I know their friends and parents and former teachers. Research is something I love most about creating this podcast almost as much as the actual interview.

This week, my guest made it a little bit easier for me. That’s because much of Isaac Fitzgerald’s life is already revealed in his New York Times bestselling book, Dirtbag, Massachusetts: A Confessional. Here, we are privy to an extremely unusual origin story. There is poverty and privilege. There is a boatload of booze, a lot of drugs, and some porn. This is all shared with Isaac’s sure handed prose and unflinching self-awareness. Dirtbag, Massachusetts came out last year in hardcover, and the brand new paperback was just published. Isaac Fitzgerald, welcome to Design Matters.

Isaac Fitzgerald):
Debbie, thank you so much for having me. I’m so happy to be here. I’m such a big fan of the podcast and of you.

Debbie Millman:
Thank you. Now, Isaac, is it true that you consider Terminator 2 to be one of the greatest action movies ever?

Isaac Fitzgerald:
I’m going to correct you, greatest movies ever. I’m sorry. I love Terminator 2. It’s right up there for me with Casablanca. I think it is a perfect, perfect movie. But yes, in terms of action movie, it is amazing.

Debbie Millman:
Why do you feel that way?

Isaac Fitzgerald):
Okay. First off, Arnold Schwarzenegger is incredible. This is one of the things that I deeply, deeply believe. And the more that we learn about him as a human being, I think the more that that is revealed. If you look at the documentary Pumping Iron from way back-

Debbie Millman:
Way back,

Isaac Fitzgerald:
It’s so easy, right? I get it. You watch Conan, you watch the first Terminator, it’s very easy to be like, okay. He was just this big strong muscly man, and they threw him on to film. But no, he actually worked very, very hard to get into Hollywood in the first place.

Second off, many people told him he would never make it because of his accent. And third, he was incredibly smart. He’s a calculated individual. It’s one of my favorite things about Pumping Iron. Was he nice in that movie? Absolutely not. But he’s getting in the heads of his competitors, and you can tell he’s just so driven.

So to see him get such a large shot, in Terminator 1, of course incredible film, he is the villain. But to see him getting a shot at basically being the anti-hero of this film, I just thought it worked so well.

The second thing that I love, and I think it’s something that drew me to it as a kid, Eddie Furlong. First off, great haircut. That’s what I talk about in the book.

Debbie Millman:
Well, you mimicked his haircut, which was my next question.

Isaac Fitzgerald:
And let’s get to that in a second. But I just want to say real quick, I think why it imprinted on me at such a young age, why I loved it so much. Of course, the action’s amazing. Sarah Connor is such a strong female lead. It’s incredible. But the thing that I really think I love about it is it’s about protecting a kid. And I think when you grow up in a home or you have a childhood where you maybe don’t feel protected, the fantasy of that movie is what if there was a giant robot, Arnold Schwarzenegger, there to protect you at all times? And who, child, adult, whoever doesn’t want that sometimes?

Debbie Millman:
Oh, okay. I get it. I totally get it.

Isaac Fitzgerald:
Yeah.

Debbie Millman:
Let’s talk about your haircut.

Isaac Fitzgerald:
Yeah. Sorry, that’s the spiritual, but let’s talk about the aesthetics.

Debbie Millman:
Your hair. You mimicked Eddie Furlong’s hair in the movie. Eddie was the young boy that Arnold Schwarzenegger was protecting. And you did this, I believe when you were in grade school. So what about his hair was so alluring to you?

Isaac Fitzgerald:
I just thought he looked so cool, and I wanted to emulate that. I think when you’re young, you see something on the screen and you think, “Maybe I could be that cool too.” And for me, what is hair except for this incredible thing that we get to change, or keep the same however we want to present. But all the time.

And as a young person who felt a little sad, I felt a little disconnected from pop culture. All my friends had been talking about this movie. At that time, I had yet to see it, and all of a sudden I’d seen a poster. I was like, “Maybe if I get this haircut, people will think that I’ve seen this movie that is apparently so cool that all my friends can’t stop talking about it.”

And I think that’s something I’ve been a little obsessed with my whole life, which is how I present. And when you’re poor, you maybe can’t buy new clothes. When you’re poor, you definitely can’t get the new shoes. But hair, even if it’s just your friends in their bathroom, was something you could make an attempt at to try and convey, “This is who I am, this is how I want to be seen by the world. I might not have Nike’s, I might not have the Reebok pumps. I might not have the right shirt, but I can do the right haircut.”

Debbie Millman:
Absolutely. I’ve written at length about how as I was growing up, we were also quite financially challenged. My mother was a seamstress, and so I learned how to sew at a very young age, and both she and I made my own clothes. But oh man, did I want a pair of Levi’s? Oh man, did I want a pair of Levi’s? It was the ’70s, and my mother offered to stitch a little red tag on the back of one of the pockets of the Modell’s dungarees, and I was like, “Mom, that would be worse. That would just be worse.”

Isaac Fitzgerald:
And it is. It’s that heartbreaking moment when you know your parents are trying their best to provide, and what a beautiful thought. And of course, I’m sure as you look back in that moment, it’s a loving memory. But when you’re a kid-

Debbie Millman:
Oh yeah, I felt so deprived.

Isaac Fitzgerald:
Yeah. And you feel crushed in that moment, and that is really tough. You’re like, “If only I had enough money to buy the right clothes, then I could truly express myself.”

Debbie Millman:
Yeah, it doesn’t work.

Isaac Fitzgerald:
And that’s right. That’s what you find out later.

Debbie Millman:
Yep. Too bad, right? Wouldn’t it be nice if somebody could just say, “You know, it’s not going to give you what you think.”

Isaac Fitzgerald:
That’s right.

Debbie Millman:
Well, in classic Design Matters interview style, I ordinarily start with a person’s origin story and then work up to their most current work. But today, I want to start our interview by talking about your recent memoir, Dirtbag, Massachusetts. And I found an interview with you on The Rumpus from 2011 wherein you stated, “I love memoirs, but I don’t think I have it in me. I don’t think I have the courage.” What changed and where did that courage come from?

Isaac Fitzgerald:
I know you hear this all the time, but Debbie, you are incredible. Your research is incredible. I love this and I love that you’re bringing this up. This is absolutely the truth.

In 2011, I’m sure I was saying this back in 2008, 2006. I would go to a party or I would meet somebody, and I would tell them about my childhood. And people would have whatever emotional reaction they have to it. Surprise, sympathy. Every once in a while though, somebody would say… Especially as I started to hang out with more and more artists, more and more writers, “Hey, have you thought about trying to tell this story?” And that’s what I always said. I love memoir, but I don’t think I have it in me to share my story, to write my story.

What changed? One was I learned how to write via craft. And it wasn’t until I was well into my twenties that I started to recognize wait, maybe writing is something you can improve at. Maybe writing is something that you can practice. Maybe if you do it over and over and over again, maybe if you read the people that you love, you can kind of just learn through osmosis a little bit, just surround yourself with the type of writing that you love. Maybe you can figure out a way to tell your own story. That was first.

But second, I think much more importantly was I learned that my story was maybe a valid one to tell, because that’s what I think I’m really saying in that moment. When somebody would ask me, “Hey, would you ever tell that story?” “No, no, no, no, no, no.” What that really meant was I didn’t think my story was important enough. Why would anybody care about the story that I have to tell? There are so many different stories out there in the world. And something I loved from a very early age was interviewing other people, and highlighting, spotlighting, turning the spotlight on other people’s stories. It’s something I loved to do from a very early age.

It wasn’t until I was maybe in my thirties that I started to realize that’s because I desperately wanted to tell my story. That’s what I couldn’t admit to myself. That’s what I’m not saying in that 2011 interview. The right answer to that is I’m dying to tell it, but I don’t think it’s important enough. I don’t know how to.

And it wasn’t until I watched many, many people, Roxane Gay is a great example. Bad Feminist is a loadstar for me and many other friends, people that I have in my life that I’m lucky enough to call friends or say that I love. I watch as they create their stories, I watch as they put their stories into the world, and I slowly start to realize maybe there’s a chance I could figure out how to do it.

Debbie Millman:
In that same interview, you said that you write like you tell stories, with a lot of bullshit. But I didn’t get the sense while reading your book, there was an iota of bullshit in it. There was no bullshit. It’s no bullshit. It’s a confessional, a no bullshit confessional.

Isaac Fitzgerald:
Well, I think again in 2011, and now we’re talking over a decade ago, which is wild. Again, you’ve read this, I haven’t thought of this interview probably in forever, if ever. It’s so interesting to see the way that my shields are up, and that’s the best way to describe it.

Debbie Millman:
I love that. Yeah.

Isaac Fitzgerald:
I’m saying, “Little old me, I’m not worthy of telling my story. Little old me, even when I tell my stories, even when I do write, don’t worry. It’s just bullshit.” The phrase I love is Irish storytelling, which of course I come from a long history of people who if the fish was this big, maybe it was a little bigger when they tell the story again. And that’s a long tradition.

But I think that was also my own way of muddying the waters and not having the strength or bravery to put myself front and center yet. And what changed in the last decade is I realized, wait a second. There is a way to tell these stories. Maybe these stories could be of use to other people. And it’s actually in the scraping away of the bullshit that I’m going to find the stories that I want to tell. And this book, it’s a short read. It’s what I love about it. I wanted to write a book that 14 year old me could stuff in their back pocket and read.

Debbie Millman:
I know. That’s why I really love that we’re talking about the paperback.

Isaac Fitzgerald:
Yeah, the paper… Yeah, exactly. This book was always supposed to be a paperback. God bless you, Bloomsbury. God bless independent bookstores. I understand more money is made off hardcovers, but I have always wanted a paperback. And so I wrote it short, but how does it get to be that way? Well, no, I wrote a lot of bullshit on the page, and then it’s about scraping that away to get to the diamond center of the story.

Debbie Millman:
You start the book with a line you knew from a young age you wanted to use someday, assuming that you know it by heart. And I was wondering if you can share it with us.

Isaac Fitzgerald:
Absolutely. “My parents were married when they had me, just to different people.” And that’s it. That line-

Debbie Millman):
It’s like right up there with, “Baby shoes, never used.”

Isaac Fitzgerald:
Listen, first lines have always been an obsession of mine. “Call me Ishmael.” First lines and last words. Those are the things that I’m somewhat obsessed with. And I knew from a very early age that in that sentence, I had something special. And even before I could allow myself to think about writing my own story, which you can tell, 2011, I wasn’t even close to being able to admit that I wanted to tell my own story. I knew just in personal interactions, it was this beautiful line, because it was part a joke, part the truth. But most important, part deflection. I could say it, the person would kind of laugh, and then I could move on and turn the attention back to them. So I knew I had this great line in it.

What happens with the book is that what happens when I don’t turn that attention to the other person and then just actually write the rest of the story after that sentence.

Debbie Millman:
You describe your parents as smart, itchy, unsteady, people both in their thirties when they met, confused and lonely and searching for some kind of salvation. But they wanted to find it the hard way. Why the hard way?

Isaac Fitzgerald:
The truth about my parents, and there’s many truths about my parents, but the truth about my parents is that they had it. They had a good life. Both of them. Maybe a little different income, maybe this that. There’s a little trouble there. But they had a family, they had love, they had security.

Debbie Millman:
They each had children with their previous spouse.

Isaac Fitzgerald:
They each had a child. It was, for lack of better word, it’s basically the American dream of that time period. They had it. So when I say the hard way, I’m almost saying it in a complimentary style. Because instead of settling for that, which clearly wasn’t satisfying them, instead of just saying, “Hey, this is the life I’m going to live. I’m going to just keep doing it.” They decided to take big risks and make, let’s be honest, messy, messy choices, and messy mistakes. But I think it was in hopes that life could be more fulfilling and life could be happier.

And that’s incredible in a way. It’s something that I actually deeply admire about them. It’s not to say it’s not complicated, but I think they chose the hard road. They could have lived a less happy life, but more stable. And they decided to roll the dice again, and it was hard and a difficult path. But I’m impressed by that.

Debbie Millman:
You were the accidental byproduct of the sin, so to speak, between two devoutly Catholic divinity students. And you state that this was your mother’s panic fling, one final push against the life that was expected of her before she settled down. Now, from everything I’ve read about your mother, this affair seems so out of character to her.

Isaac Fitzgerald :
And that’s what I think makes it so daring. No offense to my pops, love you dad.

Debbie Millman:
Wasn’t out of character for him.

Isaac Fitzgerald:
Love you, dad. You’re great. But it was pretty in character for you. But for her, I think that’s what made it such an incredible reach, and something that I think she then struggled with for the rest of her life, which you see. I think she has always struggled with the decisions that she made around this time in her life, and figuring out how to come to peace with that, and who can’t relate to that?

Debbie Millman:
Was he ready for the consequences of their affair? And it’s a two part question. A, was he ready for the consequences of the affair? And B, I assume she was madly in love with him.

Isaac Fitzgerald:
So this is what I can say. The story as I know it is that my mother had actually called it off. She had said, “Hey, we can’t do this anymore.” I think my father had been in that situation before, and he said, “No problem, but what if we took one last trip to the White Mountains?”

Debbie Millman:
It’s always that one last trip.

Isaac Fitzgerald:
That one last trip.

Debbie Millman:
It’s always the one last trip.

Isaac Fitzgerald:
Always that one last trip. And that’s what they-

Debbie Millman:
Condoms.

Isaac Fitzgerald:
And that’s what they would do. They would go to the White Mountains, they would tell their spouses that there was a divinity school trip that there wasn’t, and they would go.

And the way it’s been told to me is they were then out of touch. My mother then realizes she’s pregnant. She has a choice. She has a few choices.

Debbie Millman:
She has a few choices.

Isaac Fitzgerald:
She has a few choices. She can tell her husband it’s his. She can have an abortion. She can figure out one of the other million choices that come after that. I now know, I didn’t know this when I was writing the book, is that she and my father get back in touch. And he really was pushing for her not to get that abortion, which I didn’t know. I didn’t know. And it’s kind of beautiful, kind of fascinating. I do think she loved him very much, and I think he loved her.

What I don’t think I knew even when I wrote this book was that in a way, they were coming together to try and actually love me. These are the things that happen that you get told after you write a memoir. But I do think they realized they were in a tough spot, and the only way out was through.

Debbie Millman:
Once you were born, their wreaked havoc on their lives. They blew up their lives. You and your parents were unhoused. You lived in the Haley House, which was considered a homeless shelter in South Boston, but you loved it there.

Isaac Fitzgerald:
On paper, I’m growing up unhoused. On paper, I’m living in shelters. On paper, I’m experiencing something not many other children are experiencing. I loved it. I was surrounded by other human beings. I was so inquisitive.

I was so chipper, annoyingly chipper I’m sure. There are certain people in the shelter, I’m sure that were like, “Keep that kid away from me.” But I loved being surrounded by so many people in such a strong, caring community.

So on paper, they eventually get out of that situation and they go live in the woods. That should be, now it should be the fun childhood part, but that’s when things actually took a turn for the worst. My warmest memories as a child is living in inner city Boston in the ’80s when things were very rough, surrounded by people who had rough backgrounds, but who really loved me. And I so appreciate that.

Debbie Millman:
You and your mother moved to a town called, Athol, Massachusetts when you were eight years old. Your dad stayed in South Boston for work supposedly. You’ve written how everyone else in the state called it Rat Hole, Massachusetts or A-hole, Massachusetts. Athol also happened to have the highest teenage pregnancy rate per capita. How did you and your mother moving to the country impact your relationship with both of them? I mean, she really thought she was doing the right thing by you, I assume.

Isaac Fitzgerald:
No, that’s right. This is the thing that you see as an adult. You see how your parents were actually trying to make decisions to improve your life. But as you’re experiencing them when you’re young, you don’t understand that. And the shock of the change, and especially if you feel like you’ve gone from a happy place to a sad place, can feel overwhelming.

This is something I think about a lot. When you’re a kid, your world is your home. Also, maybe school secondary. That’s it. Those are the spaces that you occupy and those are the places that are most important to you. If an adult comes home and they’re angry, that anger fills your whole world.

Now when you’re an adult, maybe your boss was a jerk. Maybe you got cut off on the way home. Maybe X, Y, or Z, the bills aren’t being paid. There’s a million reasons why you’re feeling anxiety, why you’re feeling stressed out, why you’re feeling mad or angry. You don’t even realize that you’re feeling this small child’s whole world with that anger.

A few years can pass, and you’re having a rough patch. A few years pass, and you’re like, “Ooh, that was tough. But hey, things are getting better now.” Because when you’re older, a few years is not that long of the amount of time. When you’re eight and your mother or father both have hit a four-year rough patch, that’s half your life. That’s all that you know.

So I understand now that my mom was trying to do her best. I had been mugged, at gunpoint. Somebody had been shot on our front steps. Our neighborhood was rough. The living situation we were in was rough. She was doing her best to get me out of there with the low amount of means that she had, and this was the option. To move out there. Her parents were from that area. There was a farm, there’s a house. We can go there. I can see that now.

But when I was a kid, all I knew was that there was this place that I liked. I loved the people, I loved the community. Now it was me and my mom, and my mom was getting very sad. Of course, because she’s wrestling with this decision, which to her eight years ago is a pretty recent decision actually. But to me, I’m like, “Why is she so sad about something that happened so long ago?”

Debbie Millman:
Was she sad that your dad was now living back in South Boston while she was trying to raise you in a house next to your grandparents, in a place that she thought would be more bucolic?

Isaac Fitzgerald:
Yeah. No, I mean, listen. I think her sadness was very complex and I think there’s mental health stuff there, which I struggle with as well. But if I was to take a shot in the dark, I think she dreamed of a bigger life. And is there misbehavior on my father’s part? Absolutely. Her parents, again, also coming from rough backgrounds, so their stuff… There’s no fault to be laid at anybody’s feet, but they were definitely tough on her.

She wanted to live a bigger life, and here she was back where she grew up, in that same area where she always thought she was going to get away from. And she’s raising a kid next to these parents who are rather judgmental. There are other complex reasons why she was sad. But I think at that moment in her life, the question for her was, “How did I end up back here?”

Debbie Millman:
Yeah. It seems as if at this point in your life, your parents really lost themselves. They lost their center. Your father began to have affairs. He drank too much. He was physically abusive to you. This is going to be rough to say out loud. Your mother confessed she had considered aborting you and shared that information with you in a car ride, told you that you might’ve been better off dead. I mean, you were eight years old when she told you this.

Isaac Fitzgerald:
That’s right.

Debbie Millman::
I don’t even understand how that could possibly be something you’d ever recover from.

Isaac Fitzgerald:
Yeah. I mean the most human answer I have is I don’t know if I have yet, but I think I’m working on it. I think that’s the work of living. But no, I want to sit there for a second. It’s okay. I will say in that moment, I don’t fully comprehend what I’m hearing.

Debbie Millman:
Did you even know what an abortion was?

Isaac Fitzgerald:
I did. I think because of Catholicism, I understood what she was saying. And I understood that she was sad. And so I knew when she said maybe it would’ve been for the best. I know that she’s sharing in that moment that we’re all in a tough spot, and I think she’s questioning her decision. I got that.

But when you’re young, I don’t think you totally have an idea of what death is yet. I understood what, but I don’t think I fully grasped what she was saying. I mean, it wounded me. I want to be clear about that. It did wound me, but I don’t think I realized how hard I was being wounded in that moment.

What I really remember from that moment is how unhappy she was in recognizing that. Not fully understanding what was being said, but truly fully understanding that my mother was unhappy.

And then I think there’s a second realization, which is, “She shouldn’t be saying this to me.” I knew that. I didn’t fully comprehend what it was, but I knew that she shouldn’t be saying it to me, because there should have been another adult. There was somebody else, a friend, a parent who was maybe more sympathetic, a partner who was maybe there, who she should have been able to share that with. But that’s when I realized how alone she and I truly were.

So many years of my life have been spent being angry at that moment. I think now, I can recognize how sad that moment must have been for her, and how truly alone somebody has to feel to say that to an eight-year-old. It wasn’t coming from a vicious place. She didn’t mean to wound me. I think she wanted very much not to be. But I think she felt so isolated and so alone in that moment.

And I internalized that in a real way. It’s been something I still struggle with, absolutely self-esteem. But also, I don’t know if we want to chalk this up to be an Irish, optimistic, that same chipper kid that was running around the homeless shelter, but there was a part of me that it made my life feel special. It made me realize that there was a risk taken to bring me into this world, and that two people might’ve been making mistakes left, right, and center and constantly, but there had been another option for them too.

And it almost made me feel like there’s the saying, and I’m not trying to be glib or trite, but everything after that felt like icing. My life was mine to do what I wanted to do with it. That’s how I came to think about that moment.

Not in that moment when I was eight. But not long after, probably around 12, when I started taking more and more risks, I started to realize, “Hey, I might be in extra innings already.” There’s a weird freeness to that feeling.

And yeah, it’s tough. Obviously you shouldn’t say that to an eight-year-old. It was a defining moment in my life. But I’d be lying if I said it was all hardship on my end. It was very sad, very wounding, but in a way it was also freeing.

Debbie Millman:
It does get worse though, Isaac. I mean your mother becomes suicidal. She made a couple of serious attempts on her own life. You write how she talked about wanting to die so much, that you not only got used to it, you started thinking about it too, and rigged a wooden board by your bed, which could have killed you. Can you explain to our listeners what that was?

Isaac Fitzgerald :
Yeah. So basically when I hit my teen years, I start to have a lot of issues. There’s a lot of violence, there’s a lot of anger. A lot of bad things happened, but then we didn’t talk about them.

So my mom would attempt a suicide. I would witness it, we would handle it, but no one ever, then said, “Hey, that was a lot. We should probably talk about this.” It was a very New England, okay, onto the next thing. So I think I had so many emotions inside of me that I didn’t know what to do with. So I find drinking. I find drugs at a very early age.

But I’m also very aware of suicide, and you go back to what I was told when I was eight. I’ve been grappling now for four years, which again, when you’re 12, is a third of your life, with do I deserve to exist or not?

And so I made a contraption. We had so many knives in my house. We’re very outdoorsy. We love to camp. I still do. And so we had a lot of knives, and I got a bunch of them together, and I basically made this contraption that I would pull out from underneath my bed. And the knives were all sticking up, because sometimes I’d roll out of bed. And in my mind, suicide was a sin. But this wouldn’t be. This would be, I’m kind of giving God an option to give me an out.

And so I didn’t do it every night, but it was under my bed at all times, and I would bring it out, and I would set it up on the times when I was probably feeling sadness, and I did that probably throughout my entire middle school years. Which again, two years, if we really wanted to get into the math of it, probably not a ton of times. But when you’re a kid, it doesn’t change the fact that that’s where I was at mentally, and with no one to talk to about it.

Debbie Millman:
Did anyone care for you at that time?

Isaac Fitzgerald:
That’s a complicated question, because truly, I want to say this. I had a roof over my head. Sometimes, I was cooking the meals, but I had meals. I do think they cared. Was I neglected with massive amounts of time alone? 100%. I’m not here to pretend that that’s not true. I was on my own constantly.

But part of that was because they had to work whatever jobs they could get, and that meant they weren’t around a lot more, because they had to pay those bills. So alone, yes. Cared for, in its own way, I do believe I was. But at that point is when I start to make decisions that start to put myself in danger on my own.

Debbie Millman:
It does seem as if one of the things that helped you and comforted you was reading, and you write how your parents’ faith in literature was as strong as their faith in Catholicism, maybe stronger. And even before you learned how to read, you learned how to respect books as a second religion. Your apartment was bare except for milk crates overflowing with novels, and plays, and history books, and collections of Shakespeare. Your dad read you The Hobbit when you were five. He gave you On the Road when you were 11. He also gave you books by Charles Bukowski and Ken Kesey, books you refer to as the classics for making sure your kid turns into an upstanding citizen. You’ve said that you came to know each other through books. It seems like you came to know yourself in a lot of ways through reading and writing.

Isaac Fitzgerald:
Yeah. Books mattered to my parents. I wanted to matter to my parents. So of course, I started to care about books too. And it’s not hard to look at my entire life and realize how I put books at the burning hot center of my entire existence. But it was also a gift they gave to me. This is a perfect example, he said, “Was anyone caring about you at that time?” I was very alone, but even before my dad moved out of the city, he recorded himself reading the Lord of the Rings trilogy, because he knew how much I’d loved The Hobbit when he read it to me. And he used to send me out the tapes. I mean, perfect person? Absolutely not, but that’s an effort. You can’t-

Debbie Millman:
We’ll give them a point then. We’ll give him a point.

Isaac Fitzgerald:
That’s making an effort right there. Right? And so they believed in education, and they believed in literature. And I think they believed in making sense of oneself through seeing what else was out there in the world, and that is something that I picked up from them.

I love this quote from this play. It’s called The History Boys, and it’s a British play. And I’m not going to be able to do it verbatim, because I’m not that good of an actor, but the gist of the quote is a professor’s talking to students, and he says, “The best things about literature, about books, is you’re reading them. And you can come across a phrase or an expression of a feeling, or perhaps a deep hidden desire. And you see it there on the page. You think you are the only person that’s had that thought ever, or only had that experience in your entire life. You see it on the page. It’s like a hand comes out and grasps your own, and you feel less alone in the world.”

I know my parents believe in that power. I know they gave me that power. I’m sure we’ll get into it at some point, their reaction to the book, but I can just share right now. My father, when he reads it, writes me a letter. One of the things he said was, “Well, you can’t say we didn’t give you things to write about.” Which again, I mean, but it’s Irish. It’s very Irish, it’s very, and I do think they themselves had this ambition of living a life worthy of being put down on paper. And in their own way, I think they very much did. And I think in a weird way, they wanted that for me.

Debbie Millman:
Even with the early drinking, your teachers, your librarians all recognized how smart you were and encouraged you to apply to Cushing Academy, which was a private school. I assume you had excellent grades in order to do that. You got in. You’ve stated the school took a giant gamble not only in accepting you, but in giving you a full scholarship. Why was it such a gamble?

Isaac Fitzgerald:
I mean, one, it was only 40 minutes from where I was from. Friends could come and pick me up in their trucks. There was a chance that I was going to be not a very good student. Again, my parents instill in me this understanding that if you just show up… Because you’re absolutely right. I can just be immodest for a second. I tested well. I always got good grades. No matter how much trouble I was getting in, I never skipped school. I would always show up, because I knew in some way, the better grades I got, the less people would be on my back. That was always my thinking is, “Don’t draw attention to yourself. You can have more freedom to be a fuckup in a way, if you’re not raising all of these flags.” But when I get to this boarding school, I remember being like, “Okay, I really have to get it together now.”

Debbie Millman:
But you didn’t really, and that’s when you started snorting Adderall, and Ritalin, and partaking in other legal and illegal substances.

Isaac Fitzgerald:
And that’s what I’m saying is I remember being like, “This is going to be different.” And then I got there, and that’s when I realized a huge thing, which is, “Rich kids are fuckups too.” Because that’s what happened. In that first year, I went in with such a large chip on my shoulder. But I remember being like, “They’re giving me this scholarship. This feels like a big risk. I got to show up.” And as I go through that year, one, I realize rich kids just have better drugs, sometimes often more neglectful parents. And it’s a great awakening for me, because I had not really traveled outside of the state of Massachusetts at that point. All of a sudden, I’m meeting people from all around the world. Again, I’m back in the system that I was in the Catholic worker. All of a sudden, I’m surrounded by people with all these diverse backgrounds, all these different ways of living. I get to learn from them. I’m so excited. My mind is engaged in that way, because I’m no longer lonely in the woods. I’m now surrounded by people once again. But in my head I was like, “Oh yeah, but they’re jerks. They’re rich.” I had this real class chip on my shoulder.

And it was through my first year that I started to realize, wait a second, don’t get me wrong. Some of these kids are massive dickheads. But some of them are incredibly kind and incredibly caring. And that’s when I started going home and seeing friends from my hometown, and recognizing some of those people are still people I love to this day and I’m very much in touch with them.

But all of a sudden realizing, “Wait a second, some of them are also huge assholes,” and definitely wouldn’t like maybe some of my new friends from other parts of the world. And what does that mean? If for a long time, I think I really believed in… There was almost a saintliness to being poor. And I start to realize class is actually this more complicated thing.

Now, don’t get me wrong. I learned how to code switch. I’m one way when I’m home. I’m one way when I’m at Cushing. But I started to bridge this idea of understanding that knowing people from not my background could be really good and interesting people, widen my world in this new and incredible way. And what more do you want in an education than that? So they took a risk on me for sure, but I’m so glad they did.

Debbie Millman:
You loved bars from the first moment you drank in one. I think you were 14, but you’d been drinking since you were 12. You, as I mentioned, were experimenting with all sorts of drugs and substances. How did you not die? How did you not get addicted?

Isaac Fitzgerald:
I want to be clear, I’m not going to say I didn’t get addicted.

Debbie Millman:
Really?

Isaac Fitzgerald:
Yeah. I used a lot. I do think, and this is the first time I’ve really thought about this and tried to connect these things, but there’s something about that same mentality that I just mentioned about showing up to school. Fuck off all you want. Screw up all you want, but get your work in. Show up to class. You’re not going to get in as much trouble. I had run ins with the police. I would take cars for joy rides.

Debbie Millman:
You are really lucky you didn’t end up in jail.

Isaac Fitzgerald:
No, I know. I know. And I have many friends who did. But the joy rides is a great example. I want to be very clear, not condoning this behavior, but I would bring the car back.

And this is what I’m talking about. I have always been a big drinker. That is going to be an ongoing struggle in my life. I’m lucky in that I do not do drugs the way that I used to. But when I did, I always had these weird bumpers. “Okay, so-and-so brought this to this. Oh, hey, we’re going to go get”… “You know what guys? Good luck. I think I’m going to call it a night.” Call it self-preservation, but I don’t think that’s right because I think I was interested in self-destructive behavior at that time. I just think I had that same mentality of like, “Okay, go to class. It won’t raise red flags.” Couple day bender, go for it, man. Have fun. It starts to become a weak? No, you got to get out of there. I think I’ve always been good at setting up little responsibilities for myself to make sure that I didn’t completely go off the deep end.

It’s tough, because drugs are really fun. And when you have low self-esteem and low sense of self-worth, a lot of those drugs in a way give you that same feeling of that hand grasping that book. You feel either less alone or cocooned from a world that causes you pain. But I think I knew at that point I at least wanted to live, and so I didn’t follow the path all the way down. I always returned the car.

Debbie Millman:
And you got good grades. You got good enough grades to get a full scholarship to George Washington University.

Isaac Fitzgerald:
That’s right.

Debbie Millman:
You studied politics. What were you thinking that you would do at that point professionally?

Isaac Fitzgerald:
Again, it’s a long history of librarians and teachers showing up for me and being like, “Hey man, maybe you can do something a little bit more. Maybe you can dream a little bit bigger.” And that happens to me throughout my life. But they were like, “What about college? What do you want to do?” And all I knew was that people liked when I talked, and people were like, “Well, that’s politicians. Maybe lawyer, lawyer, lawyer, politician. So go study political science.”

So somebody just told that to me and I just stuck with it. And I did. I went to school for four years. I maintained my scholarship. I did well. I worked many different jobs, because that’s what they don’t tell you about a scholarship is they’re like, “Congrats. We’ll pay for the school and we’ll pay for the food. No walking around money.” And when you’re in a boarding school, that’s one thing. But when you’re at a college, it’s another. And so I had to work the whole way through, and I graduate and I start working for a guy. This is not in the book, but it’s in another essay. I worked for a guy, his name’s Patrick Murphy.

Debbie Millman:
Yeah. He was elected to Congress in 2006.

Isaac Fitzgerald:
That’s right. Blue wave. Hell of an American, youngest Democrat on the hill, Iraq War vet. I love him very much. But after that I was like… Basically, I just got out and I started doing the work that I studied. I realized, “I’ve wasted a college degree. I don’t want to do this at all.”

Debbie Millman:
You hated it.

Isaac Fitzgerald:
I hated it. That’s exactly right.

Debbie Millman:
Well, then you then followed a girl to San Francisco. Aside from the girl, what was your plan at that time?

Isaac Fitzgerald:
I mean, this is where we get into a real free floating time.

Debbie Millman:
Yes. Is that what inspired you to begin working with the Free Burma Rangers?

Isaac Fitzgerald:):
Well, I think this is another fun moment to share a story that’s not in the book. I moved to San Francisco. As you said, I move out there for a girl. I think she was very surprised when I showed up. I think we talked a lot on the phone, and there’d been a lot of sweet nothings, and there’d been a lot of, “Yeah, come out to San Francisco.” And then I was like, “I’m here.” She’s like, “Whoa, okay. Holy smokes.” She’s living in a place with many different roommates, not many bedrooms. So she’s trying to get me out of the house and she says, “Look, there’s this place, I don’t know if you’ve seen it. It’s on Valencia Street. There’s a sign. It says storytelling and bookmaking workshop. Why don’t you go down there?” And so I go down there.

Debbie Millman:
That’s 826, right?

Isaac Fitzgerald:
826 Valencia. I didn’t know anything about it.

Debbie Millman:
I love that you went in there blind.

Isaac Fitzgerald:
I went in there completely blind, and I walk in, and it’s very clear that they’re having an open house. And I’m like, “For people who are interested in learning how to make books.” I have read my entire life.

But up until that moment, I was not very aware of a contemporary writing scene, and I definitely didn’t realize that being an author was a way you could still make a living. I’ve grown up with books, mostly old books. Nothing about, “Oh, hey, this is a job option for you.”

And so I sit down. Quickly becomes apparent that this is a volunteer organization that is looking to get adult volunteers to work with kids. I’m 23 years old. I’ve written a kid’s book now. I love kids now, but at the time I was like, “I’m not interested.” But I knew it’d be rude. Again, this gets back to that same self… I was never that much of a jerk. I was like, “I can’t just walk out.”

Debbie Millman:
Right. I remember you writing about you didn’t want to be rude.

Isaac Fitzgerald:
Yeah, exactly. So I didn’t want to be rude. So I sat there and I looked around and I raised my hand when it came time for questions, because I asked, “Hey, what’s this?” And it’s all these different pieces of paper that are framed on the wall, and they’re covered in markings. They’re typed up, but they’re covered in markings. I said, “What are those?” And they said, “Each of those pages is a piece of a manuscript. A manuscript that eventually became a book. But we do that here because we’re a writing organization for kids. Writing is a very lonely ark, but we want them to realize either their teachers, or their parents, or volunteer here, or eventually if they become a writer or an editor can give them feedback. They don’t have to take all of it, but it can help improve their story.”

And it was the first time in my life that somebody had talked about writing as craft. Up until then, I thought you either had it or you didn’t. You lived in a white tower, and you just wrote perfect prose, and that’s how you’re a writer. That was the first time that I realized, “Wait, maybe I can take these stories.” I wasn’t ready to write my own memoir, but I was like, “Maybe I can write something that is of use to other people eventually.”

And that’s the gift that moving to San Francisco gave to me. That was the first place. I mean, don’t get me wrong. I do end up working with the Free Burma Rangers, Zeitgeist, The Armory. We can talk all about that. But 826 Valencia was where I found a community of writers. And in that moment I thought, “Maybe I could do that.”

Debbie Millman:
How long after you had that experience did it take for you to become the director of publicity at McSweeney’s, which is Dave Eggers’ publishing empire? 826 is the nonprofit organization dedicated to supporting under-resourced students with their writing skills. Started by Dave Eggers and his wife.

Isaac Fitzgerald:
Seven years.

Debbie Millman:
Seven years, wow.

Isaac Fitzgerald:
I’m really excited. This is another… Just know that I got a job at 826 Valencia. Eventually, I volunteered for six months. I became an intern. I was working at Buca di Beppo to pay the bills. I got a job as an executive assistant to the executive director of 826 Valencia. Wonderful woman, Ninive Calegari. She’s incredible. I was probably the world’s worst executive assistant. I was 23 years old. I was very bad at scheduling. I was very bad at everything.

Debbie Millman:
It’s kind of what you need to be able to be good at when you’re an executive assistant.

Isaac Fitzgerald:
So God bless Ninive. She very gently let me go, but I remained connected to the organization. So I was in that world for a very long time, and it wasn’t until I was 30 that I ended up working for McSweeney’s. Did a better job the second time around.

Debbie Millman:
I want to go back to your working with the Free Burma Rangers, because I think that was a big transformative experience in how you thought about yourself. And for those that might not be aware, the Free Burma Rangers self-describe as a multi-ethnic humanitarian service movement, working to bring help, hope, and love to people in Burma.

Isaac Fitzgerald:
That’s right.

Debbie Millman:
They also illegally smuggle medical supplies over international borders, into conflict zones to assist with medical aid for people who are being attacked by the Burmese Junta. How dangerous was this for you?

Isaac Fitzgerald:
It was dangerous for me, but not nearly as dangerous it was for the people that we were trying to help. And not nearly as dangerous for me as it was for the volunteers who worked to make that organization run. I have a lot of respect for Dave Eubank, and his family, and the people that make that organization work.

Debbie Millman:
Your life was in danger several times in that experience. What provoked you to want to do this?

Isaac Fitzgerald :
I think it has to do with that exact same kid who is pulling those knives out from underneath his bed. I knew I wasn’t going to take my own life, but I do believe I was obsessed with putting my own life in danger. I think that came from a lack of self-respect for myself, a lack of self-love for myself, and the knowledge that I was empty in a certain way.

But maybe, and this is where we get into the almost optimistic side of myself, maybe I can turn that emptiness into something that could help others. And that’s what appealed to me about the Free Burma Rangers. I could go over there and put myself in danger, and maybe it could help somebody else.

Debbie Millman:
Before you left the US to do the work, you wrote that you had to figure out how not to want to die. Did the experience change how you felt about your life?

Isaac Fitzgerald:
Yeah, I think the experience helped me value my life.

Debbie Millman:
You write this in your memoir, you say, “I know that for the rest of my life, I will, from time to time, think that the world would be better off without me. But it’s happening less as I get older. I will always be trying to stop wondering what exactly I’m good for, to instead make peace with the fact that I deserve to be alive. And from that, more calm and steady place will be better able to wrestle with what I can do for myself and others without needing the crutch of certainty.” Has publishing your memoir helped you with that?

Isaac Fitzgerald:
Yes. The memoir has helped me have a better relationship with my parents, but it’s also helped me have a better relationship with myself. I think in diving into these stories, and finding value in them in a way helped me find value in myself. This isn’t something I expected. I want to be clear about that. It was in no way a goal. But as I move through the world now, I’m feeling myself having a lighter ease.

And again, to that same point, it doesn’t mean it’s all the time. But right now, this book, part of the art of it, part of the doing it, part of the writing it was sitting down and looking at things that I realized I couldn’t look directly at for years and years and years. And there was some real relief and some real self-realizations that came from actually sitting down and looking directly at these moments and these memories.

Debbie Millman:
After leaving Burma, you returned to San Francisco and got a job you had coveted for some time working at the legendary bar Zeitgeist, which you describe as a metal bar, meets dive bar, meets German beer garden aesthetic. Why was that job so important to you?

Isaac Fitzgerald:
I loved Zeitgeist, from the second that I set foot in it. I could not have told you why at the time. But now looking back, it is so clear for me to draw a direct line from the Haley House in the south end of Boston, that shelter for the unhoused, to Zeitgeist, which was a wonderful loud bar where people from all walks of life could feel at home, could feel safe. And then above that bar, there were two floors of SEO housing.

So it was truly a community unto itself. And of course, in the moment, I didn’t realize that. But looking back and through therapy, it becomes so clear to me what I loved about that place was it reminded me of the last time I truly felt loved and safe, which was before I was the age of eight.

Debbie Millman:
You said this about working at Zeitgeist. “The bar could give me everything I wanted all in one spot. A place to drink, talk, laugh, grieve, think. A place that comforted me with the old and familiar, and exhilarated me with the fresh and strange. A place I worshiped and worshiped at.” And then you go on to write, “When you live a small life, it’s important to have small dreams. Working at Zeitgeist was mine.” Did you really think that your life was small? Do you still?

Isaac Fitzgerald:
No.

Debbie Millman:
Okay, good.

Isaac Fitzgerald:
No. Debbie’s like, “I’m going to give this man a hug.”

Debbie Millman:
Well, no. I relate to a lot of… I’m a lot older than you, but I had that same period of life from eight to 12, which I call the black years. And so I know what that does to a person. I really understand wanting more. I understand wanting to feel like you matter, hence Design Matters.

Isaac Fitzgerald::
And wanting to feel loved, and wanting to feel something new, and wanting to get away from this place where you feel so worthless.

Debbie Millman:
But it felt like that was such a big dream, and I was so happy when you get your job there. I mean, you wanted it so badly. And even your first experience there, you’re practically thrown out by the bartender who you offended by accident, trying to impress him. So it felt like it was a big dream, and it felt like that fueled more big dreams somehow.

Isaac Fitzgerald:
No, and I think that’s a beautiful way to look at it. But I think at that point… So truly, I lived on the same block as the bar. So at that point, I think… And again, I’ve never talked about this, Debbie, but you’re doing such a good job of drawing these things out of me and having me think about them in real time. And I really think this is right.

Just taking a crack at it here, but I loved the shelter. I felt so isolated and alone in the woods. Then I go to boarding school, more community, college more community. Then I move across the country. I hadn’t traveled much. All of a sudden a big move.

I think I was seeking out that kind of small structure, again, the second I got there, because it all felt so big. Boarding school for me was great, because there were rules that I broke, of course. But there was a small room that I lived in. There was a routine. I think I was looking for a return to that smallness. And so I lived on the same block. There was a bar that made me feel at home. I wanted that job so much.

I mean, that’s why, some people when they’re in their twenties, they’re moving to Hollywood, they’re going to take a crack at acting. They’re moving to New York. Even San Francisco, I was drawn to 826 for different reasons. I was drawn to Zeitgeist because I was like, “This feels safe, and this feels like a place where I can just be for a little while.” And in its own way to come around to what you’re saying, I think that was a big dream for me.

Debbie Millman:
Yeah. And it was like an intimate dream. A dream of intimacy.

Isaac Fitzgerald:
There you go. Exactly, a dream of intimacy where I could just exist and try to actually figure out who I was.

Debbie Millman:
You’ve mentioned The Armory a few times. The Armory was a building where pornography was shot. Kink.com was born there. And let’s talk about your experience working at kink.com and working in the porn business.

You were an actor. You came to the experience with quite a lot of body issues. How did you manage through the anxiety to be able to perform sexually on camera for other people to see?

Isaac Fitzgerald:
I have had body image issues my whole life. I still struggle with them. I think many of us do. It is what it is to be human. And this is one of these beautiful juxtapositions in my life that I’m actually… Again, in the moment I didn’t quite realize. But looking back, I’m so fond of. Because as a kid, I always felt like I was too big. I move out to San Francisco, I’m still feeling that way. There’s one photo in the entire book, though. You can see how rail thin skinny I am.

Debbie Millman:
Yeah, ribs showing.

Isaac Fitzgerald:
Yeah. But yet, I still had this fascination and obsession with the fact that I was too big, that I was not attractive. So how does one come from that mentality to not long after that being on camera in pornography?

And this is the most Mr. Rogers answer about a porn question you are ever going to get, but it comes back again to that community. Through the literary community that I was hanging out with in San Francisco, I began to meet sex workers. I began to meet porn workers. San Francisco’s only seven miles by seven miles. It’s a wild, wonderful city filled with artists, filled with dreamers. And I was working, one, at a bar that was truly one block away from The Armory, so a lot of these performers were coming to that bar. Also, other people, Quentin Tarantino. Many people used to come to this bar. And so that was amazing to be kind of brushing up against that.

And then also through the literary scene, a lot of these sex workers were writers, were visual artists, had their life of expression that was not just through pornography. And so these became my friends. And they were loving, encouraging people.

And so that’s what happened. I began spending time with these people. And eventually they were like, “Hey, no pressure. But if you’re interested, here’s what the job’s like. Here’s what the money would be. If you want to swing by, you could maybe,” I mean, as you know from reading the book, it was more of a, “Hey, somebody didn’t show up. We could use you in this scene.” But it didn’t change the fact that through those connections and through those friendships, I was made to be put at ease.

And the camera, instead of being voyeuristic towards me, started to make me feel, “Oh, hey, this is the job place where no one is judging me for taking off my shirt.” Obviously I’m fulfilling some type of duty here and I’m getting paid for it. So in a way, that whole situation made me feel more at ease with myself. It made me feel wanted. It made me feel like I was helping out in a way. And instead of actually being ashamed of myself, for the first time, I’m not going to say that I loved myself, but I was able to say, “Hey, I’m obviously adding value here.”

Debbie Millman:
Were you self-conscious about having sex as a performance?

Isaac Fitzgerald:
So the first time-

Debbie Millman:
You were very naive in that first time.

Isaac Fitzgerald:
I write about it in the book very, and I was in a van. And yes, I was more self-conscious of everything that was happening. But I would say the next time… So I go and I get tested, because that’s what you have to do-

Debbie Millman:
For STDs.

Isaac Fitzgerald:
Exactly. And I show up to perform. And as somebody that had consumed a lot of porn, you have certain ways. But the real thing is you show up and they’re like, there’s pizza, and everyone’s hanging out in a robe, and there’s a lot of laughing and joking, and then kind of an, “Okay, here we go.” But then there’s a nice… It’s not just like, go. They made a really nice, safe feeling space, and you would kind of ease into it.

And so I knew the director, I knew the person working the camera. I trusted these people. And so I don’t remember feeling self-conscious. Or if I did, I knew that I could ask to take a break. That was the power of that first moment in the van. I’m watching this giant hulking man over the woman, and it turns out the woman is the director. She can say stop at any moment. And then of course, I’m not going to give away too much of the book, but he reveals things about himself that are wild-

Debbie Millman:
Which was wonderful. So well written.

Isaac Fitzgerald:
That moment was such a wonderful moment for me. And so now, when I’m in that, I knew that if at any moment I felt uncomfortable, I could say something and everything would stop. And that gave me a sense of control that I wasn’t used to in my life.

And what felt amazing is that I knew everyone else in that scene felt that way too. Everyone had control to make it stop. And so that, I want to just be clear, almost rarely, rarely happened. Because I think we did all feel so safe with one another.

Debbie Millman:
Why did you stop?

Isaac Fitzgerald:
I was just in my twenties. I wish I could tell you there was this big moment, or maybe I was dating somebody who all of a sudden was very uncomfortable with it, and they drew a line in the sand. But that’s not what happened. I kept doing it. We were all hanging out. Another opportunity came up. That opportunity took me away. All of a sudden, I was working more and more. It’s this website, this culture magazine called The Rumpus. And all of a sudden, I just didn’t have as much time to… You get a couple of asks and then eventually I’m like, “Oh wait, maybe I don’t do this anymore.”

And this is true of Free Burma Rangers too. Not to equate these two extremely… One’s a Christian organization, one’s a porn company. But with both of them, I think there was a part of me that always thought I would come back, but I never did. I kept moving forward.

Debbie Millman:
When you were working at The Rumpus, you helped sculpt and sharpen pieces by authors including Cheryl Strayed, and Saeed Jones, and my wife Roxane Gay. And you’ve been described as having an innate, almost indescribable ability to know what reads well on the page. How did you hone that?

Isaac Fitzgerald:
Where did you get that quote?

Debbie Millman:
Well, I don’t have footnotes at the moment, but I can send you a link.

Isaac Fitzgerald:
Okay, okay. That’s incredibly kind. So I do have what I call progressive views on grammar. I didn’t go to school for any of this stuff. I cannot tell you a comma splice. I am not perfect at that. I don’t know the terminology. But what I do know is if you read something out loud, you can tell if it hits your ear right or if it hits your ear wrong. And so that is what I brought to The Rumpus.

And I want to be very clear, when I say I helped, sharpen is a perfect word for it. I was not making… I was working with such talented people. They were such good writers. They were turning in such beautiful, heartfelt, well-written pieces. But I could always read it out loud, and I would always either write an email back or maybe get on the phone and it would always just be, “Hey, this one sentence, I don’t know if it’s doing exactly what you want it to do.”

And that’s what gave me that… I didn’t go to school for writing, but that’s when I learned I could do that to other people’s work. Maybe I could do it to my own. So that’s how I write now. I create a giant pile of words and sentences, and then I just read it out loud over, and over, and over again until all of it hits my ear right.

Debbie Millman:
You moved back to New York and began working at BuzzFeed. You became the site’s first editor of BuzzFeed Books and co-hosted BuzzFeed News‘ morning show AM To DM, with again, the great Saeed Jones. Did you really come back for the job or did you come back for your family?

Isaac Fitzgerald:
I mean, a real fun answer is Saeed left San Francisco. He actually lived out there for a year. We’d started this new friendship, and we said this very heartfelt goodbye. And then six months later, I was living in New York. So there’s one way to look at it in which I came to New York for Saeed Jones, because I love him so much.

The job was of course what made me think I could afford it and gave me the opportunity. But 100%, the actual answer is I had been estranged from my family for almost 10 years, but my brother and his wife were having a kid. My sister was very soon to have a kid with her husband. I had turned 30, and I realized that I was already going to be the weird uncle. I’m always going to be the weird uncle. I didn’t want to be the weird uncle who lived 3,000 miles away.

And I also think at that point, having gotten through my twenties, I was able to understand the difficulties that my parents had suffered themselves in a new light. And so I was drawn back to the East Coast to say, “Let’s give this another shot.”

I loved California. I loved the West Coast. But I wanted to give my family a chance, and that was the real reason I came back east.

Debbie Millman:
During Covid, you started to leave your apartment in Brooklyn just to walk. You began to explore New York City, and realized that you’d taken the city for granted a little bit. Eventually, your walk stretched to two a day in the morning and the evening. You then set up an ambitious goal of walking 20,000 steps per day. It’s like 10 miles. What provoked you to do this?

Isaac Fitzgerald:
As we’ve been talking about, sometimes you look back on a time in your life and you can see it for what it is. That was a break in my mental health.

I was going through it, but I loved it. And that’s the truth. I immediately saw health benefits. I just want to quote this wonderful writer who I love Garnette. He talks about moving through the world at a human pace. And for him, he’s always very careful to say, “It doesn’t just have to be walking. There’s many different ways to move through the world at a human pace.” But for me, it very much was, I discovered it through walking. Leaving your phone in your pocket, not having earbuds, moving through the world at a human pace.

And I found so much comfort in exploring New York City, and just putting one foot in front of the other, in finding a life that wasn’t obsessed with everything going on in the world, especially during that time. But just focusing on where I am in the moment, and walking does that for me. I think we are all built to move through the world at a human pace. And I think when we get caught up in many different aspects of the world now, it’s so easy to get disconnected from that.

So I started walking 20,000 steps a day. I wrote about it for The Guardian, and that’s when I saw the biggest reaction to anything I’d ever written in my entire, entire life.

Debbie Millman:
Absolutely.

Isaac Fitzgerald:
And you realize that so many people are interested in just figuring out this simple way of being, and I’ve been obsessed with it ever since.

Debbie Millman:
So this success of the article sort of went viral, inspired you to launch a weekly newsletter titled Walk It Off. What do you write about?

Isaac Fitzgerald:
So I love to interview people. I love to basically take a friend for a walk, an artist that I respect. But to be honest, I’m actually hoping to reach out to other different folks working in other different industries. And I find the conversation that comes from a walk is so freewheeling and so intimate to be walking with somebody, and then just quietly record the conversation. And then I’ll take it home and I’ll transcribe it. So some people are like, “It should be a podcast.” It’s like, no, I really love then kind of taking what was said and putting it almost on a pedestal, shining it. That same with sharpening it, the way you were talking about my editing. It’s my way of finding exactly the gems in this conversation, and then I present them to the reader, and I love doing it.

Debbie Millman:
It’s a great newsletter. I love getting it.

Isaac Fitzgerald:
Thank you.

Debbie Millman:
You recently got another book deal, this time from Knopf. The book is titled American Dionysus, and this is the description I gleaned from Publishers Marketplace. I tried to get more information out from Roxane, but she said, “Just ask Isaac yourself.” So this is the description. “The author walks in the literal footsteps of John Chapman, better known as Johnny Appleseed, and speaks with the communities of people he meets along the way as he seeks to better understand American legends, both explicit and implicit, and dares to imagine more expansive possibilities for community, faith, and our shared sense of home.” So where you’ve been walking?

Isaac Fitzgerald:
Well, so I’m going to share this with you. I haven’t shared anybody, but you know I care about first lines.

Debbie Millman:
Yes.

Isaac Fitzgerald:
And so the first line of this book is, “I’ve been drinking a bit less and praying a lot more than I used to.” And it opens with me hiding from, basically they’re called bulls, but security guards at a train station, because I’d been walking along these train tracks. What I do throughout the book is I try to walk where John Chapman himself walked, which he was born in Leominster, Massachusetts, and he makes his way through Western Pennsylvania all around Ohio, and eventually ends up in Fort Wayne, Indiana near where he dies. I love Johnny Appleseed so much for so many different reasons, and I could go on and on and on about them, but-

Debbie Millman:
Well, we’ll get you back on the show for that book too. But tell us a few.

Isaac Fitzgerald:
I’ll try to be quick. What you need to know about him is one, he was a missionary of a very interesting form of Christianity at that time called Swedenborgianism, which was this almost philosopher madman from Scandinavia. And so he gets really into his belief, and his faith, and not harming creatures. That’s one of his number one things. So he will never ride a horse. He loves all animals. There’s a real St. Francis vibe to him. So I love that about him.

I also love that he’s an American legend. Most people, when I say Johnny Appleseed, they say, “Like Paul Bunion? He’s not a real guy.” But he was. He was a real guy who was born during the Revolutionary War. His father was a minute man, like a soldier. So there’s that Massachusetts background that I’m grounded to.

But the thing that I really love about him, his spirituality of course, but it’s more that he was a bit of a madman. He’s planting these trees. The legend of him, he’s just throwing seeds willy-nilly. No, it takes a lot to start an apple orchard.

Debbie Millman:
Oh my gosh, yes.

Isaac Fitzgerald:
So he would start them, but then he’d leave. When he planted those apple seeds, at one point, he has paperwork. He loses half of Ohio. But he doesn’t care. He’s not interested in money, even though he’s acquiring all this land. He doesn’t own a home. He lives off of the kindness of strangers, even though he doesn’t really need to. He sleeps in the woods.

And then the last thing that really sealed the deal for me was when you’re raised in Massachusetts especially, you get educated about him. “It’s apple pies for the settlers, for apple tarts, or all these different, it’s food.” It wasn’t.

Michael Pollan talks about this in his wonderful book, Botany of Desire. It was for apple cider and apple jack. It was alcohol. So he’s kind of this wandering boozy American saint. But I knew I’m not Ron Chernow. I’m not going to be able to write the biography on this guy. In fact, a guy named Means did a great job in 2012. But what I can do is I can walk where he walked, and talk to the people that live there now, and try and combine this wrestling that I’m having with my faith and this idea of what makes an American legend.

And then the middle part, which I love, is my mom reads Dirtbag. My mom reads the book, and she’s very loving, and beautiful kind response. But one of the things she said was, “Where are all the canoe trips? We camped a lot. Where’s chapter three, the fun camping bits?”

And well, that’s going to be in this book now. It’s about how my parents were such outdoorsy people, and at the time, I really kind of shrunk away from it. But as I come into middle age myself, I find myself drawn to the exact same things they were.

Debbie Millman:
I cannot wait to read it. When will it be out?

Isaac Fitzgerald:
I’ve got to write it first. No, no, no, no. We have a deadline, and the hope is fall of 2025. I spent this entire year in Ohio, in Indiana. I rafted the Allegheny. I’ve walked through far too many miles of highway than I’d care to admit. But I spent this whole year out in the world doing it, and now I’m going to go put it all on paper.

Debbie Millman:
We can’t wait to read it. Isaac Fitzgerald, thank you so much for making so much work that matters. And thank you for joining me today on Design Matters.

Isaac Fitzgerald:
Debbie, thank you so much for having me. It was an honor.

Debbie Millman:
Isaac Fitzgerald’s book Dirtbag, Massachusetts: A Confessional is now out in paperback. To read more about Isaac, you can go to isaacfitzgerald.net and sign up for his popular wonderful newsletter Walk It Off. You can also catch him on the Today Show talking about books.

This is the 18th year we’ve been podcasting Design Matters, and I’d like to thank you for listening. And remember, we can talk about making a difference, we can make a difference, or we can do both. I’m Debbie Millman, and I look forward to talking with you again soon.

Debbie Millman:
Stella Bugbee is the Style editor at The New York Times. How does one get to be the Style editor at The New York Times? Well, if you are Stella Bugbee, it has been a winding road through the world of New York media. Stella got her start in advertising, and later became the design director at Domino Magazine, just as print was getting overtaken by all things digital. She then led the relaunch of New York Magazine‘s The Cut, which became a wildly successful online style and culture site. Now at The Times, Stella joins me today to talk about her circuitous journey through the terrain of contemporary media. Stella Bugbee, welcome to Design Matters.

Stella Bugbee:
Hi, thanks for having me.

Debbie Millman:
Stella, I understand you were born in a giant mesa with no electricity or running water in New Mexico.

Stella Bugbee:
Yes.

Debbie Millman:
Why there?

Stella Bugbee:
They were living in Los Angeles, my parents, and looking to go back to the land. And my father tells a story that they rolled out a map of America and sort of looked for a spot that seemed remote and interesting. I did then go back and find a whole Earth catalog, I think it was from 1975.

Debbie Millman:
Great [inaudible 00:01:18].

Stella Bugbee:
That said, “You should move to New Mexico.” And I thought, “I wonder if it was really their idea or they were just responding to the zeitgeist.”

Debbie Millman:
They ended up moving to Washington DC, and then moved to Brooklyn as you went into fifth grade, I believe.

Stella Bugbee:
Sixth grade.

Debbie Millman:
Sixth grade. Sixth grade. But I understand you felt like a New Yorker well before that. When you found your spiritual resting place, standing outside Canal Jeans on Broadway. What happened when you did that?

Stella Bugbee:
So, my mom had met my stepdad while we were living in Washington, and we came to visit him and I was really into fashion. I don’t know what that even meant, but I was really into clothes. I was 10, and he took me to Canal Street outside of Canal Jeans, but there also used to be this incredible flea market on Broadway right across the street and also up the block, and there was antique boutique. And I had never seen such a concentration of youthful people dressed up in cool clothes and I thought, “I have to just live right here forever.”

Debbie Millman:
I felt the same way about the collection of stores right by Washington Square Park off of 8th Street.

Stella Bugbee:
All the shoe stores, yeah.

Debbie Millman:
Capezio, Reminiscence. And Reminiscence was my all time favorite store and I saved… My dad lived in Manhattan, my mom lived on Long Island with us, and I saved up to get a kind of not quite turquoise blue, a little bit more green in it, jeans and canvas shirt set.

Stella Bugbee:
Sounds good.

Debbie Millman:
So, there I was in these sort of turquoise-bluish-greenish jeans, the same color, short sleeve shirt and white Capezios. I just felt like that was it. There was no higher I could go fashion-wise.

Stella Bugbee:
The height to fashion for you. Yes.

Debbie Millman:
Yeah. You’ve written that you felt that you could carry the black and white striped bags stuffed with vintage clothes from Canal Jean up and down what you considered the Riviera of style, spanning Broadway from Canal to Houston. And that everything wrong in your life would be okay. What wasn’t okay at the time? Was it just being in sixth grade or parents getting divorced or…

Stella Bugbee:
I don’t know where to start. Yes, my parents were getting divorced. I am an only child. We had moved around a lot. I didn’t feel particularly settled. I had some substance abuse issues in my family. It was rough. I had a bit of a rough time early on, and there was something so soothing and escapist about seeing all this fashion and just kind of fitting in.
The other thing is that Washington DC, at that time, I don’t know what it’s like now, but it felt very financially segregated, I’ll just say. So, you kind of had to pick a lane and you had to stay in it, and it was very preppy. And even then I didn’t really particularly identify in that way, and I was just instantly felt like, “I’ll find some people here that will like me for the way I want to be.” And that was pretty obvious, just waltzing up and down that particular stretch of sidewalk. And at that point in New York, it felt really expressive. You just saw people walking around in wild outfits all the time.

Debbie Millman:
I really had this sense, as I was starting my research for today’s show, that you were a native New Yorker. And I went into my research thinking that, and then found out that no, you were born in New Mexico and then lived in Washington. I just had this sense that you were a true blue native New Yorker, as I am. But I’m glad that you’re honorary.

Stella Bugbee:
I think wherever you spend junior high school is who you are.

Debbie Millman:
I think that’s true too. Absolutely.

Stella Bugbee:
That’s so formative, that becomes you.

Debbie Millman:
Your grandmother worked at Bonwit Teller. For those that might not know or remember, was the Barneys of Los Angeles in the 1960s and ’70s. And your grandfather always carried around a beautiful Ralph Lauren bag, which I now know you carry.

Stella Bugbee:
Oh no, it was Vuitton.

Debbie Millman:
Oh, Vuitton.

Stella Bugbee:
Yeah.

Debbie Millman:
So interesting.

Stella Bugbee:
He loved Vuitton and he was very, very showy in a funny way, but also kind of dandy. I think what you’re remembering actually is a story I might’ve told you about carrying his Vuitton bag always to the Ralph Lauren show. He’s no longer with us, but I carry that bag in just as a kind of wink to myself and to him because I think he would’ve really enjoyed attending that show, so that’s my honor to him. But yeah, it’s beat up and destroyed, and I carry it anyway.

Debbie Millman:
When you were in high school, you and your poetry were featured in Sassy Magazine. How did Sassy discover your writing?

Stella Bugbee:
I had attended Bennington College’s summer program for writers, and I thought I was going to be a poet. I thought, really legitimately thought, that was going to be my life. And I had a teacher and she got me very involved in a program that worked with deaf poets, and we would translate each other’s poetry. And through that, I got into the New Rican poetry scene.

Debbie Millman:
Poetry Cafe. Yeah.

Stella Bugbee:
It’s quite a moment.

Debbie Millman:
Did you do slams?

Stella Bugbee:
I did. I wasn’t very good at them, but I did participate, and then I don’t actually know how Sassy came about, but I think somebody saw me there and they were doing a whole story about teenage poets. So, I was one of maybe three or four people featured. And I was very, very certain that that was my career. I was adamant.

Debbie Millman:
What kind of poetry were you writing?

Stella Bugbee:
Not very good poetry, actually. I mean, teenage poetry. I was really interested in poetry, actually. I think it’s still something I’m actually quite interested in and have become interested in anew, even in the last five years or so. And thinking about the way that poetry applies to what I’m doing now. I know that sounds really pretentious, but it does in terms of headlines and things like that. And I was just interested in forms. I got really into very technical, formal poetry, sestinas, things like that.

Debbie Millman:
You can send those to McSweeney’s. That’s the only poetry they accept.

Stella Bugbee:
Oh, really?

Debbie Millman:
Yeah.

Stella Bugbee:
Sestinas in particular, very hard form. But also, I loved concrete poetry, and I think that actually that’s what led me into thinking about typography, and was one of the reasons that I ended up choosing design when I ended up choosing design.

Debbie Millman:
Magazines were abundant in your house growing up, your parents had a subscription to Interview Magazine and Vogue, which you started reading when you were young. You also had a subscription of your own to Martha Stewart Living. What did you think of these magazines at the time?

Stella Bugbee:
I think that I’m someone who very much bought into the idea of aspirational lifestyle as a young child, and it was very real. You sort of felt like, “If I get Martha Stewart Living and I learn how to make cookies and make people happy and have a nice home, my life will be better.” And I think a lot of that did stem from the tumult of my earlier childhood and wanting stability and things like that.
But I really loved imagery. I think there’s something about the kind of imagery and the styling of editorial imagery that I bought into 100%. I really loved it. And whether it was Vogue or whether it was Interview, which was super cool, or whether it was Martha and food, and I don’t know, I wanted to live in those images.

Debbie Millman:
Did you have any favorite models at that time?

Stella Bugbee:
I didn’t. Models have never been the thing that interested me. I was always really interested in styling. I spent a lot of time thinking about Vogue and thinking about Old Vogue later on in my career.

Debbie Millman:
Grace Mirabella Vogue or Diana Vreeland?

Stella Bugbee:
No, Anna Vogue.

Debbie Millman:
Oh, Anna Vogue.

Stella Bugbee:
Because that was my Vogue. And I think she was really speaking to a kind of perfectionism that had a certain appeal to me at that time. The idea that you could be perfect, that you could aspire to be perfect. Now, of course, I know that that’s not true, but at the time it was alluring.

Debbie Millman:
I understand you really fell in love with design when you first saw Reagan Magazine. What intrigued you most about that, aside from the glorious typography and everything that was happening in that magazine?

Stella Bugbee:
I think it broke every rule. I was a first year art student at Parsons and trying to pick a major, and I could have gone any number of ways. I was really interested… and I was also studying writing at Eugene Lang, so I thought, “Well, do I want to be an illustrator?” That was really fun and briefly toyed with that.
But then there was such a magazine moment happening. It wasn’t just Reagan, it was Wired, it was wild. Wired was just doing the most experimental, interesting stuff with language. And I think, again, getting back to that concrete poetry side of things, I was fascinated by how far you could push language and still have it maintain readability, and what it felt like as a reader to be encountering language all blown up. And it just felt like this really experimental rule-breaking moment for typography, for language, for editorial, for creating a scene.

Debbie Millman:
Though you really loved fashion, your parents didn’t think it was a valid thing to study or to devote your life to. How come?

Stella Bugbee:
Yeah, I have said that before, but I think I would revise that. I think it just wasn’t part of our consciousness. It wasn’t that they actively would’ve said, “Don’t spend your time doing that.” It just-

Debbie Millman:
Well, if they were hippies, it might feel-

Stella Bugbee:
We didn’t know anybody who did that. They were school teachers, and came by life in a very different way and they were very literary. My mom has two MFAs in literature and it just wasn’t something that they thought it was a career in, exactly. They had no context for it, so they didn’t look down on it or something. Now that I’m a parent, I have a little more sympathy for where they were coming from. They were probably just totally unable to imagine what a person does in fashion.

Debbie Millman:
You mentioned that you went to Parsons as well as Eugene Lang, so you double majored in design and writing. Aside from poetry, what other kinds of things were you writing?

Stella Bugbee:
I initially thought I would study poetry and create writing as intensely as I studied the art. But what happened was I got into the art and I just fell in love with design, really and truly. It was like I didn’t know that a person could spend their whole life thinking about this stuff.
And once I realized that not only could you, but you could live doing that, you could make a living, it was like a real job. I kind of abandoned thinking about poetry because it felt so much less connected to what was happening in the world, and I just really wanted to be at the center of what was happening, and kind of in the center of culture. Though I loved the writing and the poetry, it felt much more niche to me at the time. So, I sort of abandoned it, to be honest. I didn’t end up graduating with the double degree. I only ended up with the BFA.

Debbie Millman:
You worked for Kate Spade when she and Andy Spade opened their first door on Thompson Street, and you said working there was a revelation. And when you were a sales girl at the original Hatbox size store, you felt like you’d been invited into a dreamed up world of creativity, an old-fashioned wholesomeness. I’m wondering what’s the biggest thing you learned from Kate Spade working for Kate and Andy?

Stella Bugbee:
Well, every detail mattered to them, and that was an important lesson. But also, you have to remember that in the ’90s, there was no internet. And so all your references, all your visual references, they came through hard work. You had to track them down, you had to accumulate a knowledge base that was yours. And they were so aesthetic and so knowledgeable and so tasteful, actually, in their own personal lives. And they were trying to take all of that knowledge and translate it into a brand, a fashion brand. And that was really cool to watch somebody do, and it was early days, small, tiny little store, and you didn’t really know what was going to come. I mean, now it all seems inevitable, but at the time it just felt very creative.

Debbie Millman:
Well, it was so different than anything else. There was so much context to the way they were creating their store and the aesthetic of their clothes and the whole Kate and Andy Spade experience.

Stella Bugbee:
I have so much more respect now even than I did at the time for how difficult it is to start a brand from scratch, especially a fashion brand, and have it resonate with people, and as quickly as that brand did. I mean, she had a background in editorial as well, and he had a background in design and advertising. And so I can look back on that and realize exactly the levers that they were pulling and all the tools they were using, and they had a ton of experience going into that building of that brand.
But it was not a sure thing. I mean, it’s an amazing endeavor to take on and have the confidence to try something like that. And then for it to succeed as wildly and as quickly as it did, just speaks to how sure-footed they were right out of the gate. And I think I got to see that up close and it was very natural to them. It seemed very natural to everybody who worked there.

Debbie Millman:
I’m glad that that brand still is around.

Stella Bugbee:
Yeah, and to see how it’s weathered these massive changes versus the small indie production that it was initially.

Debbie Millman:
You worked seven days a week when you were in college. You also had an internship with the legendary magazine designer, Roger Black, while you were at Parsons, and you worked on publications including Men’s Health and Reader’s Digest, and you said it was there that you learned graphic design was good training for decision-making. And I’m wondering if you can talk a little bit more about that.

Stella Bugbee:
Somebody was asking me the other day, “What did you like about art school? Why did you study design?” And I said that I thought a design education shows you how to solve problems. It shows you that there’s always more than one answer, and that freeing your mind up to have more than one answer for every single problem just makes you, I think, more empathetic to every problem that you’re trying to solve, and it makes you a better decision maker.
It’s like you have to make decisions really quickly sometimes, especially in editorial, and you have to sort of thought through all the other possible outcomes in order to make those decisions. I think design, really, it makes you realize you shouldn’t be too precious, I think. And working in magazines is very fast-paced, so you’re just making quick choices and then you’re onto the next magazine.

Debbie Millman:
And it’s also very subjective. There’s not only one answer to every question, but there are many that are really viable.

Stella Bugbee:
Totally. And that’s what I loved about the critique class process, and eventually I ended up teaching at Parsons, but I loved these classes where you would have a problem and everybody had the same problem and nobody had the same solution. And we had to, at that time, in those kind of classes, present three ideas and have valid reasoning behind why all three of them could work. And I saw that process play out in the actual workforce later on, but I treasure that lesson. I think it’s one of the most important things that design school, and all those internships and working at all those various magazines, taught me.

Debbie Millman:
Yeah, there’s something so interesting about going into a crit thinking your work is really solid, really good, feeling really proud of yourself and then see other people blow you away. And so you always have that, “What would that person have done?” And keeps you really striving, I think.

Stella Bugbee:
Yeah, and I think working on different magazines made me think about different audiences. And when you think about there being a different answer or a multitude of answers for any particular problem, it makes you think about solving the same problem. Let’s just say you’re basically solving the same problem for Reader’s Digest as you are for Men’s Health, but maybe for a totally different audience. So, how do you speak to what does the reader of Men’s Health need and how does the information you’re trying to design in that space speak to that reader? And how is it different than at…

Debbie Millman:
Yeah, especially with Reader’s Digest, which at the time had a bazillion subscribers. It always amazed me how many people read and subscribed to Reader’s Digest.

Stella Bugbee:
Yeah, it was wild. The other thing is, I didn’t care about either of those two publications, personally. I wasn’t invested in their content that I was working on, which I think was also a good lesson because I didn’t have to be necessarily to dissect them as problems to be solved. Right?

Debbie Millman:
Yeah. So, right out of college, you said that you got a job doing the exact thing you wanted to do, but within six months you realized you did not want to do that job, and so you called your mother and said, “I picked the wrong profession and it’s too late. Now I’m stuck for the rest of my life.” And she said, “Stella, you’re 22. You have plenty of time to change.” You disagreed and told her she didn’t understand that you had, at that time, invested so much in your career. You don’t have to tell us what the job was, but was that when you thought you should have gone to culinary school instead?

Stella Bugbee:
Well, let me be clear. I loved that job, and I loved those people and I loved that… It was really, I didn’t think I picked the right profession. It was not that any job would’ve been the right job for me.

Debbie Millman:
So, it was working in design.

Stella Bugbee:
Yeah, I was worried that being downstream from the decision-making process was upsetting to me at the time, which I’m sure is a relatable thing for a lot of young designers. And I knew even then, that the design part of it was only satisfying to me when I had some say, at least, in the content part of it, and I didn’t really know how to translate that into what… I didn’t know how to take all this stuff that I’d been doing, all this work I’d been doing, all these internships I’d had. And I loved design, but I didn’t really know how to solve that problem.

Debbie Millman:
Did you have that much confidence in design decision-making at that point to feel that you could do the bigger job?

Stella Bugbee:
I didn’t know what the bigger job was, so yes, I did. I had enough confidence to go start a company with my two colleagues and friends from college, so that I could have a little bit more control and be a little less downstream. I don’t know if that was confidence or just willfulness or what, but I-

Debbie Millman:
Drive, ambition.

Stella Bugbee:
Yeah, I think what you’re describing and what I called my mom to try to articulate, and not super successfully, was just that I wanted more control over what I was doing, and I was worried that I wasn’t going to get it for a long time in this profession. And I didn’t know how to fix that problem. I think that’s a conundrum that a lot of people come up against in design.

Debbie Millman:
Yeah, I briefly started a company, I believe I was 26 or 27, for much of the same reasons, but though I had the drive and the ambition, I didn’t have the experience. I mean, we did it and we did it fairly successfully for four or five years, but I was never proud of what we were making because I didn’t have the skills yet to understand how to make things that were better.

Stella Bugbee:
I absolutely ran up against a similar personal, sort of a lack of skills or just even experience in general. Wanting the control doesn’t mean you have the judgment yet. I knew that after that, even after doing that, even after trying to gain control over it, I actually had to go back into the workforce and get more experience and learn from others some more.

Debbie Millman:
Yeah. One of my favorite anecdotes that I read about you was when you were a very little girl, you went to a job fair and somebody asked you what you wanted to be when you grew up and you said, “In charge.” I could so relate.

Stella Bugbee:
There’s a pattern already. Yeah.

Debbie Millman:
So, you’ve had a number of really interesting jobs in that first decade of your career. You worked for Drew Hodges at SpotCo, the agency that does most of the theater campaigns for Broadway. I believe you worked on 52 campaigns that first year. You also freelanced at The New York Times Magazine. You worked at Ogilvy and Mather’s brand integration group and also began teaching, as you mentioned, at Parsons. You also worked at two independent magazines, Bene and Topic. Now, during this time, you also got really sick. Can you talk about your diagnosis and what happened after?

Stella Bugbee:
Yeah. I got sick right after college, and so that phone call that I made to my mom was also part of that. I thought, “I don’t know exactly how I’m going to work this hard, being sick.” I was diagnosed with Crohn’s disease. And so I spent a lot of years just trying to figure out how to balance the ambition that I had with the truth, which is that I was not feeling well, a lot of the time. That did affect a lot of decisions that I made, including the decision to have children earlier than I might’ve necessarily, had I not had Crohn’s disease. But other than that, I mean, I just trucked along. I wouldn’t say that I let it get me too down.

Debbie Millman:
You said that it was really intense to be sick in your early 20s because people didn’t understand you, that you were so different and in such a different place, you weren’t able to go out and party as much. How did you manage the ambition with the illness?

Stella Bugbee:
Well, also to be fair to other people, it’s not something I was talking about with anybody. So, if people didn’t understand, it’s also just not something that I was super open with it. It wasn’t something anybody was open with back then, I don’t think, as much as it is now. Now I meet people who tell me they have Crohn’s disease all the time. It’s sort of a common diagnosis. But back then I felt very embarrassed.

Debbie Millman:
Why?

Stella Bugbee:
I don’t know, because I didn’t want to be sick and I didn’t want that to define my life at all. In fact, I resented that it was there at all. You say, how did I balance it? I just didn’t really want to deal with it at all. Todd, my husband, Todd St. John, he’s also a designer. And sometimes we look back on that time in our lives and think, “Why didn’t we travel more? Why didn’t we do this or that?” But a lot of it, I think, was that there was work and then there was time where I needed to rest.

Debbie Millman:
Well, you also found yourself unexpectedly expecting twins when you were 28 years old, so that sort of changed everything.

Stella Bugbee:
Also [inaudible 00:25:40] on the travel. But I think he also worked really hard, and the two of us worked really hard in our 20s, and so we didn’t leave a lot of other time for socializing, especially if you count in the illness. There was a lot of time where after work I was tired.

Debbie Millman:
You ended up having to go on bedrest when you were pregnant. How were you feeling about where your career was going at that point?

Stella Bugbee:
I was not particularly hopeful at that point.

Debbie Millman:
I read that you thought it was a career apocalypse.

Stella Bugbee:
Yeah, I thought it was over. I thought my career was over. I didn’t really know what to expect, actually. And I think a lot of people I’ve spoken to feel that way on the cusp of their first child, of radical insecurity about whether or not they’re going to want to come back to the way that they had been working or whether they will be invited to come back into that pace. I, at the time, was working at Ogilvy, and it was really intense.

Debbie Millman:
Oh my God. I heard when Brian Collins used to bring in bags of donuts, it meant that everybody was staying overnight.

Stella Bugbee:
Yeah. I never stayed overnight, but I did eat a lot of candy late at night. Yes, I mean, I also really enjoyed that and I had incredible colleagues there and people that… I mean, for me, that was grad school, almost. It was an amazing experience, but it was very intense and not something you could go back to with Crohn’s disease and twins, clearly.

Debbie Millman:
Yeah, I look back at the pace that I had in my 20s and 30s and don’t know how I managed to stay alive. Actually, I look back on it now, I’m like, “How was that possible to stay up that night after night after night?”

Stella Bugbee:
Although it was really invigorating to work there, and David Israel and Weston Bingham and Alan Dye and…

Debbie Millman:
It’s a dream team.

Stella Bugbee:
And Brian was incredible. So, I just felt like I was in a very lucky place and I wouldn’t… If it took a lot, that’s what it took because I just wanted to be around those people.

Debbie Millman:
So, you then unexpectedly get pregnant. You’re on bedrest, you file for disability. You are considering the possibility that you’re in this career apocalypse, and there you are at 30, sitting in a sandbox with your two children, your twins, thinking you had to figure out your career, which you thought was pretty much over. And Domino Magazine calls you asking you to come in and meet with Deborah Needleman. What job did she end up offering you?

Stella Bugbee:
She needed a design director because Michele Outland was leaving, and I had thought to myself… I haven’t actually done editorial since college. I had done sort of independent projects, as you mentioned, but not at a high level. I really thought I needed to learn that. So, I was scared to go and meet with her, but we got along right away, and I loved the magazine. And I remember calling Todd and saying, “I think this is going to maybe be really hard, but it’s going to change our lives, and my life and I got to do it.” So, that was that. I started right away.

Debbie Millman:
You worked at Domino for three years and oversaw the design of every editorial page. You designed and directed the Domino Book of Decorating. You managed the art department, every aspect of the creative creation of the magazine. The magazine shut down and you left. And at that point, you got pregnant again. And at that point, you truly thought that you weren’t going to do anything ever again. Why?

Stella Bugbee:
When Domino shut down, that was a very insecure moment, I think, for everybody who worked there, and…

Debbie Millman:
It was just heartbreaking. It was such a great magazine.

Stella Bugbee:
Yeah. And it was very heartbreaking to see a whole entire staff get locked out all at once. That was sort of when I went to work in fashion for the first time. I went to work for Raul Martinez. That year that I spent working there, or a little more than a year actually, was my PhD. If Ogilvy was my master’s, then AR Media was a deep course in fashion and fashion photography and fashion branding. And I spent an entire year hanging out, reading Vogue magazines in their library, coming up with campaigns.
And so that was really a seminal, unexpected turn. It was back to branding, away from editorial, but it was… At that time, Raul was also going back to be the design director of Vogue. So, it felt like this perfect hybrid of the two worlds: branding and design and editorial, similar worlds, and fashion. And it was my first kind of real foray into the highest level of fashion.
And then I got pregnant, and then I thought I just… Every time a life change that happens, I think it’s very destabilizing. For me, it has been. Maybe some people are more prepared for things like that. I was not expecting that to happen, and I was a little destabilized and things were going great at AR. So, why did I think it was the end of my life? I didn’t see the path. I didn’t know. I think some people see their careers and their lives as a linear-

Debbie Millman:
Yeah, I don’t know anybody like that.

Stella Bugbee:
Yeah, I didn’t, and I couldn’t quite imagine what the next step would be.

Debbie Millman:
In an interview with Molly Fisher, she asked you if it was possible to be ambitious and happy, and you said you didn’t think so.

Stella Bugbee:
Yeah.

Debbie Millman:
Do you still feel that way?

Stella Bugbee:
I think that the last couple of years have been a real reckoning with ambition. Culturally, the whole culture has looked at what we think of as acceptable amount of hours to work, acceptable amount of time to spend with work, whether is work your family or is work, work. And we’ve thought a lot more about boundaries than I think we ever did when I was coming up in any of the professions that I got to work in. Yeah, I think I would revise that. Yeah, there’s a certain amount of misery that comes with ambition because you’re just always wanting something. You always want a little bit more.

Debbie Millman:
Yeah, you want more.

Stella Bugbee:
Whether you want it for yourself or you want it for the project or you want it for the world, that’s a good thing to always be striving to try to get something better or make something better, bring something out of a group of people. Whatever it is, may leave you a little wanting in the end you never quite achieve the ideal, but I’m trying to be both. I’m trying to be both happy and ambitious now.

Debbie Millman:
Same, same.

Stella Bugbee:
But I think culturally we’ve adjusted our expectations a little bit as a whole entire culture, and that’s been really interesting, and I think healthy and good, actually.

Debbie Millman:
I do too. I think there’s something really wonderful about the idea that you don’t have to go into the office every single day.

Stella Bugbee:
Yeah, or just like the horizon for what’s possible. When you have a pandemic or we had to shut down for so long, that had never happened in my lifetime, and it raised all these questions like, “Well, what is the horizon for success of anything, of a project, of a lifetime, of a relationship of a job?” If you have to put everything on hold for two years, well, that just stalls everything that you thought you were going to be doing, and maybe that was okay and it gives you a moment to reconsider what you should be thinking the horizon is for something. I don’t know if I’m making any sense, but-

Debbie Millman:
No, absolutely.

Stella Bugbee:
… that adjustment or the correction we are now in because of the ability to take that adjustment, I think was really one of the most important things that’s happened in my lifetime to the whole world. I can’t think of anything that’s had that big of an impact on how we think about time and how we spend it.

Debbie Millman:
During COVID, I remember… or during the roughest moments of COVID, I remember thinking, “I’m changing my life. I am going to do things differently. I’m having different priorities. I’m going to organize my time in a different way.” And that didn’t last.

Stella Bugbee:
What have you held onto?

Debbie Millman:
The desire to do it.

Stella Bugbee:
I feel a pretty profound change in that horizon. I think it’s okay to take a little bit longer to do things. It’s okay to be kinder to yourself and others about the time it takes to do things. And I think that’s helping balance that thing that you’re talking about is ambition and happiness.

Debbie Millman:
Yeah. Absolutely.

Stella Bugbee:
Because I think that that’s really the tension is the timeframe.

Debbie Millman:
Yeah. And I’m also aware of when I feel really happy, and it’s very rarely centered around achievement.

Stella Bugbee:
That’s good.

Debbie Millman:
Yeah. The knowledge is power, right? So, let’s talk about The Cut for a little bit. You started working at the New York Magazine‘s The Cut as a consultant in 2011. First to help relaunch New York Magazine‘s digital vertical, you ended up agreeing to join as the editorial director the next year. And in the 10 years you were there, you essentially reconstructed what was originally a Fashion Week blog and created a full-fledged magazine brand in its own right. What gave you the sense that you could do that, aside from just always wanting to be in charge?

Stella Bugbee:
Well, so New York Magazine has actually a precedent for a project like this, and that is Ms.

Debbie Millman:
Ms. Magazine.

Stella Bugbee:
And Adam Moss, who was the editor at New York Mag, I think that he thought there was space to push this, whatever he was calling, we were calling it a Women’s Vertical or whatever, into a vital internet publication. I stress the internet part of it because I think there was this permissiveness to give somebody, maybe untested, a chance, and that was the writers, that was the editors, that was the photo team. It wasn’t a whole bunch of experts coming in who’d already done a bunch of stuff. It was a bunch of young people. And we didn’t necessarily know exactly what the rules were, so that was good.
I’m not sure that I had the confidence necessarily to come in and do that, but there was a lot of interest in pushing things, and Adam was very experimental. And I had worked with David Haskell, who is now the editor-in-chief of the magazine on Topic, which was his project that you mentioned earlier. And when we worked on Topic, I remember thinking, “I just actually want to be picking the topic.”
It was Rob Giampietro and me and David. And while I was of course interested in the design, I was so much more interested in thinking about assigning stories for a specific topic, or picking the topic and then thinking about how to represent that. And so David, he knew that that’s sort of where my interests lay. Plus, I’d been working in fashion then for a year at that point before that, and it just was a strange job, and I had a strange resume, and it enabled me to pull upon everything I’d done up to that point.
It let me pull the branding and the art direction and the editorial ideas and put them all in one place, which lucky, so lucky, to be able to use all these weird experiences that didn’t necessarily add up to anything until that moment. So, it wasn’t necessarily that I had the confidence, just I had a really strange group of skills that applied in this particular instance, and then I ran at it, head on.

Debbie Millman:
I found this quote, something that Adam Moss said about you when he hired you, “The very unusual thing about Stella is that she has this big, important editorial job and has never been an editor before.” He went on to state that he, “Would’ve been unlikely to appoint a design director to run The Cut had he not already gotten to know you when you consulted.” And he stated, “What we saw then was that Stella was a natural editor with a crystal clear vision and incredible sense of story and great news judgment.”
Stella, what I love so much about this is that you succeeded by creating a magazine and a brand that you’ve described at various times as, “A smart, funny, clear-eyed look at fashion, beauty, and issues that matter most to women, that also blends a literary feeling with a punk feminist sensibility.” What could be better than that? How were you able to sell that and figure it out and then sell it in such a clear-eyed way? I mean, that’s what he said, in a clear-eyed way.

Stella Bugbee:
My main goal was to create a space where the people working on that project could say whatever they wanted to say, in the tone they wanted to say it in. So, it was always very much about the community. I used to make this arm motion where I put my arm kind of in a circle and I said, “I’m just keeping the space open so that we can do what we want and say what we want, and that we’re not being forced into a silo by some advertising category.” I think that’s really… if you look at most magazines, they were created for the purpose of advertising categories.

Debbie Millman:
And you created this for a certain sensibility, it feels like an attitude almost.

Stella Bugbee:
Yeah, psychographic, I’d say. But I firmly believe that there were people who wanted to talk about serious things and silly things at the same time in the same place, and that was fine. And I defended that urge more than anything. And it changed dramatically year over year over year. And so it wasn’t just that I had that vision from the beginning, it was sort of like, “Well, I got that done. What else can we do and how else can we grow? And who else can we bring on and what other voices can we put forth and what other challenges and ideas?”
And while that was all happening, the magazine was also feeding me incredible pieces. And I was working with the people who worked making the print magazine all the time and the editors on that. And I had an incredible partner in Lauren Kern who’s now at Apple News, and she was sort of my editorial partner on the magazine on the print side.
And once that came about, when she joined, I think that we all saw the real potential for it to be something very impactful. And again, we just all ran at it. For me, I didn’t want to squander that opportunity ever, at any moment. I thought, “What if no one ever gives me this opportunity again? I have to run at this.” And I wanted to give everybody else that sense that we got to run at this because we don’t know that this is a guarantee that we’ll always have a place to say and think and be ourselves, even with the precedent of Ms., having come out of that publication, which is really powerful. And I was operating a lot on other publications backs. I think you mentioned Mirabella, the actual Mirabella.

Debbie Millman:
Right. Grace’s magazine after Vogue.

Stella Bugbee:
Was an incredible magazine. Sassy. There was a precedent for some of what we were doing.

Debbie Millman:
Remember New York Woman?

Stella Bugbee:
New York Woman.

Debbie Millman:
Woman. Yeah.

Stella Bugbee:
New York Woman. Yeah, and in fact, I met with the editor of New York Woman early on in my time at The Cut because Pam Wasserstein knew her. And we went out for lunch. And it was important to me to note that we were part of a pretty healthy legacy actually, and we were just doing it on the internet for a new audience and building an audience in that space.
But a lot of people had tried to do what we were trying to do. And in fact, I have the very first issue of Mirabella, and I got it when we were relaunching The Cut in 2018 just as a kind of reference, and I couldn’t believe how contemporary it was and how it felt like it could literally be running now.

Debbie Millman:
Yeah. I want to talk about fashion a little bit.

Stella Bugbee:
I love fashion.

Debbie Millman:
You said that from the time you were little watching your grandmother at Bonwit Teller, you remember understanding that fashion was a form of social currency. And that people who had money looked really different from people who didn’t, and that they were treated very differently depending on what they wore. As a result, you’ve been fascinated with the way in which fashion and power overlap, and the way in which fashion and self-expression overlap. My question is, how have you incorporated expressing that fascination in the way you approach fashion and fashion journalism?

Stella Bugbee:
I think that a lot of fashion journalism is prescriptive, or at least it has been historically, and exclusionary. That’s why a lot of people have resentment toward fashion. They feel talked down to and excluded, whether it’s because they don’t fit in the clothes or they can’t afford the clothes or they’re for some reason excluded. It’s an industry and an art form that thrives on hierarchy and cast systems almost, and I don’t like that about it at all. I sort of reject that, and I kind of want everybody to feel like it’s something that they can and should embrace for themselves the way they would enjoy food or the way they would enjoy a great book or music, so that it’s a very personal, approachable part of your life.
And to go back to being in design school, for example, when I was in design school, I started seeing the world through design and it enriched my life. I got, “Oh, and this is why a chair looks the way it looks, and this is why Coca-Cola cans look the way they look.” And for me, fashion has that same thing. It’s like, “Well, you can choose to look however you want. Let’s think about that.”
And I would hope that certainly at The Cut, and perhaps less so at The Times, just because of what we’re doing at The Times, it’s very, very different. But I really wanted to start to open up a conversation for people and say, “You’re invited to this conversation if you want to be, on your own terms, and it’s fun, and you should want to cultivate a relationship to fashion and style for yourself, for your life.” Because it’s part of life, it’s really fun. So, a bit of taking away that power that fashion tends to have over people because it makes them feel excluded, that was important to me.

Debbie Millman:
One of the things that I’ve loved in quite a lot of your fashion coverage over the years is how you sort of democratize some of what we think about when we think about fashion, and also the range and the way that you put things together. But I really loved how obsessed you were for a little while there with Birkenstocks, and this was before Birkenstocks were back being Birkenstocks. And I’ve loved that you embrace both high and low at the same time. And it’s not just a matter of, “Here, we’re going to go high. Here, we’re going to go low.” You can match this up however way you want to, as long as you feel good and comfortable in whatever you’re doing.

Stella Bugbee:
I mean, I think one of the things that we were told… The magazines that I absorbed and loved so much that were so aspirational and exclusionary as a child didn’t always allow you to hold the complexity of the high and the low, of wanting to both talk about fashion and politics, of wanting to be able to indulge in something expensive, but also wear unique… Those complexities, those dichotomies, those contradictions are of life. It’s what everybody has inside of them.
And I think I was really interested in just letting all those things exist together. And I think that that’s when fashion becomes meaningful to people. One of the reasons why I cover the red carpet and what I think is interesting about, let’s say a red carpet event, is that’s where most people see the highest fashion come alive. It’s where they understand a gown. It’s not on a runway, and it’s not in their closet. It’s on their favorite star, whatever, movie star, musician, reality TV star, whomever it is.
And that’s a very fun space. I mean, it’s not stupid. It’s very fun. It’s very important that we think about the ways in which those intersections happen. So, I was very interested in collapsing some of the hierarchy around what was good and what was bad, what was high, what was low, what was accessible, what was off limits, and to whom. That’s really important.

Debbie Millman:
Is there a difference in covering a Met Gala versus going as a guest to the Met Gala?

Stella Bugbee:
Oh, sure, definitely.

Debbie Millman:
In what way?

Stella Bugbee:
Well, I’ve never been a guest at the Met Gala, to be clear. I mean, I think the most interesting thing for me about working at The New York Times is really thinking about those differences. What is the difference between covering? What is the objectivity that you bring as a reporter or an editor at The Times? How does that change your relationship to power, to the people in the room? How do you hold those people accountable when they’re not being honest? How do you-

Debbie Millman:
How do you? How do you do that?

Stella Bugbee:
By keeping yourself not a guest at the Met Gala. You have to be a little bit outside of that, and that’s the price that you have to pay. You get to sit in the room and enjoy some of those spoils, however you have objectivity.

Debbie Millman:
You see what’s really going on.

Stella Bugbee:
It’s a real… that kind of dynamic. Once you’re a guest at the table, you can’t be a journalist.

Debbie Millman:
How do you decide what you want to cover?

Stella Bugbee:
At The Times, the way the Style section works is sort of broken down roughly. We have a fashion team, we have a generalist team, so there’s news, there’s just stuff that’s happening. We got to cover this. It’s happening. And we try to set ambitious targets for that in terms of like, “Well, who’s interesting? Who do we think is pulling all the levers? Let’s go after that person in terms of let’s get a story about them. Let’s introduce them to a reader.”
And then there’s just like, “What is the reader interested in and what do we think is going to light their minds on fire? What do we think they’re going to share in their friend group chats?” That’s a big thought that’s always in my mind. And I don’t know, there’s also just a certain intangible instinct, and you never really know, but you just sort of develop over time, especially if you’re really looking at patterns over time of internet traffic. I mean, we have so much information available to us, and that’s the thing.
It’s like, “Well, you have to really read the tea leaves.” You start to think, “Well, why did that story do really well and not that one? And what’s the learning from that?” And not let that affect what you’re assigning too much, right? You have to think about what you think is interesting, what’s moving the conversation forward. And that’s the sensibility. That’s an intangible thing, actually.

Debbie Millman:
Before any publication went online, you didn’t know what people were necessarily interested in most. Yes, “Can this marriage be saved?” From Ladies Home Journal and so forth. But now, you know how many people are actually reading every single article that they’re reading and the direction that they’re going and so forth.
And in some ways, when you’re going through the paper, I still get the Sunday paper, you go through and there’s a lot of opportunity for discovery because you’re just seeing things as they pass by on the page. When you’re online, you tend to look for things like, “Thursday night into Friday morning, Modern Love will be up.” Social cues. You know when to find things, and you don’t have as much opportunity to discover unless you’re being fed, “You might also like this.” Which you have to then to decide whether or not you think it’s worth clicking. How much do stats actually matter to you? And I’m not talking about The Times. I’m just talking about you and your taste and what you believe should be published.

Stella Bugbee:
They don’t matter to me. I’m looking at them, I’m curious to see them, but I’m not going to not do a story that I believe in based on that at all. We came out of a decade, those of us who worked online, where a lot of decisions were made based on that, and I’m not sure that that was to the benefit of the content, always. And luckily, The Times really doesn’t dictate what we do in that way, which is really helpful. But I’ve developed certain instincts. I have a sense of, I think what’s going to be interesting to people and is there tension in the story? Is it a widely known subject matter? We just did a story about Barnes & Noble.

Debbie Millman:
I love that story and I love the images. It was so great to see all the different Barnes & Noble styles.

Stella Bugbee:
Well, that’s a design story, right? A total branding and design story. And several people on my team were very surprised at how big of a hit it was. But I knew it was going to be because I think there’s this huge interest in that brand, an innate interest in Barnes & Noble, why it’s not succeeding. I think actually people want it to succeed. So, what were they doing? And they’re doing something really weird, actually.
And I kind of thought, “That one will probably be a hit,” and you just develop instinct for what you think people will want to read. And I’m certainly not always right, by any means, but that’s kind of the way I use that information that I get every week, and actually every day, is just a sense of people really are interested in things that they already have emotional investment in. You write about Victoria’s Secret, people are going to read it. They’re curious about that brand, regardless of what you say about it. So, there’s certain topics that you sort of recognize will be interesting.

Debbie Millman:
You’ve written that, “Runway show going requires stamina.” Is that because of the pace?

Stella Bugbee:
Yeah, there are people who just love going to fashion shows, and I think they’re really interesting, especially if that’s your beat and that’s what you cover. But the grind of going to maybe 50 in a row, especially if you’re a visual person, you have to pace yourself. It’s a lot of images, if you’re thinking about it that way. I mean, sure, experiencing that just on Instagram when I’m not, let’s say I’m not in… I didn’t go to Milan or something. I’m experiencing it as a reader and as a viewer, it’s a lot to watch other people experience it. Imagine being there. It’s a lot of images.

Debbie Millman:
How do you feel about your own fashion when you’re watching shows or in the midst of the fashionistas?

Stella Bugbee:
Probably like most people, I have a fraught relationship with fashion. If we’re talking about what I wish I could have versus what I have. But this season, I tried a different approach, which was while I was walking around and going to shows, I started keeping a list on my phone of reminders of things that I actually like so that I wouldn’t lose sight of my own desires and my own taste, just to remind myself, “You know what? You really like this and you really like this.” And this is a hard-won, decades-long project to develop what you actually like. Don’t be too swayed just because everything is shiny.
And that’s a different approach than I’ve taken in the past, and I think that that’s been healthier. Because otherwise, you can get very wrapped up, very quickly, in kind of the dizzying aspect of all of this new, beautiful luxury, very distorted reality, which most people… I don’t think most people change their fashion every six months.

Debbie Millman:
Well, it’s just that in technology that have that sort of forced obsolescence embedded in it, which is so hard to manage emotionally because you want to sort of be stylish or in style or have the latest, greatest whatever. But that’s a lot of pressure, it’s a lot of money, it’s a lot of consumption.

Stella Bugbee:
I mean, the real hardcore fashion is for the very young, who change their fashion all the time and are trying to figure out who they are and are using style as a tool to do that, or the very wealthy, who can afford to do that. For the vast majority of us…

Debbie Millman:
And the very skinny.

Stella Bugbee:
Yes, the body that can handle that kind of change and can afford to handle that kind of change. The vast majority of us will buy a coat in 1990. I’m looking at you. I know-

Debbie Millman:
Oopsie.

Stella Bugbee:
I know you still have a coat that I admire from 1990, and keep it, right? And so how do you bridge that continuity of self year over year? That’s not something that you can sustain changing all the time, most of us. So, then you have to develop your own personal taste, which I think gets back to my goal for all of us, which is cultivate your own taste, have confidence in what you like, make your list, “This is what I actually like,” so that you’re not feeling swayed all the time or insufficient because you can’t participate for whatever reason: money, age, body, any of those reasons. It helps to have a strong foundation and understand what you actually like. And then I think you should just totally lean into that. No trends, nothing. Find yourself and enjoy yourself with fashion. That’s my main goal in life.

Debbie Millman:
Just have fun with it?

Stella Bugbee:
Is to divorce it of its power over our minds and to gain some control over that and say, “I really love this.” I love it the way I love this couch that I bought 25 years ago, and I keep recovering this couch. Well, you know what? I love this coat I bought in 1990 and I’m going to keep wearing it. I think that that’s really important, both for the Earth, for our minds, and for some semblance of control over that industry.

Debbie Millman:
You said that we can’t fix how anybody feels about their body, but we can disabuse people of the idea that certain styles are only for certain people. Do you think that designers are really paying more attention to that now?

Stella Bugbee:
There was a moment where I think we saw this little window open up and it seemed like that was going to be a priority. I’ve actually seen incredible backsliding in the last couple of years. This season was abysmal for body inclusivity. You’ll have one or two people in each show. And some brands are doing great, I should say that. But then I think with the introduction of Ozempic, it’s like everybody just gave up. I don’t know. I mean, it felt very-

Debbie Millman:
[inaudible 00:57:29] that way.

Stella Bugbee:
Yeah, it felt like market changed all of a sudden. And fashion is cyclical, and it’s not that deep, as we would like it to be. So, some of these changes that were kind of promising and exciting, we’ll see if they stick.

Debbie Millman:
Well, you had a lot of ability to help reframe the way people think about style and beauty and size at The Cut. Do you feel you’re able to do that at The Times as well?

Stella Bugbee:
The Times project is super different.

Debbie Millman:
In what way?

Stella Bugbee:
Well, it’s not a luxury sales project. We’re not making fashion shoots. We’re not really telling people what to buy so much. I mean, there’s Wirecutter, but we’re not a luxury fashion magazine. We’re a news organization. We’re part of a news organization. I don’t see my role as sorting through and telling people what to purchase. Even our critic, Vanessa Friedman, she’s not doing that. We’re not doing that. We’re taking what’s happening and we’re explaining it to people, but we’re not saying, “Here’s the 10 greatest coats you can buy right now.” That is not part of the project. So, it’s really different, and I don’t really even see that as part of my job as much as it is to document what’s happening in fashion right now.

Debbie Millman:
Right. As we’ve been talking, I realized what it was that I loved so much about your leadership at The Cut, which was I never came away from reading The Cut feeling bad about myself. And I’m not really in the same position when I’m reading The Times because it is more journalistic and it’s not as whimsical, I guess. But I hope that your voice can come through those pages as you continue to work there.

Stella Bugbee:
Well, I would certainly hope that you would never read the Style section and feel worse for wanting to know about any of that information. That’s important. And to treat the subject matter seriously, I think that’s a big important characteristic of the Style section is that we take it as seriously as anybody takes anything that they do there. But we also still have a lot of fun.

I wouldn’t want anyone to come away reading one of our stories, feeling worse about themselves or bad for wanting to know about it. And I think a lot of what we do actually is give people permission to enjoy the stuff that we’re covering. And within the context of The New York Times, that’s pretty important because there’s a lot of very serious, gut-wrenching stuff that happens in the sections other than mine. And that’s okay to then turn to us and enjoy yourself over here. I think it’s really important to say, “It’s okay. It’s okay. Come on over here and enjoy yourself.

Debbie Millman:
Yeah. So, this is my last question. You’ve had a long, illustrious, circuitous career, but you’ve also had some painful, harder times, and you’ve written about how when you look back, it looks like it was intentional, but you’re old enough now to admit that that was not the case. It seems like it was premeditated, but it was all accidents the whole time.
I think that’s really helpful for people to hear as they’re navigating their own ambition and their own career paths. It seemed like at the time, you had no idea whether you would recover from the various obstacles in your path. How do you think you were able to overcome those obstacles and what has it taught you about control?

Stella Bugbee:
Yeah, I have said that I felt like it was an accident, but actually one of the things I’ve been thinking a lot about in the last couple of years is that I looked at all these things as opportunities. So, they felt accidental or they felt like unexpected, is maybe a better word, but I was always able to look at each opportunity or each experience and say, “Well, this will complete a little puzzle piece that I’m missing. I don’t know about fashion, not really, not at the level that Raul Martinez knows about it. What can I get by working with Raul Martinez? That’s the highest level, he’s really good at it. What will I learn from this man?”
And it wasn’t necessarily clear to me what I would do with that, but I knew that it would give me this critical piece of knowledge and a way of looking at the world. And the same for Adam, and the same for Drew Hodges. I saw these people and these opportunities not necessarily in a connected way that was obvious at the time, but that they each offered opportunity for growth and to complete a sort of thing I was lacking.
And so I think that’s how, in retrospect, it makes more sense to me. It’s like, “Well…” And I would hope that that’s still the case. I still sort of think of that. I look at these incredible colleagues that I have and these people at The Times who’ve worked there for 35 years and who just know so much. And I think like, “Well, what does it feel like to put myself next to the people in this room and what can I learn from them?” That’s how it’s made sense.
It’s less that, “Oh, it’s all been accidental and oops, here I landed here.” It’s more that if you see an opportunity or if you are given any opportunity, find the little core inside there that’s going to give you the most knowledge that you can then take and apply to something else, or try to find the thing within any experience that completes a missing part of your education.

Debbie Millman:
Stella Bugbee, thank you so much for making so much work that matters. And thank you for joining me today on Design Matters.

Stella Bugbee:
Thank you for having me.

Debbie Millman:
Absolutely.

Stella Bugbee:
It’s been a pleasure.

Debbie Millman:
To see more about what’s Stella does, all you need to do is read the Style section of The New York Times. This is the 18th year we’ve been podcasting Design Matters, and I’d like to thank you for listening. And remember, we can talk about making a difference, we could make a difference, or we can do both. I’m Debbie Millman, and I look forward to talking with you again soon.

Debbie Millman:
Kevin Kelly is radically optimistic about the future. What about climate change, you might ask? Well, Kevin Kelly thinks that new technologies can foster a more favorable trajectory. What about artificial intelligence? He says, “It will usher in a new era of services and products and occupations.” In short, Kevin Kelly is betting on humanity and our extraordinary ability to adapt and innovate. Kevin Kelly is also a person who thinks a lot about the future. Almost 30 years ago, he helped co-found and was the executive editor of Wired Magazine where he currently holds the title of senior maverick. His many books include The New York Times bestseller, The Inevitable: Understanding the 12 Technological Forces That Will Shape Our Future. His most recent is Excellent Advice for Living: Wisdom I Wish I’d Known Earlier.

He’s here today to talk about his life, his career, his new book and why he’s so optimistic when so many of us are busy pulling our hair out. Kevin Kelly, welcome to Design Matters.

Kevin Kelly:
Oh my gosh, it’s such a delight to be here. Thank you so much and what a wonderful introduction. I feel like I don’t deserve it, but I am so glad to be chatting with you finally.

Debbie Millman:
Oh, absolutely, me too. I’ve been waiting for this for a long time. Kevin, in your brand new book, Excellent Advice for Living, you state that a balcony or a porch needs to be at least six feet deep or it won’t be used. How did you figure this out?

Kevin Kelly:
I was told this by Christopher Alexander, which is one of his patterns in his pattern language. And once I understood that and learned it, I checked that many times in my own experiences traveling around the world and it was absolutely true. I felt very confident to say, “This is the way.”

Debbie Millman:
Well, I want you to know that several years ago I decided to build a balcony off of my bedroom in a brownstone that I own. Now, doing that meant that I might be in some way inhibiting some of the sunlight coming in on the floor below. I didn’t want to make it so wide that it might inhibit any sunlight from coming in. And so I can tell you well beyond anecdotally, because my porch, my balcony is not at least six feet deep, we never use it.

Kevin Kelly:
Never use it, right? Exactly.

Debbie Millman:
We never use it. So when I saw that, I thought, “Oh my God, I wish I had known that earlier,” because I actually think that the way that the sun comes in, the angle that it comes in through the windows, it would not have been in any way …

Kevin Kelly:
Right, right.

Debbie Millman:
… impeded by a slightly longer …

Kevin Kelly:
Right.

Debbie Millman:
… patio or balcony, so there you have it.

Kevin Kelly:
Design matters.

Debbie Millman:
If only I could take my own advice. Kevin, you were born in Pennsylvania in 1952 and I read that it just so happens that this was the first year that the word technology appeared in the president’s State of the Union Address. When did you realize that?

Kevin Kelly:
I was doing research. I didn’t realize it growing up. I actually didn’t really have much of an interest in technology growing up, but when I was researching a book called What Technology Wants, I was really curious about where the concept of technology even arrived because the ancients didn’t talk about it and it was like, “When did we started to become aware of it?” And it was actually a fairly recent word that was rediscovered, so to speak, in the 1800s, but never really entered into the vernacular until my lifetime basically. And that’s when people started to talk about it or understand its significance.

Of course, now, it’s the main event in many ways, but that’s been a journey where when I was growing up people talked about the future and it was glorious, but they didn’t even talk about technology. They talked about flying cars, they talked about laser guidance, but they didn’t have this idea that it was a class of something, that it was a category like technology. That’s actually pretty recent.

Debbie Millman:
Well, I really wanted to understand the context in which the word was used in the State of the Union Address, what was that about, so I went back and I looked. It was President Truman. He actually says the word technical, but he says it several times. And in speaking about our potential, he states, “Our technical missionaries are out there. We need more of them. We need more funds to speed their efforts because there is nothing of greater importance in all our foreign policy. There is nothing that shows more clearly what we stand for and what we want to achieve.”

And then he goes on to say, “Our task will not be easy, but if we go at it with a will, we can look forward to steady progress. On our side are all the great resources of freedom, the ideals of religion and democracy, the aspiration of people for a better life and the industrial and technical power of a free civilization.”

Kevin Kelly:
Wow, there you go. I could not have said that better. I think he summarizes my own sentiments about the future and progress. It’s interesting that he mentions progress because that’s not a word that you hear very often these days. And It’s amazing to me that we still need to make a case for progress that you have to convince people that progress is real. In 2023, is that really something that we need to do? Because for me, part of my own journey is understanding the reality of progress, that progress is real and that came partly from a lot of time in the developing world in places like Asia as it was coming of age and seeing firsthand that, “Oh my gosh, progress is definitely real.”

Debbie Millman:
Now you mentioned as you were growing up, you really didn’t have much of an interest in technology. Your father worked in systems analysis for Time Magazine and I read that, in 1965, he took you to a computer show, but you said that you were totally bored by what you saw …

Kevin Kelly:
Oh my God.

Debbie Millman:
… and considered it pollution. And so-

Kevin Kelly:
It was … Yeah, they’re just cabinets and there was no screens, right? They’re just cabinets like refrigerators with tapes that were moving. And the output, the total output was a typewriter typing lines on sheets of paper and that was it. It was like … I’d read science fiction and I knew what computers were and these were not computers. So it was like, “No, I’m not. I have no affinity for these things and no interest in them,” and they were also very huge. They were room size and bigger and not very smart in that way. And they were literally hardly any smarter than your calculator. And it’s like, “No, I think there’s more interesting things in the world than computers.”

Debbie Millman:
You’ve written about how, when you were in high school, you don’t recall having a lot of ideas and stated that there were a lot of other kids in your school that you were very impressed with because they seemed to know what they thought. They were very glib and articulate. How would you describe yourself at that time?

Kevin Kelly:
Well, I have a bit of advice in my book that being enthusiastic is worth 25 IQ points and I’m describing myself because I was a kid that sat in the first row and asked questions the entire time and was very enthusiastic about learning and material. However, the moment I left the classroom that was done. That was over. I hardly did any homework. I did the minimal amount of homework. I was like, “No, I’m present in class and that’s what you get and then the rest of the time is my time.” So I was enthusiastic and interested and curious and that kind of curiosity is also worth a lot in terms of today’s world and that became my job as professionally curious.

Debbie Millman:
I actually think that’s one of the most important attributes to have in life, just to be curious and open-minded.

Kevin Kelly:
Right. I have another bit of advice, which is, if at all, you want to be curious about things that You’re not interested in.

Debbie Millman:
Yeah, I think that’s brilliant. I spent many decades actually, and it’s embarrassing to say this, especially to you, but I think it’s important for people to hear that most of the time up until, because I’m 62 now, I would say up until I was about 40, if I didn’t know of something, I assumed it wasn’t important. How arrogant, right? How ridiculously arrogant. And if I hadn’t heard of it, I just assumed it wasn’t important enough for me to have known. Oh, so humiliating.

Kevin Kelly:
So I’m the other way around. Now if I haven’t heard of it, I’m incredibly curious about. It’s like, “How have I not heard about that?” And I have found that one of the best remedies for this kind of curious of things you’re not interested in is YouTube. So I’ll see some weird thing recommended to me that I have no idea It’s like, “Well, if they’re recommending it, there must be some kind of a following. There must be some momentum there. Let me see what it is.” And there’ll be entire worlds connected to it and it’s like, “Oh my gosh, and now I’m interested in this. I had no idea and now I have an idea,” and that’s very, very powerful.

Debbie Millman:
It’s really amazing how much you can learn from YouTube. It is astonishing. Whenever my wife needs to fix something in the house, rather than call someone, now she goes to YouTube, she gets the directions and does it herself because there are directions to do everything.

Kevin Kelly:
Everything

Debbie Millman:
On everything, everything.

Kevin Kelly:
The combination of YouTube plus Amazon is the solution to life, right? It’s like you get on YouTube, they’ll say, “You’ll need this weird little kind of bolt to do something. Okay, well, here’s the Amazon. You’ll order it there tomorrow and you fix it and it’s like magic.”

Debbie Millman:
So after high school, you were trying to decide whether to go to art school or to MIT and you ended up going to the University of Rhode Island, but dropped out after one year and you’ve said that your one big regret in life is that you even went for one year.

Kevin Kelly:
It’s true. It’s true.

Debbie Millman:
Was it that bad?

Kevin Kelly:
It was. First of all, I shouldn’t have gone to the University of Rhode Island, but here’s the thing, is, again, this is 1969-1970, I applied to colleges having never set foot on any college whatsoever. I was just looking at a book, taking things. I’d never visited a college even for any reason. I knew nothing about the ones I’m really applying to. University of Rhode Island was a little tiny state school where most of the students were commuting and I was out of state and it was grade 13. It was literally like high school, but grade 13. And it was like, “I just need to do something. I can’t sit in a classroom anymore. I need to make something. I need to do something.”

Had there been a gap year, had there been internships, I’d probably have finished, but I needed to do something and so I dropped out and I did stuff and that was the only option I had at that time.

Debbie Millman:
You first became the resident photographer at a photography workshop in Millerton, New York and what inspired you to pursue photography and to work as a photographer?

Kevin Kelly:
I had two parts of my brain. I was a complete science geek and then I love science and I took every single science and math class that our college prep high school offered. So I doubled up in physics, biology, physical sciences, geology and all the mathematics, calculus, algebra, geometry and all that kind of stuff, but I also took every single art course and I loved art and drawing and painting and making art. And I discovered photography basically in my junior year of high school and photography was this combination of both of those. Because at that time, the only way you could do photography was to do the chemical processing yourself. You had to know chemistry to some extent. You had to know optics. It was a very technical art, but it was also art at the same time.

So photography for me was this nice melding, this nice convergence of my interest in science and art. And this was at a time when having a camera, owning a camera was very unusual. I saved some money to buy a used camera. I learned how to do photography by going to the library and getting books. It was just at the beginning when photography was coming of age and the single lens reflex was starting to happen. And so I got involved in this thing and I wanted to learn more and I read about this place in Millerton, New York where you were residents and I went there and I did photography all day every day and I learned a huge amount and that was my university.

Debbie Millman:
You then spent seven years as an independent photographer …

Kevin Kelly:
Right.

Debbie Millman:
… in the remotest parts of Asia. You lived on $2,500 a year. You traveled with a Nikkormat Camera and a bag filled with Kodachrome film through Japan, Korea, Taiwan, the Philippines, Burma, Thailand, Bangladesh, India, Sri Lanka, Nepal, Pakistan, Afghanistan and Iran. And I read that before you left, you called the National Geographic Magazine photo editor whose number you found in a phone book and asked if they needed any photographs. What did he say?

Kevin Kelly:
I remember his name Bruce McElfresh and I was maybe 20 years old and I called him up and I said, this was my first trip, “I’m going to Taiwan and Japan. Do you need any photographs?” And he says, “Well, that’s not how it works here, but when you return, show me your work.” That was amazing. That was amazing. So I did that. I went down, took a train. When I returned, my parents lived in New Jersey and I went to show my work and he was kind of, “Hmm, that’s interesting. Keep going. Show me more work next time,” and I did. And on the second time, they, being National Geographic, was interested in some of the pictures I had taken in the Himalayas and they were considering them for one of the stories.
They, in the end, didn’t use it, but what I understood and was true, was had I kept going back, had I kept doing it, had I do it a third time, I would’ve eventually had gotten some assignment. But along the way, I changed my mind about wanting to be a professional photographer because I, by that time, had started to meet some of them and I decided that I didn’t want that job. I wanted to do that as a passion on my own terms and what I wanted to photograph and I didn’t actually really want to photograph what other people wanted to be photographed.

Debbie Millman:
During that first trip, you shot over 36,000 slides.

Kevin Kelly:
Right.

Debbie Millman:
You were taking about two rolls of film, which is 70 pictures a day.

Kevin Kelly:
Right, right, right, right.

Debbie Millman:
And you’ve said that when you tell people that, they’re absolutely gobsmacked, astounded and incredulous because they didn’t understand how you could take 70 pictures a day. And this was at a time in our culture before everybody had a camera and you’ve written about how in order to take a photo, and this I, of course, remember as well, you had to previsualize what a photograph was going to look like before you shot it. And back then, did you have any sense of how much the discipline of photography was going to evolve?

Kevin Kelly:
No, I did not. So not only did I was shooting two rolls a day, which again was considered insane at the time … My family, we had a Brownie camera and my parents would do one 24-exposure roll a year. So you’d develop at the end of the year and there’d be some pictures from the 4th of July and Halloween and a birthday party and that was for the year. And the idea of two rolls a day was considered some degree of madness and-

Debbie Millman:
It was expensive.

Kevin Kelly:
It was expensive.

Debbie Millman:
Really expensive.

Kevin Kelly:
That’s the whole point. It was equivalent of like $5 today for each time you hit the shutter. And as a kid with no money, that was a lot of money. And so you had to previsualize because there was also no screen, so you don’t even know if you’re capturing and all the other adjustments like the exposure, shutter speeds were all set by hand, by manual. So you have to get it exactly right and get it focused and you don’t know if you’ve got it right until a year later when I was developing the film. And so that previsualization, which is also a term that Ansel Adams used about pre-imagining the image to the point where you see what it would look like on a paper, you imagine the whole scene in all its complexity onto the paper. That was something that I became good at.

It was something that I think is lost often now with the screens, but I had no idea that digital photography would come along. That would seem completely science fiction, and again, I wasn’t really thinking about the future that much when I was 22.

Debbie Millman:
How has the evolution of photographic technology changed the way you take photos?

Kevin Kelly:
That’s a great question and I’ve been asking that at a higher level, not just me, but how does it change how everybody takes photos. And this is in the perspective of the AI coming in. One of the things I’ve noticed is that because photography has become ubiquitous and cheap that we take more trivial things. We take more of the things that are ephemeral and passing and not as monumental, don’t have to be heroic. They’re a little bit more like the Lee Friedlander thing of serendipitous. They’re much more whimsical in general, the photography that people post say. So there’s a little bit more of a … What’s the word? They’re easier. They’re more relaxed. That’s the word I want. It’s a more relaxed photography now than before in general. And people are willing to be riskier frankly. There’s a far more risk-taking and trying things in photography now that doing so doesn’t cost anything.

Debbie Millman:
You’ve said that we can’t influence the direction of technologies, but we can influence the character. How do you think we’ve done that in the discipline of photography?

Kevin Kelly:
Yeah, I mean, if I had seen where we’re going 50 years ago saying, “Well, photography is going to become something that everybody carries around some kind of camera with them at all times. Each exposure would be free,” the question would be like, “Well, who owns the pictures?” And you could imagine several different versions of this. You could imagine under a different political system where we had a different attitude about copyright and the recent Supreme Court decision with Andy Warhol and the photographer.

Debbie Millman:
Lynn Goldsmith, yeah.

Kevin Kelly:
Right. So we could have had a different system where there was much more lax copyright ideas and people could reuse or work upon other people’s photograph without having to ask permission and that would have made a different character to photography where it was much more like you take, it’s immediately in the common and anybody can work with it. And you could imagine other versions or even harsher, where maybe to even view a photograph, you needed permission, okay?

Debbie Millman:
Mm-hmm.

Kevin Kelly:
And so you limited who could see your work. That would also have changed photography. That’s the case of changing the character of a system in which that technology operates.

Debbie Millman:
As an aside, I worked in the Empire State Building for 12 years, and at one point, the artist and designer Stefan Sagmeister came to photograph something on the Empire State Building. And the Empire State Building forbid him …

Kevin Kelly:
Yes, right.

Debbie Millman:
… to do that because the Empire State Building is copyrighted.

Kevin Kelly:
Right, exactly.

Debbie Millman:
And so you can’t take a photo of the Empire State Building and use it for any commercial purpose.

Kevin Kelly:
Right.

Debbie Millman:
But you mentioned, you just said something that I discovered in researching your work that really, really intrigued me and it was the idea of technological inevitability. And in reading your books and many articles, I came across this about the way in which technology has evolved. And you state, “When looking at the order of technologies on different continents in prehistory when there wasn’t really much influence between the continents, they actually follow roughly the same sequence. You’ll have the domestication of dogs before pottery. You’ll have the mention of sewing after pottery. There is a natural sequence which suggests that there is a certain inevitability to technologies. Once you have the previous ones, the next ones are going to happen. And I would say once you invent electricity and copper wires and switches, you’re going to invent the telephone. And once you have the telephone, you’re going to invent the internet.” So the internet was inevitable.

Kevin Kelly:
The internet was inevitable, but the character of the internet was not inevitable. This goes back to our former conversations. We still have a choice about who owns the internet, who runs it. Is it national, international? Is it run by one country or not? Is it open or closed? Those are all things that we have a choice about and they make a huge difference. But the fact that the internet arrived, it’s going to arrive on probably any planet. Where they discover electricity and wiring, they’re going to have an internet, but the character of the internet is going to be different than ours because of those social dimensions that we get to choose about.

And I fast forward this into saying AI, AI is coming. Making minds is something that evolution wanted to do many, many times. It reinvented minds in many different lines of development that were all separate from each other. So minds and artificial minds are inevitable, but the character of those, the quality that we really choose about how it’s run, who has access to it, how much does it cost, is it open or closed, these are all things that we do have decisions and choices about and they make a big difference to us.

Debbie Millman:
Would you say that in addition to the internet being inevitable, it is a mutation of technology?

Kevin Kelly:
So I wrote a book, What Technology Wants, and the short answer about what it wants is that it wants the same things that evolution wants, meaning I use the word want not consciously, but the way that a plant wants the light, it leans to the light. So these are-

Debbie Millman:
What technology seeks.

Kevin Kelly:
These are urges, tendencies. So the tendency of technologies are the same tendencies we see in evolution because it is, in fact, an extension of evolution, as evolution accelerated. And so when we look at it that way, where it’s going is towards increasing possibilities, increasing forms. So I say that the evolution of technology follows the same thing, the evolution of life, and it’s aimed in the same directions in which are towards greater complexity, greater specialization, greater mutualism. And so technology will become more complex and technology also becomes more specialized.

And so my prediction would be that, in AI, we’re going to see increasing numbers of specialized AIs to do different things, whether it’s images or language or music or equations or math proofs, that there’ll be increasing specialized versions of them just like we have specialized cameras and that there’ll be more mutualism, meaning that a lot of technology comes to depend on other technologies or may only be used by other technologies, meaning that there’ll be things that we’ll invent that the humans won’t even use like they’ll be invented for other technologies to use. That’s mutualism where they are embedded in the system itself.

And so my view is that those are the inevitable things and they’re not at the species level. So I would say, in evolution, any planet in the galaxy that had a gravity like Earth’s and an atmosphere like Earth, that evolution will have quadrupeds. That’s inevitable because that’s just a physically elegant solution, four legs, very, very stable. But a zebra is not inevitable. That species is completely stochastic, completely random. So species are never predictable or inevitable, but the larger blueprint is. So the internet is, but a website is not inevitable. Telephones were inevitable, but the iPhone, in particular, is not necessarily inevitable. And so we can say certain AIs are going to be inevitable, but ChatGPT-4 is not necessarily inevitable.

Debbie Millman:
I had my own little epiphany as I was thinking about this inevitability and the way in which the order of technologies on different continents …

Kevin Kelly:
Right, right.

Debbie Millman:
… in prehistory all were sort of on the same timetable. And in many ways, while this might seem trivial, I’ve spent most of my career in branding and I believe that the discipline of branding was also inevitable and that you have the same kind of trajectory, if you think about brands beyond consumerism. First, you get religious symbols …

Kevin Kelly:
Right.

Debbie Millman:
… in different continents all around the same time. So you have the symbols in the Middle East, you have the symbols in Brazil or in South America. You have symbols that popped up all around the same time. About 10,000 years ago, all of a sudden humans started to create a symbol to signify their relationship with this higher power. Higher power had nothing to do with it.

Kevin Kelly:
Right.

Debbie Millman:
We created those. And then over time, again, we had no way of knowing what was happening on these different continents. We get flags, family crests …

Kevin Kelly:
Right.

Debbie Millman:
… brand marks of ownership on animals. And then before you know it, Coca-Cola is in every country in the world.

Kevin Kelly:
Right.

Debbie Millman:
But I’ve always wondered what triggered those first religious symbols in so many places at the same time with no one else knowing about it.

Kevin Kelly:
Yeah, yeah. It’s a great question and It’s a great image too of the first person to make a symbol on rock and to say, not just me, but all of us here that this represents us or what we believe, that’s an incredible step.

Debbie Millman:
Right?

Kevin Kelly:
Yes. It’s an incredible step. It’s a kind of an abstraction, which is really very, very powerful, but yeah, that would be interesting if maybe some of the earliest cave drawings were actually branding exercises.

Debbie Millman:
Well, I think they were. I would contend that they are because we were creating an organized system of being able to perceive reality that was a shared reality.

Kevin Kelly:
So maybe the wonderful ochre handprints or maybe those are the brand of view, the brand of me, the brand of humans.

Debbie Millman:
Yes, so the notion that most inventions and innovations are co-invented in multiple times simultaneously and independently is one of the properties of something that you call the technium and I was wondering if you could define technium for our listeners.

Kevin Kelly:
Yeah, yeah. So we talked earlier at the very beginning about technologies, plural, that we have a microphone and we’ve got a camera and we’ve got cars and even materials, Teflon, Kevlar. We understand these to be technologies, although it’s broader, because in fact, technologies would include things like a calendar and timekeeping. These are technologies too. But if we think of these as independent little things and in our own lives, our life is a witness to a parade of new technologies as they’re invented. But in fact, the reality is much more complicated because these new things that are being invented rely on other technologies to make them or even to input them like they’re eating them, they’re consuming them.

And so we have really something that’s much more like a rainforest of different technologies that are interdependent, codependent on each other. You can’t do farming today without computers and satellites and telephones and logistics and you can’t do those logistics unless you have food for the workers. And so there is a complete ecosystem of these technologies that are codependent on each other. And the important idea about this ecosystem, which I call the technium, is that the technium itself, the forest itself has certain biases, certain tendencies that the individual components don’t have, that the tendencies are not found in the individual components. It’s a little bit like a beehive, which I was a beekeeper and so the bees live only six weeks, but the hive can have a memory of years.

So there are attributes of the hive that you can’t find in individual bees no matter how hard you look. That’s because systems have behaviors themselves. All systems have certain antics and biases and tendencies. And so I’m saying we have a system of technologies called the technium that’s not just culture, it isn’t Earth. It’s actually active, it’s an agent, it’s doing things and it has certain tendencies and urges and recurring patterns that are not found in the individual technologies that make up and all the technologies together make up this technium. And so the question that I ask is, what are some of those behaviors of the technium at large? And that’s what I get the question, what does technology want?

Debbie Millman:
You’ve said that the technium is an extension of the same self-organizing system responsible for the evolution of life on this planet. How so?

Kevin Kelly:
I would say in my definition of things that are created by minds, which is what technology is that that would include the dams that beaver make, the nests that birds make, the homes that termites make because they are being created from their neurons. Their neurons are measuring the honeycomb. Their brains are assembling the nest. This way of looking at technology is something that behaves in the same way as evolution does. So you can map the genealogy of different inventions and showing how they mutate. There’s a little mutation which is picked up and it becomes more common. And that is then the origin of the next one. There’s like offspring in children.

So it’s behaving almost identical to biological evolution with one big caveat, which is that, unlike biology, it’s very, very, very rare for anything to go extinct in the technium, but otherwise, the behavior of this as it progresses through time is very, very similar to biology and we see bits of the technium in the sense of things being made from the mind already occurring in the animal kingdom. And so for me, we can view technology as origins that’s not human made, that actually the origins are actually at the Big Bang. It’s the same origins of the beginning of our universe and life of these self-organizing systems. And so the mathematics of the energy component of technology follows the same kind of laws that evolution does. So whenever we can measure about evolution, we can apply to the technium and see that it’s also very similar.

Debbie Millman:
So if you think about birds making nests or beavers creating their dams, there isn’t a manual that they get.

Kevin Kelly:
Right.

Debbie Millman:
When they are creating them, it’s very much instinctual. So they have an ability to be instinctively creative.

Kevin Kelly:
Right.

Debbie Millman:
And-

Kevin Kelly:
There actually is a little bit more leeway. While a lot of it is intuitive, instinctive, but we know from birdsong and stuff, they actually can learn and change. So it’s not 100% reflexive. There are elements of individual creativity even in those acts.

Debbie Millman:
And so it makes me wonder and I’m just formulating this as we speak, so it might not be quite as eloquent as I want it to be, but if we, as humans, have an ability to be creative and that’s something that many people think that all humans are born with, the whole notion of folks like Rick Rubin or Elizabeth Gilbert talking about creativity coming through us, the best creativity coming through us, not bias, I’m wondering if there’s some correlation there with this innate instinctiveness in creating the best possible art or invention.

Kevin Kelly:
Yeah, I think there is. And I think one of the things that AI has shown us is that creativity rather than being a high-order rarefied quality is actually very primitive. It’s actually elemental. It’s so elemental that we can actually make machines do it. Rather than it being something that is layered on top of consciousness and awareness, it actually precedes all those and that it’s actually so elemental and fundamental that we’re capable of programming it into machines and so that machines can be creative, certainly with that lowercase creativity of doing something novel. Maybe not through the breakthroughs yet, but certainly at the lowercase. And I think animals have shown that they are capable of having a lowercase creativity in certain cases.

So that to me says that yes, this is elemental foundational level of creativity is something that’s very fundamental to all living systems and that’s what living systems that try to learn and adapt. You could say that that’s one variety of creativity. And I think what we’re seeing is that is something that’s portable, that’s something that we can move and it’s not just the province of … Humans don’t own it.

Debbie Millman:
Yeah. I want to talk quite a bit about AI, but I also want for our listeners to be able to understand something that you just mentioned which is called Uppercase Creativity or lowercase creativity. So I’m going to read very specifically something that Kevin has said so that folks understand. “Scholars of creativity refer to something called Uppercase Creativity. Uppercase Creativity is this stunning field-changing, world-altering rearrangement of that major breakthrough brings. Think special relativity, discovery of DNA, Picasso’s Guernica. Uppercase Creativity goes beyond the merely new. It is special and it is rare. It touches us humans in a profound way far beyond what an alien AI can fathom.” And we’ll come back to the AI conversation momentarily because there’s a bunch of other things that I want to talk to you before that.

So we were talking a little bit about … You mentioned the Big Bang. That’s a door I can’t help but go through. So you’ve written that at the core of the origin of life and its ongoing billion-year metabolism is its ability to replicate and copy information accurately and life copies itself to live, copies to grow, copies to evolve. Life wants to copy. So my question, especially given your earlier experiences in Jerusalem … You know where I’m going?

Kevin Kelly:
Yeah.

Debbie Millman:
… do you believe in God? And if so, how does that connect to the notion of evolution on this planet?

Kevin Kelly:
Sure, sure. So I do believe in God, and if listeners want to bear with some of my personal theology, it goes like this. It seems to me there’s only two major possibilities when we think about where did all this, the universe and everything in it, which is quite big as we look out into the telescopes with web and beyond, where did they come from? And so the general two answers are, well, it has always been. It somehow self-created itself. The universe has always been. Or the second one, it was that it began by itself in some weird way. Why? Who knows? And then there’s the other story which is, well, God made it. And then you say, “Well, where did God come from?” Well, he’s always been or always self-made. And all I can say is none of those are satisfactory, but I find the God version to be a lot more interesting and entertaining.

So I prefer the God explanation and my explanation of God is that God was a self-created being, the only self-created thing. And in order to understand itself, it manifests itself as the universe in order to understand what it is. And evolution is the way in which this unfolds, it’s God discovering itself by making things with freewill like itself. And we are made in the image in the sense that we are now in the process of discovering who we are and we’re going to make other things like robots in order to understand what we are. We’ll give these other beings some degree of freewill just as we have freewill to understand ourselves. And so this is replicating process.

And so for me, the godhood is a kind of all-encompassing being that’s served perfect, but becoming more perfect, which again logically doesn’t make any sense. What does that even mean, where if you are infinite and becoming more infinite? But the idea is that it’s not static. It is a process that itself is becoming more God-like by having a universe, by understanding itself it’s a way of looking at itself. So that’s my short version of the theology. I don’t expect anybody else to believe it, but that’s my view.

Debbie Millman:
You’re a Christian?

Kevin Kelly:
Yeah.

Debbie Millman:
You had a religious epiphany …

Kevin Kelly:
Right.

Debbie Millman:
… in Jerusalem in the 1970s. Can you just share a bit of a high-altitude explanation of what happened?

Kevin Kelly:
I don’t know if I can explain it.

Debbie Millman:
Yeah, that’s a good point.

Kevin Kelly:
But I can tell you the short … There’s a couple versions of it. By the way, the first time I told the story about it was on This American Life and I don’t think I’ve been able to tell it as well since. The short version is that I was working in Iran during the Khomeini revolution, got kicked out, went to Jerusalem to photograph Easter and had a conversion experience in Easter where I really believed that Jesus was the cosmic Jesus. Cosmic Jesus, again, taking that view of the godhood and understanding that, when you have a freewill, we’re going to discover this ourselves when we make robots that have free wills, is that, when a robot that you made decides to do harm, the question is, what are the consequences? Should the robot absorb it? Does the maker of the robot have any degree of capability? And how do we satisfy the need for justice while still also be loving?

And for me the answer is that the godhood, the creator takes on the penalty itself. It absorbs the penalty in part in order to relieve the being with freewill from eternal guilt and the burden of having to suffer the consequences of doing harm. And so for me, that’s the cosmic Jesus and that-

Debbie Millman:
So that everybody is forgiven?

Kevin Kelly:
Right. And so that set me off on a course of an assignment that I believe I got, which was to try and live as if I was going to die in six months. And that set me off on a different course where I graduated from photographing and traveling and I was trying to prepare for this short time of no regrets and trying to deal with things to be ready. And what I didn’t understand at the time, but did later on, was this was providing me with a rebirth experience where I actually went through the whole thing and then didn’t die, but was reborn in a very, very visceral, tangible way that I could not have believed.

And so what was interesting about having six months to live was that I could only do that by denying a future. So every day, I was giving up the future. I was not thinking about … I wasn’t taking photographs because what’s the point? You’re not going to be there in six months. And that restricting of the future was another lesson, because when it came out of it on the other side, I realized that having a future was one of the most human things that was really necessary for our own humanity, was to have something in the front of us and that, if you take that away, you take away a lot of humanity.

Debbie Millman:
Yeah, that’s really the only thing that differentiates us from other species, is our ability to imagine …

Kevin Kelly:
Right.

Debbie Millman:
… a scenario or a future.

Kevin Kelly:
And so I began much more interested in thinking about the future after that.

Debbie Millman:
It’s interesting because you had this sense that you were going to die and it does seem like that six months was a death of sorts and that you were rebirthed in a new way …

Kevin Kelly:
Right, right.

Debbie Millman:
… thinking about time in an entirely new way. Did you have a sense that this was more a metaphysical death or did you believe that it was going to be a physical death and that you might get hit by a car or be involved in some …

Kevin Kelly:
Right.

Debbie Millman:
… accident and no longer exist?

Kevin Kelly:
I was taking it very literally that I was preparing for the complete death where I would go to sleep that night and not wake up. That was the assignment to me, was to prepare in every way as if this was a complete physical reality. So I was acting as much as I could to be responsible in taking that seriously in every respect. So when I went to bed that night, I was prepared to physically die.

Debbie Millman:
Initially, you thought that, with six months to live, you would climb Mount Everest or go scuba diving or get in a speedboat and see how fast you could go.

Kevin Kelly:
Right. That would be the natural inclination to live life to the fullest, but in fact, I surprised myself because I wanted to see my parents and my brothers and sisters and do ordinary things. Yeah, that was a surprise to me.

Debbie Millman:
You found the ordinary quite exotic when you went back.

Kevin Kelly:
Yes, and that’s I think part of the marvel of life, is finding the extraordinary and the ordinary and finding the ordinary and the extraordinary and I think that was a gift.

Debbie Millman:
You wrote about what you did when you were back home with your parents. You said that you helped around the house, you cut shrubs, you worked on a deck, you moved furniture, you washed dishes. Were you bored doing those things or were you feeling very fulfilled by doing those things?

Kevin Kelly:
I was a little bored, because after three months, I got on a bicycle and rode across the US to visit my brothers …

Debbie Millman:
Right.

Kevin Kelly:
… and sisters. So no, I get bored pretty easily.

Debbie Millman:
You returned home again on October 31st from a 5,000-…

Kevin Kelly:
Right.

Debbie Millman:
… mile trek on your bicycle to visit your siblings. Nobody knew this entire time that you were in a race against the clock, so to speak …

Kevin Kelly:
Right.

Debbie Millman:
… and that you were expecting to die on November 1st, but you didn’t die. Did that surprise you when you woke up on November 1st? Did you think like Groundhog Day or did you-

Kevin Kelly:
No, no, that’s what I was saying, I literally felt like I was being born. When I was opening up my eyes, the experience from the visceral, from my whole body was a gift like being born. Because as I was opening my eyes and coming to, I realized that I had a future again, that I had everything. And so it was, yes, a surprise in that sense. It was … I mean, surprise is not the exact word. It was a gratitude, it was an appreciation. It was like, if you were conscious and you were born, what would that feeling be? How would you describe that? If you were, instead of being born as a baby, you were born as an adult, there would be an exhilaration that you would feel and that’s what I felt.

Debbie Millman:
You had your religious epiphany when you were 27 and you thought you only had six months to live. After you realized that you were not going to die, you created a countdown clock on your computer to count down the days you had left after figuring out your anticipated life expectancy based on some Medicaid actuary charts …

Kevin Kelly:
Right.

Debbie Millman:
… that told you that your new projected age of dying was going to be 78.68 years old. I believe you’re now 70?

Kevin Kelly:

Debbie Millman:
According to the date, duration, calendar, you figured out the estimated last day of your life was now going to be January 1st, 2031. How do you think about that day now?

Kevin Kelly:
Well, so the thing about it is the good news is that my longevity has been increasing. So now, when I look at the tables, it’s like 80, 81 or something. And there’s also something about it. The longer you live, the higher your chances of living longer and then there’s medical advances. And so in some senses, in the last couple of years, I haven’t been losing any dates. I’ve actually been able to maintain the same 5,080 days. And so that’s been a bonus, some gravy, but I think I run it just to sharpen my commitment and my focus during the day, because each day, if I have 5,080 days to do everything on my list, then is doing what I am right now, is it what I want to do? And the answer is, in this case, yes, absolutely, but it helps me focus in that way.

Debbie Millman:
I went and did the same thing after reading about you doing this. I have about 10,000 days left.

Kevin Kelly:
There you go.

Debbie Millman:
I am projected to live until 91, which means only two-thirds of my life is over. I have another big chunk, a big third. What’s interesting is that my grandmother lived until 91 and her sister lived until 91. My mother is currently 81, still going.

Kevin Kelly:
Yeah, yeah, yeah.

Debbie Millman:
So I’m feeling good about that and so the 10,000 days is something now I’m thinking about.

Kevin Kelly:
Well, see, you may say 10,000 days is a lot, but to me, for all the things I want to do, even 10,000 days doesn’t seem like enough.

Debbie Millman:
No, it doesn’t, it doesn’t, it doesn’t. Are you afraid of dying?

Kevin Kelly:
No, because I’ve already rehearsed it. I’m not looking forward to it at all. I don’t want it, but I’m not afraid of it.

Debbie Millman:
Are you afraid of anything?

Kevin Kelly:
I’m afraid of being wrong about so many things. There are lots of things that I believe that I’m sure will be totally wrong. It’s a different kind of fear, but in terms of actual things that exist today that I am afraid of, no.

Debbie Millman:
From what I understand, you haven’t been wrong about that much. I think the one article … No, no, no, the one article that I think you were really embarrassed about was something called The Roaring Zeros or something like that.

Kevin Kelly:
Yeah, yeah. No, there’s plenty of things I’m sure, beliefs that I have that I’m sure I’m wrong about that people in the future will look back and be embarrassed. My descendants will be embarrassed by what I believed.

Debbie Millman:
Well, fortunately, I think there’s going to be enough other good stuff to cover that stuff up. I want to talk a little bit about your use of technology. In 2010, when you wrote What Technology Wants, you stated that you didn’t have a smartphone, Bluetooth, Twitter. Your kids grew up without TV as you did. You had no cable. At the time, you said you didn’t have a laptop or traveled with a computer. Now, I know now that most of the above you now have.

Kevin Kelly:
Right, right, right, right, right.

Debbie Millman:
When did you decide to dive into social media and what has your experience been of it?

Kevin Kelly:
Right. So I have social media, but not on my phone.

Debbie Millman:
Right.

Kevin Kelly:
I have it on my desktop and that works for me in terms of hearing the people I follow or thinking about. So for me, it’s very, very useful. I have a laptop which I use when I travel, but it is primarily again just to do email. I’m an email old school person. So I don’t know, I find it pretty easy to manage or to unplug things. I know people, not everybody feels that same way, but for me, there hasn’t been a problem. We didn’t have TV in our household, not because of the content, because we were actually one of the first families that got the ISDN, and then later on, we were the first with Netflix discs.

My main objection to it was the commercials. Our kids grew up without the commercials and that was the main. And the second thing was also seeing things on our demand rather than having to watch when things were being shown. So it was this idea of content on demand without advertisements, which is streaming these days …

Debbie Millman:
Right.

Kevin Kelly:
… right?

Debbie Millman:
So the inevitable.

Kevin Kelly:
Right, exactly. That’s what we wanted. Because I do remember a great moment, when my oldest daughter was maybe eight or something, no, six or eight, she came to me and she said … Because we had borrowed a VHS tape, a Disney tape, and she came to me and said, “Daddy, daddy, there’s a program in my program.” I said, “Well, let me go see,” and it was an advertisement, interrupted her program. She had no idea what it was and we had a teaching moment about what the commercials are really about. So that was the objection. And these days, we were talking about YouTube, one of the best bargains in the world is YouTube Premium. If you don’t have it, it’s like crazy because there’s no commercials, there’s, no ads on YouTube. It’s worth, whatever, I’m paying not to see ads.

And until recently, I went off of Google, which I was a very early, one of the first Google users, went off the Googles because they didn’t offer a version of Google where you paid to not see ads, those sponsored links. So I went to a version of a search engine, it was with Neeva and I’m now going to you.com where you can pay and you don’t see the sponsored ads. So I am totally in favor of controlling what you see by supporting the site in other ways than giving my attention. I’d rather give the money than give my attention.

Debbie Millman:
You stated that the complexity of social media is akin to biology …

Kevin Kelly:
Right.

Debbie Millman:
… and that it’s not a coincidence that we speak of things going viral.

Kevin Kelly:
Right.

Debbie Millman:
And I’m wondering if you can elaborate a little bit more on why you feel that way.

Kevin Kelly:
I wrote a whole book, my first book called Out of Control, which was about decentralized systems and the parallels between the world of the born and the world of the maid and how when things are complex and complicated enough we can import the behavior of biological systems to manage them, to make them work, to evolve them and adapt them, to make them more alive and organic. And we’re seeing that and one of the ideas is that very large systems like the internet can have an immune system, whereas you cannot ever completely eradicate spam, but you can keep it down to a minimum, just like you have infections or you have cells in your own body. You don’t ever actually eliminate them. You just keep it down to a manageable level.

The general principle is that these systems, when we take some of these biological principles into these complicated systems, we can make them more like a living system, which makes them better for us.

Debbie Millman:
I’d like to read a quote of yours that I found in my research about the state of social media. You state, “We cannot use something for hours a day every day and have it not affect us. We have hints, but don’t really know. As we discover how it works, a wise society would modulate how this technology is used by adults and children. As we begin to understand its tendencies, harms and benefits, we can devise incentives to continually redesign the tech to enhance democracy and wellbeing. All this must be done on the fly, in real time, because what we’ve learned over the past a hundred years is that we can’t figure out, we can’t predict what technologies will be good by simply thinking and talking about them. New technologies are so complex they have to be used on the street in order to reveal their actual character.”

That is one of the most cogent statements I’ve encountered about the quagmire of social media, Kevin, and I’m wondering, how can we best manage our relationship with social media? Do you believe that we are addicted and that it’s all a dopamine game and we’re all searching for constant gratification through our devices?

Kevin Kelly:
I think there’s an element to it, but I think the whole point of social media is obviously there’s more going on than just that. And I also don’t believe that everybody that is inherently addictive. I think there are categories. A lot of the studies on social media used right now is based on the US and the US is peculiar in so many ways. Other countries don’t necessarily have the same problems that we have with social media. We don’t have enough data from their use to know whether this is a human thing or just an American thing. And what we do know from the studies in health say is that you don’t want to base policy on just one or two health studies of a thing. We just don’t know enough. It’s so complicated. We need hundreds of studies before we can say, “Definitely, this or that,” and making a policy level.
And right now, we just don’t have enough studies about social media to understand where the harm is coming from exactly. And the third thing I would say about it is, whenever we’re evaluating new technologies, we always have to say, “Compared to what?” “Compared to the existing technology. So yes, dental fillings may cause some harm, but compared to what? Compared to cavities? They’re way an improvement.” The same thing with say influencing elections. I think there’s an overestimation of the role of the social media. You want to say, “Compared to what? Compared cable TV? Compared to Fox News?”

Debbie Millman:
Yeah, it’s interesting to think about the self-driving cars and the outrage that people had about one car accident.

Kevin Kelly:
Right, “Compared to what?”

Debbie Millman:
There are a million car accidents a year, right?

Kevin Kelly:
Right.

Debbie Millman:
Something like that?

Kevin Kelly:
Right. So the idea would be, are we going to prohibit human drivers until they’re 99.99% safe. No, we’re giving a pass to human drivers that we don’t expect or the pass that we’re not giving to the new technologies. “The self-driving cars, how safe are they compared to what?” “Compared to the old. Compared to what we have right now.” And so the same thing with whatever other issues in social media like bullying. “Okay, compared to what? Compared to what happens in the middle school hallway?” And so-

Debbie Millman:
The junior high school gym in my case.

Kevin Kelly:
Exactly. “Compared to what?” So we tend to evaluate new technologies at a higher double standard than we do with the existing technology. And part of what my idea of proactionary stance to technology is that we want to constantly evaluate the old technology too. The FDA gives a pass for approval of a drug, but it should be about reevaluating it all the time in the context of new evidence and the way it’s being actually used. And so we want constant evaluation and I think we should make policy based on evidence, evidence-based policy. A lot of the policy in AI is now being made on imaginary harms. People are imagining what could go wrong. They’re imagining the harms and they’re going to make policy based on those imaginations and that’s very, very dangerous and harmful to the technology.

Debbie Millman:
Speaking of new technologies, on May 4th, 2022, you veered from the type of daily art you were posting on your Instagram page.

Kevin Kelly:
Right.

Debbie Millman:
Rather than making daily art on your own, you began to use AI to help make a new type of images.

Kevin Kelly:
Right.

Debbie Millman:
What has that experience been like for you?

Kevin Kelly:
Well, part of what I was doing for the year posting a piece of art that I made every day was I would sit down and literally have no idea what I was going to make and I had one goal, which was to surprise myself. I wanted to make something, I was like, “Where did that come from?” I didn’t know that or I didn’t have that in my mind. It came out of the drawing or painting. And that was really fun. And so then when the AI came along, it was easy to do that part of being surprised, but it turned out to be really, really hard to get it to obey you. The AIs are easy to surprise and hard to follow your orders.
And so what I’ve been trying to do is get them to go in certain directions and have things I can imagine. Surprise part is easy, but getting them to do something great is really, really difficult. They call this new art or job of prompting. You’re constantly nudging them and you’re trying to figure out what they want to hear and you’re guessing. It’s like working with a donkey. It’s really hard to get them to go in certain directions. And here’s what the epiphany that I had recently. So I’ve been making for a year, I’ve done this, I’m using Mid-Journey and Dall-e and Stable Diffusion and recently Photoshop has a built in, which I think they’re going to open AI. But anyway, there’s the fourth one, Photoshop.

And what I realized is that there are images, art that I could imagine, but I didn’t have any words for and a lot of great art you can’t put into words. And that means that, even though theoretically the AIs could make any possible image, they cannot. These large language models cannot make art that’s not tethered to language. It’s bound to things that you can describe. So there’s this whole world of art that I have in my mind that I don’t have words for. Therefore, the AI can’t make it. I can draw because I’m able to transcend language in my mind, but they can’t. And so that was an epiphany that the current crop of AI are incapable of making images that transcend language, which is some of the best art in the world.

Debbie Millman:
I recently heard about the job title prompt engineer …

Kevin Kelly:
Right.

Debbie Millman:
… and investigated what that was like. It still seems that all of the AIs, as you put it because it’s going to be more than one or is more than one, aren’t really self-directed and that’s what John Mato once said about the computer, the inherent flaw of the computer was that it could do nothing on its own. It had to be directed by us to do it.

Kevin Kelly:
I think that is true currently. We might see abilities to make it self-directed and the question is, well, how long will it go before it putters out or stops itself? But you’re right. Right now, that is absolutely true. There is no self-directed and what amounts there are is very limited. And that’s one of the things that I’ve also observed is that they have very short attention spans.

Debbie Millman:
But you’re having a lot of fun with it.

Kevin Kelly:
I’m having a lot of fun, but they have short attention spans. So one of the first things we want to do, I had a friend, science fiction writer, we want to make a book, illustrate a book. And the problem was is that it could develop a character and then forget about it two seconds later. It’s like, “No, no, no, come on, you need to remember this.” The new versions of ChatGPT have a little bit more memory, but they’re still just not engineered or not capable of sustaining attention over long periods of time to the same thing. So that’s another failing of them currently as they have short attention spans.

Debbie Millman:
There have been so many headlines about the future of AI in the New York Times.

Kevin Kelly:
Right.

Debbie Millman:
The New York Times I think published over 60 articles on the AI alone in the last 30 days. Some of them with titles including “How Could AI Destroy Humanity?”, “Big Tech is Bad,” “Big AI Will Be Worse,” and the pessimistic, “AI Poses Risk of Extinction, Industry Leaders Warn.”

Kevin Kelly:
Right.

Debbie Millman:
That was an actual headline in the New York Times, “AI Poses Risk of Extinction, Industry Leaders Warn.”

Kevin Kelly:
Right.

Debbie Millman:
How accurate do you think these headlines are?

Kevin Kelly:
Yeah, they remind me very much of headlines. I should go back and read the New York Times when it was talking about the internet, but we’d certainly heard similar … I wouldn’t say they’re that drastic, but we did hear very dire warnings about the internet and there was, I remember, a Time Magazine cover about, “If the internet continues, spam will take over the world and destroy the internet.” They were saying, “Well, look, how much spam we have right now. If everybody has email, then spam will just kill it.” Of course, the solution was we had spam filters and that spam filters even being embedded at the level of Google. So that’s what’s happening, is that Google is basically filtering the spam before it even reaches you.

So we developed technologies to deal with that issue and that’s what we’re going to do with AI, is there are certainly going to be new problems, biases, prejudices. These are real, but we can invent technologies and solutions that will solve them. They’ll make new problems of their own. So we’re not looking forward to a problem-free future That’s utopia, which I don’t think is possible or desirable, but what I call protopia where we are going to have more problems, but the solutions to those problems are more technologies. So I’m optimistic about that protopia, not because I think our problems are smaller than we thought, but because I think our capacity to solve them is even greater.
And so that’s the missing part, is our ability to keep solving these problems that come up. And if we can never get better at it, then yes, I would agree with the pessimists, “It’s at the end. We’re done,” but the thing is that these new technologies also help us to create new solutions at an even faster rate than before.

Debbie Millman:
I came of age as a designer in that time between doing old school hands-on …

Kevin Kelly:
Right.

Debbie Millman:
… drafting table graphic design and then morphing and migrating to an Apple computer. And in that time, there were many, many people, older designers than I was that were absolutely vehement, that nothing creative could come out of a computer …

Kevin Kelly:
Right.

Debbie Millman:
… that …

Kevin Kelly:
It was cheating.

Debbie Millman:
… this was … Yeah, yeah, and then of course, when the iPhone came out, everybody was talking about how this was going to ruin the discipline of photography. And this is another quote I found from you, “We might’ve expected professional occupations in photography to fall as the smartphone swallowed the world and everybody became a photographer with 95 million uploads to Instagram a day and counting. Yet the number of photography professionals in the US has been slowly rising from 160,000 in 2002 before camera phones to 230,000 in 2021.” So I think that you talk about the tech panic cycle and I think we’re in one of those right now with a number of different technologies.

Kevin Kelly:
Yeah, yeah, and we’re dwelling on AI because that is the most recent one, but there are others that cause panic cycles including genetic engineering, embryo selection. These are things that are going to come and we’ll be facing those very squarely soon, genetic sequencing of newborns and all kinds of things are going to be in front of us and there are people … Here’s the problem. The problem is that it is very easy to imagine how things don’t work. That’s entropy. That’s the easiest most probable things or things fail, things don’t work. So seeing the path where things break is easy. Seeing the path where things work in a new way for the first time is hard. It’s improbable, okay? It requires a lot more energy and effort.
And so we tend to take the easy path of just quickly imagining all the ways that these things break and are going to harm us. And going the other direction of imagining the ways in which there’s unintended benefits rather than harms is harder. And I think there are less people doing it. So what I’m trying to spend my time on is coming up with those possible paths where there’s a future ahead of us that I want to live in at least. And I think we benefited in today’s generation from people who thought about Star Trek, the communicator. What an inspiration that was for people making the iPhones. They could see it in their head, “There it was. We can make that come true.” And I think the fact that it was imagined made it easier to make it come true.

And I think it’s hard for us to really have a future that’s going to be really great unless we imagine it first. I think it’s hard to get there inadvertently. And what I’m looking for is we don’t want to ignore the problems. They need great attention and I’m glad there’s many people focused on their problems, but we just need a few more who are focused on the opportunities and who can articulate what one of those good futures might look like to help us make them achievable.

Debbie Millman:
Kevin, before I let you go, I want to talk about your new book. It is a delicious book. It is called Excellent Advice for Living: Wisdom I Wish I’d Known Earlier. And you’ve said that Excellent Advice for Living is an inadvertent book and that writing a book of advice was never on your bucket list. What made you decide to publish this book?

Kevin Kelly:
It was born on the internets and it came from a habit that I had of jotting down great sayings by other people. One, I just loved the form, the format of proverbs, just that condensation, the little kind of zip file that you have to unpack. And at some point, many years ago, I began writing down my own versions of things and it was just for the joy and pleasure of trying to compress something into a whole book of wisdom into a single sentence. And then at some point, I realized that as I was getting older that there were things I really had wished I’d known earlier. And so I thought, “Well, I should give these to my young adult children because we weren’t very preachy and I never really gave advice in that way and they would probably benefit from hearing this younger rather than later.”

So I wrote down 68 of them on my 68th birthday to give to my kids and I posted them, not expecting very much just because I’d written them and they went viral and bounced around to such an extent that I was encouraged to do the same thing a year later, 69 and 70. At some point, they made it to the New York Times op-ed page and so I thought, “Okay, there’s something here. I should put them all together in a way that makes it handy to hand someone rather than have to search through the internet to look for them.” And so it was originally to help me. I think of these as reminders, reminding myself of things in a way that I can repeat to myself that I thought would be handy for my kids to help them repeat and change their behavior.

And so some of them are just channeling the ancients and others are very practical things that probably won’t make sense in 10 years, but it could be practical right now.

Debbie Millman:
You stated that when you want to change your own behavior, you need to repeat little behavior modifying mantras as reminders and I do the same thing. I’d like to share some of my favorites from your book. Some are a little too hard, hit a little too hard, if you know what I mean, but that’s a good thing. So here’s some of my favorites, “When you are anxious because of your to-do list, take comfort in your have-done list.”

Kevin Kelly:
Right, right. The paper version of to-do list are good for that because you can see your have-dones.

Debbie Millman:
Yes, that’s why I like to check things off.

Kevin Kelly:
Yeah, exactly.

Debbie Millman:
This one is really good, “A great way to understand yourself is to seriously reflect on everything you find irritating in others.”

Kevin Kelly:
We are a package of contradictions and opposites.

Debbie Millman:
Right?

Kevin Kelly:
Yeah.

Debbie Millman:
A couple of these are pieces of advice that I am taking into the podcast now in terms of how I think about things. So the next two are, “A worthy goal for a year is to learn enough about a subject so that you can’t believe how ignorant you were a year earlier,” and this goes all the way back to that thinking when I was 40 that anything I didn’t know about was not important to know.

Kevin Kelly:
Well, for me, that thing has been learning about the elements.

Debbie Millman:
Oh really? The periodic table?

Kevin Kelly:
The periodic table elements. I was shocked by how ignorant I was of the elements, these basic building blocks of the universe and elements that I had no clue even existed, their names, their profiles. It’s like, “How could I miss? This is universal. This is like any galaxy, any planet, anywhere in the world. They’ll know this, but I don’t know them.” And so I’ve been reading more and more about the elements and hearing about the history of their discovery. It’s just like I’m shocked by how ignorant I was.

Debbie Millman:
Good. That’s a good thing, right?

Kevin Kelly:
Yeah.

Debbie Millman:
“Rule of three in conversation. To get to the real reason, ask a person to go deeper than what they just said, then again and then once more. The third time’s answer is the one closest to the truth.” So you’ll be seeing me apply that in the podcast. And then I have three more. This is something I’m working on too “Forgiveness is accepting the apology you’ll never get.”

Kevin Kelly:
Oh, yeah and it’s a gift to yourself.

Debbie Millman:
Yeah. That’s why I said before, “Everyone will be forgiven.” “Superheroes and saints never make art. Only in perfect beings can make art because art begins in what is broken.”

Kevin Kelly:
Yeah, yeah. If people think, “Well, I can’t make it because I’m not enlightened, I’m not there,” no, no, no, no, that’s exactly where you want to start.

Debbie Millman:
“Everyone’s time is finite and shrinking. The highest leverage you can get with your money is to buy someone else’s time. Hire and outsource when you can.” I love that.

Kevin Kelly:
That took me so long to understand. As a whole earth do-it-yourselfer, everything that was like the highest quality, but when I realized that the billionaires with all the money cannot buy more time. And so it is the most precious and scarcity that we have, and getting someone else to give you their time, oh my gosh, it’s worth anything.

Debbie Millman:
Yeah. I think so much about time now. I don’t know if you saw the article a couple of days ago, I think it was in nature.com that scientists are beginning to believe that time immediately after the Big Bang …

Kevin Kelly:
Yeah, yeah, I saw that.

Debbie Millman:
… was slower …

Kevin Kelly:
Right, right.

Debbie Millman:
… than time now. And since the universe is expanding at an accelerated rate, I’m wondering if that correlates with time feeling like It’s going faster too.

Kevin Kelly:
I asked that exact question five days ago to Brian Green.

Debbie Millman:
And?

Kevin Kelly:
So I said, “Brian, my understanding is that, from the Big Bang, the universe is expanding, space is expanding and that, compared to now, the universe was very tiny. Does that mean that time is also expanding and that, compared to now, a billion years, it went very fast?” He said, “No. So the standard theory is that space expands in time, that time is constant, the speed of light is constant, because if it wasn’t constant, the speed light wouldn’t be constant.” He says, “The standard theory right now is that, no, space expands, but time does not.” He says, “There are some other alternative theories about a flexible time, but they’re all considered not proven.” So I was very disappointed because …

Debbie Millman:
I am too …

Kevin Kelly:
… the same thing …

Debbie Millman:
… Kevin.

Kevin Kelly:
… I was thinking, “Oh, well, a billion years ago, it was only a second now.”

Debbie Millman:
That 10,000 days might just go on forever. In an interview with Tyler Cowen, he gave you a piece of advice and he said, “Tell me if this is good or bad, minimize deathbed regret.” And you felt it was good and you went on to say that the people that you respect the most in your circle are still asking themselves at 70 years old, “What am I going to do when I grow up? Who am I? What am I here for? Should I be doing this?” “That’s actually why I respect them so much because they’re still constructing their lives rather than, say, discovering it or finding it. They’re constructing it,” and I think that’s a really wonderful metaphor. And I wanted to share that with our listeners because so many people that I encounter that listen to the show are always worried about when they’re going to be able to find their purpose or make their mark or do the thing that they were meant to do. And I think that that’s a wonderful way of thinking about the long game or the long now.

Kevin Kelly:
Sure. I think that that’s a direction, not a destination, that awareness of becoming what I say the only and that it’s a lifetime duty, it’s a lifetime chore, a lifetime assignment that you’ll spend all your life to get there and it’s not somewhere you arrive. It’s like an asymptote, you keep approaching it and ideally on the day before you die, you feel like, “Okay, I fully become myself.” So-

Debbie Millman:
Yeah. People talk about making it and I say, “Why would you want to peak until the day before you die?”

Kevin Kelly:
Right.

Debbie Millman:
“You don’t want to be a has been.”

Kevin Kelly:
You don’t want to arrive up too early.

Debbie Millman:
Right. Kevin, I want to end the show today by reading a little bit more from your interview with Tyler Cowen about your new book. And this is one of the most beautiful things I’ve encountered in a while and I want to read it in its entirety. You state, “I think there is one little piece of advice at the very end which is your goal in life. Your goal in life is to be able to say, on the day before you die, that you have fully become yourself. I want to emphasize the idea of fully becoming yourself and the difficulty and the challenge to discover what that is, but how powerful it is. And that’s true whether you’re starting a company or becoming an artist or a teacher, whatever it is.

And the reason why I’m very pro on technology is that I think it enables us, helps us generally to become more of ourselves. We all have mixtures of talents that need external tools to help us express things. I am interested in increasing that pool of possible tools in the world, so that all of us have some chance to really express our genius and fully become ourselves.” And, Kevin, then you conclude by saying, “It’s going to take all your life to figure that out. Life is to figure it out. Every part of your life, every day is actually an attempt to figure this out.”

Kevin Kelly:
So thank you for helping me figure it out today.

Debbie Millman:
Thank you. Kevin Kelly, thank you so much for making so much work that matters and thank you for joining me today on Design Matters. It has been an absolute honor.

Kevin Kelly:
And a real delight. Thank you for inviting me.

Debbie Millman:
Kevin Kelly’s most recent book is titled Excellent Advice for Living: Wisdom I Wish I’d Known Earlier. You can find out more about Kevin Kelly and all of the extraordinary things he’s doing, only some of which we touched on today on his website, kk.org. This is the 18th year we’ve been podcasting Design Matters and I’d like to thank you for listening. And remember, we can talk about making a difference, we could make a difference or we can do both. I’m Debbie Millman and I look forward to talking with you again soon.

Debbie Millman (00:00:00):

Chip Kidd has been on the podcast before. Four times, actually. I went back to the archives and counted. He’s been on to talk about a novel he wrote. He’s been on to talk about the fabulous book covers he’s been designing at Knopf for decades. He’s been on with Chris Ware to talk about graphic novels.

Debbie Millman (00:00:19):

More recently, he’s been on to talk about his book, Go: A Kidd’s Guide to Graphic Design. That book is now out in paperback, and there’s so much more to talk about like his Batman exhibits, and his cameo in the last Star Wars movie, just to mention, two of his latest projects. Chip Kidd, welcome back to Design Matters.

Chip Kidd (00:00:44):

Thank you so much. I can’t believe you wanted me back again, but I-

Debbie Millman (00:00:48):

Of course.

Chip Kidd (00:00:50):

I’m so grateful, and I just want to say thank you for creating Design Matters. What an incredible, incredible achievement. It’s just-

Debbie Millman (00:01:01):

Thank you.

Chip Kidd (00:01:01):

Yeah. Thank you. And I’m proud to call you my friend.

Debbie Millman (00:01:03):

Oh, Chip, you know that I call you my brother.

Chip Kidd (00:01:07):

Well, all right. Then, that-

Debbie Millman (00:01:10):

You’re my family.

Chip Kidd (00:01:10):

I’m proud to call you my sister then.

Debbie Millman (00:01:12):

Absolutely. Absolutely. And hi there, Mrs. Kidd.

Chip Kidd (00:01:15):

Hi, mom.

Debbie Millman (00:01:16):

Chip, I want to start by asking you about something that I seem to have missed in our four previous interviews, which I’ve subsequently regretted, and wanted to ask you about now. You designed the original Jurassic Park book cover in 1990, which subsequently was used in the 1993 movie directed by Steven Spielberg.

Debbie Millman (00:01:40):

And since then, that same logo has been part of the five additional movies. The most recent being the blockbuster summer hit Jurassic World Dominion. It’s also on thousands, if not millions of merchandising and promotional items. Is it true that the original Jurassic Park book logo was really dark green?

Chip Kidd (00:02:07):

Oh, yeah. First of all, just to clarify, the original book jacket is just the typography and then the drawing of the dinosaur. And the drawing of the dinosaur, which I did both, but the drawing of the dinosaur is what they used for the logo. So, the lettering is by somebody else and all of that.

Debbie Millman (00:02:25):

Okay. Yes. We must be accurate about every bit of the credit.

Chip Kidd (00:02:28):

Yeah, I think so.

Debbie Millman (00:02:29):

Absolutely.

Chip Kidd (00:02:31):

But yes, I don’t know what I was thinking with a couple things with that cover. The drop shadow on his name, why is it there?

Debbie Millman (00:02:42):

Design regrets.

Chip Kidd (00:02:43):

Maybe somebody had said his name needs to pop more or something. But yeah, from a distance, the dinosaur looks like it’s black. But then when you get up real close to a first edition in the unforgiving light of day, you can see that it’s a dark green. And I think what I was thinking was something about primordial ooze. Yeah.

Debbie Millman (00:03:09):

What is the strangest thing you’ve seen the logo on?

Chip Kidd (00:03:13):

A human body.

Debbie Millman (00:03:15):

Really?

Chip Kidd (00:03:15):

Oh sure. Yeah.

Debbie Millman (00:03:16):

So, people have tattooed.

Chip Kidd (00:03:17):

Oh yeah, yeah, yeah.

Debbie Millman (00:03:18):

I thought you were going to say something about the toaster. I know there’s a Jurassic Park toaster.

Chip Kidd (00:03:23):

Well, which you were so sweet to give me. They made a toaster that upon putting the piece of bread in and pushing the button, when it pops up, the logo is on it. And I will admit, I have it in the box, but I haven’t opened the box.

Debbie Millman (00:03:39):

It’s probably worth more not opening it.

Chip Kidd (00:03:46):

The kind of guy I am, but yeah.

Debbie Millman (00:03:46):

All of the history of the logo and the identity is now shared in another new book that’s come out about Jurassic Park that actually has been published by Topps, the card company.

Chip Kidd (00:04:01):

It’s actually been published by Abrams.

Debbie Millman (00:04:04):

Okay.

Chip Kidd (00:04:04):

But Abrams publishes these… and they’re beautifully done, these collections of Topps collector cards. So, they’ve done Star Wars, and Wacky Packages and Mars Invades. So, then, they were going to do Jurassic Park, and the editor of this series is my dear friend, Charlie Kochman at Abrams. And he suggested, I guess, to Topps and including Universal, that I write an afterward.

Chip Kidd (00:04:32):

And so, I did, and they had to vet everything. And I basically just explain again how this happened with photographic evidence, and they published it. So, for me, it’s a very meaningful hallmark for me because it’s the first time that Universal Pictures is acknowledging that I did this because I’m never in the movie credits and-

Debbie Millman (00:05:02):

Haven’t received a penny of the proceeds.

Chip Kidd (00:05:02):

That is certainly true. So, there it is. It’s in print with the stamp of approval by Universal Pictures. I’m glad that it’s at least acknowledged that way. I did two Ted talks and the first Ted talk was basically like, this is who I am and this is what I do. And I very much wanted to make creating Jurassic Park a big part of that because I want this… I was going to say I want to own it. I want to own the fact that I did it.

Debbie Millman (00:05:38):

Absolutely, as you should. It’s one of the most recognizable logos of the 20th century. And now, it’s continuing into the 21st. It’s so interesting that they rebooted the movie. They rebooted it with all new actors, only in this third movie are Laura Dern and some of the rest of the cast back. But the logo has been there-

Chip Kidd (00:05:59):

But the logo is the same.

Debbie Millman (00:06:00):

… for all six movies. That’s incredible.

Chip Kidd (00:06:02):

It is. It’s amazing.

Debbie Millman (00:06:03):

Even the Star Wars logo has changed a bit over the years. But the Jurassic Park logo hasn’t.

Chip Kidd (00:06:08):

No.

Debbie Millman (00:06:09):

And the new book is really beautiful. One thing I found in my research that I didn’t see in any of the previous times that I’ve interviewed you is a fax that Michael Creighton actually sent to Sonny Mehta, which it has the normal heading of a fax, the to, from, the date, et cetera. And then, in giant typewritten letters, it says, “Wow, fantastic jacket.” And I thought that was pretty cool too.

Chip Kidd (00:06:38):

Yeah. Boy, those were the days, faxes.

Debbie Millman (00:06:40):

Faxes. Chip, you were born in Shillington, Berks County in Pennsylvania. And I know as a child, you were enthralled by pop culture. And I love to remind you that in the prologue to your first monograph, you stated, “I did not grow up yearning to become a book designer. What I wanted to be was Chris Partridge on The Partridge Family.”

Chip Kidd (00:07:05):

Absolutely.

Debbie Millman (00:07:06):

I still don’t understand why you were so fascinated with Chris, especially since two actors played the same character.

Chip Kidd (00:07:13):

I know. And that was fascinating too.

Debbie Millman (00:07:14):

What was it about Chris that enthralled you so?

Chip Kidd (00:07:17):

I wanted to be a drummer, and that I did sort of become. But the idea that he’s eight years old or whatever it is, and he’s the drummer of this band. I was just obsessed with that show.

Debbie Millman (00:07:32):

I was, too.

Chip Kidd (00:07:33):

And the music was so good. In that sense, it was sort of like The Monkees. It would be so easy to write it off, but the music was terrific.

Debbie Millman (00:07:42):

Yeah. I think the music actually holds up. I think Point Me in the Direction of Albuquerque is one of their great unsung hits that deserves a lot more recognition. I loved that show. There was something about the dynamic of this family without a dad, with-

Chip Kidd (00:08:02):

Which they never talk about.

Debbie Millman (00:08:04):

Never, never. With these little kids being part of a big band. I had a massive crush on Susan Dey, but I also had a bit of a crush on Danny Bonaduce as well. I love them all. Bobby Sherman, still to this day. I love Bobby Sherman.

Chip Kidd (00:08:21):

Right. Yeah.

Debbie Millman (00:08:23):

Your mom was very supportive of your interests. And I think in many ways was the catalyst to a lot of what you ended up loving. I know she made you Batman costumes every year for Halloween. And talk about how she influenced your thinking about cartoons, and comics, and characters.

Chip Kidd (00:08:48):

Well, it was my mom and my dad. Actually, when it came to the cartoon characters, it was much more dad than mom. Because he wasn’t trying to taunt my brother and I, but he would tell us that he had Superman #1. He had the Superman #1 comic and the Batman #1 comic.

Chip Kidd (00:09:07):

And he had all this stuff when he was a kid, but then it all got tossed into the paper drive for World War II. But he was a terrific cartoonist who pursued chemical engineering instead. But I remember going up into the attic in the house that I grew up in, and just poking around, and I would find his old chemistry textbooks, and he would have cartoons in the margins.

Chip Kidd (00:09:34):

And I was just fascinated by that. I think the difference between my parents and me is that I felt I could pursue an actual career doing something creative. Whereas, I think for them, they were much more pragmatic. Like I said, my dad was a chemical engineer. My mom was what used to be called a personnel manager, which we now called human resources.

Chip Kidd (00:10:02):

And they both did creative things on the side for fun. And I wanted to do a creative thing as my main job, hopefully, for fun that hopefully, to get a salary. My mom, her brilliant creative thing was she was a seamstress. When we were really little, she would make our clothes, my brother and I, brother Walt. And she would make our clothes, and there would be these little junior league fashion shows.

Chip Kidd (00:10:29):

And we’re like three and five years old, tramping down the runway in these little onesies that she made, and it’s so funny. But yeah, then when we went to elementary school for Halloween every year, my brother and I would think up what we wanted to be. And for about, I’d say five to eight years, they would figure out what we wanted to be.

Chip Kidd (00:10:54):

It was Batman and Robin right away. Then, for me, Captain America, Zorro, Captain Marvel, the DC Captain Marvel, my brother wanted to be Hawkman one year. There were these dolls, the silver knight and the gold knight. They were like GI Joes, but they were knights, and had all this armor, and he wanted to be, I think, the gold knight. So, they were very nurturing, and loving, and sweet in this regard. Yeah.

Debbie Millman (00:11:26):

You recently gave one of the costumes to Anderson Cooper, talk about why, and the worldwide sensation that that costume has become.

Chip Kidd (00:11:41):

Well, I thank you. You’re exaggerating a little bit.

Debbie Millman (00:11:46):

Not really.

Chip Kidd (00:11:47):

I had designed book jackets for Anderson’s mother, Gloria Vanderbilt for what seemed like forever, since 1991. And that came about because she was published by Knopf. And somehow, her jackets started getting assigned to me, and that’s how I got to meet her. And she was just amazing, and fascinating, and sweet, but this window into this whole other world.

Chip Kidd (00:12:19):

One of the book covers that I designed for her was called A Mother’s Story, which was her memoir of her older son with Wyatt Cooper taking his own life. I was just tremendously affected by that. And so, through the years, she would make a book, and I would do the cover. And then, Anderson was publishing his first memoir, which was just after Katrina.

Chip Kidd (00:12:45):

And he wasn’t out yet. And it was published by HarperCollins. So, for me, that was a freelance job, and that’s how I met him. And he was just amazing. I went to his office at CNN, and I’ll never forget he had a mouse pad that was the Wonder Twins from Super Friends, Zan and Jayna, shape of this and form of that. And I’m like, “Oh my God, it’s the Wonder Twins.”

Chip Kidd (00:13:13):

He’s like, “You know what the wonder twins are?” I said, “Yes, I love the Wonder Twins.” So, I did the cover of that book. And then, in the middle of the pandemic, I got an email from him. I think it was like June 2020, that he was going to be working on a history of his family, The Vanderbilts. And it was going to be the Schwartz and all thing.

Chip Kidd (00:13:45):

And he was inspired to do it because he had conceived a child through a surrogate, Wyatt. So, long story short, I did the cover. He really liked it. He sent me this text video of him with the book. I hadn’t seen it. And he wanted me to do the end papers too. And I made it coordinate with the jacket and all this stuff.

Chip Kidd (00:14:08):

And he was all excited, and I wrote to him and I said, “Could I come by your house, and meet Wyatt, and get you to sign a book for me?” And he said, “Sure.” And then, I started thinking, I have a couple of bits of these costumes that survived over the years, amazingly, that my mom made.

Chip Kidd (00:14:31):

I have the Batman cape, and I have the Robin tunic, but I had this other blue cape that was… I’m pretty sure it was used for my brother’s gold knight costume. But it looks like a Batman cape. And I thought I’m going to take this and give it to him then. And then, I had this vintage Batman, Japanese, 1966, like a Halloween mask, but it’s for a little kid. It’s small. And I thought I’m going to bring that too.

Chip Kidd (00:15:00):

And so, I did, and it was just the most lovely experience, but hilariously, I thought… and he starts filming, and there’s the nanny there. It’s like, that’s it. It’s like us three or four. I’m wanting to take pictures, but I’m thinking this is a private thing. But he starts taking pictures, and he starts taking little movies and stuff. And I said-

Debbie Millman (00:15:27):

And so, the baby is in the actual costume and he’s-

Chip Kidd (00:15:32):

Yes, he’s in the mask and the cape. There’s something about capes. And by, I guess last fall, he would’ve been 18 months. So, you’d put the cape on him, and then he’s just running around. There’s just something magical about that that I think literally empowers a child. For whatever reason, I don’t know. But he starts filming that. And then, I’d like, “Can I?” He’s like, “Sure.”

Chip Kidd (00:15:55):

So, I start filming and taking pictures. And then, he signed a book for me, and he signed a book for my mom, and we just had a lovely, I don’t know, it was like an hour, hour and a half. And I just thought that was just a lovely private thing. And I’m going to have to figure out a way to tell my mom, but I’m just going to wait because I knew, and Debbie, you know my mom.

Chip Kidd (00:16:23):

As soon as I tell her, she’s going to want to get on a bus, and come up to New York, and see little white… and I should say in the past, I was supposed to have lunch with Gloria. I believe it was the fall of 2016. And Gloria had suffered a fall, and she couldn’t do it. And so, she wrote to me, “I’m so sorry.”

Chip Kidd (00:16:46):

And Anderson wrote to me and said, “Look, I’m really sorry that she can’t do it, but is there anything that I could do?” And my mom and my aunt Syl were coming to New York. So, we were his guest at CNN for two hours. He’s just the best. He is exactly what you see on TV. He’s just a great, great guy.

Chip Kidd (00:17:10):

But anyway, so I just thought, I’m going to tell my mom, but I was just putting it off because I’m sure she was going to call the local paper and have them put it on page one. And so, the following week, my mom goes to this meeting of… she’s on one of these committees for the local symphony, for the Redding symphony, it’s the lady’s committee or whatever they call it.

Chip Kidd (00:17:34):

And one of these women said, “Well, that’s really something about Anderson giving the cape that you made for Chip to his little boy.” And my mom is like, “What are you talking about?” The previous day, he had gone on CBS Sunday Morning. I think it was Gayle King said, “What are you going to do? Are you going to take him out for Halloween?”

Chip Kidd (00:17:59):

And he said, “I’m not sure, but if we do, I have the perfect costume.” And he told the whole story. And so, that cat was out of the bag. And then, he told it again on Drew Barry Moore. And he told it again on Stephen Colbert. And I just-

Debbie Millman (00:18:15):

Your mom is now getting orders for little Batman costumes.

Chip Kidd (00:18:18):

No, I got the biggest kick out of it. But I should add, that evening after I had given him that stuff, he texted me and he’s like, “Are you sure you want to give this away? Because if you want it back, I will totally understand.” And I said, “This means so much to me that you have this and that he has it.” And I said, “Oh, and by the way,” and I sent him a couple other pictures of the stuff that I still do have.

Debbie Millman (00:18:45):

Well, it’s giving whole new life to these wonderful things that were handmade with lots and lots of love.

Chip Kidd (00:18:51):

Yeah, exactly.

Debbie Millman (00:18:53):

Talk about your love of Batman. You’ve been called a bat maniac, which I’d never heard. I’d never heard that term until I did the research for this show. What fuels it? What fuels that passion?

Chip Kidd (00:19:06):

I feel at this point, it’s such a universal thing. But I think the gateway drug was the Adam West 1966 TV show. And the fact that I have a brother who was two years older, I think I was two when the show came out. So, he would’ve been four. We were the perfect audience for it at the perfect time.

Chip Kidd (00:19:29):

And it was just so mesmerizing as a kid, and exciting, and like this crazy other world where they… I think it’s the escapist aspect of it. And part of that is that he’s a billionaire. You start to fantasize, like it would cost money to be Batman to do it properly with the car and all of that. And then, as I was growing up, there were all these other… the show came and went. That was pretty quick.

Chip Kidd (00:20:03):

But then, the comic books really picked up on the much darker origins of the strip. And DC Comics was very good about constantly reprinting the original stories. So, that was a revelation to me, that it was dark, and scary, and the Joker was really scary, and killing people in mysterious ways, and announcing it on the radio, and just fascinating. And I don’t know, I just never got over it.

Debbie Millman (00:20:36):

Which is your favorite Batman portrayal? Aside from Adam West.

Chip Kidd (00:20:40):

Right. The cop out answer is the voice actor, Kevin Conroy, on the animated series. I think he’s near perfect. I think in terms of the movie portrayals, it’s just so hard to say, because at this point, there’re so many. I was very impressed with Robert Pattinson, I would say, yeah.

Debbie Millman (00:21:03):

Yeah. My nephew too. He’s-

Chip Kidd (00:21:04):

I was impressed with him, and I thought the costume was great. Yeah. And this is a whole other geeky discussion. I think Christian Bale was the best Bruce Wayne. Again, I love the millionaire playboy carefree aspect of that. So, that’s his disguise that you would never guess that he was this other thing. And they did away with that in the most recent movie. And I wasn’t so crazy about that.

Debbie Millman (00:21:31):

You recently curated an art show at Artspace in Louisiana titled Batman: Black and White. And it features an extraordinary selection of over 150 original Batman drawings that you commissioned from artists, including Alex Ross, Frank Miller, Neil Gaiman, Ross Chest, even Gloria Vanderbilt.

Debbie Millman (00:21:53):

And the project really began back in 2012. When DC comics invited you to write a story for their Batman: Black and White anthology comics title, which was based on their hugely popular 1996 publication, how did it grow into an exhibit of this significance?

Chip Kidd (00:22:14):

It was a total accident, and I don’t know how easy this… or effectively I can explain this on a podcast. But basically, when issue number one that had my story in it came out, by then, I think it was October 13. It was New York Comic-Con, and they issued it with different covers. And one of the covers is what’s called a blank variant.

Chip Kidd (00:22:40):

So, it’s this uncoded card stock cover that is just blank white, except it has the logo of the comic on it. And the idea was, is they do it to this day, you get that version, and you go to a convention, or you go to a show, or you go to whatever where there’s artists, and wait in line, and get Neal Adams to draw on it, or get your favorite artist to draw on it.

Chip Kidd (00:23:09):

And so, as is my temperament, I became completely obsessed. I started buying these things up on eBay, just thinking of like, “Who?” And it was a really interesting exercise. And first of all, there had been people who I wanted to draw a Batman for me for a long, long time who don’t normally draw a Batman.

Debbie Millman (00:23:31):

Like who?

Chip Kidd (00:23:32):

Well, Art Spiegelman, this Dutch cartoonist, Joost Swarte. So, a lot of the raw artists, Charles Burns, Kim Deitch, Gary Panter. It was this strange opportunity to at least tug on their sleeve and say, “Would you do this?” And 165 people said yes.

Debbie Millman (00:23:54):

Isn’t that incredible?

Chip Kidd (00:23:55):

It is.

Debbie Millman (00:23:56):

What surprised you most as you were collecting these pieces of art from these extraordinary artists?

Chip Kidd (00:24:05):

What surprised me the most? Well, what surprised me is what they’ve come up with. Some people would say, “What do you want?” And then, others would have some crazy idea that they just wanted to do. One of the most recent ones that I got over the pandemic is by this amazing artist who goes by R. Kikuo Johnson. He’s just a brilliant illustrator.

Chip Kidd (00:24:29):

And he does covers for The New Yorker, and he just released a new graphic novel. He uses a very clear line, and I had been wanting to get in touch with him for years to try and publish a graphic novel by him at Pantheon. Finally, he did a cover for The New Yorker called Waiting. And it’s this sole Asian woman alone. I don’t know if you remember it, on the subway track, looking at her watch.

Chip Kidd (00:24:54):

With this furtive look on her face like, “Train, please get here now.” And it was just so timely and moving. And that’s what finally nudged me to like, “Come on, get ahold of this guy.” But he’s like, “Yeah. All right. I actually have an idea for that.” So, I’ve sent him the book with a return slip, and it’s brilliant.

Chip Kidd (00:25:20):

So, Batman is laying on his back, and he’s trapped by this giant chicken that has the Joker’s head on it that’s menacing him. And it’s brilliantly done, but it’s like, “Where the hell did that come from?” What does this mean? And he’s just like, “I’ve just always been fascinated by this idea.”

Debbie Millman (00:25:46):

Interesting. Well, that’s what makes him the brilliant genius he is.

Chip Kidd (00:25:51):

He is. He is, indeed.

Debbie Millman (00:25:52):

There was also a rather risqué cover of Batman and Robin kissing.

Chip Kidd (00:25:58):

Yes. That’s Art Spiegelman.

Debbie Millman (00:26:00):

Talk about that, if you can.

Chip Kidd (00:26:01):

That’s a reference to his, I guess, infamous New Yorker cover where he has the Hasidic man kissing the African-American woman. Plus, he did it in color. That was the interesting thing. If people wanted to do things in color, that was fine with me.

Debbie Millman (00:26:17):

You’ve written extensively about Batman, your books about the Cape Crusader include Batman Collected, Batman Animated, which garnered two of the comic book industry’s highest awards, the Eisner Awards and Batman: The Complete History. Do you anticipate a Batman: Black and White will also become a book?

Chip Kidd (00:26:37):

I would love that, but the problem is it would be a permissions nightmare. I’ve actually pursued it. It got as far as somebody at DC had drawn up a release form, I got a bunch of the artists to sign it, but there was a bunch of them that would not sign it. They’re like, “If you want to use this in a book, fine, but there’s no way…” because I can’t remember what the release language was.

Chip Kidd (00:27:01):

But it was basically, the artist can’t republish it without DC’s permission, and DC can’t republish their art without their permission. One day, I will try and self-publish it just so that it exists, but that would be a lot of work. But I’d really like to do that.

Debbie Millman (00:27:18):

Yeah. I think it should be. It should be made, or maybe a catalog from the shows.

Chip Kidd (00:27:23):

Yeah.

Debbie Millman (00:27:24):

Batman is not the only comic character you have worked with. You have also designed the trilogy, Superman: The Complete History and Wonder Woman: The Complete History for Chronicle Books, several books about the art of Alex Ross, which are magnificent, Peanuts: The Art of Charles M. Schulz, and so many more. One of your upcoming projects is a book titled Spider-Man: Panel by Panel. Tell us about that.

Chip Kidd (00:27:55):

Well, that is going to be again, that’s Abrams and my friend, Charlie Kochman, who made the connection, because it all has to be sanctioned by Marvel. Spider-Man first appeared in a comic book called Amazing Fantasy #15 in 1962. And that was an immediate hit. And then, Spider-Man #1 quickly followed. And so, what we’re doing is a photographic reexamination of both of them.

Chip Kidd (00:28:29):

So, going super close up with the camera because by now, my God, a copy of Amazing Fantasy #15 just sold for like $3 million. It’s just insane to try and find original. But Charlie hunted down or found a collector, who had this that had not sealed it in Plexiglas, who allowed us to photograph it. So, it will allow the fans to see what it was like to have this comic book in 1962 up close.

Chip Kidd (00:29:01):

It’s almost like you’re under the covers in your bedroom with a flashlight looking at it. That’s the kind of effect. And plus, some mysterious donor had the original art by Steve Ditko to the Spider-Man origin story from Amazing Fantasy #15, and donated it to the Library of Congress. They were going to allow us to photograph it, but COVID restrictions prevented that, but they’re photographing it to our specification. So, you’ll get to see the original art, which is always so fascinating.

Debbie Millman (00:29:36):

Speaking of original art, in 2019, you collaborated with JJ Abrams, different from Abrams book publisher, JJ Abrams, the man on the comic Spiderman #1, which featured a unique die cut. How did that project come about? And how did you go about making that cover?

Chip Kidd (00:29:58):

JJ is a friend. Well, he hired me through Paramount Pictures to do a print campaign for a movie that he was producing called Morning Glory. And this was quite some time ago. The movie didn’t do much business, but the experience was great, and the print campaign turned out really well. And we became friends from that.

Chip Kidd (00:30:22):

And he and his son, one of his sons, Henry, I guess pitched to Marvel, we want to do our own take on Spider-Man, and it’ll be six issues long. The first one had three or four variants, and they asked me to do one of the variants. And so, I researched what had been done before in terms of really zooming in on the Spider-Man mask, and the classic eye.

Chip Kidd (00:30:48):

And so, I decided to do that, but I wanted to see if they would allow a die cut whole so that when you open it up, there’s something else revealed underneath. I did what you’re really not supposed to do as a freelancer. I sent it to JJ first, before sending it to Marvel. And so, he fell in love with it, and Marvel didn’t want to spend the money because it’s extra money.

Chip Kidd (00:31:13):

And JJ insisted. And so, he prevailed, and it totally sold out. And so, then the Marvel art director approached me and said, “Well, actually, we’re doing a new Wolverine #1, and we’re doing a new Spider-Woman #1, can you do die cut covers for those?”

Debbie Millman (00:31:31):

One of the most unique things about you is how you’re able to make things happen through the sheer will and creativity of your spirit. And one of my favorite stories that I really want you to share with our audience, because it really is about manifesting a reality that you want to make happen is your experience with JJ Abrams, and your cameo in the last Star Wars movie. If there was ever a story about persistence, and grit, and manifesting something that you want more than anything, this is the story.

Chip Kidd (00:32:18):

Well, I have to say, it’s hard for me to talk about this. It’s really a story about a friend helping another friend grieve. So, my wonderful, beautiful husband, Sandy McClatchy had be… we’ve been together for 20 years, and he became ill, and I was a caregiver. And through that time, JJ would write periodically because he had met him, and we had spent time, and how are you doing, and how is he doing?

Chip Kidd (00:32:53):

And so, by the summer of 2018, I was alone. And I got this notion actually from Chris Ware who had visited the set of The Force Awakens. Because when he was over in England getting some sort of award, and they were filming that back then, and Chris had told me about this experience. And I just wrote to JJ out of the blue and said, “You know, actually, I’m going to be in London for a while this fall, could I come by the set, and maybe be a Storm Trooper or something?”

Debbie Millman (00:33:30):

Or something.

Chip Kidd (00:33:32):

And he wrote, he wrote back and he said, “We’ll figure something out for you. And I’m going to hand you over to my, my AD, Josh, and you can work it out with him.” And so, for two weeks, November into December of 2018, I was on the set in Pinewood, and they’ve thrown together this costume for me. But they also-

Debbie Millman (00:33:58):

So, you weren’t a Storm Trooper, you actually-

Chip Kidd (00:33:59):

No, I wasn’t. Yeah, I wasn’t a Storm Trooper.

Debbie Millman (00:34:01):

You show up on screen as not you, but you know-

Chip Kidd (00:34:03):

Right. I mean-

Debbie Millman (00:34:04):

… your face is Chip Kidds’ face.

Chip Kidd (00:34:07):

I have a beret and a leather trench coat. The thing is if you don’t know to look for me, I’m actually in it three times. But if you don’t know to look for me, blink and you’ll miss it. But I’m in what passes for the Cantina scene, where three of the leads are sneaking through trying to evade Kylo Ren, but it’s Daisy Ridley, and Oscar Isaac, and Anthony Daniels is C-3PO are sneaking through this bar. And as the band is playing, and I’m sitting at the bar chatting with this giant creature thing. And that was just wild.

Debbie Millman (00:34:46):

So, not only did you have this wonderful costume made for you, I know that they also gave you a book to hold.

Chip Kidd (00:34:53):

They gave me a prop book. They took my book, Go, and they made a Star Wars version of it. It was just so touching, the effort that they went to. And that was all JJ.

Debbie Millman (00:35:06):

I know you’ve been a Star Wars fan since you were quite young. And when you were a little boy, you made a Star Wars scrapbook. Talk about that. Why are you laughing?

Chip Kidd (00:35:19):

Yes. I made this scrapbook and it had, for some reason, David Prowse, who was the physical embodiment of Darth Vader, I guess was doing this tour. This was way before Comic-Cons existed. This would’ve been the late 1970s. And he came to our local department store, Boscov’s, and I waited in line, and got him to sign it. And this scrapbook that I had that… it was not a scrapbook, it was a notebook.

Chip Kidd (00:35:46):

It was a spiral notebook that had Darth Vader on the front. And then, I started putting stuff in it. Many years later when I was helping my parents to move, I found it in their storage unit. So, when I went over on the set, I gave it to JJ as a present.

Debbie Millman (00:36:04):

Could you imagine what little Chip Kidd would’ve thought when he was making that scrapbook that one day, you’d end up on not only on the set, but in three scenes in the movie, the final chapter of this-

Chip Kidd (00:36:21):

What can one say?

Debbie Millman (00:36:23):

… nine-film saga?

Chip Kidd (00:36:25):

Yeah.

Debbie Millman (00:36:26):

I know that it’s a hard story in that you were grieving quite terribly during that time. But I also think it’s a really beautiful story about manifesting something that you really want to help your spirit.

Chip Kidd (00:36:42):

Yeah. And something that he was willing to giving.

Debbie Millman (00:36:44):

Yeah. Shows JJs generosity, for sure. I want to talk about Go, but I also want to talk about so many of your other books. You attended Pennsylvania State University where you graduated in 1986 with a degree in graphic design, which you’ve written about in The Cheese Monkeys and in The Learners, your novels. Afterwards, you were hired as a junior assistant designer at Knopf where you still work today all these years later.

Chip Kidd (00:37:12):

Yeah.

Debbie Millman (00:37:13):

In addition to working as the associate art director now, you are also editor at large for their graphic novels division. I think it’s safe to say that you’ve designed over 2,000 book covers, book jackets.

Chip Kidd (00:37:28):

I would think at this point, yeah.

Debbie Millman (00:37:31):

Yeah. Because in our last interview, which was several years ago, it was at the 1,500-, 1,600-mark. So, I was trying to do the math. So, the covers include work for Cormac McCarthy, David Sedaris, Donna Tartt, Whoopi Goldberg, Oliver Sacks, John Updike, James Ellroy, who stated that you are the world’s greatest book jacket designer, and he’s not lying, time out.

Debbie Millman (00:37:53):

New York stated that the history of book design can be split into two eras before graphic designer, Chip Kidd, and after. So, I’d like to talk about some of your recent covers because you really are in a whole new zone now with some of the work that you’re doing, which is magnificent. First, you designed Billy Jean King’s memoir, All In, which immediately became a New York Times bestseller. What was that process like? What is it like to work with these legends, living legends?

Chip Kidd (00:38:22):

Well, I’ll tell you. The process was so different because it was by then, we were in the pandemic. And I was down in a little studio in my apartment. So, it was all virtual. I think had the world not changed, I would’ve been taking meetings with her at the office. And as it was, there was a lot of Zoom. It’s interesting when you work with somebody at that level, they have a team.

Chip Kidd (00:38:55):

And she very much wanted the team involved. And it turned out fine, but it was just a lot of time, talking to this person, and that person, and then explaining why I was doing what I was doing, but she was great. And she knew Charles Schulz, and they were friends. And so, I don’t know, somebody did their homework, and knew that I had that history.

Chip Kidd (00:39:23):

So, I think that helped. The big question was what image of her would we put on the front? And we, as a publisher, really, really wanted a vintage action shot of her on the court. And she was saying, “But that’s not who I am anymore. I’m an activist now. That was 30 years ago, 40 years ago.” And so, you have to listen, no matter who the author is.

Chip Kidd (00:39:57):

You have to listen to them if they have strong ideas about what they want. And so, we tried, I tried a couple of options where, “All right, here you are now on the front, but look at this amazing shot of you nailing this.” And so, she, I guess acquiesced is the word. And so, we put a big photo of her now on the back, and this great action shot on the front. And I think it really did what it was supposed to do.

Debbie Millman (00:40:30):

Rodrigo Corral, another great book designer puts up a lot of rejected covers on his Instagram, which is so interesting to see. Many, many, many times, I think some of the rejected covers are far better than what ended up going to market.

Debbie Millman (00:40:47):

How do you present different options to a client, whether it be Knopf, whether it be one of your freelance clients, that shows a range of work that both provides the type of work that the client might be expecting to see, but then also, takes them to a whole other place that surprises them?

Debbie Millman (00:41:13):

Because that’s really what you’re known for. You’re known for breaking paradigms, doing work that’s never been done before. How do you get clients to feel safe enough to take those risks?

Chip Kidd (00:41:25):

Because in most cases, we’ve been working together for so long. So, like Haruki Murakami just trusts me. This latest new one for Cormac McCarthy, he just trusts me. Now, sadly, after doing this for almost 36 years and counting, a lot of the authors are gone. Michael Crichton John Updike-

Debbie Millman (00:41:49):

They had it in their contracts that you were their designer for their book.

Chip Kidd (00:41:53):

Some of them did, Oliver Sacks. I think if you have a reputation that you’ve built up over a long time, people will at least look at what you’ve done, thoughtfully consider it. And then, it goes from there. The editor has a say, the publisher has a say, sales has a say, marketing. But I think with me, I have a certain reputation. So, they’ll at least take it seriously. But again, no matter what kind of reputation I have, if the author doesn’t like it, that’s just it. And you have to start over.

Debbie Millman (00:42:34):

How often does somebody like Murakami or Cormac McCarthy say, “Mm-mmm, sorry, Chip. This isn’t a winner?”

Chip Kidd (00:42:42):

It happened with Cormac McCarthy on the road. And that’s hard to explain. What it came down to was that book was so personal to him. And it was an allegory about something else in his life that he started micromanaging it in a way that he didn’t, on the other four books that I designed for him. He didn’t want his name on the front, which made our editor in chief’s head explode. And it can become very tricky.

Debbie Millman (00:43:12):

You recently worked on three book jackets for Haruki Murakami, First Person Singular, Murakami T, and Writing as a Vocation.

Chip Kidd (00:43:22):

Yeah.

Debbie Millman (00:43:23):

Were they all different types of experiences?

Chip Kidd (00:43:27):

Completely, completely.

Debbie Millman (00:43:27):

In what way?

Chip Kidd (00:43:28):

Well, and what I love about designing for him is that you start from scratch every time. Those are three completely different books. So, First Person Singular is short stories. Murakami T is this little gift book that’s about his t-shirt collection. And he’s got all these stories about them. It’s really interesting. And then, the new one that’s coming out this fall is Writing as a Vocation. It’s precisely what it’s about. It’s about his writing process.

Chip Kidd (00:43:58):

So, those are three completely different things. And you just have to consider what’s the book about, and how are you going to convey to the reader what’s Murakami doing now. The new one, Writing as a Vocation, I made the letter M into a huge labyrinth. So, writing as is going into the labyrinth, and then coming out at the bottom is a little arrow, a vocation. And so, the visual metaphor is going through all these starts, and stops, and false endings to get finally where you need to go.

Debbie Millman (00:44:36):

Do you start by sketching? Do you start on the computer? How do you work?

Chip Kidd (00:44:40):

You know what? I’ve never been a sketcher. Back in what, a sophomore in college, one of our graphic design classes, we had to keep a sketchbook. And that was work. Doing the actual assignments, that was much easier than actually having to document them in a sketchbook because it’s just not my temperament. I do all the sketching up in my head.

Chip Kidd (00:45:07):

And if there’s something that I need executed by somebody else, like a photographer, what have you, then maybe I’ll make a sketch and say, “Hey, we want a monkey raising his hand or something like that.” But-

Debbie Millman (00:45:18):

It’s so interesting when people work in their heads like that. My wife, Roxanne writes an entire essay in her head before she starts typing.

Chip Kidd (00:45:27):

Now, that is amazing because writing is a whole other thing for me. Yeah, no, no. I need to be at the keyboard, and writing, and writing in InDesign.

Debbie Millman (00:45:39):

Well, what’s interesting is that you’re not only just a designer, you’re also a writer and an editor. You’ve written several novels, and you’ve edited two important books over the last year, Original Sisters by Anita Kunz and Our Colors by Gengoroh Tagame. How do you pivot back and forth between these different vocations?

Chip Kidd (00:46:01):

I’m hugely grateful for it. Especially, in the last two years, I’ve been so grateful to have work to do, because I was just in isolation for so long down in my place in south Florida. And how do you pivot? I’m a fan of all of it. I really love it. And so, that really helps. I can’t imagine how people work on things that’s assigned to them that they don’t want to do. And that’s most people.

Chip Kidd (00:46:36):

Occasionally, I’ll have to do a book cover for something that I’m not all that interested in, but I can get interested in it. Computer coding in 1940 or whatever, that’s not something normally I would-

Debbie Millman (00:46:51):

You and Michael Bierut have that ability to find something interesting about anything.

Chip Kidd (00:46:54):

Well, anything that’s thrown at me.

Debbie Millman (00:46:58):

How do you go about finding and inquiring books? Because you do that, you look for graphic novels to publish.

Chip Kidd (00:47:05):

It’s a totally organic process. In the case of Original Sisters by Anita Kunz, I had known her for a long time. I had known her work for a long time. I think she’s absolutely brilliant. It had never occurred to me to publish any of her work because she’s not what we call a sequential artist. She’s not a graphic novelist, which is mainly what I’m looking for.

Chip Kidd (00:47:27):

And so, a couple months into the pandemic, I got this proposal from her on email. And she had originally called it The Originals. I was stunned. It’s a book of portraits of women in history, some of whom you know, but a lot of whom you don’t, and then her researching of them. And so, you have people to bounce things off of.

Chip Kidd (00:47:51):

And so, I sent it to some of my colleagues and said, “I think this is kind of great. What do you think?” And they’re like, “Yeah, we think this is really kind of great.” And so, that’s a submission. The Gengoroh Tagame, Our Colors, I pursued that, and we had published him previously and very successfully. So, that makes it much easier to do the next project.

Debbie Millman (00:48:14):

How involved are you in the editing process when you acquire a book?

Chip Kidd (00:48:18):

That’s a really good question. Sometimes not at all. Sometimes intensely, like I’m publishing this graphic novel by this guy, Wonderful Toronto, a cartoonist and illustrator named Maurice Vellekoop. And he was just in town, and we were working on that, and it’s really one of the first graphic novel, because usually, we get them fully formed. And I’ll have a couple of ideas.

Chip Kidd (00:48:45):

And we have a copy-editing department that’s going to take care of that stuff. But with this, the book by Maurice Vellekoop is called I’m So Glad We Had This Time Together, and it’s a memoir, and he had a difficult family, and they were very conservative, and he was gay, and he wanted to be an artist, and they were all upset about that. We’ve been working on this thing for 10 years.

Chip Kidd (00:49:10):

I think it’s finally going to come out in the spring of what, ’24, but that this is one I’ve really been putting input into, really, actually editing. Usually, editing a graphic novel, for me, means being an ambassador for it, into the publishing house. And you have all these duties that you have to do. You have to do an audio presentation for the salesforce so they can listen to it in their car or now, at home. That’s part of the editorial process at Pantheon and Knopf.

Debbie Millman (00:49:44):

You have a book that has been recently published. It is the paperback version of Go: A Kidd’s Guide to Graphic Design. Congratulations.

Chip Kidd (00:49:55):

Thank you.

Debbie Millman (00:49:55):

What made you decide to create a book about graphic design for kids in the first place?

Chip Kidd (00:50:00):

Well, as I’ve said in every interview about this, it was not my idea. I cannot claim ownership of the idea. It was this amazing woman named Raquel Jaramillo, who by now is much better known by her pen name, R.J. Palacio. And she had been a book cover designer of great renowned. She did everything for Thomas Pynchon. And then, she became an editor at Workman.

Chip Kidd (00:50:27):

And she called me, I don’t even remember what year it was, 2010, 2011 and said, “Do you want to have lunch? There’s a project I want to talk to you about.” And I said, “Sure.” And I just thought it would be a book cover that she wanted me to do. And so, we met and she said, “Okay. Unless I’m mistaken, no one’s ever created a book to teach graphic design to kids.”

Chip Kidd (00:50:51):

And as soon as she said it, this flash went off in my head, I’m like, “Oh my God, you’re right. I can’t think of one.” And she said, “Yes. And I think you should do it.” I probably said this in the last interview we did about this, but I thought, “Okay, I don’t know any kids. I don’t relate to kids. I don’t like kids. Sign me up.” Because I just thought nothing is going to put me outside of my comfort zone like this.

Chip Kidd (00:51:26):

But what was great about it, and at time is frustrating was okay, rethink all of this. I learned these things in college, but now, what do I say to a 10-year-old? It forced me to rethink about what graphic design is, about what the components are, how to teach somebody about it, who doesn’t have a lot of life experience.

Debbie Millman (00:51:53):

How do you go about doing that? How do you go about teaching somebody something where they don’t really have the construct in which to potentially envision it on their own?

Chip Kidd (00:52:06):

One of the things that Raquel said from the beginning was don’t talk down to them. Don’t talk down to your audience. And I had figured that out with kids, despite all of what I just said. It’s like talk to them like they’re a peer and not like they’re 10. And they’re going to take you a lot more seriously, and listen more effectively to what you have to say.

Chip Kidd (00:52:29):

And then, it’s imagination. I have to think about, “Okay, if I was 10, what would I be able to comprehend about this?” And I’m sure I’ve also said in the other podcast about it, the challenge became not so much what to put in the book, but as to what to leave out. Because when I learned about graphic design in college, we studied the history.

Chip Kidd (00:52:55):

There are all these important historical moments and contributions in the history of graphic design, which is mainly the 20th century, that I did not want to get into with a 10-year-old, war propaganda, pornography, sex sells. And in fact, I didn’t want to make any of it about selling something, really.

Debbie Millman (00:53:18):

That’s hard.

Chip Kidd (00:53:18):

Yeah. It is hard.

Debbie Millman (00:53:19):

It’s really hard.

Chip Kidd (00:53:21):

We touched on it a little bit, but not really. It’s more about form, and content, and concept, and typography. Think about the alphabet. Do you realize what a miracle the alphabet is, and how it’s used? But message sending and-

Debbie Millman (00:53:40):

It’s really, for me, a blueprint for creating visual language in a lot of ways. I learned a lot reading it. I learned about numbers and the history of numbers.

Chip Kidd (00:53:50):

I learned a lot too, because I had to look all this stuff up. Because I thought, “All right, who created the written word?” That’s pretty important. And I didn’t know. You do a lot of research, and then you figure out, all right, now I’ve got to explain this to a 10- to 12-year-old kid.

Debbie Millman (00:54:09):

Had Raquel written Wonder at that point?

Chip Kidd (00:54:12):

She was writing it at the time, which I didn’t even realize until towards the end because she… I forget the context, but we put the cover of Wonder in Go, which I think was a way of showing something metaphorically without showing it literally.

Debbie Millman (00:54:33):

Well, that’s one of the things I love about the book that there are visual examples for everything that you talk about. So, people can, not just read it, but actually see it, and learn it from examples.

Chip Kidd (00:54:45):

Yeah. And they’re all examples of real actual printed work.

Debbie Millman (00:54:48):

So, did Raquel also edit it?

Chip Kidd (00:54:51):

Yeah.

Debbie Millman (00:54:51):

Because she has that way of talking through the eyes of a child that so-

Chip Kidd (00:54:58):

And she actually had children. So, every now and then, I can’t think of it… oh, there’s a spread where I’m trying to teach the difference between sincerity and irony to a kid, and using two different words, and then depicting the words in different ways. It was something like fastidious and filthy. I think it was a different one, but she was like, “Let’s not use fastidious. That’s too complicated.” And so, we changed it.

Debbie Millman (00:55:30):

A word with many syllables.

Chip Kidd (00:55:31):

Right. And then, there are the projects for the reader to do at the end. And she was really great about coming up with some of those.

Debbie Millman (00:55:39):

Yeah. They’re really fun. You added new material to the paperback version. Talk about what is different.

Chip Kidd (00:55:44):

Well, what’s different is the timeline in the front. And I have to say, Workman approached me about doing this. And again, it was the middle of the pandemic, and I get this email from them out of the blue, and they said, “We never did a paperback version. Do you want to?” And I said, “Sure.” And they said, “We’ll treat it as a new publication, and you can fiddle with it a little bit.”

Chip Kidd (00:56:10):

We have four extra pages that we can put in it because now, we don’t have the end papers, and you can use. And so, I expanded, there’s a timeline, just a couple little highlights of the history of graphic design. Then, I was able to put two more spreads of them in.

Debbie Millman (00:56:27):

What things did you add?

Chip Kidd (00:56:29):

I added the on-off button, which I didn’t even realize is a combination of a one and a zero. And I ended with the street painting both in Washington and in New York city of Black Lives Matter in the street because that was just such a brilliant use of graphic design. At that point, there was a different editor I was working with because Raquel had left to pursue her career. And I said, “Is this too political?” They said, “Well, let me check, and we’ll get back to you.” And they said, “Let’s do it.”

Debbie Millman (00:57:05):

That’s great. It’s an opportunity to teach kids, while they’re learning about graphic design, about the power of imagery, and what this means to our society and our culture.

Chip Kidd (00:57:16):

Yeah.

Debbie Millman (00:57:17):

I have one last question for you.

Chip Kidd (00:57:20):

Okay.

Debbie Millman (00:57:21):

Thor: Love and Thunder will have just come out when this interview is published. Are you excited about seeing the film, and any predictions for the storyline?

Chip Kidd (00:57:33):

Well, I don’t know if I’m allowed to say this, but I’m excited about seeing it because I’m going to see it with you. I’m trying to think what I’ve heard. I haven’t tracked this one that much. I know that Jane becomes the new Thor or at least at some point.

Debbie Millman (00:57:51):

Yes.

Chip Kidd (00:57:51):

Which is a theme in the comics, and that Christian Bale plays some crazy freaky villain.

Debbie Millman (00:57:58):

Creepy looking villain.

Chip Kidd (00:57:59):

Yeah. Very creepy looking.

Debbie Millman (00:58:00):

Speaking of creepy, I actually wanted to ask you about your new cover that you’re designing for Bret Easton Ellis next spring. It’s coming out. It’s called The Shards, sounds rather sinister as well.

Chip Kidd (00:58:10):

Yeah. It’s a very personal book for him. It’s a prequel to Less Than Zero. I’m thrilled with the cover. I think he is too because he just post… I think he just posted it on Twitter. It’s really interesting. I would say it’s one of the first cinematic covers that I’ve done that involves sequential imagery. I’m really excited about it.

Debbie Millman (00:58:35):

I’m running to Instagram after this interview.

Chip Kidd (00:58:39):

And again, my God, I’ve worked with him and for him since, I think The Informers in 1995, ’96.

Debbie Millman (00:58:48):

I lied. I do have one last question for you before we sign off. You also have designed the upcoming Cormac McCarthy books because there’s two. And I have seen those, listeners, and they are magnificent. Talk just a little bit if you can. Give us a little tease about what you’ve done with these novels.

Chip Kidd (00:59:11):

Well, first of all, as a publishing house at Knopf, we were just so thrilled that he delivered this manuscript. He’s been working on it for a long time. He’s 88 years old. We didn’t know if we were ever actually going to get it. It’s complicated. It’s a two-book story. And one of the books is called The Passenger. And the other book is called Stella Maris.

Chip Kidd (00:59:33):

And they’re the story of a brother and a sister. It’s complicated, but there’s mathematics. There’s deep sea diving. There’s the atomic bomb. There are all these themes in it. And the brief to me was we’re going to publish them individually. Then, we’re going to publish them together in a box. It all has to look like it goes together, but both the individual jackets and the box set, when they’re together, the books have to look like they belong together.

Debbie Millman (01:00:04):

And when they’re apart, they have to look like they can stand on their own.

Chip Kidd (01:00:08):

Right. To me, they also have to look like they need each other, which is a big theme in the book.

Debbie Millman (01:00:14):

Will they be coming out at the same time or are they coming out separately?

Chip Kidd (01:00:17):

Staggered over three months. So, The Passenger comes out in October of ’22. The second, Stella Maris comes out in November of ’22. And then, the box hit comes out in December.

Debbie Millman (01:00:31):

Chip Kidd, thank you so much for making so much work that matters in the world. And thank you for joining me today on Design Matters.

Chip Kidd (01:00:38):

Well, thank you my friend, and my sister, Debbie Millman.

Debbie Millman (01:00:42):

Chip’s upcoming exhibit, Batman: Black and White, will be opening at MICA in Baltimore this fall. And his latest book, Go: A Kidd’s Guide to Graphic Design, can be found wherever books are sold. You can keep up with all things Chip Kidd and all his latest projects at chipkidd.com. I’d like to thank you for listening. And remember, we can talk about making a difference, we can make a difference, or we can do both. I’m Debbie Millman, and I look forward to talking with you again soon.

Debbie Millman (00:00:00):

Chip Kidd has been on the podcast before. Four times, actually. I went back to the archives and counted. He’s been on to talk about a novel he wrote. He’s been on to talk about the fabulous book covers he’s been designing at Knopf for decades. He’s been on with Chris Ware to talk about graphic novels.

Debbie Millman (00:00:19):

More recently, he’s been on to talk about his book, Go: A Kidd’s Guide to Graphic Design. That book is now out in paperback, and there’s so much more to talk about like his Batman exhibits, and his cameo in the last Star Wars movie, just to mention, two of his latest projects. Chip Kidd, welcome back to Design Matters.

Chip Kidd (00:00:44):

Thank you so much. I can’t believe you wanted me back again, but I-

Debbie Millman (00:00:48):

Of course.

Chip Kidd (00:00:50):

I’m so grateful, and I just want to say thank you for creating Design Matters. What an incredible, incredible achievement. It’s just-

Debbie Millman (00:01:01):

Thank you.

Chip Kidd (00:01:01):

Yeah. Thank you. And I’m proud to call you my friend.

Debbie Millman (00:01:03):

Oh, Chip, you know that I call you my brother.

Chip Kidd (00:01:07):

Well, all right. Then, that-

Debbie Millman (00:01:10):

You’re my family.

Chip Kidd (00:01:10):

I’m proud to call you my sister then.

Debbie Millman (00:01:12):

Absolutely. Absolutely. And hi there, Mrs. Kidd.

Chip Kidd (00:01:15):

Hi, mom.

Debbie Millman (00:01:16):

Chip, I want to start by asking you about something that I seem to have missed in our four previous interviews, which I’ve subsequently regretted, and wanted to ask you about now. You designed the original Jurassic Park book cover in 1990, which subsequently was used in the 1993 movie directed by Steven Spielberg.

Debbie Millman (00:01:40):

And since then, that same logo has been part of the five additional movies. The most recent being the blockbuster summer hit Jurassic World Dominion. It’s also on thousands, if not millions of merchandising and promotional items. Is it true that the original Jurassic Park book logo was really dark green?

Chip Kidd (00:02:07):

Oh, yeah. First of all, just to clarify, the original book jacket is just the typography and then the drawing of the dinosaur. And the drawing of the dinosaur, which I did both, but the drawing of the dinosaur is what they used for the logo. So, the lettering is by somebody else and all of that.

Debbie Millman (00:02:25):

Okay. Yes. We must be accurate about every bit of the credit.

Chip Kidd (00:02:28):

Yeah, I think so.

Debbie Millman (00:02:29):

Absolutely.

Chip Kidd (00:02:31):

But yes, I don’t know what I was thinking with a couple things with that cover. The drop shadow on his name, why is it there?

Debbie Millman (00:02:42):

Design regrets.

Chip Kidd (00:02:43):

Maybe somebody had said his name needs to pop more or something. But yeah, from a distance, the dinosaur looks like it’s black. But then when you get up real close to a first edition in the unforgiving light of day, you can see that it’s a dark green. And I think what I was thinking was something about primordial ooze. Yeah.

Debbie Millman (00:03:09):

What is the strangest thing you’ve seen the logo on?

Chip Kidd (00:03:13):

A human body.

Debbie Millman (00:03:15):

Really?

Chip Kidd (00:03:15):

Oh sure. Yeah.

Debbie Millman (00:03:16):

So, people have tattooed.

Chip Kidd (00:03:17):

Oh yeah, yeah, yeah.

Debbie Millman (00:03:18):

I thought you were going to say something about the toaster. I know there’s a Jurassic Park toaster.

Chip Kidd (00:03:23):

Well, which you were so sweet to give me. They made a toaster that upon putting the piece of bread in and pushing the button, when it pops up, the logo is on it. And I will admit, I have it in the box, but I haven’t opened the box.

Debbie Millman (00:03:39):

It’s probably worth more not opening it.

Chip Kidd (00:03:46):

The kind of guy I am, but yeah.

Debbie Millman (00:03:46):

All of the history of the logo and the identity is now shared in another new book that’s come out about Jurassic Park that actually has been published by Topps, the card company.

Chip Kidd (00:04:01):

It’s actually been published by Abrams.

Debbie Millman (00:04:04):

Okay.

Chip Kidd (00:04:04):

But Abrams publishes these… and they’re beautifully done, these collections of Topps collector cards. So, they’ve done Star Wars, and Wacky Packages and Mars Invades. So, then, they were going to do Jurassic Park, and the editor of this series is my dear friend, Charlie Kochman at Abrams. And he suggested, I guess, to Topps and including Universal, that I write an afterward.

Chip Kidd (00:04:32):

And so, I did, and they had to vet everything. And I basically just explain again how this happened with photographic evidence, and they published it. So, for me, it’s a very meaningful hallmark for me because it’s the first time that Universal Pictures is acknowledging that I did this because I’m never in the movie credits and-

Debbie Millman (00:05:02):

Haven’t received a penny of the proceeds.

Chip Kidd (00:05:02):

That is certainly true. So, there it is. It’s in print with the stamp of approval by Universal Pictures. I’m glad that it’s at least acknowledged that way. I did two Ted talks and the first Ted talk was basically like, this is who I am and this is what I do. And I very much wanted to make creating Jurassic Park a big part of that because I want this… I was going to say I want to own it. I want to own the fact that I did it.

Debbie Millman (00:05:38):

Absolutely, as you should. It’s one of the most recognizable logos of the 20th century. And now, it’s continuing into the 21st. It’s so interesting that they rebooted the movie. They rebooted it with all new actors, only in this third movie are Laura Dern and some of the rest of the cast back. But the logo has been there-

Chip Kidd (00:05:59):

But the logo is the same.

Debbie Millman (00:06:00):

… for all six movies. That’s incredible.

Chip Kidd (00:06:02):

It is. It’s amazing.

Debbie Millman (00:06:03):

Even the Star Wars logo has changed a bit over the years. But the Jurassic Park logo hasn’t.

Chip Kidd (00:06:08):

No.

Debbie Millman (00:06:09):

And the new book is really beautiful. One thing I found in my research that I didn’t see in any of the previous times that I’ve interviewed you is a fax that Michael Creighton actually sent to Sonny Mehta, which it has the normal heading of a fax, the to, from, the date, et cetera. And then, in giant typewritten letters, it says, “Wow, fantastic jacket.” And I thought that was pretty cool too.

Chip Kidd (00:06:38):

Yeah. Boy, those were the days, faxes.

Debbie Millman (00:06:40):

Faxes. Chip, you were born in Shillington, Berks County in Pennsylvania. And I know as a child, you were enthralled by pop culture. And I love to remind you that in the prologue to your first monograph, you stated, “I did not grow up yearning to become a book designer. What I wanted to be was Chris Partridge on The Partridge Family.”

Chip Kidd (00:07:05):

Absolutely.

Debbie Millman (00:07:06):

I still don’t understand why you were so fascinated with Chris, especially since two actors played the same character.

Chip Kidd (00:07:13):

I know. And that was fascinating too.

Debbie Millman (00:07:14):

What was it about Chris that enthralled you so?

Chip Kidd (00:07:17):

I wanted to be a drummer, and that I did sort of become. But the idea that he’s eight years old or whatever it is, and he’s the drummer of this band. I was just obsessed with that show.

Debbie Millman (00:07:32):

I was, too.

Chip Kidd (00:07:33):

And the music was so good. In that sense, it was sort of like The Monkees. It would be so easy to write it off, but the music was terrific.

Debbie Millman (00:07:42):

Yeah. I think the music actually holds up. I think Point Me in the Direction of Albuquerque is one of their great unsung hits that deserves a lot more recognition. I loved that show. There was something about the dynamic of this family without a dad, with-

Chip Kidd (00:08:02):

Which they never talk about.

Debbie Millman (00:08:04):

Never, never. With these little kids being part of a big band. I had a massive crush on Susan Dey, but I also had a bit of a crush on Danny Bonaduce as well. I love them all. Bobby Sherman, still to this day. I love Bobby Sherman.

Chip Kidd (00:08:21):

Right. Yeah.

Debbie Millman (00:08:23):

Your mom was very supportive of your interests. And I think in many ways was the catalyst to a lot of what you ended up loving. I know she made you Batman costumes every year for Halloween. And talk about how she influenced your thinking about cartoons, and comics, and characters.

Chip Kidd (00:08:48):

Well, it was my mom and my dad. Actually, when it came to the cartoon characters, it was much more dad than mom. Because he wasn’t trying to taunt my brother and I, but he would tell us that he had Superman #1. He had the Superman #1 comic and the Batman #1 comic.

Chip Kidd (00:09:07):

And he had all this stuff when he was a kid, but then it all got tossed into the paper drive for World War II. But he was a terrific cartoonist who pursued chemical engineering instead. But I remember going up into the attic in the house that I grew up in, and just poking around, and I would find his old chemistry textbooks, and he would have cartoons in the margins.

Chip Kidd (00:09:34):

And I was just fascinated by that. I think the difference between my parents and me is that I felt I could pursue an actual career doing something creative. Whereas, I think for them, they were much more pragmatic. Like I said, my dad was a chemical engineer. My mom was what used to be called a personnel manager, which we now called human resources.

Chip Kidd (00:10:02):

And they both did creative things on the side for fun. And I wanted to do a creative thing as my main job, hopefully, for fun that hopefully, to get a salary. My mom, her brilliant creative thing was she was a seamstress. When we were really little, she would make our clothes, my brother and I, brother Walt. And she would make our clothes, and there would be these little junior league fashion shows.

Chip Kidd (00:10:29):

And we’re like three and five years old, tramping down the runway in these little onesies that she made, and it’s so funny. But yeah, then when we went to elementary school for Halloween every year, my brother and I would think up what we wanted to be. And for about, I’d say five to eight years, they would figure out what we wanted to be.

Chip Kidd (00:10:54):

It was Batman and Robin right away. Then, for me, Captain America, Zorro, Captain Marvel, the DC Captain Marvel, my brother wanted to be Hawkman one year. There were these dolls, the silver knight and the gold knight. They were like GI Joes, but they were knights, and had all this armor, and he wanted to be, I think, the gold knight. So, they were very nurturing, and loving, and sweet in this regard. Yeah.

Debbie Millman (00:11:26):

You recently gave one of the costumes to Anderson Cooper, talk about why, and the worldwide sensation that that costume has become.

Chip Kidd (00:11:41):

Well, I thank you. You’re exaggerating a little bit.

Debbie Millman (00:11:46):

Not really.

Chip Kidd (00:11:47):

I had designed book jackets for Anderson’s mother, Gloria Vanderbilt for what seemed like forever, since 1991. And that came about because she was published by Knopf. And somehow, her jackets started getting assigned to me, and that’s how I got to meet her. And she was just amazing, and fascinating, and sweet, but this window into this whole other world.

Chip Kidd (00:12:19):

One of the book covers that I designed for her was called A Mother’s Story, which was her memoir of her older son with Wyatt Cooper taking his own life. I was just tremendously affected by that. And so, through the years, she would make a book, and I would do the cover. And then, Anderson was publishing his first memoir, which was just after Katrina.

Chip Kidd (00:12:45):

And he wasn’t out yet. And it was published by HarperCollins. So, for me, that was a freelance job, and that’s how I met him. And he was just amazing. I went to his office at CNN, and I’ll never forget he had a mouse pad that was the Wonder Twins from Super Friends, Zan and Jayna, shape of this and form of that. And I’m like, “Oh my God, it’s the Wonder Twins.”

Chip Kidd (00:13:13):

He’s like, “You know what the wonder twins are?” I said, “Yes, I love the Wonder Twins.” So, I did the cover of that book. And then, in the middle of the pandemic, I got an email from him. I think it was like June 2020, that he was going to be working on a history of his family, The Vanderbilts. And it was going to be the Schwartz and all thing.

Chip Kidd (00:13:45):

And he was inspired to do it because he had conceived a child through a surrogate, Wyatt. So, long story short, I did the cover. He really liked it. He sent me this text video of him with the book. I hadn’t seen it. And he wanted me to do the end papers too. And I made it coordinate with the jacket and all this stuff.

Chip Kidd (00:14:08):

And he was all excited, and I wrote to him and I said, “Could I come by your house, and meet Wyatt, and get you to sign a book for me?” And he said, “Sure.” And then, I started thinking, I have a couple of bits of these costumes that survived over the years, amazingly, that my mom made.

Chip Kidd (00:14:31):

I have the Batman cape, and I have the Robin tunic, but I had this other blue cape that was… I’m pretty sure it was used for my brother’s gold knight costume. But it looks like a Batman cape. And I thought I’m going to take this and give it to him then. And then, I had this vintage Batman, Japanese, 1966, like a Halloween mask, but it’s for a little kid. It’s small. And I thought I’m going to bring that too.

Chip Kidd (00:15:00):

And so, I did, and it was just the most lovely experience, but hilariously, I thought… and he starts filming, and there’s the nanny there. It’s like, that’s it. It’s like us three or four. I’m wanting to take pictures, but I’m thinking this is a private thing. But he starts taking pictures, and he starts taking little movies and stuff. And I said-

Debbie Millman (00:15:27):

And so, the baby is in the actual costume and he’s-

Chip Kidd (00:15:32):

Yes, he’s in the mask and the cape. There’s something about capes. And by, I guess last fall, he would’ve been 18 months. So, you’d put the cape on him, and then he’s just running around. There’s just something magical about that that I think literally empowers a child. For whatever reason, I don’t know. But he starts filming that. And then, I’d like, “Can I?” He’s like, “Sure.”

Chip Kidd (00:15:55):

So, I start filming and taking pictures. And then, he signed a book for me, and he signed a book for my mom, and we just had a lovely, I don’t know, it was like an hour, hour and a half. And I just thought that was just a lovely private thing. And I’m going to have to figure out a way to tell my mom, but I’m just going to wait because I knew, and Debbie, you know my mom.

Chip Kidd (00:16:23):

As soon as I tell her, she’s going to want to get on a bus, and come up to New York, and see little white… and I should say in the past, I was supposed to have lunch with Gloria. I believe it was the fall of 2016. And Gloria had suffered a fall, and she couldn’t do it. And so, she wrote to me, “I’m so sorry.”

Chip Kidd (00:16:46):

And Anderson wrote to me and said, “Look, I’m really sorry that she can’t do it, but is there anything that I could do?” And my mom and my aunt Syl were coming to New York. So, we were his guest at CNN for two hours. He’s just the best. He is exactly what you see on TV. He’s just a great, great guy.

Chip Kidd (00:17:10):

But anyway, so I just thought, I’m going to tell my mom, but I was just putting it off because I’m sure she was going to call the local paper and have them put it on page one. And so, the following week, my mom goes to this meeting of… she’s on one of these committees for the local symphony, for the Redding symphony, it’s the lady’s committee or whatever they call it.

Chip Kidd (00:17:34):

And one of these women said, “Well, that’s really something about Anderson giving the cape that you made for Chip to his little boy.” And my mom is like, “What are you talking about?” The previous day, he had gone on CBS Sunday Morning. I think it was Gayle King said, “What are you going to do? Are you going to take him out for Halloween?”

Chip Kidd (00:17:59):

And he said, “I’m not sure, but if we do, I have the perfect costume.” And he told the whole story. And so, that cat was out of the bag. And then, he told it again on Drew Barry Moore. And he told it again on Stephen Colbert. And I just-

Debbie Millman (00:18:15):

Your mom is now getting orders for little Batman costumes.

Chip Kidd (00:18:18):

No, I got the biggest kick out of it. But I should add, that evening after I had given him that stuff, he texted me and he’s like, “Are you sure you want to give this away? Because if you want it back, I will totally understand.” And I said, “This means so much to me that you have this and that he has it.” And I said, “Oh, and by the way,” and I sent him a couple other pictures of the stuff that I still do have.

Debbie Millman (00:18:45):

Well, it’s giving whole new life to these wonderful things that were handmade with lots and lots of love.

Chip Kidd (00:18:51):

Yeah, exactly.

Debbie Millman (00:18:53):

Talk about your love of Batman. You’ve been called a bat maniac, which I’d never heard. I’d never heard that term until I did the research for this show. What fuels it? What fuels that passion?

Chip Kidd (00:19:06):

I feel at this point, it’s such a universal thing. But I think the gateway drug was the Adam West 1966 TV show. And the fact that I have a brother who was two years older, I think I was two when the show came out. So, he would’ve been four. We were the perfect audience for it at the perfect time.

Chip Kidd (00:19:29):

And it was just so mesmerizing as a kid, and exciting, and like this crazy other world where they… I think it’s the escapist aspect of it. And part of that is that he’s a billionaire. You start to fantasize, like it would cost money to be Batman to do it properly with the car and all of that. And then, as I was growing up, there were all these other… the show came and went. That was pretty quick.

Chip Kidd (00:20:03):

But then, the comic books really picked up on the much darker origins of the strip. And DC Comics was very good about constantly reprinting the original stories. So, that was a revelation to me, that it was dark, and scary, and the Joker was really scary, and killing people in mysterious ways, and announcing it on the radio, and just fascinating. And I don’t know, I just never got over it.

Debbie Millman (00:20:36):

Which is your favorite Batman portrayal? Aside from Adam West.

Chip Kidd (00:20:40):

Right. The cop out answer is the voice actor, Kevin Conroy, on the animated series. I think he’s near perfect. I think in terms of the movie portrayals, it’s just so hard to say, because at this point, there’re so many. I was very impressed with Robert Pattinson, I would say, yeah.

Debbie Millman (00:21:03):

Yeah. My nephew too. He’s-

Chip Kidd (00:21:04):

I was impressed with him, and I thought the costume was great. Yeah. And this is a whole other geeky discussion. I think Christian Bale was the best Bruce Wayne. Again, I love the millionaire playboy carefree aspect of that. So, that’s his disguise that you would never guess that he was this other thing. And they did away with that in the most recent movie. And I wasn’t so crazy about that.

Debbie Millman (00:21:31):

You recently curated an art show at Artspace in Louisiana titled Batman: Black and White. And it features an extraordinary selection of over 150 original Batman drawings that you commissioned from artists, including Alex Ross, Frank Miller, Neil Gaiman, Ross Chest, even Gloria Vanderbilt.

Debbie Millman (00:21:53):

And the project really began back in 2012. When DC comics invited you to write a story for their Batman: Black and White anthology comics title, which was based on their hugely popular 1996 publication, how did it grow into an exhibit of this significance?

Chip Kidd (00:22:14):

It was a total accident, and I don’t know how easy this… or effectively I can explain this on a podcast. But basically, when issue number one that had my story in it came out, by then, I think it was October 13. It was New York Comic-Con, and they issued it with different covers. And one of the covers is what’s called a blank variant.

Chip Kidd (00:22:40):

So, it’s this uncoded card stock cover that is just blank white, except it has the logo of the comic on it. And the idea was, is they do it to this day, you get that version, and you go to a convention, or you go to a show, or you go to whatever where there’s artists, and wait in line, and get Neal Adams to draw on it, or get your favorite artist to draw on it.

Chip Kidd (00:23:09):

And so, as is my temperament, I became completely obsessed. I started buying these things up on eBay, just thinking of like, “Who?” And it was a really interesting exercise. And first of all, there had been people who I wanted to draw a Batman for me for a long, long time who don’t normally draw a Batman.

Debbie Millman (00:23:31):

Like who?

Chip Kidd (00:23:32):

Well, Art Spiegelman, this Dutch cartoonist, Joost Swarte. So, a lot of the raw artists, Charles Burns, Kim Deitch, Gary Panter. It was this strange opportunity to at least tug on their sleeve and say, “Would you do this?” And 165 people said yes.

Debbie Millman (00:23:54):

Isn’t that incredible?

Chip Kidd (00:23:55):

It is.

Debbie Millman (00:23:56):

What surprised you most as you were collecting these pieces of art from these extraordinary artists?

Chip Kidd (00:24:05):

What surprised me the most? Well, what surprised me is what they’ve come up with. Some people would say, “What do you want?” And then, others would have some crazy idea that they just wanted to do. One of the most recent ones that I got over the pandemic is by this amazing artist who goes by R. Kikuo Johnson. He’s just a brilliant illustrator.

Chip Kidd (00:24:29):

And he does covers for The New Yorker, and he just released a new graphic novel. He uses a very clear line, and I had been wanting to get in touch with him for years to try and publish a graphic novel by him at Pantheon. Finally, he did a cover for The New Yorker called Waiting. And it’s this sole Asian woman alone. I don’t know if you remember it, on the subway track, looking at her watch.

Chip Kidd (00:24:54):

With this furtive look on her face like, “Train, please get here now.” And it was just so timely and moving. And that’s what finally nudged me to like, “Come on, get ahold of this guy.” But he’s like, “Yeah. All right. I actually have an idea for that.” So, I’ve sent him the book with a return slip, and it’s brilliant.

Chip Kidd (00:25:20):

So, Batman is laying on his back, and he’s trapped by this giant chicken that has the Joker’s head on it that’s menacing him. And it’s brilliantly done, but it’s like, “Where the hell did that come from?” What does this mean? And he’s just like, “I’ve just always been fascinated by this idea.”

Debbie Millman (00:25:46):

Interesting. Well, that’s what makes him the brilliant genius he is.

Chip Kidd (00:25:51):

He is. He is, indeed.

Debbie Millman (00:25:52):

There was also a rather risqué cover of Batman and Robin kissing.

Chip Kidd (00:25:58):

Yes. That’s Art Spiegelman.

Debbie Millman (00:26:00):

Talk about that, if you can.

Chip Kidd (00:26:01):

That’s a reference to his, I guess, infamous New Yorker cover where he has the Hasidic man kissing the African-American woman. Plus, he did it in color. That was the interesting thing. If people wanted to do things in color, that was fine with me.

Debbie Millman (00:26:17):

You’ve written extensively about Batman, your books about the Cape Crusader include Batman Collected, Batman Animated, which garnered two of the comic book industry’s highest awards, the Eisner Awards and Batman: The Complete History. Do you anticipate a Batman: Black and White will also become a book?

Chip Kidd (00:26:37):

I would love that, but the problem is it would be a permissions nightmare. I’ve actually pursued it. It got as far as somebody at DC had drawn up a release form, I got a bunch of the artists to sign it, but there was a bunch of them that would not sign it. They’re like, “If you want to use this in a book, fine, but there’s no way…” because I can’t remember what the release language was.

Chip Kidd (00:27:01):

But it was basically, the artist can’t republish it without DC’s permission, and DC can’t republish their art without their permission. One day, I will try and self-publish it just so that it exists, but that would be a lot of work. But I’d really like to do that.

Debbie Millman (00:27:18):

Yeah. I think it should be. It should be made, or maybe a catalog from the shows.

Chip Kidd (00:27:23):

Yeah.

Debbie Millman (00:27:24):

Batman is not the only comic character you have worked with. You have also designed the trilogy, Superman: The Complete History and Wonder Woman: The Complete History for Chronicle Books, several books about the art of Alex Ross, which are magnificent, Peanuts: The Art of Charles M. Schulz, and so many more. One of your upcoming projects is a book titled Spider-Man: Panel by Panel. Tell us about that.

Chip Kidd (00:27:55):

Well, that is going to be again, that’s Abrams and my friend, Charlie Kochman, who made the connection, because it all has to be sanctioned by Marvel. Spider-Man first appeared in a comic book called Amazing Fantasy #15 in 1962. And that was an immediate hit. And then, Spider-Man #1 quickly followed. And so, what we’re doing is a photographic reexamination of both of them.

Chip Kidd (00:28:29):

So, going super close up with the camera because by now, my God, a copy of Amazing Fantasy #15 just sold for like $3 million. It’s just insane to try and find original. But Charlie hunted down or found a collector, who had this that had not sealed it in Plexiglas, who allowed us to photograph it. So, it will allow the fans to see what it was like to have this comic book in 1962 up close.

Chip Kidd (00:29:01):

It’s almost like you’re under the covers in your bedroom with a flashlight looking at it. That’s the kind of effect. And plus, some mysterious donor had the original art by Steve Ditko to the Spider-Man origin story from Amazing Fantasy #15, and donated it to the Library of Congress. They were going to allow us to photograph it, but COVID restrictions prevented that, but they’re photographing it to our specification. So, you’ll get to see the original art, which is always so fascinating.

Debbie Millman (00:29:36):

Speaking of original art, in 2019, you collaborated with JJ Abrams, different from Abrams book publisher, JJ Abrams, the man on the comic Spiderman #1, which featured a unique die cut. How did that project come about? And how did you go about making that cover?

Chip Kidd (00:29:58):

JJ is a friend. Well, he hired me through Paramount Pictures to do a print campaign for a movie that he was producing called Morning Glory. And this was quite some time ago. The movie didn’t do much business, but the experience was great, and the print campaign turned out really well. And we became friends from that.

Chip Kidd (00:30:22):

And he and his son, one of his sons, Henry, I guess pitched to Marvel, we want to do our own take on Spider-Man, and it’ll be six issues long. The first one had three or four variants, and they asked me to do one of the variants. And so, I researched what had been done before in terms of really zooming in on the Spider-Man mask, and the classic eye.

Chip Kidd (00:30:48):

And so, I decided to do that, but I wanted to see if they would allow a die cut whole so that when you open it up, there’s something else revealed underneath. I did what you’re really not supposed to do as a freelancer. I sent it to JJ first, before sending it to Marvel. And so, he fell in love with it, and Marvel didn’t want to spend the money because it’s extra money.

Chip Kidd (00:31:13):

And JJ insisted. And so, he prevailed, and it totally sold out. And so, then the Marvel art director approached me and said, “Well, actually, we’re doing a new Wolverine #1, and we’re doing a new Spider-Woman #1, can you do die cut covers for those?”

Debbie Millman (00:31:31):

One of the most unique things about you is how you’re able to make things happen through the sheer will and creativity of your spirit. And one of my favorite stories that I really want you to share with our audience, because it really is about manifesting a reality that you want to make happen is your experience with JJ Abrams, and your cameo in the last Star Wars movie. If there was ever a story about persistence, and grit, and manifesting something that you want more than anything, this is the story.

Chip Kidd (00:32:18):

Well, I have to say, it’s hard for me to talk about this. It’s really a story about a friend helping another friend grieve. So, my wonderful, beautiful husband, Sandy McClatchy had be… we’ve been together for 20 years, and he became ill, and I was a caregiver. And through that time, JJ would write periodically because he had met him, and we had spent time, and how are you doing, and how is he doing?

Chip Kidd (00:32:53):

And so, by the summer of 2018, I was alone. And I got this notion actually from Chris Ware who had visited the set of The Force Awakens. Because when he was over in England getting some sort of award, and they were filming that back then, and Chris had told me about this experience. And I just wrote to JJ out of the blue and said, “You know, actually, I’m going to be in London for a while this fall, could I come by the set, and maybe be a Storm Trooper or something?”

Debbie Millman (00:33:30):

Or something.

Chip Kidd (00:33:32):

And he wrote, he wrote back and he said, “We’ll figure something out for you. And I’m going to hand you over to my, my AD, Josh, and you can work it out with him.” And so, for two weeks, November into December of 2018, I was on the set in Pinewood, and they’ve thrown together this costume for me. But they also-

Debbie Millman (00:33:58):

So, you weren’t a Storm Trooper, you actually-

Chip Kidd (00:33:59):

No, I wasn’t. Yeah, I wasn’t a Storm Trooper.

Debbie Millman (00:34:01):

You show up on screen as not you, but you know-

Chip Kidd (00:34:03):

Right. I mean-

Debbie Millman (00:34:04):

… your face is Chip Kidds’ face.

Chip Kidd (00:34:07):

I have a beret and a leather trench coat. The thing is if you don’t know to look for me, I’m actually in it three times. But if you don’t know to look for me, blink and you’ll miss it. But I’m in what passes for the Cantina scene, where three of the leads are sneaking through trying to evade Kylo Ren, but it’s Daisy Ridley, and Oscar Isaac, and Anthony Daniels is C-3PO are sneaking through this bar. And as the band is playing, and I’m sitting at the bar chatting with this giant creature thing. And that was just wild.

Debbie Millman (00:34:46):

So, not only did you have this wonderful costume made for you, I know that they also gave you a book to hold.

Chip Kidd (00:34:53):

They gave me a prop book. They took my book, Go, and they made a Star Wars version of it. It was just so touching, the effort that they went to. And that was all JJ.

Debbie Millman (00:35:06):

I know you’ve been a Star Wars fan since you were quite young. And when you were a little boy, you made a Star Wars scrapbook. Talk about that. Why are you laughing?

Chip Kidd (00:35:19):

Yes. I made this scrapbook and it had, for some reason, David Prowse, who was the physical embodiment of Darth Vader, I guess was doing this tour. This was way before Comic-Cons existed. This would’ve been the late 1970s. And he came to our local department store, Boscov’s, and I waited in line, and got him to sign it. And this scrapbook that I had that… it was not a scrapbook, it was a notebook.

Chip Kidd (00:35:46):

It was a spiral notebook that had Darth Vader on the front. And then, I started putting stuff in it. Many years later when I was helping my parents to move, I found it in their storage unit. So, when I went over on the set, I gave it to JJ as a present.

Debbie Millman (00:36:04):

Could you imagine what little Chip Kidd would’ve thought when he was making that scrapbook that one day, you’d end up on not only on the set, but in three scenes in the movie, the final chapter of this-

Chip Kidd (00:36:21):

What can one say?

Debbie Millman (00:36:23):

… nine-film saga?

Chip Kidd (00:36:25):

Yeah.

Debbie Millman (00:36:26):

I know that it’s a hard story in that you were grieving quite terribly during that time. But I also think it’s a really beautiful story about manifesting something that you really want to help your spirit.

Chip Kidd (00:36:42):

Yeah. And something that he was willing to giving.

Debbie Millman (00:36:44):

Yeah. Shows JJs generosity, for sure. I want to talk about Go, but I also want to talk about so many of your other books. You attended Pennsylvania State University where you graduated in 1986 with a degree in graphic design, which you’ve written about in The Cheese Monkeys and in The Learners, your novels. Afterwards, you were hired as a junior assistant designer at Knopf where you still work today all these years later.

Chip Kidd (00:37:12):

Yeah.

Debbie Millman (00:37:13):

In addition to working as the associate art director now, you are also editor at large for their graphic novels division. I think it’s safe to say that you’ve designed over 2,000 book covers, book jackets.

Chip Kidd (00:37:28):

I would think at this point, yeah.

Debbie Millman (00:37:31):

Yeah. Because in our last interview, which was several years ago, it was at the 1,500-, 1,600-mark. So, I was trying to do the math. So, the covers include work for Cormac McCarthy, David Sedaris, Donna Tartt, Whoopi Goldberg, Oliver Sacks, John Updike, James Ellroy, who stated that you are the world’s greatest book jacket designer, and he’s not lying, time out.

Debbie Millman (00:37:53):

New York stated that the history of book design can be split into two eras before graphic designer, Chip Kidd, and after. So, I’d like to talk about some of your recent covers because you really are in a whole new zone now with some of the work that you’re doing, which is magnificent. First, you designed Billy Jean King’s memoir, All In, which immediately became a New York Times bestseller. What was that process like? What is it like to work with these legends, living legends?

Chip Kidd (00:38:22):

Well, I’ll tell you. The process was so different because it was by then, we were in the pandemic. And I was down in a little studio in my apartment. So, it was all virtual. I think had the world not changed, I would’ve been taking meetings with her at the office. And as it was, there was a lot of Zoom. It’s interesting when you work with somebody at that level, they have a team.

Chip Kidd (00:38:55):

And she very much wanted the team involved. And it turned out fine, but it was just a lot of time, talking to this person, and that person, and then explaining why I was doing what I was doing, but she was great. And she knew Charles Schulz, and they were friends. And so, I don’t know, somebody did their homework, and knew that I had that history.

Chip Kidd (00:39:23):

So, I think that helped. The big question was what image of her would we put on the front? And we, as a publisher, really, really wanted a vintage action shot of her on the court. And she was saying, “But that’s not who I am anymore. I’m an activist now. That was 30 years ago, 40 years ago.” And so, you have to listen, no matter who the author is.

Chip Kidd (00:39:57):

You have to listen to them if they have strong ideas about what they want. And so, we tried, I tried a couple of options where, “All right, here you are now on the front, but look at this amazing shot of you nailing this.” And so, she, I guess acquiesced is the word. And so, we put a big photo of her now on the back, and this great action shot on the front. And I think it really did what it was supposed to do.

Debbie Millman (00:40:30):

Rodrigo Corral, another great book designer puts up a lot of rejected covers on his Instagram, which is so interesting to see. Many, many, many times, I think some of the rejected covers are far better than what ended up going to market.

Debbie Millman (00:40:47):

How do you present different options to a client, whether it be Knopf, whether it be one of your freelance clients, that shows a range of work that both provides the type of work that the client might be expecting to see, but then also, takes them to a whole other place that surprises them?

Debbie Millman (00:41:13):

Because that’s really what you’re known for. You’re known for breaking paradigms, doing work that’s never been done before. How do you get clients to feel safe enough to take those risks?

Chip Kidd (00:41:25):

Because in most cases, we’ve been working together for so long. So, like Haruki Murakami just trusts me. This latest new one for Cormac McCarthy, he just trusts me. Now, sadly, after doing this for almost 36 years and counting, a lot of the authors are gone. Michael Crichton John Updike-

Debbie Millman (00:41:49):

They had it in their contracts that you were their designer for their book.

Chip Kidd (00:41:53):

Some of them did, Oliver Sacks. I think if you have a reputation that you’ve built up over a long time, people will at least look at what you’ve done, thoughtfully consider it. And then, it goes from there. The editor has a say, the publisher has a say, sales has a say, marketing. But I think with me, I have a certain reputation. So, they’ll at least take it seriously. But again, no matter what kind of reputation I have, if the author doesn’t like it, that’s just it. And you have to start over.

Debbie Millman (00:42:34):

How often does somebody like Murakami or Cormac McCarthy say, “Mm-mmm, sorry, Chip. This isn’t a winner?”

Chip Kidd (00:42:42):

It happened with Cormac McCarthy on the road. And that’s hard to explain. What it came down to was that book was so personal to him. And it was an allegory about something else in his life that he started micromanaging it in a way that he didn’t, on the other four books that I designed for him. He didn’t want his name on the front, which made our editor in chief’s head explode. And it can become very tricky.

Debbie Millman (00:43:12):

You recently worked on three book jackets for Haruki Murakami, First Person Singular, Murakami T, and Writing as a Vocation.

Chip Kidd (00:43:22):

Yeah.

Debbie Millman (00:43:23):

Were they all different types of experiences?

Chip Kidd (00:43:27):

Completely, completely.

Debbie Millman (00:43:27):

In what way?

Chip Kidd (00:43:28):

Well, and what I love about designing for him is that you start from scratch every time. Those are three completely different books. So, First Person Singular is short stories. Murakami T is this little gift book that’s about his t-shirt collection. And he’s got all these stories about them. It’s really interesting. And then, the new one that’s coming out this fall is Writing as a Vocation. It’s precisely what it’s about. It’s about his writing process.

Chip Kidd (00:43:58):

So, those are three completely different things. And you just have to consider what’s the book about, and how are you going to convey to the reader what’s Murakami doing now. The new one, Writing as a Vocation, I made the letter M into a huge labyrinth. So, writing as is going into the labyrinth, and then coming out at the bottom is a little arrow, a vocation. And so, the visual metaphor is going through all these starts, and stops, and false endings to get finally where you need to go.

Debbie Millman (00:44:36):

Do you start by sketching? Do you start on the computer? How do you work?

Chip Kidd (00:44:40):

You know what? I’ve never been a sketcher. Back in what, a sophomore in college, one of our graphic design classes, we had to keep a sketchbook. And that was work. Doing the actual assignments, that was much easier than actually having to document them in a sketchbook because it’s just not my temperament. I do all the sketching up in my head.

Chip Kidd (00:45:07):

And if there’s something that I need executed by somebody else, like a photographer, what have you, then maybe I’ll make a sketch and say, “Hey, we want a monkey raising his hand or something like that.” But-

Debbie Millman (00:45:18):

It’s so interesting when people work in their heads like that. My wife, Roxanne writes an entire essay in her head before she starts typing.

Chip Kidd (00:45:27):

Now, that is amazing because writing is a whole other thing for me. Yeah, no, no. I need to be at the keyboard, and writing, and writing in InDesign.

Debbie Millman (00:45:39):

Well, what’s interesting is that you’re not only just a designer, you’re also a writer and an editor. You’ve written several novels, and you’ve edited two important books over the last year, Original Sisters by Anita Kunz and Our Colors by Gengoroh Tagame. How do you pivot back and forth between these different vocations?

Chip Kidd (00:46:01):

I’m hugely grateful for it. Especially, in the last two years, I’ve been so grateful to have work to do, because I was just in isolation for so long down in my place in south Florida. And how do you pivot? I’m a fan of all of it. I really love it. And so, that really helps. I can’t imagine how people work on things that’s assigned to them that they don’t want to do. And that’s most people.

Chip Kidd (00:46:36):

Occasionally, I’ll have to do a book cover for something that I’m not all that interested in, but I can get interested in it. Computer coding in 1940 or whatever, that’s not something normally I would-

Debbie Millman (00:46:51):

You and Michael Bierut have that ability to find something interesting about anything.

Chip Kidd (00:46:54):

Well, anything that’s thrown at me.

Debbie Millman (00:46:58):

How do you go about finding and inquiring books? Because you do that, you look for graphic novels to publish.

Chip Kidd (00:47:05):

It’s a totally organic process. In the case of Original Sisters by Anita Kunz, I had known her for a long time. I had known her work for a long time. I think she’s absolutely brilliant. It had never occurred to me to publish any of her work because she’s not what we call a sequential artist. She’s not a graphic novelist, which is mainly what I’m looking for.

Chip Kidd (00:47:27):

And so, a couple months into the pandemic, I got this proposal from her on email. And she had originally called it The Originals. I was stunned. It’s a book of portraits of women in history, some of whom you know, but a lot of whom you don’t, and then her researching of them. And so, you have people to bounce things off of.

Chip Kidd (00:47:51):

And so, I sent it to some of my colleagues and said, “I think this is kind of great. What do you think?” And they’re like, “Yeah, we think this is really kind of great.” And so, that’s a submission. The Gengoroh Tagame, Our Colors, I pursued that, and we had published him previously and very successfully. So, that makes it much easier to do the next project.

Debbie Millman (00:48:14):

How involved are you in the editing process when you acquire a book?

Chip Kidd (00:48:18):

That’s a really good question. Sometimes not at all. Sometimes intensely, like I’m publishing this graphic novel by this guy, Wonderful Toronto, a cartoonist and illustrator named Maurice Vellekoop. And he was just in town, and we were working on that, and it’s really one of the first graphic novel, because usually, we get them fully formed. And I’ll have a couple of ideas.

Chip Kidd (00:48:45):

And we have a copy-editing department that’s going to take care of that stuff. But with this, the book by Maurice Vellekoop is called I’m So Glad We Had This Time Together, and it’s a memoir, and he had a difficult family, and they were very conservative, and he was gay, and he wanted to be an artist, and they were all upset about that. We’ve been working on this thing for 10 years.

Chip Kidd (00:49:10):

I think it’s finally going to come out in the spring of what, ’24, but that this is one I’ve really been putting input into, really, actually editing. Usually, editing a graphic novel, for me, means being an ambassador for it, into the publishing house. And you have all these duties that you have to do. You have to do an audio presentation for the salesforce so they can listen to it in their car or now, at home. That’s part of the editorial process at Pantheon and Knopf.

Debbie Millman (00:49:44):

You have a book that has been recently published. It is the paperback version of Go: A Kidd’s Guide to Graphic Design. Congratulations.

Chip Kidd (00:49:55):

Thank you.

Debbie Millman (00:49:55):

What made you decide to create a book about graphic design for kids in the first place?

Chip Kidd (00:50:00):

Well, as I’ve said in every interview about this, it was not my idea. I cannot claim ownership of the idea. It was this amazing woman named Raquel Jaramillo, who by now is much better known by her pen name, R.J. Palacio. And she had been a book cover designer of great renowned. She did everything for Thomas Pynchon. And then, she became an editor at Workman.

Chip Kidd (00:50:27):

And she called me, I don’t even remember what year it was, 2010, 2011 and said, “Do you want to have lunch? There’s a project I want to talk to you about.” And I said, “Sure.” And I just thought it would be a book cover that she wanted me to do. And so, we met and she said, “Okay. Unless I’m mistaken, no one’s ever created a book to teach graphic design to kids.”

Chip Kidd (00:50:51):

And as soon as she said it, this flash went off in my head, I’m like, “Oh my God, you’re right. I can’t think of one.” And she said, “Yes. And I think you should do it.” I probably said this in the last interview we did about this, but I thought, “Okay, I don’t know any kids. I don’t relate to kids. I don’t like kids. Sign me up.” Because I just thought nothing is going to put me outside of my comfort zone like this.

Chip Kidd (00:51:26):

But what was great about it, and at time is frustrating was okay, rethink all of this. I learned these things in college, but now, what do I say to a 10-year-old? It forced me to rethink about what graphic design is, about what the components are, how to teach somebody about it, who doesn’t have a lot of life experience.

Debbie Millman (00:51:53):

How do you go about doing that? How do you go about teaching somebody something where they don’t really have the construct in which to potentially envision it on their own?

Chip Kidd (00:52:06):

One of the things that Raquel said from the beginning was don’t talk down to them. Don’t talk down to your audience. And I had figured that out with kids, despite all of what I just said. It’s like talk to them like they’re a peer and not like they’re 10. And they’re going to take you a lot more seriously, and listen more effectively to what you have to say.

Chip Kidd (00:52:29):

And then, it’s imagination. I have to think about, “Okay, if I was 10, what would I be able to comprehend about this?” And I’m sure I’ve also said in the other podcast about it, the challenge became not so much what to put in the book, but as to what to leave out. Because when I learned about graphic design in college, we studied the history.

Chip Kidd (00:52:55):

There are all these important historical moments and contributions in the history of graphic design, which is mainly the 20th century, that I did not want to get into with a 10-year-old, war propaganda, pornography, sex sells. And in fact, I didn’t want to make any of it about selling something, really.

Debbie Millman (00:53:18):

That’s hard.

Chip Kidd (00:53:18):

Yeah. It is hard.

Debbie Millman (00:53:19):

It’s really hard.

Chip Kidd (00:53:21):

We touched on it a little bit, but not really. It’s more about form, and content, and concept, and typography. Think about the alphabet. Do you realize what a miracle the alphabet is, and how it’s used? But message sending and-

Debbie Millman (00:53:40):

It’s really, for me, a blueprint for creating visual language in a lot of ways. I learned a lot reading it. I learned about numbers and the history of numbers.

Chip Kidd (00:53:50):

I learned a lot too, because I had to look all this stuff up. Because I thought, “All right, who created the written word?” That’s pretty important. And I didn’t know. You do a lot of research, and then you figure out, all right, now I’ve got to explain this to a 10- to 12-year-old kid.

Debbie Millman (00:54:09):

Had Raquel written Wonder at that point?

Chip Kidd (00:54:12):

She was writing it at the time, which I didn’t even realize until towards the end because she… I forget the context, but we put the cover of Wonder in Go, which I think was a way of showing something metaphorically without showing it literally.

Debbie Millman (00:54:33):

Well, that’s one of the things I love about the book that there are visual examples for everything that you talk about. So, people can, not just read it, but actually see it, and learn it from examples.

Chip Kidd (00:54:45):

Yeah. And they’re all examples of real actual printed work.

Debbie Millman (00:54:48):

So, did Raquel also edit it?

Chip Kidd (00:54:51):

Yeah.

Debbie Millman (00:54:51):

Because she has that way of talking through the eyes of a child that so-

Chip Kidd (00:54:58):

And she actually had children. So, every now and then, I can’t think of it… oh, there’s a spread where I’m trying to teach the difference between sincerity and irony to a kid, and using two different words, and then depicting the words in different ways. It was something like fastidious and filthy. I think it was a different one, but she was like, “Let’s not use fastidious. That’s too complicated.” And so, we changed it.

Debbie Millman (00:55:30):

A word with many syllables.

Chip Kidd (00:55:31):

Right. And then, there are the projects for the reader to do at the end. And she was really great about coming up with some of those.

Debbie Millman (00:55:39):

Yeah. They’re really fun. You added new material to the paperback version. Talk about what is different.

Chip Kidd (00:55:44):

Well, what’s different is the timeline in the front. And I have to say, Workman approached me about doing this. And again, it was the middle of the pandemic, and I get this email from them out of the blue, and they said, “We never did a paperback version. Do you want to?” And I said, “Sure.” And they said, “We’ll treat it as a new publication, and you can fiddle with it a little bit.”

Chip Kidd (00:56:10):

We have four extra pages that we can put in it because now, we don’t have the end papers, and you can use. And so, I expanded, there’s a timeline, just a couple little highlights of the history of graphic design. Then, I was able to put two more spreads of them in.

Debbie Millman (00:56:27):

What things did you add?

Chip Kidd (00:56:29):

I added the on-off button, which I didn’t even realize is a combination of a one and a zero. And I ended with the street painting both in Washington and in New York city of Black Lives Matter in the street because that was just such a brilliant use of graphic design. At that point, there was a different editor I was working with because Raquel had left to pursue her career. And I said, “Is this too political?” They said, “Well, let me check, and we’ll get back to you.” And they said, “Let’s do it.”

Debbie Millman (00:57:05):

That’s great. It’s an opportunity to teach kids, while they’re learning about graphic design, about the power of imagery, and what this means to our society and our culture.

Chip Kidd (00:57:16):

Yeah.

Debbie Millman (00:57:17):

I have one last question for you.

Chip Kidd (00:57:20):

Okay.

Debbie Millman (00:57:21):

Thor: Love and Thunder will have just come out when this interview is published. Are you excited about seeing the film, and any predictions for the storyline?

Chip Kidd (00:57:33):

Well, I don’t know if I’m allowed to say this, but I’m excited about seeing it because I’m going to see it with you. I’m trying to think what I’ve heard. I haven’t tracked this one that much. I know that Jane becomes the new Thor or at least at some point.

Debbie Millman (00:57:51):

Yes.

Chip Kidd (00:57:51):

Which is a theme in the comics, and that Christian Bale plays some crazy freaky villain.

Debbie Millman (00:57:58):

Creepy looking villain.

Chip Kidd (00:57:59):

Yeah. Very creepy looking.

Debbie Millman (00:58:00):

Speaking of creepy, I actually wanted to ask you about your new cover that you’re designing for Bret Easton Ellis next spring. It’s coming out. It’s called The Shards, sounds rather sinister as well.

Chip Kidd (00:58:10):

Yeah. It’s a very personal book for him. It’s a prequel to Less Than Zero. I’m thrilled with the cover. I think he is too because he just post… I think he just posted it on Twitter. It’s really interesting. I would say it’s one of the first cinematic covers that I’ve done that involves sequential imagery. I’m really excited about it.

Debbie Millman (00:58:35):

I’m running to Instagram after this interview.

Chip Kidd (00:58:39):

And again, my God, I’ve worked with him and for him since, I think The Informers in 1995, ’96.

Debbie Millman (00:58:48):

I lied. I do have one last question for you before we sign off. You also have designed the upcoming Cormac McCarthy books because there’s two. And I have seen those, listeners, and they are magnificent. Talk just a little bit if you can. Give us a little tease about what you’ve done with these novels.

Chip Kidd (00:59:11):

Well, first of all, as a publishing house at Knopf, we were just so thrilled that he delivered this manuscript. He’s been working on it for a long time. He’s 88 years old. We didn’t know if we were ever actually going to get it. It’s complicated. It’s a two-book story. And one of the books is called The Passenger. And the other book is called Stella Maris.

Chip Kidd (00:59:33):

And they’re the story of a brother and a sister. It’s complicated, but there’s mathematics. There’s deep sea diving. There’s the atomic bomb. There are all these themes in it. And the brief to me was we’re going to publish them individually. Then, we’re going to publish them together in a box. It all has to look like it goes together, but both the individual jackets and the box set, when they’re together, the books have to look like they belong together.

Debbie Millman (01:00:04):

And when they’re apart, they have to look like they can stand on their own.

Chip Kidd (01:00:08):

Right. To me, they also have to look like they need each other, which is a big theme in the book.

Debbie Millman (01:00:14):

Will they be coming out at the same time or are they coming out separately?

Chip Kidd (01:00:17):

Staggered over three months. So, The Passenger comes out in October of ’22. The second, Stella Maris comes out in November of ’22. And then, the box hit comes out in December.

Debbie Millman (01:00:31):

Chip Kidd, thank you so much for making so much work that matters in the world. And thank you for joining me today on Design Matters.

Chip Kidd (01:00:38):

Well, thank you my friend, and my sister, Debbie Millman.

Debbie Millman (01:00:42):

Chip’s upcoming exhibit, Batman: Black and White, will be opening at MICA in Baltimore this fall. And his latest book, Go: A Kidd’s Guide to Graphic Design, can be found wherever books are sold. You can keep up with all things Chip Kidd and all his latest projects at chipkidd.com. I’d like to thank you for listening. And remember, we can talk about making a difference, we can make a difference, or we can do both. I’m Debbie Millman, and I look forward to talking with you again soon.

It’s easy to look at Elissa Altman’s career and think she’s wholly defined by the subject of food.

There’s her work in publishing houses, in which—following culinary school—she began as an editorial assistant and rose to the highest echelons of the industry, bringing a slew of cookbooks to market; she has penned innumerable food columns for newspapers; she launched the James Beard Award–winning blog Poor Man’s Feast; she subsequently released the bestselling book of the same name, and other titles with culinary cores.

But just like an optometrist wields a refractor, when you study a writer through different lenses, a more complete portrait begins to emerge—and one of the most striking (and defining) ways to look at Elissa Altman is through her mother.

After all, it’s how she found a fascination with food in the first place. As she has written, “My mother calls my supposed cooking ability the hidden family secret. I call it a form of self-defense—plain and simple—against a family legacy of quick-frozen peas and dried soup mix.”

Altman’s mother is no chef. And she’s the diametric opposite of her daughter in almost every other possible way: Altman’s mother has long adored feminine fashion; Altman long preferred the stylings of her father’s suits and wingtips. Her mother pursued a career in entertainment, being a former TV singer and model; Altman pursued an English degree at Boston University. Her mother sought a mini version of herself in her daughter; Altman took after her father in appearance, demeanor and interests, and longed for a loving 1970s television mom.

As for the things that define writers, they tend to use them as optical devices to visualize and interpret the world at large. Yes, Altman’s work often focuses on food—and food is often used as a means to explore relationships. The past and present. Where we’ve been and where we’re going. And her mother, long a fixture of Altman’s writing, has recently taken center stage in Motherland: A Memoir of Love, Loathing and Longing, which gives us, as readers, a window into Altman’s complex relationship with her, and perhaps insights into our own familial stories.

Moreover, Altman has never shied from tackling the less-than-appetizing sides of food in her writing, approaching the subject in all its brutal honesty, and she takes the same approach when writing about life. And that is what elevates her work to the cathartic and often universal. A recipe is not always just a recipe, and a life story is not always just a life story.

“We are all complicated, challenged beings,” she told For Women Who Roar, “and all of that complexity allows memoir to be what it is at its best: reflective of the human condition, in all its extreme messiness.”

As a complement to this episode of Design Matters, here is a look at Altman’s three most recent—and defining—books.

—Zachary Petit, Design Matters Media Editor-in-Chief

Poor Man’s Feast: A Love Story of Comfort, Desire and the Art of Cooking Simple
Say the Critics: “Delightful. … A wealth of food tales about foodies and food phobics, cooks and kitchen disasters, cooking successes and failures—all in clear, pleasing prose. … Poor Man’s Feast deserves a place on the shelf with the finest food writers.” —New York Journal of Books

Official Copy:
“Born and raised in New York to a food-phobic mother and a food-fanatical father, Elissa learned early on that fancy is always best. After a childhood spent dining at fine establishments, from Le Pavillon to La Grenouille, she devoted her life to all things gastronomical. She served rare game birds at elaborate dinner parties in an apartment so tiny that the guests couldn’t turn around and bought eight timbale molds while working at Dean & DeLuca, just to make her food tall.

“Then, Elissa met and fell in love with Susan—a frugal, small-town Connecticut Yankee with a devotion to simple living—and it changed her relationship with food, and the people who taught her about it, forever.

“Told with tender and often hilarious honesty, and filled with 26 delicious recipes, Poor Man’s Feast is a tale of finding sustenance and peace in a world of excess and inauthenticity, demonstrating how all our stories are inextricably bound up with how we feed ourselves and those we love.”

Treyf: My Life as an Unorthodox Outlaw
Say the Critics: “Gives eloquent voice to the universal human desire to belong. A poignant and life-affirming family memoir.” —Kirkus Reviews

Official Copy: “Treyf: According to Leviticus, unkosher and prohibited, like lobster, shrimp, pork, fish without scales, the mixing of meat and dairy. Also, imperfect, intolerable, offensive, undesirable, unclean, improper, broken, forbidden, illicit.
 
“Fans of Augusten Burroughs and Jo Ann Beard will enjoy this kaleidoscopic, universal memoir in which Elissa Altman explores the tradition, religion, family expectations and the forbidden that were the fixed points in her Queens, New York, childhood. Every part of Altman’s youth was laced with contradiction and hope, betrayal and the yearning for acceptance: synagogue on Saturday and Chinese pork ribs on Sunday; bat mitzvahs followed by shrimp-in-lobster-sauce luncheons; her old-country grandparents, whose kindness and love were tied to unspoken rage, and her bell-bottomed neighbors, whose adoring affection hid dark secrets.
 
“While the suburban promise of The Brady Bunch blared on television, Altman searched for peace and meaning in a world teeming with faith, violence, sex and paradox. Spanning from 1940s wartime Brooklyn to 1970s Queens to present-day rural New England, Treyf captures the collision of youthful cravings and grown-up identities. It is a vivid tale of what it means to come to yourself both in spite and in honor to your past.”

Motherland: A Memoir of Love, Loathing and Longing
Say the Critics: “Rarely has a mother-daughter relationship been excavated with s
uch honesty. Elissa Altman is a beautiful, big-hearted writer who mines her most central subject: her gorgeous, tempestuous, difficult mother, and the terrain of their shared life. The result is a testament to the power of love and family.”—Dani Shapiro, author of Inheritance

Official Copy: “After surviving a traumatic childhood in 1970s New York and young adulthood living in the shadow of her flamboyant mother, Rita, a makeup-addicted former television singer, Elissa Altman has managed to build a very different life, settling in Connecticut with her wife of nearly 20 years. After much time, therapy and wine, Elissa is at last in a healthy place, still orbiting around her mother but keeping far enough away to preserve the stable, independent world she has built as a writer and editor. Then Elissa is confronted with the unthinkable: Rita, whose days are spent as a flâneur, traversing Manhattan from the Clinique counters at Bergdorf to Bloomingdale’s and back again, suffers an incapacitating fall, leaving her completely dependent upon her daughter.

“Now Elissa is forced to finally confront their profound differences, Rita’s yearning for beauty and glamour, her view of the world through her days in the spotlight, and the money that has mysteriously disappeared in the name of preserving youth. To sustain their fragile mother-daughter bond, Elissa must navigate the turbulent waters of their shared lives, the practical challenges of caregiving for someone who refuses to accept it, the tentacles of narcissism, and the mutual, frenetic obsession that has defined their relationship.

“Motherland is a story that touches every home and every life, mapping the ferocity of maternal love, moral obligation, the choices women make about motherhood, and the possibility of healing. Filled with tenderness, wry irreverence and unforgettable characters, it is an exploration of what it means to escape from the shackles of the past only to have to face them all over again.”
 

In 2015, when I was the editor of PRINT magazine and Debbie Millman was its creative director, we raised the hackles of our corporate overlords when we decided to do an issue on text—a seemingly odd move for a magazine focused on visual culture. But the issue explored the fascinating intersection between the two, and in addition to pieces we had commissioned on the design of braille, text messaging, the history of Lorem ipsum and even a profile of the cue card writer at SNL, Debbie brought another idea to the table: an article on emojis—told on the left-hand page in text, and the opposite page in emoji—by a writer named Zoe Mendelson.

I had some editorial paranoia about how much interest and intrigue there could be to a dialogue about emojis … and I was proven delightfully wrong when this energetic, intensely talented writer filed the piece.

Mendelson hails from Chicago, and as this episode of Design Matters explores, early on a viral column she wrote for Fast Company led to her becoming “the emoji girl”—something I would feel guilty having perpetuated in the pages of PRINT had her work around the subject not been so good. Moreover, Mendelson says that today, she has made her peace with that chapter of her life—it culminated in a key project in Mexico City, where she now lives, and it amplified her voice to the world at large. Her writing has appeared in The Los Angeles Times, Wired, Slate and the Huffington Post, among other outlets.

Throughout her life, she seems to have always rejected casually accepting the status quo. She abhors nihilism. She exudes passion. And that passion is no more apparent than in the project she has been focused on bringing to life for the past couple of years: Pussypedia. It began as an argument, evolved into a Kickstarter, and today is a “free, bilingual encyclopedia of the pussy, made for you to understand. Pussypedia aims to address the lack of quality, accessible information about our bodies on the internet. Pussypedia is a community-sourced project: the product of people all over the world working together. It is a platform meant to facilitate our ability to collectively generate high quality, accessible information.”

To explore all of Pussypedia, click here. (And to support or contribute to Pussypedia, click here.)

For the emoji curious, Mendelson’s PRINT article of yesteryear is below. And finally, for more from Mendelson, keep an eye on the curious site called Absinthe. We’re brewing up something exciting.

—Zachary Petit, Design Matters Media Editor-in-Chief

“Tower of Babble”
Decoding the failed set of vector files we don’t want to admit we use every day.

The BBC recently called emoji the UK’s fastest-growing language. But is emoji a language? Language hinges on a convention of signification, a system of obeyed rules agreed upon by users. Symbols must have a fixed meaning. Emojis are so ambiguous as to render their meanings fluid and subjective.[1] Emoji is a broken set of symbols that, like an organism with a beneficial genetic mutation, has flourished in its failure.

When the original set hit iPhones, their most salient quality was their inexplicable randomness. Emojis intended to provide a collection of one-tap shortcuts for things we commonly text. But a floppy disk? A fried shrimp? How often could even the Japanese text about fried shrimp? The arbitrary nature of the set constituted such an extreme failure that the original task became irrelevant. Their genetic mutation was their arbitrariness. It propelled them from app to global phenomenon by endearing them to us and exploding their repertoire of uses.

Consider the praying hands: easily a high five or, if you please, a plausible vagina. The leaning pineapple could mean pineapple or lean. The face baring teeth and squinting eyes is either a grin or grimace. They can denote literally or connote metaphorically. They can play on homonyms (a bee could mean a bee or the verb be); metonymy (the pen for the “the written word”); or synecdoche (the Statue of Liberty can refer to New York). The problem (and the fun part) is that in a transaction of meaning the receiver must discern which.

This is their paradox: Their arbitrariness is both their greatest asset and shortcoming.

Emoji can do gold-medal representative acrobatics but at the end of the day, they fail at the point of transfer and thus perhaps at communication. But if so, what are we doing when we send each other emojis, if not communicating?

Even where emojis fail at semiotic nuance, they succeed as pragmatic communicative gestures. On the most basic level, no matter how specifically misinterpreted, their very presence serves to communicate a friendly, informal tone.

To grasp at objective clarity while “speaking” emoji, one must err on the side of extremely literal or extremely pictorial. Neither strategy is foolproof. And both require a bit of reverse engineering—a consideration of the emojis available before deciding what is possible to “say.” This counts as a feature similar to language. We often don’t have concepts for phenomena for which we lack words—for example, a German friend once asked me, “What do you call that feeling when you just got out of work and it’s a really nice day outside?”

Sure, you cannot say exactly what you want or whatever you want to say in emoji and assume another person will interpret it with reasonable ease and without losing any intended meaning. But, language, the language we rely on, isn’t entirely reliable, either.

1. Each emoji, surprisingly, does have an original, intended fixed meaning, and in a perhaps misguided, perhaps fascist effort, Unicode plans to tweak them to make their meanings more obvious and standardized.

To read the emoji version of this article, click here.
 

The stag.

When she looks back on it now, it’s a moment imbued with tremendous weight. As a kid, Jocelyn K. Glei could more often than not be found playing in the wilderness of rural Virginia with her friends. And then one day, as she was running home alone, there it was: a massive male deer, grazing in the woods. She hid behind a log among the flora and gazed upon it, frightened, yet in awe.

It feels close to a cinematic moment, and one’s mind fictively fills in the details—streaks of sun breaking the green canopy, the deer pensively munching leaves and shoots, its muscles tensing and its head snapping to attention at any errant footfall; Glei, 5 years old, holding her breath. 

She observed the creature for a series of frozen moments before it pranced off, sealing a memory that today represents freedom, innocence, wonder. And it’s a moment seemingly made more rare day by day since, given the evolving norms of parenting—and, moreover, the endless barrage of digital distraction in which we now live.

Which brings us to a second key moment in Glei’s upbringing: the day her family got their first computer. She was a teenager, and it changed her life, offering not just an outlet for her creativity but also a porthole to her future in digital media. She experimented with the art of curation via her first zine. She explored and absorbed the machine’s tools. And despite having self-diagnosed herself as having “Peter Pan” Syndrome as a kid, she grew with it.

Glei attended Boston University and studied French, screenwriting and American literature, and after graduating and spending time at a small web design firm she moved to New York City and volunteered her skills at the upstart website Flavorpill. She rose from volunteer to senior editor and New York City managing editor to global managing editor. After a stint at a music site on the West Coast, she moved back to New York and had perhaps another seminal moment in life—she met Behance co-founder Scott Belsky.

Belsky was at work on the soon-to-be bestselling book Making Ideas Happen, and he needed someone who could help him out with some editorial aspects of the title. Glei and Belsky had an immediate bond, and Belsky soon asked Glei if she’d be interested in working on a burgeoning Behance initiative dubbed 99%. The core thesis of the project was the Edison quote that genius is 1% inspiration and 99% perspiration, and with a website and conference for creatives, Glei became the driving force that would empower so many to pursue, and have a realistic shot at, their goals and dreams. (Following the dawn of the Occupy Wall Street movement, 99% evolved into 99U, the ‘U’ for “university.”)

Glei’s own creativity was seemingly fully unleashed, and she thrived, orchestrating brilliant conferences with the top minds in the design and creativity fields, stocking the site with stimulating content and extrapolating the lessons of creative gurus for the masses in a medley of ways, such as the books she edited for 99U, Manage Your Day-to-Day, Maximize Your Potential and Make Your Mark. Throughout her tenure, she worked obsessively, intensely and comprehensively (as she has noted, it wasn’t enough for her to simply curate the program for the 99U conference—she insisted on managing details like the music playlists for the breaks, too).

All the while, by studying and sharing the wisdom of the aforementioned gurus, a funny thing happened: She became one herself.

And that’s why what happened next is perhaps so important.

She had a bit of a breakdown.

As Glei has written, she had become obsessed with her own productivity and output—to the point that she’d get home every night around 8 p.m., open a beer and order some takeout, and then do it all over again. And again. Her relationships suffered. Her health suffered. At the end of the day, she was utterly and completely exhausted, “a burnt out husk of a person,” as she has described it.

To those who knew Glei for her prolific output and sage advice, it might have indeed seemed surprising. But unsurprisingly for someone who specialized in moving from idea to execution, she decided to actually do something about it. And perhaps with the zeal with which she took on her work projects, she turned her focus inward—consulting an acupuncturist, a psychotherapist, a physical therapist, a life coach, a personal trainer, a shaman, a Reiki healer.

And over time, she healed.

Her most recent project, RESET, focuses on the distillation of what she learned as she sought to stop and recalibrate her own life—and how others might do the same.

Rarely do gurus reveal vulnerability, those stress cracks that run through life. Via a carefully curated persona, the sum toll of their life and output tends to look flawless.

And more often than not, that’s a lie. (After all, a persona is a persona.)

In Glei, the creative world has a powerful ally—one who is not ashamed to reveal vulnerability, and one who shows the rest of us that it’s OK to wave a white flag, reflect and reset, and that it in fact can be a miraculous thing. That in a hyper-paced society, slowing down can be a miraculous thing. That in a perpetual “yes” career culture, saying “no” can be a miraculous thing.

As Glei told Creative Mornings, “If creativity is self-expression, then every idea is a chance to move deeper into yourself.”

Perhaps an indirect yet poignant reminder to listen and absorb the world and all the gurus around you—but to also always look within and assess what you find there. You never know what glimpses of yourself you might catch in those ethereal woods.

—Zachary Petit, Design Matters Media Editor-in-Chief
 

As a cub reporter for The San Francisco Examiner in 1957, Lewis H. Lapham’s first assignment was the stuff of nightmares for many the aspiring journalist. Some reporters take up the pen because they want to delve into the vast underbelly of politics; others want to go behind the scenes of films and sporting events; still others yearn to document anything that might yield them a prize or enduring fame.

Lapham’s stated goal? Simply put, as he has said, “I couldn't imagine anything more exciting to do than to try to put words on paper.” He wanted to learn to write. So when his editor gave him a fluff assignment to cover a flower show in Oakland, he did just that: He wrote.

A basic newspaper article tends to run around 300–600 words. Lapham went to the show—and then he returned to his desk, hit the page, and turned in 4,000 words to his editor.

There aren’t many cut from the literary cloth like Lewis H. Lapham. And in a TL;DR hummingbird era when in-depth articles that would otherwise be regarded as magazine pieces of modest length are relegated to the dreaded moniker of “longreads,” words have become “content” and art and design pieces have become “assets,” the Laphams of the world seem perhaps more critical than they ever have before.

A predilection for the written word seems to have long surged within him. At the age of 6, he made a deal with his mother: She agreed to read him Moby-Dick, but if he couldn’t keep up with the book, they would switch back to something more suited to a child of his age, such as Peter Rabbit. Outside the confines of his home, Lapham would regularly observe his grandfather, the mayor of San Francisco, living a life of public service—and doing it in a way that was uniquely his, pledging to only serve a single term so that he could call the shots as he saw fit, to the irritation of the establishment.

Lapham went off to school, intending to be an historian. But after he returned home from Yale and Oxford (where he had studied with author C.S. Lewis), his father—who had worked as a journalist before moving on to financially greener pastures as a banking and shipping executive—wasn’t thrilled about his son’s new plans. Lapham stayed true to them.

He spent the 1960s writing for Life and The Saturday Evening Post, the latter of which even sent the young journalist to India to cover The Beatles’ Transcendental Meditation studies at the ashram of Maharishi Mahesh Yogi. (As the only journalist permitted inside, he would later document the experience in detail in the book With the Beatles in 2005.)

Lapham then joined Harper’s in 1971 and took its helm in 1976—kicking off a rare, career-defining pairing of an editor brilliantly in sync with his publication. Leading a magazine that began in 1850, maintaining and growing its circulation and hiring the next generation of writers to follow in the footsteps of Herman Melville, Jack London, Roald Dahl, Horatio Alger, Mark Twain and J.D. Salinger is no small feat. But Lapham did so masterfully, winning a host of National Magazine Awards—the industry’s equivalent of the Academy Awards—for everything from feature writing to essays to fiction to criticism, including the top honor or General Excellence in 1983 and 2006, the year he retired from Harper’s.

After leaving Harper’s, the man who once fancied a future as an historian arguably came full circle when he founded the nonprofit Lapham’s Quarterly, a journal in which every issue carries a theme—such as music, luck, death, magic shows, celebrity, the future—and is comprised, brilliantly, of abridged historical texts, alongside contemporary prose on the subject. The result is comprehensive, stirring, often cathartic studies of massive topics. And again, his editorial oversight delivers, with pieces from the Quarterly finding homes in Best American Travel Writing, Best American Essays, Best Food Writing.

The magazine was a finalist for a National Magazine Award in 2011, and Lapham’s own writing won one in 1995, with his output being recognized for showcasing “an exhilarating point of view in an age of conformity.” And that is what Lapham has always been—in addition to, in some ways, seeming a bit like the last of his kind.

The last of the great working journalists who grew up a cub reporter charged with procuring daily bourbon from people in City Hall for the veteran journalists on the beat. The gadfly, a thinker hailing from a long line of thinkers to prod and challenge authority and the world around him with eloquence and elongated word counts. An editor living by his own rules, an unrepentant chainsmoker, puffing away with “a childish unwillingness to go along with authority, really.” A believer in his craft, and a keeper of the transcendent power of the past—as he told The Millions, it’s a cultural shame that writers don’t wield the power that they once did: “To be a writer was an important thing. There was the belief that writers could change the world. And the heroes were people like Camus, Yeats, even Auden, and Hemingway, Mailer. The notion that literature was going to come up with important answers. Solzhenitsyn—the novel as heroic. That’s an idea that comes out of the 19th century. That’s Victor Hugo in exile from the Second Empire in France. That’s what Flaubert was trying to do. Balzac was trying to do the same thing. Dickens. William Dean Howells in this country, Twain—the writer was a heroic kind of figure, or at least had that possibility.”

When he had to write about a flower show, he wrote 4,000 words. And today, that is an important thing.

—Zachary Petit, Design Matters Media Editor-in-Chief

Books by Lewis H. Lapham
Age of Folly: America Abandons Its Democracy
Money and Class in America
With the Beatles
Pretensions to Empire: Notes on the Criminal Folly of the Bush Administration
 

The name “Pamela Paul” sometimes awakens emotions in writers.

Fear! What if The New York Times Book Review, which she edits, eviscerates my novel?!

Bitterness! Who is she to serve as judge, jury and executioner of the literary masses today?!

Jealousy! Who don’t I have that job?!

But for all of the above, said complainants likely do not know about Bob—who we’ll get to in a moment—or Pamela Paul at large.

As Debbie Millman notes in this episode of Design Matters, in an upbringing that seems tailor-made for the career that would follow, Paul’s mother named her after the 18th-century book considered to be the first English-language novel, Samuel Richardson’s Pamela. Moreover, Paul grew up in a home built in the 17th century … that had served as her town’s first library.

To this day, she recalls the first book that was hers, and hers alone: The Pocket Book. One wonders what it was about this tiny tome that sparked an all-encompassing lifelong literary hunger, nigh obsession—“passion” being too tame a word for the place that books hold in Paul’s life.

Unfortunately for Paul, when she was growing up books did not hold the elevated position in society that they do today. Reading was not a noble, intellectual pastime; rather, it was akin to watching TV—a pulp pursuit. Which was unfortunate for the perpetual reader. As was the fact that her consumption of books outpaced her parents’ ability to spend money on them for Paul and her seven brothers.

Pinging between her mother’s home in Long Island and her father’s on the Upper West Side of Manhattan, Paul babysat. She folded sweaters in a store. Worked in a bakery. Even assembled catalogues in a South American import warehouse. All for one goal: to obtain more books. She’d pore over the opinions of the city’s literary critics, and hungered for titles receiving top marks.

And that brings us to Bob. In high school, Paul attended a summer program in rural France. Like most teens, she had failed to keep a consistent (and quality) diary, but she had brought a journal with her, nonetheless. After she finished reading Franz Kafka’s The Trial, she took it out, wrote “Book Journal” on its first page, and logged her premiere entry. And throughout her entire life, somehow, she has not stopped: After finishing a book, she logs the title, author and date in that same journal, her (now-a-bit-beat-up-and-rough-around-the-edges-but-still-kicking) Bob—her Book of Books.

Though she was seemingly on a predestined path, Paul strayed from it. At Brown, she studied history. She nearly worked at … Quaker Oats. And then, a book—of course it was a book—upended her life in a lucky, much-needed chaos. Thalia Zepatos’ A Journey of One’s Own: Uncommon Advice for the Independent Woman Traveler persuaded her to make a random move abroad, to Thailand. There, she taught at schools part-time. She explored the countries around her. She sought herself.

Later, arriving back in New York, she found work in marketing, and in 1988 she also found a husband. She followed him to London, and began doing some writing for The Economist—but just shy of their first anniversary, they divorced. Ironically, the pain of the relationship’s end would eventually lead to catharsis and, in 2002, Paul’s first personal contribution to the world of books that had defined her life: The Starter Marriage and the Future of Matrimony, a work of nonfiction exploring the trend of childless marriages that expire before five years. Alongside the unexpected coining of a pop term in “starter marriage,” Paul found herself catapulted onto the talk show circuit, being asked about her personal life and her own failed marriage—even though she only mentioned her journey in the introduction to the book. She was now learning, in real time, the strange things that a life of reading, no matter how intense or devoted, cannot prepare one for as an author contributing to that history of letters.

Meanwhile, her starter marriage complete, she happily married again at 33, and around the time her first child was born, she got an invitation: to review The Lady and the Panda for The New York Times Book Review. Later, a friend asked her if she knew anyone who would be interested in being the Children’s Book Editor for the Review. She eventually realized that, yes, she did: It was her. A couple of years after accepting the gig, her life came full circle—the girl who knew the names of all the top critics in New York growing up was offered the ultimate position: editor of the Review, in charge of all of The New York Times’ book coverage.

Along the way, more books followed: Pornified, about the cultural toll of the industry; Parenting Inc., about the parenting industrial complex of products targeting those with new offspring; By the Book, a collection of her best New York Times Book Review interviews with authors.

With her latest book, the full circle in her life widens, deepens and multiplies. Paul has spoken before about how she adores books for the simple fact that they transport us, as readers, to myriad eras, locales and legends. She has dubbed books time machines. And her Bob is in many ways a time machine of her own life, a cipher. Perhaps she never knew until it was time to explore it; perhaps she always knew. But with its titles, names and dates, Bob was a memoir. Paul just needed to add some words to connect the dots. Thus was born My Life With Bob: Flawed Heroine Keeps Book of Books, Plot Ensues, which The Economist deemed the book that she was put on Earth to write.

One gets the sense that given how deeply Paul loves books, it must be sort of akin to a spiritual endeavor for her to write them. In her work, and especially in My Life With Bob, she brings that care, that respect for the form, to the page, and truly delivers.

… Which may be to the ire, perhaps, of scribes whose books were not favorably embraced by The New York Times Book Review. Those with that aforementioned spot of fear, bitterness. Those who have not stepped back, assessed her life and career and realized that Paul is genuine. Many people take up flags for the sake of having flags to wave. Many seek to form passions simply for the sake of having passions; to have things to talk about on a stage or set; to have something to bandy about in books.

In Paul’s home, there are books everywhere. Her books. Her husband’s books. Books belonging to her kids. Paul even selected her Japanese platform bed because it can be used, well, to store more books.

Pamela Paul’s story is not one of wise branding. This love of books: It’s real. And it’s real in an era where so many things are not.

—Zachary Petit, Design Matters Media Editor-in-Chief

Books By Pamela Paul

My Life With Bob: Flawed Heroine Keeps Book of Books, Plot Ensues

Parenting, Inc.: How the Billion-Dollar Baby Business Has Changed the Way We Raise Our Children
 
The Starter Marriage and the Future of Matrimony