Book Club

7 takeaways from Book Club’s ‘Dirtbag, Massachusetts’ author discussion

“It was so important to me that this memoir didn’t feel like a bow on top of a package. Life is an ongoing conversation.”

Isaac Fitzgerald, author of the new memoir “Dirtbag, Massachusetts,” said for years that he’d never write about his childhood. 

When he sold a proposal for a collection of essays to his publisher, he’d intended to write a series of stories on pop culture, music, and television that would draw very minimally from his own life. But then he started writing, and he couldn’t help but be drawn to his personal experiences. 

As it turns out, the collection of essays he’d pitched was perfect for how he wanted to convey the story of his life — not as a linear path, but as a reflection on key moments. 


“When it comes to the big moments, I wanted to be able to zoom in and focus on those. The essay format allowed me to chop it up and focus on these very important details throughout my life without having to tell all of my life story,” the writer shared. “It was so important to me that this memoir didn’t feel like a bow on top of a package. Life is an ongoing conversation.” recently hosted a discussion with Fitzgerald and Nicole Brinkley, a bookseller at Oblong Books in Rhinebeck, N.Y., about his memoir. They talked about how he feels about getting vulnerable on the page, how therapy helped him navigate this writing journey, and why being an avid reader is important for any writer. 

Read on for takeaways from their discussion, and get more Book Club updates here.

Isaac Fitzgerald put himself into the mindset of a reader to write this book.

The “Dirtbag, Massachusetts” author set out to write a book that would have an important message, but wouldn’t leave readers feeling like they were being lectured. 

“I tried to approach it from a reader’s perspective. I wanted to make stories that people would enjoy reading,” I wanted to make a book that still had lessons in it, but didn’t feel like, “Alright, time to eat the broccoli.’”


Because this memoir is so vulnerable, Fitzgerald had to constantly remind himself not to shy away from his discomfort with his own story. 

“When you look at the thing you’re trying not to look at, when you talk about the thing you’re trying not to talk about that’s when you’re gonna come up with an interesting story. I kept finding that out time and time again with ‘Dirtbag, Massachusetts,’” he said. 

Going to therapy gave Fitzgerald the tools to write this book. 

Throughout the talk, Fitzgerald gave shoutouts to his therapist, who he said helped him process a lot of the work he needed to write this memoir. 

“Within myself, there was an ongoing, making the same mistakes over and over and over again,” he said. “Only when I started therapy, about three years ago, that I started recognizing the pattern. That’s when I realized while I was trying to write these pop culture essays, I realized actually, no, it’s going to be about my childhood.”

Finding family in queer spaces helped Fitzergerald become a better person.

During his years living on the West Coast, Fitzgerald found a welcoming environment among the queer community. As a straight and cisgender man, it was those relationships that helped him work through his understanding of his own masculinity and tolerance for others. 


“It is on me to do the reading or to be curious and try to figure out ways to educate myself when it comes to wanting to be, and I don’t even need to say a better man, just a better human,” he said. “But what I was lucky enough to have was that I was moving in these spaces where people in my life cared about to have these conversations.” 

Everyone should be open to changing their environment to learn more about the world. 

One of his earliest eye-opening experiences was getting a full scholarship to Cushing Academy, a private boarding school in North Central Massachusetts. There he was exposed to people from all over the world and learned to expand his worldview. Admission to private school isn’t the only way to become more open, Fitzgerald noted, but he believes it’s especially important for young men to get opportunities to become more comfortable with people of all walks of life. 

The Catholic Worker Movement in Boston played a big part in his childhood, too. 

Fitzgerald’s parents raised him in the Catholic Worker in Boston, a progressive Catholic movement that the writer described as “all the faith, not so much the institution of Catholicism.” Being in those spaces as a child meant that he was raised around a lot of open conversations he wasn’t encountering in other spaces of lower socioeconomic class, something he says he’s never taken for granted.

Navigating failure has been a big part of his life.

Growing up in a low-income household and dealing with instability in his childhood made him more comfortable with the possibility of failure, Fitzgerald shared. Rather than allowing that to stop him from pursuing life, he adopted the mentality that he could keep “swinging for the fences” because he “had nothing to lose.”


“It’s such a cliche thing to say, but it is about how you get up, dust yourself off, and then keep going,” he said. 

Fitzgerald wrote this memoir as a “letter to his parents.” 

Fitzgerald was careful to have discussions with key people in the book prior to publication, but since the book’s release, he’s had to have tough conversations with his parents about his perception of his childhood.

“Overwhelmingly, my family has been incredibly supportive. Not everyone who has a story like mine gets the love and support that I’ve gotten,” he shared. “[This book] was me trying to figure out how to talk to them about something, I couldn’t talk with them directly about. Those conversations have been happening, and I’m so, so grateful for it.”

For writers, it’s important to honor the books and writers that influence your work. 

Fitzgerald named “Another Bullshit Night in Suck City,” a memoir by Nick Flynn about how he reconnected with his estranged father while working in a homeless shelter in Boston, as one of the inspirations for his own memoir. Flynn’s book was recommended by readers as one of the best books set in Massachusetts and comes highly recommended by Fitzgerald, too.  

“So many of the things that I went through, Nick had also grappled with and so that was the book that I picked up at a very young age,” he said. 

“My dad gave me a lot of books to read when I was younger. It’s important to honor the books that came before, and so many different books inspired ‘Dirtbag, Massachusetts.’”