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The Daily Stoic

Why Struggling Is the Point | David Epstein

07 Jun 2026

Transcription

Transcript generated automatically by AI and may contain errors.

Chapter 1: What are desirable difficulties and why are they important?

0.031 - 28.943 Ryan Holiday

Welcome to the Daily Stoic Podcast, designed to help bring those four key Stoic virtues, courage, discipline, justice, and wisdom into the real world. You think you want everything to go your way. You think you want them to be easy. You think you want green lights. And I'm not sure that you do. Look, I'm not saying that some challenges aren't frustrating, that obstacles aren't painful.

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29.523 - 52.875 Ryan Holiday

But obviously, a core idea in Stoic philosophy is that some forms of struggle and adversity make us better. Psychologists call this desirable difficulties. And it's actually the theme of today's conversation with the great David Epstein. We broke up his episode into a handful of sort of chunks rather than doing sort of one long episode.

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52.915 - 76.998 Ryan Holiday

And if you read his book, Range, which I loved, his book, Sports Gene, which is really good, or his new book, Inside the Box. I think you'll see it's a theme of his work, how certain kinds of limits and friction and challenges can sharpen us rather than hold us back. And that's what we're going to talk about here. An obstacle isn't always in your way. Sometimes it... is the way.

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77.659 - 96.958 Ryan Holiday

And I think you're going to like this conversation. As I said, David Epstein is one of my favorite writers. I rave about his stuff all the time. He's a former reporter at ProPublica, a senior writer at Sports Illustrated, and he's written for many years about performance, human potential, learning, and hidden advantages, sometimes in breadth and sometimes in specialization.

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96.978 - 118.971 Ryan Holiday

You can follow him on Instagram at David Epstein. You can get signed copies of Range and Inside the Box online. But let's get into this idea of desirable difficulties. You know what silently kills sales teams? The inability to see what's happening in their pipeline. And part of the reason they can't do that is because they use software or CRM that's so complicated that people don't even log in.

119.011 - 139.342 Ryan Holiday

I do this all the time. You get some tool and you're like, I'm going to use it. And then... then it's so complicated you don't use it. And that's where today's sponsor, Pipedrive, comes in. It's an easy, intelligent CRM loved by growing sales teams, and most important, actually used by them. Pipedrive gives your team one complete, trusted record of every customer and deal.

139.783 - 162.912 Ryan Holiday

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162.892 - 181.633 Ryan Holiday

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181.734 - 198.834 Ryan Holiday

And some of the kids, I don't know if I call them kids, but some of the Gen Z kids on my staff had to tell me about it. They really love it because you can find vintage stuff and collectible stuff online. I was looking at some videos of people selling vintage band tees and records and watches. And it's real people selling.

Chapter 2: How can challenges enhance our learning process?

424.178 - 438.86 David Epstein

Instead of just executing procedures, they're forced to match a strategy to a type of problem. And when they all were tested on new problems— The mixed practice group blew the block practice group out of the water. It was like the equivalent of taking a kid from the 50th percentile and moving them to the 80th.

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439.441 - 458.933 David Epstein

They studied the same thing, but in an order that made it more difficult for that one group that kind of forced them to do the hard mental work. One you might like, in particular, it comes from some of Seneca's wisdom is docendo discomus, which is by teaching we learn. So there are studies where people are told that they're going to have to teach some material.

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458.913 - 472.788 David Epstein

And even if they don't, the best is actually if you do have to teach it. But even thinking you're going to have to teach it causes you to organize it more coherently in your mind. And so you're much more attentive to like, what are the main ideas? How are things connected?

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472.828 - 480.256 David Epstein

And so that, you know, that old wisdom of like, you learn what you teach turns out to be now, centuries later, scientifically validated.

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480.317 - 488.025 Ryan Holiday

You're understanding it going into, you're going to have to understand it at a level that allows you to explain it to someone else. So you can't just sort of, oh yeah, yeah, I think I get it.

488.005 - 498.689 David Epstein

Yeah. So you're not just thinking of like memorizing things. How can I coherently structure this? And the weird thing is you'd think, well, I can just I can just do that. Right. I'll just I'll just coherently structure this time. But it just doesn't work.

498.709 - 498.89 Ryan Holiday

Yeah.

498.91 - 505.525 David Epstein

You know, you actually have to put yourself in that spot of I'm going to have to teach this. So it's a good idea to if you really want to learn something to try to teach it to someone.

505.505 - 526.288 Ryan Holiday

When Theodore Roosevelt was president, he would take his kids on these walks actually through Rock Creek Park, which I know is near you. And the rule of the experience was if they ran into an obstacle or impediment, they were not allowed to go around it. So if they came to a river or a stream or a pile of rocks or a tree that fell down, they were not allowed to go around.

Chapter 3: What role do tests play in effective learning?

961.297 - 971.055 Ryan Holiday

And so you're developing reps, right? Like you're getting comfortable with an uncomfortable thing. And then when it happens in a big way, it's not unfamiliar to you.

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971.035 - 989.297 David Epstein

You just remind me of a line I probably haven't thought about in 20 years back when I was like reading Nietzsche, which I haven't read in a long time, where he says something like, gosh, I hope I don't brutalize this. It's something like, if your friend asks for a bed, give them a bed, but give them a bed that's cold and hard because life is cold and hard or something like that.

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989.497 - 998.709 David Epstein

And, you know, whatever, I would give my friend a fine bed if they came over. But the idea that you want to be prepared for this stuff, right? You don't want to be surprised when things get hard.

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998.949 - 1015.111 Ryan Holiday

Well, there's actually an idea with the Spartans where what they would do is if they were faced with this predicament, they would give their friend the comfortable bed and they would take the uncomfortable bed. The idea of exposing, forcing challenges on other people other than your kids is not your thing. role, right?

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1015.191 - 1019.761 Ryan Holiday

But the idea of, yeah, getting comfortable with cold and hard things is a good place to be.

1019.781 - 1030.945 David Epstein

I mean, I worry for sure more with my kid about adversity deficit than I do about too much adversity, for sure. They both have cause for concern, but I'm more worried that he won't have enough adversity in the early going.

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