Of the four people who have won two Pulitzer Prizes for fiction, only one has done it with back-to-back novels: Colson Whitehead. The first came in 2017 for The Underground Railroad, a genre-defying reimagining of slavery in which the titular railroad is rendered as a literal, subterranean train system.
The second came three years later, for The Nickel Boys, a stark and devastating account of abuse at a segregated reform school in Jim Crow–era Florida, based on the real-life Dozier School for Boys. That novel cemented Whitehead’s place as one of the most important American writers of his generation. It also nearly broke him.
Writing The Nickel Boys, Whitehead later said, was emotionally depleting. The last two months of the process left him depressed, “staring off into space” after each workday. He immersed himself in the stories of the boys who had lived and died at Dozier, studied photos of the school, and spent his days writing about cruelty, violence, and the failure of America to reckon with its own past. He never visited the site—by the time the characters came to life on the page, the idea of going revolted him.
That combination—historical rigor and creative freedom—is a hallmark of Whitehead’s work. His books jump across genres and tones: he’s written a satirical coming-of-age story (Sag Harbor), a post-apocalyptic zombie novel (Zone One), a comic noir crime caper (Harlem Shuffle), and a nonfiction book about the World Series of Poker (The Noble Hustle). He’s written fiction and criticism, horror and humor, fantasy and reportage. “You can do anything if you’re good enough,” he often says. The only rule he sets for himself is: don’t write the same book twice.
Still, certain themes recur. In book after book, Whitehead returns to questions of injustice, identity, survival, and what it means to live in America. “There are corners of America that we never see, never think about and never hear about,” he told 60 Minutes. “There are people walking around with stories no one cared to listen to. And if we put the effort in, maybe we can discover them.”
He nearly didn’t become a novelist at all. After graduating from Harvard, Whitehead got a job at The Village Voice, fact-checking and freelancing. His first attempt at a novel—a theoretical story about a Gary Coleman–like child star—was rejected 25 times. “It sucked,” he later admitted. But the experience convinced him he had no other choice. He wrote another novel, and another, and another.
Over time, he built a reputation as a daring and unclassifiable writer. Then came The Underground Railroad, and his career exploded. The novel spent 49 weeks on the New York Times bestseller list, won the National Book Award and the Pulitzer, and was adapted into an acclaimed limited series by Barry Jenkins. It sold more than two million copies.
Success hasn’t made writing any easier. “Every book is terrifying,” Whitehead says. “You have your hopes and wishes for the project, and then your limitations as an artist. And if you’re lucky, you find a path in the middle.”
He still approaches each new book the same way. First comes the idea, often sparked by a newspaper article, a photograph, or a fragment of history. Then comes the research—books, archives, maps, conversations with his mother. He outlines meticulously, always knowing the ending before he begins. And then, finally, the writing.
Colson Whitehead’s daily writing routine
“I try to write eight pages a week,” he told The Toronto Star. “It could be Monday, Tuesday, and then Saturday and Sunday. Or Thursday through Sunday. But eight pages—that’s 30-something a month. In a year, that’s a good amount.” He works at home, where he can pace, nap, cook, and listen to loud music. Cafés don’t work, he jokes: “You can’t nap or weep spontaneously.”
The first line is critical. “Even in death the boys were in trouble,” begins The Nickel Boys. “The first time Caesar approached Cora about running north, she said no,” opens The Underground Railroad. These sentences often come months in advance, jotted down on his phone at 4 a.m., waiting for the right book to arrive.
The voice of the narrator takes longer. Sometimes it clicks quickly—Whitehead says he found the tone for The Nickel Boys and The Underground Railroad almost immediately. Other times it takes 80 or 90 pages to figure out. Once he has it, he goes back and rewrites from page one to bring the early chapters in line with the new voice. “Maybe the narrator is very expansive,” he says. “Maybe very curt. But once I know, I know.”
He doesn’t write every day, and he doesn’t believe in romanticizing the grind. “Some people say write every day,” he says. “That seems sort of fascistic and not very fun.” Instead, he alternates between periods of high productivity and long stretches of doing nothing—watching movies, cooking, reading comic books, playing video games. “I’m the most productive, laziest person I know,” he says. “And that’s the greatest compliment.”
“I always wake up, look at my computer, and say, ‘Don’t screw it up today, Colson,’” Whitehead told The Toronto Star. He writes from home, where he can nap, cook, pace, and blast music from a 3,000-song playlist. He outlines each book in advance and always knows the final page before he begins. He writes in spurts—four or five hours a day, aiming for eight pages a week. “Writing every day,” he says, “seems a little joyless.” Some books come easily. Others don’t. But once a book is underway, he disappears into it: “I don’t go out. I forget to eat. I sleep very little. And once it’s done, I veg out and play video games for six weeks.”
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