We spend a lot of time weighing the cost of risking too much. Jimmy Chin has spent most of his life on the harder question, which is what it costs to risk too little, quietly, for twenty or thirty years, until the years are gone.

Jimmy Chin is an Academy Award-winning director, a National Geographic photographer, and a New York Times bestselling author. He made Free Solo, Meru, The Rescue, and Nyad, he skied off the summit of Everest, and he lived out of the back of a Subaru from 21 to 28. Then he turned fifty, started looking at his life in chapters, and went looking for people who could tell him what success meant to them at the start and what it means to them now. Those conversations became his new book, Rules to Live By: How Extraordinary Lives Define What Really Matters.

Here's what we get into:

• The question Jimmy says he has been asking since he was ten years old, and why the answer keeps moving while the question never does
• What one of the world's great cellists realized in the middle of a technically flawless performance, and where it sent him afterward
• Why the founder of a three-billion-dollar company looked at his own growth numbers and felt sick, and the one sentence of his Jimmy channels at every crossroads
• The difference between a kid wanting a parent alive and a kid wanting a parent to feel alive, and what it takes to hold both at once
• What a seven-year-old said to her father at thirteen thousand feet that he is still thinking about six years later

If you have hit the season where the boxes are checked and the question underneath them has gotten louder, this one is for you.

You can find Jimmy at: Website | Instagram | Episode Transcript

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Nicholas Epley studies how people misjudge each other, avoid conversations with strangers, and miss out on life-affirming relationships. It all started when he noticed something on a silent Chicago train that changed how he thinks about the strangers he avoids and the people he loves but never calls. The thing stopping him wasn't what he expected.

Epley is a professor of behavioral science at the University of Chicago Booth School of Business, where he's spent over fifteen years studying why smart, socially wired people routinely misread each other. His research on human connection has appeared in the New York Times and on NPR, and he teaches an MBA course called Designing a Good Life. His new book is A Little More Social.

What you'll explore in this conversation:

• Why the experiment that convinced Nicholas to talk to a stranger on a silent train started with him assuming it would go badly
• The specific belief researchers found sabotages more conversations than shyness, rudeness, or bad timing combined
• What his team discovered when they photographed people's resting faces, and why it explains a train car full of strangers staying quiet
• A kind word tends to land better than a polished one, according to decades of research on how we actually judge each other. Nicholas breaks down why
• Acting more outgoing than you feel might not cost the energy you'd expect, even for people who've called themselves introverts their whole lives

If there's someone you've been meaning to reach out to, or a stranger you keep talking yourself out of talking to, this conversation makes the case for testing that instinct instead of trusting it.

You can find Nicholas at: Website | LinkedIn | Episode Transcript

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She measured everything about her illness. The measuring turned out to be part of what kept her sick.

Giorgia Lupi is an information designer and a partner at Pentagram in New York, and one of the few people alive who can take raw data and turn it into something you understand in your bones and feel in your body. In 2020, a mild COVID infection set off four years of long COVID, chronic fatigue syndrome, POTS, mast cell activation, and a level of disability that left her housebound, out of work, and eating eight foods for an entire year.

Giorgia did what she does. She tracked every symptom, every test, every prognosis, and limitation. Then she published 1,374 Days, a visual op-ed in the New York Times built from her own symptom data, and readers with chronic illness wrote to say it was the first thing they could hand to the people who loved them.

That, however, was just the beginning of a story of recovery that was about to take a wild, transformative turn. One that would find her rethinking her approach to measuring what was wrong and shifting to the opposite, realizing, all too often, that what we measure reinforces our reality.

In this conversation, you'll explore:

• The number of practitioners she saw over four years before a single one offered to coordinate her care, and what her body did in that exact moment, before any new treatment was tried
• What she took off her wrist and archived on her hard drive, after believing for years that it was the thing keeping her safe
• The first entry in the new spreadsheet she opened in 2024, and why something that small was the turn
• Why the online illness communities she went to for support sent her home more frightened every time, and what she went looking for instead
• How she started charting a different kind of data, and finding new answers that not only refuted much of the dire prognosis she’d been given, but also, slowly, brought her back to life.
• Why her working definition of recovery now, which is not the one she wrote down while she was sick, is not "getting back to normal"

A note on how we held this one. Giorgia is careful, and so are we. This is her story and not a protocol, her symptoms were real, documented in labs, and measurable, and nobody in this conversation is suggesting anyone thinks their way out of illness.

If you have ever looked fine from the outside while something underneath was quietly giving way, this is a conversation about what your body might be trying to tell you before it has to shout.

You can find Giorgia at: Website | Instagram | Episode Transcript

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