For Michael Lewis, literary stardom was never in plan, mostly because there was no plan.
“I didn’t know what I wanted to do with my life when I was in college,” the bestselling author of Moneyball, The Big Short, and The Blind Side, said speaking at the National Book Festival in Washington, D.C. on Sept. 2. “When I got out, I didn't have any plan … It didn’t occur to me that I would have to.”
An art history major at Princeton who was in search of a job, Lewis found himself somewhat dubiously moored in a port wholly foreign to the listless Liberal Arts student: Wall Street. Tapped as a bond salesman at Salomon Brothers in the 1980s, Lewis witnessed the the bull rush of the stock market boom that defined the decade and fueled his first book, Liar’s Poker.
His latest, The Undoing Project: A Friendship That Changed Our Minds, explores the human nature of decision-making through the work of a pair of Israeli psychologists, but its development is the result of a familiar charmed fortuitousness that followed Lewis’ career. Here are three insights on writing that Lewis shared with the substantial crowd.
1. Know Your Audience
Attracted to the craft following his senior thesis at Princeton, Lewis said he began writing by first pitching magazine pieces.
“I didn't know what I was doing,” he said. “I didn't know anybody who wrote for a living. It was a quixotic enterprise.”
Lewis said he thumbed through the Writer’s Market (WD Books) for the addresses of editors and publications he could pitch, eventually landing in travel magazines.
“For some reason, I got into my head that the easiest thing I might be able to break into was in-flight magazines,” he said. “I was volunteering at a soup kitchen on the Bowery [in New York] and I thought the street people were so interesting. I wrote a piece about New York homeless people, and I sent it to all of the in-flight magazines in America.
“I remember I got this letter back from Delta Airlines and it said, ‘You know, we kind of like the piece, but you do understand what we are in the business of doing. We’re trying to get people to go places, not flee them.’ So it took me a while to figure out the market.”
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2. Be Lucky
Lewis credits a significant portion of his success to sheer luck.
“There is an incredible serendipity in my career,” Lewis said. “The fact that I wanted to be a writer and I got this job in the very best place on Earth to write about Wall Street in the 1980s. I was given the leisure by my parents to fart around for two or three years after college. If they hadn’t done that, I doubt I would have become a writer.”
Penning columns about Wall Street under the nom de plume of his mother’s maiden name, Lewis began stacking up clips when he got a phone call from Ned Chase—famous book editor at Simon and Schuster and father of actor Chevy Chase—who had uncovered Lewis’ identity and advised him to write a book, which became Liar’s Poker.
Perhaps even more auspicious was how the author discovered the central narrative for his book, The Blind Side. Pitching a story to The New York Times Magazine about the teacher who changed his life, which happened to be his high school baseball coach, Lewis traveled to Memphis to interview his old teammate, Sean Tuohy.
While talking with Tuohy, Lewis encountered Michael Oher, a homeless teen and gifted athlete who would become the focus of a book about the rise of the left tackle in professional football.
“It is typical of how I find stories in that you’ll see that it’s just chance. I chance into stories,” he said.
3. Don’t Fear the Alien
Coincidentally, shortly after meeting Oher, the success of Moneyball had made Lewis acquaintances with several NFL executives, who were interested to see a version of Moneyball written about football.
Because of the league’s salary cap and free agency, the author discovered that among the highest paid positions on the team was that of left tackle, an insurance policy to protect the blind side of the quarterback.
By this time, Oher’s natural talent at the position had been discovered by college coach Nick Saban. So Lewis saw the elements of a story: an undervalued teen with highly valued talents fostered by the care of a mother.
“Once I realized that, I had a story. And this always happens, I had it for six months before I had the nerve to say, I’m going to write it,” he said. “I often think there is someone better to write this. There's always some part of me that thinks it’s alien to me, so I really shouldn’t be the one to do it.
“But the truth is the fact that it’s alien to you is why you should do it. Because it enables you to get across to other people to whom it’s alien the stuff about it that’s interesting.”