Isaac Fitzgerald has been a firefighter, worked on a boat, and was once given a sword by a king. He is also the New York Times bestselling author of “Dirtbag, Massachusetts,” a coming of age memoir recounting his early years in Boston, an ongoing search for forgiveness, and a more expansive definition of family and self.
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.