A Pilgrimage With Isaac Fitzgerald

Down the length of Fire Island with the most gregarious member of the literary internet.

Photo: Remi Morawski
Photo: Remi Morawski

The writer Isaac Fitzgerald was walking across a parking lot one day this summer when he looked up to find an airplane falling out of the sky. “Jesus fucking Christ!” he cried. (“Excuse my language,” he added primly.) It was a small blue propeller plane, but in that moment it most resembled a leaf tumbling end over end. After a sickening interval — that moment when vastly divergent futures have yet to fork — the stunt plane finally righted itself. It flew onward. Then it began a yet-more-tortuous series of swoops and twists.

It was an apt metaphor for the year he, and many of us, had just lived through: unpredictable, surreal, plunging, soaring. As an essayist and editor, Fitzgerald had long served as a kind of genial barkeep of the literary internet — an avuncular, boozy presence with killer taste in books. In the past 18 months, that reputation had only grown: Fitzgerald had published a best-selling children’s book, finished an essay collection, and maintained a semi-regular book-recommendation segment on the Today show. But he had also experienced a painful breakup with his fiancée, the writer Alice Sola Kim, and survived a plague.

Last summer, prompted by a health alert from his iPhone about how sedentary he was becoming, Fitzgerald set himself the goal of walking 20,000 steps, or roughly ten miles, a day. (Fitzgerald, who has no kids and has lowered his cost of living in order to be what he calls a “time millionaire,” could afford this luxury.) It worked wonders. His mind felt sharper. His body changed shape in ways that pleased him. His world widened, and the pall of the pandemic seemed to lift.

He gradually ventured farther and farther from home. He walked (and skateboarded) seven miles from Brooklyn to Manhattan. He walked through a cemetery. He walked to a shipwreck. He began documenting these walks, first on Twitter, then on a weekly Substack newsletter titled Walk It Off. (Tagline: “That was tough. Let’s go for a walk.”)

In the canon of contemporary writers who write about walking (Rebecca Solnit, Will Self, Frédéric Gros, Teju Cole, Garnette Cadogan), Fitzgerald is unusually down-to-earth. His approach is relaxed, undogmatic. He does not wax on about the Baudelairean flaneur or the Elkinian flaneuse. He does not partake in psychogeographic games. He often stops to drink a beer at random bars; he will pause to admire a headstone in the shape of a grizzly bear and ponder, “Is it wrong to consider a gravestone sexy?” In other words, he is not trapped in his own head. That, to him, is the point of walking. “For me, it’s the opposite of sitting in your bed staring at the ceiling, thinking about a million things,” he said.

Fitzgerald also began going on walks with friends, many of whom are famous writers: Marlon James, Susan Choi, Saeed Jones, Josh Gondelman. On one walk, with the novelist Raven Leilani, she described how, in the same year, she had lost both her father and her brother and had published a best-selling novel. “It was a mindfuck,” Leilani told Fitzgerald. “ ‘How are you doing?’ felt like the most ridiculous question. No one was saying the real answer. And when you can’t give the real answer, you feel isolated.”

This past July, Fitzgerald embarked on his longest pandemic walk yet: a two-day amble down the length of Fire Island. Although we had never met, he agreed to let me tag along. Planning to camp on the beach, Fitzgerald carried a bicycle-messenger bag and, inside it, a $5 plastic tarp, a knife, and an old hammock.

We began our walk at the base of the Robert Moses Bridge. After jumping into the cold, churning sea, we turned eastward, following the waterline, where the sand was firmest. The sky turned the color of cockles, and a light rain began to fall. We stopped at a lighthouse, where Fitzgerald listened with interest while an old man spent 20 minutes describing the workings of the lens of the lantern. To each person we passed, Fitzgerald asked, “How we doing?” (Always that strangely inclusive formulation: How we doing?)

In Kismet, we stopped for lunch at a bar with Frankie Valli playing on the jukebox. Fitzgerald was still damp with rain. His shoes were filled with sand. He ate a bad lobster roll and drank two ales. “I am so happy right now,” he said.

Fitzgerald’s life hasn’t always been so carefree. As a young child, he lived in a shelter for the unhoused and then in low-income apartments in the South End of Boston before he and his mother moved to “a small gray drafty farmhouse” in rural Massachusetts. His father was rarely around, and his mother, “scooped out with loneliness,” once tried to commit suicide. Fitzgerald began dropping acid at the age of 12; at 15, he and his friends formed a fight club. (This period of his life is recounted in his forthcoming essay collection, Dirtbag, Massachusetts.) After college, he worked a series of odd jobs, including stints as a bartender at a biker bar, “the world’s worst sushi chef,” the body man for a congressman, and a model for Kink.com. He chose to be radically openhearted, unlike many of the adults he had grown up around. “I knew I didn’t want to be a person who was bitter and mad all the time,” he said.

Fitzgerald wandered into the book world one day in 2006, when, after moving to San Francisco, he volunteered at a storytelling workshop at 826 Valencia, the nonprofit co-founded by Dave Eggers. He eventually became the managing editor of The Rumpus, an online literary magazine, where he edited Cheryl Strayed’s “Dear Sugar” column and Roxane Gay’s early essays. Fitzgerald’s success at The Rumpus led to a job as the first editor of BuzzFeed Books, which brought him to New York. Shortly after being hired, Fitzgerald announced that BuzzFeed Books would publish only positive reviews — “Why waste breath talking smack about something?” he famously declared — which prompted a scathing rebuke by Tom Scocca in a Gawker piece titled “On Smarm.” (Fitzgerald, true to form, refused to talk smack about Scocca. “I think that piece is really good!” he told me.)

That afternoon, a vicious thunderstorm erupted. In desperation, we ducked beneath the eaves of a cabin run by the Appalachian Mountain Club. Inside was a cluster of people playing Scrabble. “We’re not supposed to let you in because of COVID,” said a woman as the rain lashed us. “It’s all right, girl!” Fitzgerald said. “No sweat!” The rain continued unabated, so we abandoned our plans for camping, opting instead for a cheap hotel in town. We ended the night at a dive bar, where Fitzgerald stayed late, drinking pink fizzy cocktails and talking to strangers.

The following day, the skies cleared. Walking through the community of Seaview, we passed an old man pushing a dog in a baby carriage. “How we doing?” Fitzgerald asked.

“I’m lost,” the man said cloudily.

“What are you lookin’ for?”

“I don’t know.”

Fitzgerald asked the man’s name, and the dog’s name, and stayed by the man’s side until he found his way home.

Strayed describes a phenomenon she calls “life at foot speed.” It is the act of moving slowly enough that chance entanglements can occur with people and places. Walking, seen in this light, feels at once freeing and communal, two qualities that have been in short supply of late. Fitzgerald’s newsletter — his whole way of being in the world, in fact — is an ode to life at foot speed.

On our walk, Fitzgerald ultimately made it as far as Cherry Grove. The goal had been to reach the Pines, but more rain was coming, and with a smile and a shrug, he decided to cut the trip short. Walking off a bad year is a fluid endeavor — there is no set terminus. He gave me a hug, then rushed off to catch the ferry, sand still sticking to the backs of his legs.

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