Quixotic Quagmires

The Malcolm Gladwell Interview His books were some of the first I ever read because we had copies of Outliers, Blink, and Tipping Point all around my childhood home. Then when I was getting into writing, I learned how to open essays by studying his New Yorker profiles. So I wanted to ask him how he tells stories, makes his audiobooks, and manages to be such a prolific writer. Timestamps: 00:00 Introduction 00:38 How are puzzles similar to writing 04:55 Why specificity matters more than knowledge 12:28 How Malcolm wrote his new book 17:02 Stop readers from leaving 19:28 What he learned from John le Carré 23:58 What he learned from Michael Lewis 27:15 You should engineer your curiosity 30:59 Why memory is underrated 33:37 Give readers a big why 38:15 How to make readers cry 41:29 What audio formats mean to him 45:57 Leave room for uncertainty 48:37 Pace your story like a runner 53:02 Say more with fewer words 55:24 Malcolm’s advice for beginner writers Here's what stuck out to me: 1) “I will turn down a story if I do not think it has intrinsic interestingness.” 2) Most of Malcolm's writing life doesn't revolve around sitting at the keyboard: “Most of my days are spent either reporting or arranging to report.” 3) Writing books requires you to pace yourself. It's like running: “In mile one, you could run much faster, but you deliberately don’t because you want to last for mile ten.” 4) "Other people have stories. Go and find out what they are." You don't need to come up with stories on your own if you're curious enough to ask questions and wait patiently until a story emerges. Doing so removes the pressure to manufacture a story from a blank page. 5) Malcolm's spent tons of time with Paul Simon and was repeatedly struck by the depth of his reference archive. He's like a walking LLM, with unlimited resources for summoning facts, riffs, and musical ideas. 6) 'Granularity' is the thing you want from the people you interview for a book. The most important person won't always give you that. Sometimes, it's the person on the front lines or the periphery of a situation. 7) Audiobooks shouldn't quote people the author interviewed. They should have the original tape from the original interview so the listener can hear it right from the source. He says: “Why bother reading someone’s quote when it’s audio? Play the tape. Let’s hear them speak.” 8) Audiobooks are so core to his work that he thinks about the audio experience before he even writes the first word of the book. 9) Sometimes, in an audiobook, the emotional register is better set by a song than prose. That's why Malcolm's new audiobook opens with music by Drew Holcomb. In 2.5 minutes “he accomplishes something I couldn’t do in the book.” 10) Delay your conclusions when doing research: “The penalties associated with premature conclusions are so large.” For example, Gladwell regrets how quickly he embraced the Broken Windows theory as an explanation for crime in New York. 11) You don't need to be good at every part of writing in order to be an outstanding writer. For example, if you have a strong voice and lively characters, you don't need an elaborate plot. He says: "Just give us enough plot to activate another part of our brain.” The point is that every part of your book should support the thing you're uniquely good at. 12) It was interesting to hear Malcolm reflect on his earlier writing and confess that he got too cute with coming up with fun names for things. 13 Is laughter slightly overrated in our current culture? Gladwell says: "Getting someone to laugh is far easier than making them cry.” 14) Interview your parents before they die: "Think about how many people, when asked about their parents after they’ve passed, say, 'I never talked to them about that. I wish I had.'” 15) If Malcolm were teaching a class on writing, he'd make kids skip class in order to sit down with their parents, record them speaking for 45 minutes, and then run the conversation through an AI transcription service. Then they'd bring the transcript back to class and write a short article about the conversation. "That's where we’d start on day one. We would then build from there." I've shared the full conversation with @Gladwell below. If you'd rather watch the full thing on YouTube, or listen to the episode on Apple / Spotify, check out the reply tweets. Enjoy!