Michael Lewis is the New York Times bestselling author of multiple books of nonfiction, including Moneyball, The Big Short, Flash Boys, and most recently, The Undoing Project. At Authors@Wharton, a speaking event with award-winning Wharton professor Adam Grant, Michael offered this sage advice on writing and storytelling.
Rule #1: Interesting things happen to people who can tell interesting stories about themselves.
Developing a narrative impulse about your own life is incredibly enriching. Most people don’t. Most people walk in a room and don’t see the story of their life. If you were observed closely, you are a very good character. A lot of people are good characters if they’re watched closely. So watch.
Rule #2: If you want to tell good stories about just your own life, observe it.
Observe what’s around you, take time. Back off it a little bit. Have some detachment about it. People think that important people are busy, so if they’re busy they must be important. That’s not a good strategy. You can’t be really busy all the time and notice the things that lead to stories.
Rule #3: Pay attention to the way you tell the story of your own life.
If you are always the victim, or something bad is always happening to you, you might notice patterns. I’ve found the happiest people and the best storytellers often find gratitude in life. You can find your good fortune if you look for it.
Rule #4: Admit contradictory evidence.
Cheap storytelling is a cheap pattern writing machine. If there’s something that violates the pattern, if you incorporate it into the story, often it makes the story even richer. It’s at first blush uncomfortable, because you had this neat story. Sometimes the better stories are messier. Don’t be afraid to see the complexity. For a story to rise to the level where I want to tell it in print, it’s got to have a bunch of ingredients that anecdotes about your life don’t necessarily have to have. Although the ability to tell the anecdote is a requirement to tell the story in the first place, it’s got to have a character who interests people, who they want to follow.
Rule #5: If you create a character who the reader will follow, it’s amazing where they will follow him.
They will learn about collateralized debt obligation, if they get interested in Steve Eisman or Michael Burry. They will learn about baseball statistics, even if they have no interest in baseball, if they are interested in Billy Beane or Scott Hatteburg or Chad Bradford. Be very alive to the situation in which the character finds themselves. All these books start with a character in a situation that I find interesting.
Rule #6: Tell stories you are passionately interested in and see important meaning in.
If you’re telling a story just to sell something, and you’re not actually interested in the story, that will quickly become apparent to the people who are listening. But if you yourself are interested and see some important meaning in it, people want that, and they will listen. The test for me is I always have a feeling: the feeling this story is so important that I have an obligation to it. I’ve been lucky to be in a situation where I’ve been gifted this material. I now have the job of not screwing it up in print. That’s the spirit in which I go into every book. I’ve got to have that because it gets miserable in the middle of it. They’re a pain in the ass to do. You have to realize there’s some higher obligation behind this.
Rule #7: Don’t think in terms of perfection, think “is it jumping off the page?”
When I’m editing, I try to edit on paper, on a phone, on my computer, because each time you see it differently. I’ll have a couple glasses of wine and then read it, that really helps. It’s just different states of mind. Is it alive when you’re seeing it fresh?
Rule #8: Have the nerve to be yourself—you can’t learn voice.
You can’t be someone else. The goal is to be the best you. Stop reading [other writers’] stuff, and comparing it, because it’s going to be different anyway, right? Having the nerve to be yourself is very valuable. Even if you don’t naturally have a strong literary voice, try not to sound like someone else.
Rule #9: Figure out what you’re trying to say and don’t overtax the reader with how you say it.
If some kid came to me and said, “Give me stuff to read you think will help shape me into a better writer,” I would hand them things like George Orwell’s journalism and essays. Prose that illustrates the power of simple clarity. You want the reader to feel like you’re not wasting his time.