Michael Lewis on the Crafts of Writing, Friendship, Coaching, Happiness, and More (#427)

“The secret to doing good research is always to be a little underemployed. You waste years by not being able to waste hours.”
— Amos Tversky

Michael Lewis is the best-selling author of many books, including Liar’s Poker, Moneyball, The Blind Side, The Big Short, The Undoing Project, and The Fifth Risk. Both of his books about sports became movies nominated for Academy Awards, as did The Big Short, his book about the 2008 financial crisis. He lives in Berkeley, California, with his wife and three children.

His critically acclaimed podcast, Against The Rules, returns with season two on Tuesday, May 5. Last season, Michael explored the attack on referees in sports, financial markets, newsrooms, courts of law, and the art world.

This time around, Michael focuses on coaches: why the role of coach has expanded beyond sports in American life and why everyone seems to love coaches. Each episode examines a different kind of coach. From money coaches and voice coaches to college coaches and even the one who changed his own life, Michael delves deep inside the vast world of the coach. Can a good coach level the playing field? What is the secret to effective coaching? What role do coaches have in creating unfairness? Can everyone be coached or are some people beyond help?

Please enjoy! 

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform.

This podcast is brought to you by UCAN and Readwise. More on both below. 

#427: Michael Lewis on the Crafts of Writing, Friendship, Coaching, Happiness, and More


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What was your favorite quote or lesson from this episode? Please let me know in the comments.


Want to hear an episode with another iconic writer? Listen to my conversation with Malcolm Gladwell in which we discuss routines, habits, and tools, how to make your stories relatable, and why he eats as little as possible in the morning. 


  • Connect with Michael Lewis:

Website | Podcast


Note from the editor: Dear listeners, the timestamps will be added shortly.

  • A story about the first time I was (kindly) rejected by Michael Lewis.
  • How handing in a book report almost got Michael kicked out of middle school.
  • What Michael’s thesis advisor at Princeton thought about his writing as an undergrad.
  • How did Michael develop the ability to write without studying it directly?
  • What was it about writing that got Michael hooked enough to keep submitting content to various publications even when he’d get more rejections than acceptance?
  • Was it a hard decision for Michael to give up a high-paying job at Solomon Brothers to gamble on a career as a first-time author in 1989?
  • Unintended consequences: Michael wrote Liar’s Poker as a cautionary tale with humorous overtones, but a lot of young people entering the workforce read it as a how-to book.
  • In his own life, how does Michael think about ambition? By what metric does he measure success?
  • Maximizing self-satisfaction, optimizing the writing process, and learning to sing.
  • When you’re a developing writer, there’s no underestimating the value of having an honest, earnest editor on your side who isn’t afraid to give you impolite feedback — whether it’s Michael Kinsley or John McPhee.
  • On the merits of productive laziness.
  • One good question Michael asks himself to help determine if a potentially worthwhile project should proceed.
  • An example of how feeling an obligation to the material resulted in a project that grew from an idea for a few pages in a magazine about baseball to a book about the way markets value people: Moneyball.
  • How has Michael self-consciously cultivated the narrative that he’s “one of the happiest people” anybody knows (including fellow writer Walter Isaacson), and how does this direct his interactions with others?
  • Since Michael’s perpetually cheerful disposition disarms conversations that invite complaints before they even begin, what conversational prompts emerge instead?
  • Who are Daniel Kahneman and Amos Tversky — the subjects of Michael’s book The Undoing Project — and what has he taken away from studying their somewhat tempestuous relationship?
  • Among the small group of friends with whom Michael shares his work in progress, how does he phrase his requests for feedback?
  • Michael gives us a sneak peek of what we can expect from the upcoming episode of his Against the Rules podcast in which he interviews The Inner Game of Tennis author Timothy Gallwey and delves into why the coaching methods outlined there can be applied across disciplines — from playing tuba to hitting a softball.
  • Now that he’s dipped his toes in the waters of podcasting, are we going to see a decrease in Michael’s literary output?
  • What does Michael’s exercise regimen look like? How does pandemic exercise differ from non-pandemic exercise?
  • Books Michael has gifted most.
  • What would Michael’s billboard say?[00:00]
  • Parting thoughts.