Something to listen toGetting ahead
Don't try to change yourself all at once
A 35-minute podcast episode on how Yul Kwon took on his childhood anxiety in small steps
Why it’s worth your time
Becoming more confident at work can seem to require a personality you don't have. Yul Kwon describes a childhood of severe anxiety and how he changed it by setting himself one small, uncomfortable thing at a time and putting himself in rooms where being nervous was normal. He's candid that therapy helped too, and the first part of the conversation is a practical, generous account of how it added up.
Building confidence one small stretch at a time
- Listen to the episode.
The part about change comes first, when Steve Levitt asks how an anxious kid became a high achiever, and it runs until the break. After the break the conversation turns to how Kwon used game theory to win Survivor, which is fun but a different subject. That first part, about 15 minutes, suits a commute.
- Pick one stretch for this week.
Choose something at work that makes you slightly nervous and takes a minute, like asking one question in a meeting where you'd usually stay quiet, or introducing yourself to someone on another team. Do it once this week.
Good moments for this: before a meeting you usually sit quietly throughwhen a new role asks for a bolder youafter a meeting where you held back
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Making it work for you
Every workplace is different. Here’s what to think about before you start, and what might get in the way.
Things to think about
Kwon signed up for a drama class partly because, there, the others were likely to be nervous too. At work, a small working group, a lunch session or a volunteer role can be a gentler room to practice speaking up than the big weekly meeting.
What might make this harder
Keep the stretches small and pair them with real help. Kwon says therapy helped him enormously and he wishes he'd found it sooner, and that the small steps he took on his own still apply.
Questions people ask
What is the Yul Kwon episode of People I (Mostly) Admire about?
Economist Steve Levitt talks with Yul Kwon, a lawyer, tech leader and Survivor winner, about getting past severe childhood anxiety through small daily stretches and changes of surroundings, then about how he used game theory to win Survivor.
How do you change yourself in small steps?
Pick one slightly uncomfortable thing you can do today, do it, and pick another tomorrow. Kwon also suggests changing your environment, since that's often easier than relying on willpower.
How can I become more confident at work?
Practice in small, low-stakes moments: one question in a meeting, one introduction, one opinion stated plainly. Confidence often follows the behavior instead of arriving first.
What it says, and how it holds up
Yul Kwon's career reads like a list of things that take nerve: Marine Corps officer candidate school, law firms, McKinsey, a frozen yogurt chain, Facebook, Google, and a season of Survivor that he won. Levitt, who knew him only through work, expected to hear that school came easily. Instead Kwon describes serious social anxiety, bullying and severe OCD as a boy, and a decision in middle school that he didn't want to be the same person in five years. What he did about it was deliberately small: raise a hand in class one day, sit next to a stranger and say hi another.
What he describes comes down to a few habits. Break the change into pieces you can do today and tomorrow. Change your surroundings, since willpower on its own is a hard way to do it. Keep going when an attempt flops. Kwon is careful not to oversell: he doesn't think anyone can remake themselves completely, only that people are more flexible than they assume.
Later in the conversation he turns the same instinct on his career, calling himself a quitter and describing what he calls a portfolio theory of his career, optimizing for different things at different times because no single job gave him everything. He also admits he may have switched too often. His check on whether change is working is gentler than a five-year plan: picture the person you were four years ago looking at you now, ask what they'd think, and whether you'd be happy with that. Small stretches tend to help most with fears you can practice against, and they can do much less in a workplace that punishes the attempt. If speaking up on your team gets you talked over or marked down, that's more likely a problem with how the team runs than with your nerve, and more courage on your part may not change it.
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Picked by Truest and described in our own words. The original belongs to its creator. Last updated October 9, 2026. We sell a career membership; where that’s relevant above, we say so.