Books

Q&A: Isaac Fitzgerald on his memoir ‘Dirtbag, Massachusetts’

“I was trying to make a story that spoke to other peoples’ lives, in a hope that they could feel just a little less alone.”

By Dialynn Dwyer

July 19, 2022

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Isaac Fitzgerald knew from a young age that he had a great opening line for his own story: “My parents were married when they had me, just to different people.”

Over the years, he’d use it to deflect from sharing more. He’d usually get an awkward laugh, and then he’d move the conversation on. 

But now, with the release of his debut memoir “Dirtbag, Massachusetts,” the sentence serves as the anchor and kickoff for a series of essays that delve, without shying away, into his childhood and the years that followed. In the book, which publishes Tuesday, Fitzgerald recounts growing up in a homeless shelter in Boston and in rural Massachusetts; examines the ideas of home, safety, and belonging; and reflects on life experiences ranging from working as a bartender in San Francisco to the time he spent smuggling medical supplies into Burma.

Fitzgerald — who was the first books editor at Buzzfeed, frequently shares reading recommendations on “The Today Show,” and is the author of the popular Substack newsletter “Walk It Off” — told Boston.com it is both moving and wild to have the opening line he’s held close for years now be the start of a deep examination of his childhood and family.

“That is now the opening line of something that is really about my relationship with these two people and their relationship with each other, and where our relationship used to be and where our relationship is now. … It’s still a growing, ever-evolving thing,” Fitzgerald said. “So the thing that I can only hope for is that those lines of communication stay open and that we get to move forward as a family.

“And I’m very happy to report, because this stuff isn’t in the book, but the book is bringing some really important and really loving conversations that I maybe wasn’t expecting,” he said. “And that’s been brilliant too.”

But, the author stressed, he still thinks it’s a funny line. 

Below, Fitzgerald shares more with Boston.com about his new memoir, what he hopes readers take away from it, and the way stories can be “lifelines.”

This interview has been edited for clarity and length. 

Boston.com: “Dirtbag, Massachusetts” is being called a “memoir in essays.” How — and why — did you decide to approach your story with this structure? What did it allow you to do differently than a typical memoir?

Isaac Fitzgerald: When I first sold this book, I was viewing it as a collection of essays that would not be connected, that would be about all sorts of different things. The essay that’s in the book that’s a really good example of that is the “Hold Steady” piece. It’s very much about my time in San Francisco. It’s about my love for my friend, Jef, but it was also about The Hold Steady, the band, and Craig Finn’s solo music career.

So I was picturing, actually, a lot of things like that. Where I dove into one thing that I was interested in or that I loved, but then would kind of go into my own past or my own personal connection with that thing. 

But then what happened, and this is what happens … you sit down to write and the piece changes. So that’s what happened. I realized that I kept alluding to my childhood in sort of pieces, but I was not actually exploring it. … I had a conversation with myself that I needed to face about my childhood. About how my parents, and my family, how we all kind of exploded apart and then, in an interesting way, started on our journey to coming back together as I got older. 

So … that’s when I realized, OK I need to find the moments in my life that have been extremely important touchstones and then do therapy, talk about the book and the things that emerge. … What I wanted to focus on was the emotional, gripping things that I think would be of interest to a reader. So that’s why essays were the choice for me. … I wanted that freedom to move around. 

One of the essays in the book is also called “Dirtbag, Massachusetts” — how did that rise to the top for what you wanted to call the book?

The name of the book actually came first. And that is, credit where credit is due, [due to] my friend, Jason Diamond, who is a wonderful writer. He and I were on a road trip up to Boston. He had a book event that was happening, so he had asked me to do a conversation with him … And while we’re driving, I crack this joke about the town that I lived in called Athol, Massachusetts. Everyone else in the state would be harsh on it, calling it “Rathole Massachusetts” or “A**hole, Massachusetts.” And I went, “You can’t call a book, A**hole, Massachusetts,” almost as a joke. 

And he said, “Dirtbag, Massachusetts” would make a really great title. 

That was still back when I was thinking these will be all these separate essays. 

But as I started to write it, it became clear to me that I was getting at more of my own personal experience, but also the experience of what it is to be in the state of Massachusetts, [in the] north, central, one of the more northern parts of the state. That’s when I realized … now I have to write an essay that encapsulates my experience there. So … the title came first and then I wrote that piece to match it. And again, it was a lot of work. That part of my life played such a formative moment — my love for that area, but also how getting out of that area changed my life. And that became the core piece. 

Early in the book, you talk about your experiences spending time in Haley House in Boston and the importance of sharing community. What do you think the broader public doesn’t understand about the community that exists for those struggling with homelessness? 

There’s three different things. The first place my mind goes is dignity. People that are struggling with being unhoused — it’s because of a lack of support, it’s because there’s a lack of infrastructure, it’s because so many people just need a little help. And I feel like more and more we are stepping away from having any kind of safety net from either the state or federal government. I just think the way this whole country continues to struggle with this issue is a lot of hand wringing about the situation, but not a lot of action that can actually help … You could set up places for people to live and give that dignity to really start a life. So that’s one of the things that’s so important to me.

Then we get into, in the face of that lack of support, what happens? Well, people are still generous. People care about their community. That’s what I love about the Catholic Worker; that’s what I love about that support system. It’s: Here are people who are not waiting for somebody else to grapple with this issue. Here are people who are willing to roll up their sleeves and tackle it themselves and do what they claim, which is love thy neighbor and give that support. So that’s one of the things — that’s what I absolutely love. 

When you’re a kid, you don’t know you’re growing up in a special situation. But getting to grow up within the Catholic Worker gave me so much love, gave me so much support. I got to watch what it means for adults — because when you’re a kid, who are the people you’re looking up to? You’re just looking up to the adults in your own life. And so I got to watch as adults truly cared for one another, truly assisted each other, truly helped one another out. And I think that’s had such an impactful, impactful thing on me. 

So the first is dignity, second is community, and then — I feel like it’s the whole special thing that I wish more people understood — it’s how it makes you feel to be a part of that community. 

That is to say, my parents were having a very hard moment. But I got to watch — they are not without faults in other parts of their lives — as they, through community, got their own dignity. They were so quick to then turn around and help those around them. 

And that to me is the real secret of it all. That you will actually feel good; it’s not just about sacrificing and going out and trying to help. 

So for somebody like me, the child that I was in that situation to benefit so much from the love and support from all these other adults — who were trying to help us out in that moment, who were volunteering their time in that moment, who were volunteering food in that movement to help us — that is something that I now carry with me everywhere. The generosity of spirit. Once you’ve received that generosity, you realize how impactful you can be by giving it to other people. 

So those are the things that I wish people [understood]. A little bit of dignity will go such a long way. The community can be so loving and supportive. And if you join a community like that and you’re helping people find their own dignity, you will find more of your own dignity within yourself. 

One of the things that really jumped out to me throughout your book is the way you reflect on stories that are told or inherited in families, and the role of storytelling — both in forming one’s identity and in building community and connecting to others. What do you hope readers could learn from or take away from the stories you have shared from your own life? 

That was so much at the core. Like I said, I started thinking it might be these disparate, separate essays. And as I realized more and more I was going to have to focus on my own life, that’s when I’d sit down and I’d say, OK, which stories … were told to me and really shaped who I thought of myself as a person and which ones are worth keeping and worth putting down? And then realizing my own stories, OK, when I am bulls******g myself? When am I putting too much of a nice glossy shine on things? 

That for me is a core part of the book: stories as lifelines. Stories as the way we form how we see the world, but also how we see ourselves and the importance of stories and, especially, that maybe the stories you’re told are not truthful. Or maybe they are, but they’re not to you, not your experience. And they don’t have the power that we’ve maybe given them in certain instances. So that for me was part of it. 

And then to be so grandiose as to say what I hope people take away from mine, when I realized what this book was becoming, what I wanted was to have a copy of the book, like a paperback copy my 14-year-old self would have folded up in his own back pocket. 

I was trying to make a story that spoke to other peoples’ lives, in a hope that they could feel just a little less alone …  If this book has anything in it that allows the reader to feel a little less alone, a little more seen, then that is such a blessing. That means that I have done what I have set out to do. And if that happens … that reflects back and also makes me feel better and more a part of the world. It makes me feel less alone. So if the book can even do that just a little bit, that will mean so much to me. 

You write about forgiveness and the importance of honest and vulnerable self-reflection in order to grow. It seems we’re in a period of history when that is what is needed to move through the challenges — like the resistance to facts and history — we’re facing in this current moment. I wondered, how much did recent current events (like the Me Too movement, the pandemic, the racial justice protests of 2020, the Jan. 6 insurrection) influence you when you were putting together this book? 

I wrote a lot of this book with a toothache that I couldn’t get seen by a dentist … because it was lockdown. So I was literally sucking on a piece of ice all day while my tooth was just throbbing in pain, trying to write some of this stuff. So [it] influenced in a lot of different ways, one being that it was just really uncomfortable a lot of the time. 

But two, to more of the spirit of your question, I think conflict is a very important part of life. And that’s actually a lesson it’s taken me a long time to learn. I think because there was so much conflict in my early childhood, I did my damndest to avoid it all the time. And how I could do that was be polite, be nice. I just really worked toward avoiding conflict. 

And the complicated moment that we find ourselves in now, which at times can feel very very hard and very very difficult, I still think it’s extremely important. The conversations that have come out of the racial justice movement and the protests of [that] summer are so important and such a long time coming, would be one way to say it. But there are also conversations that have already been happening for a long time. 

And that’s what I think is so important about it — same with the Me Too movement — what we are talking about are hard, important conversations that need to happen and are important for society to move forward.

I don’t think there’s any perfect moment we’re all walking towards. I don’t think that’s the way society, humanity, the world, life … I just don’t think that’s the way the world works. But what is important is that we do have these conversations. And that there is at least some openness to being vulnerable, to admitting when one is wrong, to understanding that past actions could have incredible effects like you could not have even comprehended. And with that work, we’re able to get to these moments of, again, not perfection, but at least of understanding.

And to bring it back down to a very small thing … if I had written this book when I was 25, it would have been a book that was just about how angry I was at my parents. But having written it — I started it at 35, I’m now 39 — it is about what it means to have conversations with my parents now about what happened. And it’s not going to be some neat and tidy bow … No. It’s still difficult; it’s still hard. But there’s a better understanding there and that allows for more communication. 

Do you have a favorite essay from the book?

It shifts, it grows, it changes. But right now … the “Forgive Me” essay I think is one of my favorites just because of how much it does dive into the Church as a structure and form of religion, but also the ideas behind it, which I think the Catholic Worker gets to. It is about loving your neighbor. It doesn’t have to be about ambiance and spectacle. It can be about these very simple, very grounded ways by which we connect with each other and love one another. And I think that, while it is a very long and complicated essay, I think that’s the one that really sings for me right now. 

[Read an excerpt from “Dirtbag, Massachusetts” here]

What was the hardest essay to write and why?

The opening and the closing essays were the last ones that I wrote. And it does not take a therapist, although I very much love mine, to find out why that is. Those are the two essays where I’m really getting into some difficult and hard things around my family and around my childhood. And in a way, I almost wrote them as one essay and then broke them up and had them bookend the book. 

The first one is called “Family Stories,” which is kind of all the stories that were in a way told to me. And then the last one is called “My Story” when I get into … what happened. And what was difficult about those [is] it’s hard to look back at that and to jump back into those feelings. But also, like I said, this is a story about a family breaking apart. But it’s also a story about a family coming back together. So I have a relationship with my father, I have a relationship with my mother, I have a relationship with my siblings and their children. So no matter how much distance one might feel, it was important to me that I wanted to protect the family as well. 

And so that’s what really made those essays difficult to write. It doesn’t get to all just be anger. Like I said, the book I’d write at 25 would be angry. The book I wrote now is, “OK, so why were my parents going through that?” Trying to better understand. They are full, three dimensional, human. They were, at times, trying to do the best that they could with the situation that they were in. 

So that became a big part of that project and became a big part of the book and that’s part of the story around the book. The fact of the matter is now I’m having conversations, especially with my mother, where I feel extremely close to her right now … This book has in a way made room for communication that we didn’t really have room for before. And that’s been such a wonderful, powerful thing. So those essays were the hardest to write, but I also think those essays are probably affecting my real life more than anything else in the book. 

Is there anything else you want to say?

The joy for me is other people now reading [the book]. I’m just so excited for it to be in other people’s hands. So I’m so looking forward to it being the [August] Boston.com Book Club pick because I know I’m going to get to sit down and have a conversation and get questions from readers. And I can’t wait for that.