685: David Epstein - The Freedom Trap, Narrative Values, General Magic, The Nobel Prize Winner Who Simplified Everything, Wearing the Same Thing Everyday, and Why Constraints Are the Secret to Your Best Work

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The Learning Leader Show with Ryan Hawk

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My guest: David Epstein is the #1 New York Times bestselling author of Range and The Sports Gene. A former investigative reporter at ProPublica and senior writer at Sports Illustrated. His new book is called Inside the Box: How Constraints Make Us Better.

Notes

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Key Learnings

The easier move is to let it go. David found a factual error in Ryan's new/my new book. David was supposed to read it and write a blurb on it - but went further and challenged a factual error. The kind move, what great leaders actually do, is being willing to point things out, even if it could cause a little friction.

There is such a thing as too much autonomy. After Range became mega viral, David optimized for autonomy. He individualized his whole life. He no longer was writing about what others assigned him. A year later, he realized there is a thing as too much autonomy. He missed the structure of a work day, the deadlines, the annoyances of working with other people's schedules. This total freedom ended up feeling terrible. "The great thing about being committed by your own choice is that you can stop wondering how to live and start living." This quote by Mihaly Csikszentmihalyi hit David when he was on a dating app for book topics, just swiping and swiping. That day he said, "I'm really interested in constraints. I need some myself. I'm writing a book proposal on this." Two weeks later he was 10 times more interested because he decided to dive into it.

Cal Newport says "system shutting down" at the end of his workday. It seems silly, but when you have all that freedom, you need something to close the workday so you can recover and be ready for the next day.

Your brain is made for preventing you from having to think whenever possible. Cognitive scientist Daniel Willingham says thinking is energetically costly. So when your calendar is too open, all you'll do is what's convenient. Your brain will be lazy. The path of least resistance.

The mere urgency effect: when schedule and structure is too open, people do things that seem urgent even if they're unimportant. When you're too unstructured, you end up doing huge volumes of low value stuff just to have checked off doing something.

What David's workday looks like now:

• Batching work: people at work check their email on average 77 times a day. The way people are usually doing that is they're toggling all the time between email and something else. When you do that, it lowers your productivity and massively increases your stress.
• David doesn't start his day with his inbox. He'll check it at the end of the workday because emails can take him away from the most important work at the beginning of the day.
• Stress + Rest = Growth. The workday ends when David's son gets home. When writing, you have to program in rest, just like you would if you were an athlete in training.

Daniel Kahneman said writing "Thinking Fast and Slow" was the worst few years of his life. David had lunch with Kahneman and praised the book. Kahneman said, "Never again." He said it was so isolating. He was used to working with a partner or multiple partners and colleagues. He felt so isolated that he said he'd never write a book again, or if he did, he would write it with somebody else. And that's what he did. And David could empathize with that.

David made a one-page architectural outline for how "Inside the Box" would look. If it's not on that page, it is not in the book. He wrote as small as possible to try to defeat his own system. The book's 20% shorter than his other two. He thinks it's much tighter writing. He was so much more efficient that he doesn't feel nearly as burned out.

After a mega hit book, two things matter: (1) A lot is out of your control, and (2) Identify as a craftsman. David's colleague at Sports Illustrated told him, "If a book about genetics and vampires comes out the same day, you're screwed, and there's nothing you can do about it." He was right. But David very strongly identifies as a writer now, as a craftsman. He's taken fiction writing courses just to learn about craft. With Inside the Box, he did a structural experiment that he found so engaging because he was focused on the craft itself, not just the commercial outcome.

"Docendo discimus" - by teaching, we learn. This is a quote from Seneca. If people think they're going to have to teach certain material, they organize it more coherently in their own mind. They start pulling out main ideas and attaching different ideas together. Teaching it is even better, but just making someone think they're going to have to teach it makes them learn in a much more coherent way.

Narrative values: the recurring themes that give coherence to a life. David went back and looked at his life and identified: curiosity, open-mindedness, diligence, and resilience. Now that he's started telling his story in that way, it shows up everywhere. But going forward, he also wanted some things in his story that he didn't have. So he identified forgiveness in particular because that has not been a strong suit for him.

Ben Helfgott: the only living Olympian to have survived a concentration camp. Almost everybody in his family was killed in the Holocaust. He just preached forgiveness all the time. When David saw what Ben did, these petty grudges he's holding are nothing. You're just poisoning yourself when you hold these grudges. So David decided he wanted forgiveness to become one of his narrative values.

Herbert Simon won the highest award in computer science, psychology, and the Nobel Prize in economics. His quote serves as the epigraph of the book: "It is a myth, widely believed but not less mythical for that, that people are most creative when they're most free."

Simon coined the term "satisficing." It's a combination of satisfy and suffice. It means having good enough decision rules. He contrasted that with maximizing. From a mountain of psychological research, it is almost always bad to be a maximizer. Maximizers are less happy with their decisions, less happy with their lives, more prone to regret. There's not much evidence they actually make better decisions most of the time.

Simon was a proactive satisficer. He said you need three sets of clothing: one on your back, one in the wash, and the next one ready to wear. He simplified all the decisions in his life so he could save cognitive bandwidth for the really important ones. He famously said, "The perfect is the enemy of the good."

Choose when to choose. Choose when to save and when to use your cognitive bandwidth.

Good enough doesn't mean you have low standards. It means you're saving your bandwidth for the most important things.

"How you do anything is how you do everything" is completely wrong. This is one of David's least favorite quotes. It's wrong. Herbert Simon did the same mundane thing, the same breakfast every day, the same socks, so he could crush it in his work. He wasn't doing everything the way he was doing his work.

The Fredkins Paradox: We spend the most energy on the least important decisions because we agonize when the options are really similar. General Magic: They invented the smartphone in 1990. The iPhone would not exist without them. They had infinite degrees of freedom. They could do anything. When the device came out, it didn't solve a clear customer problem. It had a 200-page manual. They sold 3,000 units in the first six months.

Meanwhile, people inside General Magic who bit off much smaller chunks had success. One low-level engineer started Auction Web. His bosses said no, too small. He left and changed the name to eBay. Another created Graffiti. He said "I'm going to solve a clear customer problem. Busy professionals want contacts and calendars on the go." He did just a calendar, contacts, and a memo pad. That was the Palm Pilot. By doing way less. By doing something, not everything.

Tony Fadell (the "podfather"): "If you don't have constraints, make up constraints."

Bill Gurley said, "We have a saying in venture: more startups die of indigestion than starvation." When Tony co-founded Nest, he made his team work inside a literal box. He made them prototype the box before they had the product. If it didn't fit in that box, it was not a priority.

Reflection Questions

1. What area of your life has too much freedom right now? Where could you add a constraint (a deadline, a ritual, a boundary) that would actually make you more productive or creative?
2. If you had to pick three narrative values that run through your life story, what would they be? Are they the ones you want, or do you need to add an aspirational value like David did with forgiveness?
3. What's one decision you're maximizing (trying to find the perfect choice) when you should be satisficing (good enough and move on)? How much time and energy would you free up if y