Isaac Fitzgerald, DIRTBAG, MASSACHUSETTS: A Confessional

Isaac Fitzgerald, DIRTBAG, MASSACHUSETTS: A Confessional

Zibby interviews New York Times and USA Today bestselling author Isaac Fitzgerald about his gritty and humorous memoir-in-essays Dirtbag, Massachusetts: A Confessional. Isaac talks about his book’s unexpected but incredible reception across the country (thanks to indie booksellers!), his arduous, months-long writing process, and his story’s most memorable moments, like his childhood in a Catholic Worker community and the boarding school that saved him from a self-destructive path. The two also talk about their challenges with body image and how writing about them has helped others as much as it has helped them.


Zibby Owens: Welcome, Isaac. Thank you so much for coming on “Moms Don’t Have Time to Read Books” to discuss Dirtbag, Massachusetts: A Confessional.

Isaac Fitzgerald: Thank you so much for having me on.

Zibby: It’s my pleasure. Your book has gotten so much press. You must be so excited. Tell me what that has been like. Then I want you to tell listeners more of what it’s about and all that, but first, the preface.

Isaac: For me, it has been a wild year. I feel extremely grateful for that. Publishing, as we know, can be a real topsy-turvy world. I’ve had different jobs in it for quite some time, in the publishing industry. I really tried to go in with low expectations. That’s kind of a philosophy in all of life. I try to set the bar low. Then if things go better than that, it’s exciting. With the launch of this book, it really came down to, I was just thrilled for it to be out in the world and to find the right readers and the readers that could connect with it. I never expected for that to be such a large number of readers or for so many people to connect with this book in such a major way. The last six months, I’ve been on the road a lot. It’s been difficult. It’s been hard. It’s something that I really love doing, is traveling, but once you’re doing it for a long, long time, it starts to get a road-ragged, as I would say. Overall, it’s just been such a phenomenal experience. While we come to the end of the year, I’m happy to take a little bit of a rest, but I’m really grateful for everything that happened.

Zibby: Do you feel like the reception of it was different in Massachusetts?

Isaac: That’s a great question. The book is kind of sneakily about California and a few other places, so I definitely got love from different parts of the country. I would say, if anything — this might get me in a little trouble — the Massachusetts reaction and New England reaction was very in line with what I was expecting, which was a healthy bit of skepticism. Luckily, I like to think I won some readers over. Coming from New England, there’s a little bit of a, let’s keep it buttoned up. We don’t talk about that kind of stuff. Luckily, I found, especially for me, I would say the largest supporting group were independent booksellers, the independent booksellers not just in Massachusetts, but through New England. I was able to go to a conference that they had last year. They just really turned up the support. That stuff matters. Like I said, it’s such a topsy-turvy game. The fact that they were putting it in the windows and that they read it and really loved it is how I think it found its audience in that area.

Zibby: That’s awesome. I’m opening an indie bookstore.

Isaac: No kidding. When? Where?

Zibby: In Santa Monica in February.

Isaac: That’s wonderful. Congratulations. I’ll have to come visit.

Zibby: You’ll have to come visit.

Isaac: Obviously, it goes without saying we all love independent bookstores, but right now especially, it feels like there’s this real turn into, not only do they function as spaces for authors to come and interact with the community, but they actually are community centers themselves. That’s so important. Then the other part of it is I think after many, many years of, “This algorithm recommends this. This is the best-of list,” or this or that, I really feel this year, what I saw a lot of was people in local communities really trusting their independent booksellers the right book in the right hands. If there’s another one in Santa Monica, a new independent bookstore, that makes me really happy. Congrats.

Zibby: Thank you. We’re actually going to do shelves that are author-curated, so it would be your five or ten favorite books or something like that.

Isaac: That’s such a great idea. I’m sure you’ve got a lot of folks, but I would love to .

Zibby: If you want to do one, we would love it. That would be great.

Isaac: That would make me so, so happy.

Zibby: We’re actually a little low on men.

Isaac: I’m ready. Sign me up. It’s right here. It’s official. I’m in.

Zibby: Great. Back to your book, your whole memoir, why did you write it? Why did you want to share it? Which pieces of this were you like, “I have to get this out. I want people to know X, Y, or Z”?

Isaac: The funny story here is that for many, many years, I said I was never going to write about my childhood. I’ve always loved books. I grew up with a huge love of reading. I really do have my parents to thank for that. I knew that writing was something — it took me a while. I’m not one of those folks that was really gifted with it. My approach to it was much more craft. Work, work, work. Practice, practice, practice. Over the years, get better and better and better. For the longest time, in my twenties especially — I would meet you at a party. We would talk. I was very open about my past. I would tell some stories. Every once in a while, somebody would say, you should really — I was always just like, oh, you know. This book, when it sold, was actually supposed to be a bit more of just pop culture commentary, a sprinkling of my own stuff. The book that I compare it to and the book that inspired it, and she’s a good friend of mine, but Roxane Gay’s Bad Feminist. Incredibly powerful essays, but very separate, come from a lot of things that she’d written in the past, which I did as well in Dirtbag. That was my setup, was that kind of approach.

Then as I sat down to write it, basically, a year went by. I was really struggling. Let’s be very clear about this. This book missed deadline many, many times. One of the problems was I would try to start writing about this idea that I had, and all of a sudden, I’d have seven paragraphs about my father or seven paragraphs about something in childhood. I kept trying to push that aside, push it aside, focus on the thing. That’s kind of when it started to dawn on me that maybe — obviously, not an original thought here, but it takes life to learn things. Maybe the things that I don’t want to talk about, the things that I’m trying to kind of turn away from, that might actually be where the interesting stories are. After, no lie, it was a year that I sat, and then basically, another six months passed, about another eighteen months. I called my editor at Bloomsbury, Nancy Miller, wonderful woman, and I said, “I think this book might be a little bit more about my childhood than I expected it to be.” Nancy said, “Yeah, I’ve been waiting about eighteen months for you to figure this out.”

Then that’s when a lot of things really clicked into place for me. The themes that came out of this book were not the themes that I was trying to get into when I started this project or when I sold the proposal. It really did have a lot more to do with community, family, faith than I expected it to at all. I wish I could sit here and tell you that I had this perfect idea and I knew exactly what I was trying to put out in the world and how to figure out how to get readers to connect with these stories, but it really was a lot of fumbling in the dark — I’m sure many people can relate to this as well — and then almost overworking it and not being willing to let it go because there was almost this fear of sharing these deeply personal stories in the world. Luckily, I have a lot of people in my life who are really caring and really patient and who gave me some really great feedback and some really great help with edits and things like that. Eventually, the book got to this place where I was willing to let it go.

Zibby: I’m glad that you didn’t say it was easy and you just cranked it out, and there it was in perfection. I think your experience is more reflective of the pain involved in writing a memoir and how hard it is to write the stuff that scares you.

Isaac: It’s something I’m so, so grateful for. If I had written this book when I was twenty-five, one, my writing would’ve been a lot worse, but two, and I would argue much more importantly, it would be this book that’s kind of like, my parents are the worst. The world is mean and hard. Having written it ten years later, I’m so grateful and thankful for the kind of introspection, the maturity, the growing up that I did in that time that allowed me to realize, okay, my parents were having a difficult time. Yes, some of their choices were not fantastic, but now that I am that same age, can I not see that not all adults have everything figured out? Sometimes we make very, very big mistakes, and that’s okay. I’m really happy, in a weird way, that it took me as long as it did to get down on the page.

Zibby: I could feel some of that perspective, too, when you were like, well, it made sense why we would leave the city. It should’ve been pretty and easy and a nicer life. They wouldn’t have known that it would be so horrific. Maybe they could get over the fact that we were moving back to my mom’s town where her mother couldn’t stand her or whatever.

Isaac: That’s absolutely right. For those that are listening who are like, “What is happening? What is this book even about?” I can do a quick —

Zibby: — There we go. Yes, I should’ve gone back to that.

Isaac: No, that’s all right. You asked it earlier, and I kind of missed it. It’s Dirtbag, Massachusetts. It’s a collection of essays, but there really is through line. I try to build an overarching story. One could almost call it episodic. You’re moving through my life, for the most part. Some scenes are jumping around in time. It starts very early on. The elevator pitch I can give is it’s how my family exploded apart and then, in a very new shape, eventually, over years and years and years, came back together. A part of that explosion, a part of the beginning of that is, we grew up in inner-city Boston involved with Catholic Worker. It’s started by Dorothy Day. It’s this socialist, Catholic, very grassroots, “give your shirt to your neighbor” type situation for the unhoused. My family was unhoused, and so I grew up in the Catholic Worker in this beautiful, vibrant — on paper, you’re like, oh, a kid’s in a living situation for the unhoused. That’s got to be really hard. Those were actually some of the best years of my life in the inner city.

Then my parents make the decision to go out to rural Massachusetts. Like you were just saying, on paper, again, that should be like, oh, you’re going to the country. You’re going to have a yard. Actually, things became much, much worse. The book goes from there and reactions I have in my twenties trying to pretend like my childhood is in the past and not affecting me at all, realizing that, actually, a lot of the trauma I experienced was making me make some very, very bad — I don’t even want to say bad, but sometimes difficult, sometimes hurtful to myself or to those around me decisions. That’s the concept of Dirtbag, Massachusetts. You should know it’s Dirtbag, comma, Massachusetts in name of this town that I lived in in my teenage years. It was called Athol, Massachusetts. I’ll give you one guess what everyone else in the state called Athol, Massachusetts. It turns out you can’t call a book that.

Zibby: Did you try?

Isaac: Yeah, I talked about it with them. A real shout-out here because I think it’s important. It’s smart. You can. Let’s be honest. Technically, of course, you can, but it makes it hard to promote in any kind of way. It makes it really hard to search for. They were like, “Hey, that’s not a great idea.” Jason Diamond, who’s a wonderful author and very good friend of mine — I’m very lucky. I was just offhandedly telling him that. He didn’t miss a beat, immediately turned to me and was like, “You should call it Dirtbag, Massachusetts.” It was him. It’s a great title. Full shout-out, it all came from Jason Diamond.

Zibby: Amazing. There was such a turning point in your life before and after you went to boarding school. It almost seemed very unlikely, given the narrative, that that’s where you would end up for high school. Can you just talk a little bit about that? What would’ve happened had you not gone? Do you ever think? Was this your sliding-doors moment?

Isaac: Listen, I think all of us as human beings have a million sliding-door moments all the time. If one thinks too much about it, you could do nothing but stare at the ceiling and wonder. That was a big one for me, for sure. You’re absolutely right. After we move out to the country, things get really tough for my parents. I also then grow a little older. Let’s be honest, I’m around the age of twelve, I myself then become very difficult reacting to the years before and the experiences around me. What was lucky is that I was at a public school, wonderful school, where the teachers, librarians, secretaries kind of saw — they could tell. They could tell that there was trouble at home, but they could also tell that if there was a situation where I was given a chance, I might be able to succeed academically. As much trouble as I was getting in at school, I always made sure that my work was getting done, that my grades were up, and so I got a full scholarship to this boarding school. Before that, I had no interest — interest isn’t even the right word — dream of going to college. I felt like a very straight path — I probably would’ve stuck around the area that I live where — I want to be very clear. There’s a really strong community there. It’s a really beautiful part of the state. It is still a very low-income part of the state, but we’re talking about a low-income part of a very rich state. I talk about class and how these poor communities and very wealthy communities really bump right up against each other in the book. That’s always going to be something that fascinates me. I always want to give a shout-out because that area is beautiful and does have such a strong community, but I think myself and what I was going through at the time, I would’ve been on a self-destructive path in that area.

What boarding school gave me was this chance to get out of my house and get away from a few of my bad habits. Let’s be very clear. No matter where you go, there you are. I still was getting into a ton of trouble, but I think the biggest gift that the boarding school gave me — of course, education and this ability to then get a scholarship for college. I was there for four years. The biggest thing it did was just expand my horizons. I had barely been out of the state at that point in my life. Here was a school where a lot of kids came from not just all over the country, but internationally as well. All of a sudden, my world opened up in all of these incredible ways. It’s funny. Don’t get me wrong. If you talked to me when I was probably fifteen, sixteen, there’s a lot I would’ve complained about. I really recognize what those teachers, secretaries, and librarians at my public school did for me in helping me achieve that. Then I understand what that school did in terms of broadening my horizons. A lot of my friends who did stick around have incredible stories themselves in, whether they stay in the community and the way they helped shape that community now or in — my best friend growing up ends up going to West Point. We’re still best friends to this day. We’ve lived very, very different lives at this point. There are these wonderful stories out of that area, but myself, I was drawn to the self-destructive path that I was on. I like to think I would’ve figured it out. I want to give myself that grace. I want to believe that I still could’ve figured things out, but I think it would’ve been a much harder journey.

Zibby: Interesting. You also wrote really openly about your body and your weight and the different fluctuations. You even included a photo of, “Oh, wow, look at what I looked like then. I can’t even believe it,” which was lovely. Thank you. I just feel like we don’t get enough of that. Of the thousand books that a woman might discuss her body, there might be one. I feel like that’s maybe the percentage. I don’t know. I made that up. Talk to me about sharing all that, what you feel about it, and what the response has been to your relationship with your own weight and body.

Isaac: That essay that you’re mentioning is probably one of the — like I said, a lot of this is new material, but some of it are pulled from these older essays that I published. Again, I reshaped them and made it so that it ran with a smoother narrative within the collection. That, I believe, is probably the oldest essay in the book. Just speaking for myself, not speaking for any other readers, but what really sticks with me is how that essay is still as relevant to me today as it was when I originally published it. It’s an essay that a lot of people connect with. It’s probably one of the essays that I get written about the most from all sorts of different folks. I think it’s one of the fundamental — sorry, my philosophy major is jumping out here a little bit. I think one of the fundamentals of the human experience is, how do we feel at peace in our own bodies? How do we feel love for our own bodies or even just not itchy in our own skin? To try and find peace. The tough thing that I mention in the essay is you will have these moments of, oh, this is it. I look good. I feel good. I love myself. Then a day, two days later, all of a sudden, you’re just like, ugh! It can all come apart.

I try to capture that in this essay. For me, when I first published that essay, I remember being a bit scared putting it out into the world, but I knew that — it’s not like I knew, but I basically had a theory from talking to so many people. At that point in my life, I was at least, probably, thirty. I was starting to figure out, wait a second, I’m not the only person. Actually, it’s not even a small — my theory is it might just be almost everyone that grapples with this. When I put it out into the world, the feedback I got really, really showed that to be true. That is why body image issues are going to be something that I’m always trying to write about. Just to speak on it, I think it’s something that men should feel — I think we’re seeing way more of it now, way more of it, but a lot of acceptance in themselves to feel okay sharing these different kinds of thoughts. The more people are talking about it, the less alone other people will feel with it. For a long time, there was this feeling of, hey, we don’t talk about that kind of stuff. Just either hit the gym or don’t, but don’t talk about it. I’m excited as I get older as a reader that I’m seeing more and more of it out there in the world.

Zibby: The first essay I ever published, I was fourteen, and I wrote about what it had felt like to gain twenty pounds the year my parents got divorced. I wrote it in Seventeen magazine. Not exactly your caliber of place to publish.

Isaac: No, , and you were fourteen. Look at that. That’s amazing. Keep going.

Zibby: Like you, I got so many letters to the magazine. I feel like that’s the only reason why I’ve kept writing for however many years. I’m forty-six. People are so desperate, I feel, to feel seen. Desperate sounds negative. Eager. People are just so eager because of all the interior conversations just to feel like, gosh, thank god someone said something that I feel and don’t say.

Isaac: Again, I think it helps you move through the world in a more loving manner because all of a sudden, you recognize you’ve got these rough voices in your head, but wait, so does everybody else. Everyone’s dealing with this. I love that. Can I ask, did you just submit it? Sorry, I promise not to turn the .

Zibby: No, it’s okay.

Isaac: Did you just submit it to them? Did you have somebody? You knew somebody there?

Zibby: I did not know anybody there. My mother is on the nosier side of things. I wrote it. I used to write all the time. I wrote it. I printed it to go grab, but my mother somehow intercepted it off the couch and read it, not in front of me, and then came into my room holding it and was like, “You have to send this to a magazine. I bet this will help other girls.” I was like, “What? Why would I do that? I didn’t even want you to read it.” She’s like, “I really think it’d help people.” Together, we sat there and opened it up and found the address and mailed it in. Then they took it. I know. It was so amazing. I couldn’t believe it. Then they had me go to the office. I had to pose with a scale. They waxed my eyebrows off. I was like, this is terrible. What am I doing here?

Isaac: They were doing that a lot back then.

Zibby: It was pretty exciting.

Isaac: I’m sure there’s all sorts of different levels to that story and to your mom and that relationship as well. What a brave thing to do at such a young age. Then also, to get that feedback, not just this thin, oh, you did a good job, but to actually have readers write letters that were meaningful and that you felt that kind of connection, so it’s no wonder you then are writing the rest of your life, having this love of that kind of connection because that’s a really real thing. That’s impressive.

Zibby: Like you, I think that it can’t be underestimated, the power of someone early on identifying something in you that they see of value, whether it’s, you’re smart enough, why don’t you try going to this school? You know what? You’re good at that. Keep writing. Keep doing this. It’s huge. So many people on the podcast are like, I had this one teacher who really believed in me. That’s all it was. It changed their lives.

Isaac: This is just something I believe in completely. The power of somebody believing in you or the power of even just positive support, even if it’s coming in the form, hey, there’s something that you might need to work on here, but said in this positive way, is something that I really, really believe in. Especially when you’re young, there’s so much pressure to figure out the world. Figure out the world. Even since we’re little babies, it’s just a little learning machine that we have. We’re just trying to wrap our head around the world. Then again, the world gets bigger and bigger. You learn that all problems are much more complex. You’re always constantly trying to figure that out. Especially when you’re young, there’s this want to be like, okay, I’ve got it. I’ve got my handle on it. This is the way the world is. Okay. That can feel comforting in certain ways, but in other ways, it means you’re almost against changing. That’s the beauty of when somebody comes into your life and says, hey, just for the record, this is all going to be changing all the time, but you’re going to do a good job with X, Y, and Z. It’s okay to grow and change in these ways. That kind of support can really change the trajectory of somebody’s life.

Zibby: Totally. I totally agree. By the way, I loved your children’s book, which I read with my kids. How did you end up doing that? That came first. How did that happen?

Isaac: This is great. This is a great, great story. I could tell it for an hour. I’m going to give you the quick version.

Zibby: You have three minutes.

Isaac: I promise. The book’s called How to Be a Pirate. It’s illustrated by Brigette Barrager, who’s this incredible illustrator out there on the West Coast. She also did Uni the Unicorn. Every time I’m doing a reading in a school and I , the kids go, oh! It’s such an incredible book. She’s such a great illustrator. The way that book comes to be, much like we’re talking about here, a lot of my process is an idea just kicking around in my head forever and ever and ever. A lot of these essays, even when I was saying I don’t want to write it, these thoughts and these memories were still kicking around in my head. How to Be a Pirate came from this place of, I wanted to make a tattoo book for kids. That was it. That was the idea. It hadn’t really baked much more than that, but it had been kicking around for me in my head for years. I had a friend who had a kid. Their kid called me the stamped man. My brother was starting to have kids. They were like, what are these? I just wanted to figure that out. Much to the themes that we’re talking about, community, a little bit of luck, but a lot of positive support — I moved to New York City from San Francisco. Rough move. Kind of had forgotten about winter. Big mistake. Everything was hard in that moment. Then get through the winter.

Next summer, I’m out in my backyard. This is true. I’m not talking down the block. I’m talking about two backyards. There was a guy in his backyard drinking rosé. Then I’m in the next lot in my backyard drinking rosé. We get to talking. We talk and talk and talk. Eventually, he’s like, “Hey, why don’t you just come around the block? Come to the house.” I walk in the house. There’s kids’ books everywhere. Here’s the thing. The guy’s name was Jon Scieszka. It’s Jon Scieszka. He wrote The Stinky Cheese Man: And Other Fairly Stupid Tales, The True Story of the Big Bad — these nineties books that shaped my — thing is, if you look at his name, the way it’s — I just didn’t know how it was ever pronounced as a kid. There’s a lot of S’s, Z’s, and C’s. All of a sudden, I was like, holy crap. We become friends. I’ve got this idea for a kids’ book. The one thing I don’t want to do is step on his toe. Jon Scieszka, everybody that meets him probably is like, I have a kids’ book idea. I waited thirty times. Then I said kind of what I just said to you.

Then he just looks me dead in the eyes. He says, “Isaac?” I go, “Yeah.” He goes, “That’s a stupid idea for a kids’ book.” I’m crushed. I’m like, oh, no, I overstepped my boundaries. Then he say, “But if you come over here every other Friday for the rest of the summer, I will teach you how to take this weird idea that you have that’s very much an adult trying to teach a kid something, which kids don’t want, and turn it into a book that a child might actually be interested to read.” I won’t take you through everything that he taught me in that moment. That can be a story for next time. That support and that love and that trust — the first time I walked over there, all those kids’ books I’d mentioned in his library were out. They were on couches, on the floor, on coffee tables. He’s like, “I’m going to go to the backyard and drink some rosé, and you’re going to read all these books.” It was this very Karate Kid-style thing that happened. He really taught me how to write a children’s book. The reason that book is so good and the reason kids like it is because of the incredible way that Jon Scieszka thinks about young readers.

Zibby: Wow, back to somebody encouraging you.

Isaac: I won’t lie. I’m very proud of Dirtbag, Massachusetts, but How to Be a Pirate, the way it connects with kids means so much to me.

Zibby: I couldn’t believe when I realized you were the same person. I was like, no way.

Isaac: That makes me very happy too.

Zibby: Isaac, thank you so much for coming on. This was really fun. It was great getting to know you. Thank you.

Isaac: Zibby, absolute pleasure. Talk to me about Santa Monica and the bookstore idea.

Zibby: Yes, I will.

Isaac: I’m here to help. Then hopefully, next time I’m out there, we can see each other in person.

Zibby: Sounds good. Thank you. Buh-bye.

Isaac Fitzgerald, DIRTBAG, MASSACHUSETTS: A Confessional

DIRTBAG, MASSACHUSETTS: A Confessional by Isaac Fitzgerald

Purchase your copy on Bookshop!

Check out the merch on our new Bonfire shop here.

Subscribe to Zibby’s weekly newsletter here.

You can also listen to this episode on:

Apple Podcasts