If form follows function, then the traditional memoir could never contain the motley and multihued life of Isaac Fitzgerald, a frequent visitor on NBC’s Today showwho penned the bestselling children’s book How To Be a Pirate. “While I’ve tried to live with intentionality,” says the gentle and genial author, “this book revealed that a lot of time I’ve just been…trying out different things.” That understatement captures Fitzgerald’s utter lack of grandiosity: In Dirtbag, Massachusetts (Bloomsbury, July 19), he exhibits a devilish derring-do tempered always by his natural modesty. Each chapter reaffirms the lesson of one of his favorite sayings: “Life’s mistakes are my co-pilot.”

Mistakes or not, they’re all deftly recounted with the care of a storyteller, and by book’s end, a tale of human grace emerges. “I grapple with emotions in story form,” he says, “even if my life has been grappling in the dark.” Fitzgerald’s grappling took place in many disparate arenas:actual grapples, bloody and bruised, in a real-life fight club; barbacking in a San Francisco biker dive; erotic performing in pornographic films; smuggling supplies to internally displaced peoples in Southeast Asia.

Fitzgerald grew up Catholic (his mother worked for Cardinal Bernard Law, the archbishop of Boston) and indigent, but he was not unhappy—until the ripe old age of 8, when his family moved to the country. What followed were unsafe escapades filled with trauma, self-loathing, violence, and drunkenness. A respite came when he secured a scholarship to a venerable prep school; thereafter the book thrums with ethical lessons accrued while navigating far-flung places. Fitzgerald receives unexpected generosity from unlikely outcasts, all serving to fortify the author’s inborn humility.

While Dirtbag, Massachusetts is not exactly a memoir, Fitzgerald nails the genre in his subtitle: A Confessional. Not only does this evoke his Catholic background (plus one odd experience he endured in the actual confessional booth), it captures the soul-baring tone of the book: raw, unflinchingly candid, never out to impress—only reveal. Fitzgerald discussed it by telephone from his home in Brooklyn; our conversation has been edited for length and clarity.

Was writing this book cathartic or—to use a less grand term—an unburdening, of sorts?

There’s a real draw in writing a memoir to make yourself look better than you are. [Laughs.] Of course! You’re in control! But that’s the beauty of a confessional: Behind the lattice and the shadowy figure, you’re talking directly to God, and here’s where you can be honest. No reason to hold back—you’re gonna be forgiven. In fact, I think that with all my other writing, what drove me was a hope for the unburdening you mention; I’ve learned that the real place to find that is in therapy. What I discovered (though probably already knew) in writing Dirtbag, Massachusetts is that if you try to make yourself look good, you end up with a boring memoir.

And this book is anything but. So you set out to write a traditional memoir?

Actually what I sold to my publisher was a collection of cultural essays—what I turned in is so different from the original proposal. But as I wrote I found myself drawn more and more to my childhood, and I realized that what I’d thought was my being an adult was just me reacting to that childhood over and over again. For many years I made sure that I was not going to write a memoir. I was reading a lot in the ’90s, and—let’s be honest—there were a lot of sad White boy childhood memoirs in the ’90s. So while I knew I could write an entertaining essay about Star Wars, it became clear that I needed to focus on this first. It just poured out on the page.

Explain the title.

One of the places I lived was Athol, Massachusetts. [Laughs.] Exactly—everyone calls it Asshole, Massachusetts. A poor rural area—but beautiful—in a relatively rich state. And the name fit. But you can’t call a book Asshole, Massachusetts, and a friend said: “Why don’t you just call it Dirtbag, Massachusetts?” And that was the moment when I knew it was going to become more memoir-based—dealing with where I was from and all that.

You write that you went from being “poor city mouse to poor country mouse”—and then got a scholarship to a wealthy boarding school.

My first year at boarding school I had such a thick Boston accent—an accent that, up until that point, I was proud of! But not there, so I’d sit in my room and practice pronouncing my R’s. And of course, the next year Good Will Hunting comes out and suddenly that accent was cool. I’d return to Athol and people who never spoke that way suddenly had that accent. [Laughs.]

You have a talent for upending conventional expectation. Your time in porn was where you learned how to be moreintimate in life. The violence of your teenage fight club taught you more tender ways to express love.

It makes me so happy that that comes across. I’ve come to learn that places like “the childhood home,” “the Catholic church,” you know…all those places that are typically sold as safe spaces—they were not for me. I love a bar—it’s a space I’ve always sought out. Where I found a place to be myself, at home, safe—they were those places that are usually sold as places to be avoided. The porn set. Biker bars. Fight club. For me they were a place to be myself without admonishment.

Plus your time on the frontlines of real danger: dodging landmines with the Free Burma Rangers [a humanitarian mission operating in Myanmar, Sudan, and Iraq] when you felt for “the first time in a long while I don’t feel like dying.”

The sense of purpose you can get out of life came clear to me with FBR. Maybe that work was not my purpose, exactly. But it was about opening myself up to the idea that through helping others you can learn self-worth. Because there’s never going to be that perfect moment where you turn the final page and it’s like, yeah, I’m safe, I feel like everything’s good. It’s always mixed with the bad. You have to make the effort to be curious and to forgive. The FBR is an organization (and I’m not a smart enough person to say why or why not) that’s not perfect. But do I know that at a certain moment in my life they were providing help to humans who truly needed it? Yes.

Despite your turn from Catholicism, it seems like there’s still a deeply religious person in there.

You’re 100% correct. Am I an atheist? Yes. But do I pray every time I touch the ocean? Yes. I believe in gratitude. If the only reason you’re a good person is that you’re scared you’re going to hell, that’s not saying much. I believe in forgiveness and growth. A good percentage of us are just out there trying our best. I find that my life is more full when trying to move through the world believing that people can change.

Which is akin to your belief in stories—there can be character redemption in the third act.

After all, what is the Bible? It’s a collection of stories. I have to believe in humanity. There’s a way to live that you can be curious about yourself, but you have to extend that curiosity to other people. What a flat world it would be otherwise!

Steven Drukman is a playwright and writer in New York.