‘Underground Railroad’ Author Stops at ’Wick

National bestselling author Colson Whitehead visited the Upper School on Monday, Sept. 18, to discuss literary journeys, his life as a writer, and his National Book Award and Pulitzer Prize-winning novel The Underground Railroad.
 
Whitehead is this year’s visiting author — on campus to speak to Upper School students and faculty from both Brunswick and Greenwich Academy, all of whom read The Underground Railroad this past summer as a prelude to discussion and written exploration in English classes.
 
He joins the recent ranks of John Irving, Column McCann, and Wes Moore as distinguished and award-winning writers who’ve had their work featured at Brunswick.
 
Whitehead — childhood adorer of The Twilight Zone, comic books, science fiction, and Stephen King — considered himself a writer upon entering Harvard College in the late 1980s.
 
But there was a problem: He didn’t have one piece of writing to his name.
 
“I wore black and smoked cigarettes, but never actually sat down and found the courage to write,” Whitehead said — his self-deprecating, deadpanned sense of humor on display throughout his remarks.
 
He did finally write two five-page stories, which he used to audition for creative writing classes at Harvard, but he was rejected.
 
“That was good training for the future,” he said.
 
He claims to have gotten his lucky break after graduating and landing a job at The Village Voice, the famed alternative weekly in New York City.
 
It was there he learned the tricks of the trade, earning bylines for critiques in the television, music, and film sections. He soon felt ready to try his hand at fiction.
 
But the rejection slips stuffed his mailbox after he completed his first novel — a story exploring black imagery and pop culture in a way similar to the television sitcom Diff’rent Strokes
 
“I began having bizarre thoughts during that period, thinking I wasn’t cut out to be a writer,” he said.
 
He thought about other career paths and harked back upon his parents’ generational belief that it was “an able-bodied black person’s duty to make something of himself, to lift up the race.”
 
“As I sat in my dirty apartment, watching too much reality TV, I realized it didn’t matter if nobody liked what I was doing,” Whitehead said. “I had no choice but to start over and do it again.
 
“And it went better the next time.”
 
Whitehead read two passages from The Underground Railroad — a novel he envisioned nearly 17 years ago, after remembering a moment of his childhood, when he thought the railroad literally existed underneath the Earth.
 
“I would have screwed it up if I had written it then,” he said. “I needed to write more books, become more technically sound as a writer, and bring more wisdom of my years to the subject.”
 
The novel was finally published in 2016, adding the Carnegie Medal for Fiction, the Heartland Prize, and the Arthur C. Clarke Award to his lengthy list of honors.
 
And yet, Whitehead is quick to deny that The Underground Railroad plays a larger role in America today or that he wrote it to change the world.
 
“I write books for myself. I try to execute an idea or artistic imperative that seems compelling to me,” he said.
 
“If I’m lucky, other people understand what I’m getting at or connect with what I’m doing.” 
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