The long walk with Isaac Fitzgerald

When Isaac Fitzgerald was a child growing up in the South End of Boston, he used to escape with his father to New Hampshire, where the two would spend hours hiking deeply wooded trails through the White Mountains. 

“And we would walk, and he would tell me a story and talk, because he knew if he stopped talking that I would be like, ‘Wait a second. I’m 6 [years old] and we’re in the middle of the woods,’ and I would sit down and quit. I would revolt,” the New York City-based Fitzgerald said recently while standing in my backyard, having just completed a story-filled walk of our own en route to my favorite tree, which I guess is something you have once you hit a certain age. 

Last year, in June, Fitzgerald started to leave his NYC apartment after three months of fairly intensive quarantine amid a worsening pandemic, setting off on foot to explore a city that he had in some ways started to take for granted. Eventually these walks stretched to two a day, in the morning and evening, with Fitzgerald setting an ambitious goal of walking 20,000 steps per day, which led to a November essay in the Guardian centered on how transformative this routine had become.

The essay, which Fitzgerald said generated a larger response than anything else he had written up to that point, helped shape his decision to launch Walk It Off, a new weekly Substack newsletter in which he (you guessed it) takes walks, recounting the sites, sounds and people he encounters along the way. If it sounds like a simple idea, it is. But Fitzgerald said that is precisely the point.

“I think a lot of us, especially this last year, have spent a lot of time stuck inside staring at a screen, but there’s something about, ‘Hey, just go for a walk. Get outside.’ Whatever form that takes for you, you just move through space, and you change and feel a little better,” said Fitzgerald, who will occasionally take Walk It Off on the road, beginning with this Columbus trip, during which he took a stroll with longtime friend Saeed Jones that will appear in a coming edition. “So, for me, Walk It Off, for one, is just about that joyful experience. And, two, hopefully I’ll actually have somebody with me on many of the Walk It Offs. … It’s about that human connection, which is why I launched it right now, as things start to open back up again. I want to get out there. I want to see people. I want to talk to them. I want to see the interesting things that they’re interested in. I want to be out in the world.”

For Fitzgerald, getting to this point has also required walking away from some things, particularly in the last couple of years, which has been a period of near-constant transition. In 2019, he walked away from both his job as books editor at BuzzFeed and AM to DM, a live morning show from BuzzFeed News he co-hosted with Saeed Jones. Then, in the midst of the pandemic, he walked away from a relationship, which he detailed in a September 2020 essay published in the New York Times.

And yet, Fitzgerald said he couldn’t be happier than he is at this particular moment, describing his path to becoming a writer as wholly improbable. “The joke I make, and, again, every job is of a purpose and important, but without the internet [and the writing doors it opened], I’m a gas station attendant, for sure,” he said. “Don’t get me wrong. I’m a charming gas station attendant and everybody likes me. And maybe in my older years I get voted to the school board, even though I don’t have kids.”

Part of this improbability can be traced to Fitzgerald’s upbringing. He said he wasn't raised in a family of means, and as a way of describing the area in Western Massachusetts he moved to after spending his early years in Boston, he recalled an illustrated map of the state, where different regions were labeled on the basis for which they were known. “So it was like, ‘Here’s cranberries. Here’s this,’” Fitzgerald said, his hands tracing an imaginary map. “Then you got to my little section and it just said ‘Here be dragons.’ Like, we had the highest teenage pregnancy rate per capita. We were a mess.”

At home, Fitzgerald experienced similar struggles. He grew up in the Haley House, a halfway house on the South End of Boston, raised by young parents who had it rough. “They figure it out eventually,” Fitzgerald said, “but those weren’t the easiest years.”

One thing the writer did have going for him, though, was that both of his parents were book lovers, who instilled in him a fondness for reading beginning at an early age, when he would frequent the public library to check out books like Rule of the Bone by Russell Banks and Maniac Magee by Jerry Spinelli. 

“Surprisingly, I was drawn to kids with abandonment issues, characters that had rough, unstable home lives,” Fitzgerald said, and laughed. “But when you’re a kid, books are just books, and you don’t think about where they come from. You just love them, and they help you escape whatever situation. And I love that feeling of my brain taking me somewhere else, and not being in the moment that I’m in.”

This love of reading is what would eventually help Fitzgerald escape those hardscrabble early years, the knowledge and sense of curiosity the hobby formed in him helping him gain admission to George Washington University on a scholarship, where he studied politics. Following graduation, Fitzgerald landed a job with Patrick Murphy, who would then be elected to Congress in 2006.

Shortly thereafter, Fitzgerald became disillusioned with politics, though, leaving the field and moving to San Francisco on a whim, where he worked for a stretch at Buca di Beppo ("It's like the Olive Garden but worse,” he said) before landing his dream gig manning the door at the bar Zeitgeist, where employees were expected to remain cool but Fitzgerald couldn’t quite shake his affable nature. “You’re supposed to be like, ‘ID? ID?’ he said, adopting a robotic deadpan. “And I’m up there like, ‘Hi! Welcome to Zeitgeist!”

Even in these years, Fitzgerald said he never really considered giving it a go as a writer, owing to a notion of the profession that he’d held from childhood.

“I thought writing was a gift from God, and you were touched by the universe, God, whatever language you want to use, and you lived in an ivory tower, wrote beautiful prose, hit print and sent it to New York, which is where they put a cover on it,” he said.

This illusion was shattered when Fitzgerald attended a bookmaking class at 826 Valencia, a nonprofit organization dedicated to supporting the writing skills of under-resourced students, not realizing in that moment that it was an event geared toward children.

“And it became very clear very quickly that this was an open recruitment to get adults to work with kids, to help them with their bookmaking and storytelling. But in my head I’m like, ‘I can’t get up and walk out. I’ll look like an asshole, like I hate kids,’” Fitzgerald said. So he stayed, and in the process he was directed to the various page proofs that were marked up by editors and then framed and hung on the wall. “And that was the first time I’d ever heard the idea that writing is craft. It was even the first time I thought about that idea that books are something that are made. They’re not just these escape portals. They are something you can build yourself.”

In the months and years that have followed, Fitzgerald has immersed himself in this craft both as a writer and an editor, working for places like the Rumpus and BuzzFeed to help sculpt and sharpen pieces by the likes of Roxane Gay and Jones, owing to an innate, almost indescribable ability to know what reads well on the page. Parts of his approach are also drawn from his blue-collar roots, with Fitzgerald comparing his editing and writing styles with the neighborhood mechanics that dotted the South End. “I’m just tinkering and banging at it, trying to wrestle certain things into shape,” he said.

Throughout this time, Fitzgerald also worked to uncover his own voice as a writer, describing a key turning point as “High for the Holidays,” an essay published by BuzzFeed in 2013 in which Fitzgerald recounts climbing Mount Kilimanjaro with his sister and estranged father. The essay, like its author, is both big-hearted and impossibly open, qualities that he said required time to properly dial in.

“I would argue that was the first time I was writing instead of doing an impersonation of someone I admire, which is also an important step in all of this,” said Fitzgerald, whose forthcoming memoir, Dirtbag, Massachusetts: A Confessional, is due early in 2022. “It felt like that was the first essay where I allowed myself to be as earnest … as I actually am. A lot of the writers I admire, there can be this coolness, which is part of what I loved, and why I tried to impersonate it. But it felt like the first time I found my own voice because I was saying, ‘Hey, man, the fact of the matter is you’re not that cool. You’ve got a lot of feelings, boy.’ And I finally let that shine through.”

Walking, in a way, is also central to that particular essay, with Fitzgerald describing how he often followed his father up the mountain, or his father followed him, the two taking turns staring at each other’s feet but never really reconnecting or making amends for the past, which is part of the reason that the younger knows what he has to do in some future edition of Walk It Off.

“It will be one of the tougher ones, and I won’t do it for a while for all kinds of reasons, but eventually I’m going to have to ask my dad to go on a walk. He has to be one of the people I feature, and I’m sure we’ll talk about some difficult things, but also some lovely and pleasant things,” Fitzgerald said, going on to recall the childhood hikes the two used to take together in the White Mountains. “Even though I felt a little dragged along at the time, looking back on it, I can recognize it for what it was, which was him getting out of the city, which was him getting into nature, and this wonderful connection he and I got to build around it. And 30 years later, it’s just funny that I’m coming to do the exact same thing. I got it from my dad. That dude loved to go get lost, and I love to go get lost.”