Adam Moss is a painter, but he will tell you, as he does in the introduction to his new book, that he feels silly saying so. The former editor in chief of New York magazine started to dabble around 2017, but it wasn’t until he left the magazine in 2019, following a storied 15-year run at the helm, that he really got into it. “I really wanted to be a good painter. What a fucking idiot I was,” Moss tells me. His quest to understand how art is created—which serves as the driving force behind his new book—is “the consequence of my struggles to paint,” he says.

The Work of Art is a case study in creativity featuring preeminent artists of our time who span genres and mediums, from filmmakers to painters to chefs. Moss interviewed more than 40, many during the worst of COVID, asking them to walk him through the process of making a specific work of art and drawing on what he calls “process artifacts” to chronicle their thinking (e.g., the original outline Gay Talese used to write his iconic write-around of Frank Sinatra; David Mandel’s whiteboard exploring how the last season of Veep might end). Some conversations appear as Q&As, others as mini profiles or monologues; but all home in on, and try to deconstruct, the often intangible process of creation. “Some people really enjoy being put on the couch this way. A lot of people—no one ever asks them these questions,” Moss says. “They ask them who they’re dating and they ask them what the project means,” but “how they made it—in practical terms and also, more importantly, psychological terms—that’s kind of virgin territory for a lot of people.”

Throughout the book, Moss is trying to figure out what all of these artists, regardless of genre, have in common—a shared trajectory, perhaps, or a set of characteristics key to the act of creating. Early on, Moss tested out his idea for The Work of Art on a friend, Michael Cunningham, whose own chapter focuses on his Pulitzer Prize–winning novel, The Hours. “I wanted to see if my conceit would work—that the artifacts of something’s beginnings might yield insight into how an artist’s mind works,” Moss writes in the book. Combing through Cunningham’s archives together, they eventually found a memo he wrote to himself in the midst of writing, “a kind of free-associative list that actually verbalizes some of the questions he was having,” Moss recalls. “Including a great little line: ‘Call it The Hours?’”

Not everyone passed the test. “A number of people failed to work for the book for two big reasons,” says Moss, explaining that some weren’t introspective enough (or were even superstitious about discussing their practice) and others didn’t have artifacts from the process. “I was very lucky to get Amy Sillman, because she did actually keep every iteration,” he adds. “Most painters don’t work like that.”

Moss began his career in journalism as a copyboy at The New York Times. He next worked at Rolling Stone, then Esquire, and eventually started the short-lived but beloved weekly magazine 7 Days. He returned to the Gray Lady years later as editor of The New York Times Magazine. His book is not a memoir about his time in journalism—“I’m really not that interested in myself,” he says—but glimpses of what such a work might have looked like are sprinkled throughout, in footnotes and introductions to subjects. In one footnote, Moss recalls creating the 9/11 issue at the Times Magazine in a mere 72 hours—“a collage of fragmentary imprints of that freighted day, which was deeper and even more artful than many we’d taken months to make—probably the most meaningful (to me) of my whole career.” In another, he tells the story of then publisher Arthur Sulzberger Jr. pulling him aside after Moss made the mistake of approving a photo in the magazine that employed S&M imagery, a decision the paper then had to distance itself from in an editor’s note. (“Not a smart move, but I hope you ignore the note and just continue what you’re doing,” Sulzberger said, according to Moss.)

One of the works of art in Moss’s book is a Times front page from May 2020, which saw the paper memorialize nearly 100,000 COVID deaths by filling A1 with the names of 1,000 people who’d lost their lives to the virus. Moss had wanted to include a public memorial in the book—he’d thought of Maya Lin and the Vietnam Memorial—and then this cover happened. “And I thought, Well, this is the Vietnam Memorial, except it’s in the pages of a newspaper that I used to work in, where something like this was, I mean, really inconceivable,” says Moss. It was “a little atypical for the book, but I was interested in it anyway,” he adds. In his interview for the book, Dean Baquet, then the paper’s executive editor, rewards Moss’s instincts. “I actually thought that page was trying to portray a feeling. Nobody was going to read it name by name. It was like a Rothko,” he tells Moss. “And the longer you look at a Rothko, the sadder you get.”

Moss’s pages, too, evoke a feeling—the frenzy of the creative process—and provide a tinge of nostalgia. With the book’s layers of small type, arrows directing you through graphics, and annotations and dialogue in footnotes, the reading experience is not unlike the one you’d have with New York in the Moss era. (In fact, one of the designers of this book, Luke Hayman, previously worked as the magazine’s design director.) “Very early on in my career, I developed an interest, which I’m not sure that all editors have,” says Moss, “to continue to use a magazine as a canvas to try new things. I was always interested in new story forms—always. [It] just kind of was a fetish, almost.” This book, says Moss, made use of some of those magazine tools. “A reader comes to a book with different sets of expectations, but can we push it?” asks Moss. “If I had done it as straight text, I think the book would be much less interesting, but also it would not feel as much an expression of me.”

When I recently met Moss at a downtown restaurant not far from New York’s old office, it had been five years, almost to the day, since he’d stepped down from the magazine. Under his leadership, New York didn’t just navigate the transition from city weekly to digital publisher; it thrived in it, launching a number of online verticals—The Cut, Vulture, The Strategist, Grub Street, Intelligencer—that function as stand-alone properties, with some also serving as sections in the print magazine (which, since 2014, has published every other week). Moss, like the magazine he edited for 15 years, is obsessive and curious, with a twinkle in one eye and knowing skepticism in the other. 

“I had gotten older,” Moss, now 66, says after I ask why he left New York. “There was more and more that the editors were bringing me that I didn’t relate to, didn’t understand, because they came out of the experience of a younger generation of staff members, which would translate to a younger generation of readers,” he adds. “The only way I know how to edit a magazine is by editing for myself.” And he was sick of the responsibilities that came with being a boss, particularly the one requiring him to spend a lot of time on business strategy. “I was still doing journalism, but I wasn’t doing it enough,” he says. A bicycle accident in 2017 also put things into perspective. “For the first time, I imagined myself being fragile, perishable. So I felt I had another chapter, but not that many more,” he explains.

Does he miss New York? “I miss the people generally. I miss specific people specifically. I miss the ‘let’s put on a show’ aspect of it,” says Moss. He doesn’t miss the news cycle much, though, and has enjoyed being “liberated from the gerbil world,” as he puts it. Still, his brain remains in editor mode. “It forms everything into stories and almost everything into narrative. And so I don’t turn that off,” he says. “And I’m glad I can—he never listens to me, but I can just write a little note to [New York editor in chief] David Haskell and say, ‘Hey, have you thought of this?’” He’s also been consulting for other journalism operations, including The Washington Post’s Opinions section. (Editorial page editor David Shipley is his friend and former colleague.) “I’m kind of like a constant, relatively well-informed focus group,” Moss says of his role.

Otherwise, he’s been enjoying his free time. “I go to museums. I go to movies. I hang out with my friends. I go to painting classes,” Moss says. “My quixotic painting thing is really a big part of my life. I don’t want to pretend otherwise, even though I am embarrassed.” (So much so that he has yet to share his work publicly.)

I ask him if he’s found the answer he set out for. “I’ve gotten one part of the answer, which is that the work of art is the work…. It’s the most banal observation, but that it’s not about the thing you make; it’s about the making. It took me three years to figure out that that was actually true,” he says. “And let me tell you, it has changed my life.”