Why Struggling Is the Point | David Epstein

Summary

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Podcast Summary: The Daily Stoic

Episode: Why Struggling Is the Point | David Epstein

Date: June 7, 2026
Host: Ryan Holiday
Guest: David Epstein

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Overview

This episode explores the vital concept of "desirable difficulties"—the idea that encountering and engaging with challenges is not just unavoidable but essential for real learning and personal growth. Drawing on insights from Stoic philosophy, modern psychology, and personal anecdotes, author David Epstein and Ryan Holiday discuss why struggle shapes us, how to intentionally seek discomfort, and practical strategies for building resilience in ourselves and our children.

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Key Discussion Points & Insights

1. The Concept of "Desirable Difficulties" (04:04–07:53)

• Definition: Desirable difficulties are learning challenges that make the process slower and more uncomfortable but embed knowledge and increase adaptability over the long run.
  • “Learning tactics that make learning slower in the short term, often more frustrating, but make it stickier and more flexible in the long term.” — David Epstein (04:04)
• Generation Effect: Testing yourself before learning actually primes the brain; making mistakes boosts retention (“hyper correction effect”).
• Interleaving: Mixing different types of problems or subjects is more effective than "blocked" or repetitive practice, even though it feels harder.
  • “That group, slower, more frustrating... when they all were tested on new problems, the mixed practice group blew the block practice group out of the water.” — David Epstein (06:38)
• Teaching to Learn: The phrase docendo discimus (“by teaching, we learn”) is validated by studies showing that preparing to teach helps structure information better.
  • “So you’re not just thinking of memorizing things. You’re thinking about, how can I coherently structure this?” — David Epstein (07:43)

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2. Childhood, Parenting, and the Value of Struggle (08:00–10:44)

• Roosevelt's Obstacle Walks: TR made his children overcome obstacles rather than go around—both for physical and mental conditioning.
  • “If they ran into an obstacle or impediment, they were not allowed to go around it—they had to figure out a way to go over it.” — Ryan Holiday (08:07)
• Modern Parenting Contrasts: Discussion of "snowplow" (removing all obstacles) vs. "helicopter" parenting; parental instincts to make things easy can backfire.
  • “You went from like helicopter to snowplow. Right. Just clear the road.” — David Epstein (09:39)
• Risk and Growth: Citing Jonathan Haidt's research, Epstein notes that teens break bones less often today—reflecting overprotection rather than innate safety.
  • “A 15-year-old boy has about the same odds of breaking their arm now as a 50-year-old man. Whereas a generation ago… a 15 year old boy was way more likely because they’re doing dangerous things.” — David Epstein (09:39)
• Accepting Risk for Growth: Epstein describes consciously letting his child take some risks to promote development, with the line: “As long as you don’t break your head, yes. It’s okay. We’ll fix anything else.” (10:20)

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3. Struggle in Everyday Life — Adults Need It, Too (11:21–15:46)

• The Problem of Convenience: Modern life removes natural friction; working from home or technological solutions mean fewer real-world difficulties.
  • “I just don’t think convenience as our regnant value is actually the way that people thrive.” — David Epstein (11:21)
• Intentionally Seeking Discomfort: Both speakers describe their efforts to put themselves into uncomfortable, unfamiliar, or “beginner” situations.
  • Epstein attends dance classes with much younger people: “Not only am I older, nobody cares what other stuff you’ve done. Right. Total beginner... and it’s scary.” (13:33)
• Low-Stakes Practice: Epstein advocates “low-stakes practice for awkwardness,” like talking to strangers in elevators, to build confidence for higher-stakes challenges.
  • “Low stakes practice for awkwardness... great low stakes practice. So I’m a big fan of low stakes practice for awkwardness and low stakes.” — David Epstein (14:46)
• Avoiding "Adversity Deficit": Both express concern that avoidance of small difficulties now will leave you unprepared for real adversity later.
  • “Do you want, when that happens, for it to be the first time you are dealing with it in a serious way, or do you want to go, I deal with shit like this all the time?” — Ryan Holiday (15:16)

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Notable Quotes & Memorable Moments

• “An obstacle isn’t always in your way. Sometimes it is the way.” — Ryan Holiday (00:00)
• “The more wrong you are, actually, the more likely you are to retain the information. It’s called the hyper correction effect.” — David Epstein (04:42)
• “You learn what you teach turns out to be now, centuries later, scientifically validated.” — David Epstein (06:50)
• “It’s low stakes practice for awkwardness. Right? And I’ve always been a fan of that.” — David Epstein (14:33)
• “I worry for sure more with my kid about adversity deficit than I do about too much adversity.” — David Epstein (16:35)

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Timestamps for Important Segments

• Desirable Difficulties & Learning Science: 04:04–07:53
• Roosevelt, Parenting, and Obstacles: 08:00–10:44
• The Modern Ease Epidemic & Adult Discomfort: 11:21–15:46

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Closing Reflections

The conversation underscores that struggle, friction, and even awkwardness are not just inevitable but necessary if we want to build wisdom, resilience, and the ability to adapt. By reframing challenges as opportunities—whether in school, at work, or in our personal lives—we strengthen our capacity to handle life’s harder tests when they come.

Summary Takeaway:
Seeking out difficulty and embracing discomfort—deliberately and safely—makes us better, braver, and more adaptable humans, echoing both ancient Stoic wisdom and the latest in psychological science.

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Transcript

[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, that, 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. 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. 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. You can follow him on Instagram Avid Epstein. You can get signed copies of Range and Inside the Box. But let's get into this idea of desirable difficulties. The Painted Portrait My bookstore here in Bastrop, Texas has a porch on the back and it is painted. We actually just repainted it and then we were sort of trying to fix it up a little bit. It's been sort of an afterthought. But we try to make it a little bit nicer. And we bought some new outdoor furniture. Some chairs, a rug, some string lights, you know, just some stuff that the employees and I myself can hang out on. You know, this is the best time of year in Texas. It's cool and nice. Days are still long, but not so long. Anyways. Where'd we get all the furniture? We got it from Wayfair. Outdoor seating, grills, major appliances, storage, patio lights, rugs, decor. Wayfair is your one stop shop for home installation and assembly. Services are available for a truly seamless experience. Wayfair deals with the hard part so you don't have to with over 20 million five star reviews, you can hear from real customers before you buy. Patio season is here and these deals won't last. Head over to Wayfair.com right now to get your outdoor space ready for way less. W A Y-F A I R.com Wayfair

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[David Epstein]

Yeah, that's a term psychologists use. First, the psychologist Robert Bjork to describe learning tactics that make learning slower in the short term, often more frustrating, but make it stickier and more flexible in the long term. So things like, you know, we think of tests as only for evaluation. But in fact, before you even study something or try to learn it, you should take a test on it. You should quiz yourself. It doesn't matter if you get everything wrong. It's so. It feels terrible, but it actually primes your brain for the subsequent learning. It's called the generation effect. So when I'm with my kid, I always ask him to guess things before I tell him because it doesn't matter if he gets of course, now he makes me guess everything too. But it primes your brain to then retain the information. And the more wrong you are actually, the more likely you are to retain the information. It's called the hyper correction effect.

[Ryan Holiday]

Isn't there probably also something in Just like tests are stressful and getting comfortable, being stressed and challenged has benefits too. You know what I mean? It's not just like, oh, you're taking the test so that they can track whether you're retaining the knowledge or not. But like, life is full of tests, metaphorically and otherwise. Yes. And like, when people are like, oh, I'm just bad at taking tests, it's like, seems like you're going to have a hard time just being a person then. Yeah, because like, we all have shit that we're bad at and you have to figure out how to get good at the things that you're bad at. That for sure, for sure.

[David Epstein]

But on a tactical level, like if you take two people and you give one a half hour to study the material, and the other half hour, you know, they take a test, they know nothing about it, and then they see the answers, the retention, like a week

[Ryan Holiday]

later, they had to come face to face with not knowing a thing. And then they learned the thing after they learned that they didn't know it.

[David Epstein]

Yeah, there's some priming of your brain that's like, I don't know this, I'm ready to receive it now. And so a few of the other desirable difficulties, one called interleaving, or people call mixed practice if they want to use English. You know, psychologists, not so good at marketing their ideas, but it basically means like, if you have a bunch of things you're trying to study material, math problems, styles of a painter, whatever, instead of studying all one type at once, you should mix them all together and then instead of, it forces you to create these more generalized mental templates where you understand the structure of a problem. So to give an example, there was a randomized study that put middle school classrooms and either they got what's called blocked practice, where it's like problem type aaaaa, bbbbb, et cetera, or interleaved mixed practice, where it's like you threw all the problem types in a hat and draw them out at random. That group slower, more frustrating. They often rate their own learning lower in that kind of condition. Instead of just executing pro, 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. 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 discimus, which is by teaching, we learn. So there are studies where people are told that they're going to have to teach some material, 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? And so that, you know, that old wisdom of, like, you learn what you teach turns out to be now, centuries later, scientifically validated, you're understanding that going

[Ryan Holiday]

into it, 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. Yeah, yeah, I think I get it.

[David Epstein]

Yeah. So you're not just thinking of, like, memorizing things. You're thinking about, 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.

[Ryan Holiday]

Yeah.

[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.

[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.

[David Epstein]

Yeah, yeah.

[Ryan Holiday]

And. 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. They had to figure out a way to go over it effectively. And so he's basically just taking his kid out, his kids out on an obstacle course every day, and that. That he thought this was great for sort of physical fitness, but also kind of mental stimulation. And then, of course, it's a metaphor for life.

[David Epstein]

I love that. Next time you're in my area, I want to take you over to Boulder Bridge where I can show you an old picture. Because I went on, like, a guided nature walk in Rock Creek of Roosevelt, and there's this one kind of bouldering spot that's really picturesque where he would take people who were visiting from other countries and, like, clamber up it and then laugh at them trying to do it. So you can see people in, like, formal clothing trying to get up these rocks.

[Ryan Holiday]

He'd be like hey guys, I think we gotta take our clothes off to ford this stream. What the president. But that was his kind of thing. Is he. I think he just, he loved challenges and he loved like having to do hard stuff.

[David Epstein]

And he also lost a gold ring right by that bridge and put an ad in the newspaper. So there's like an you know a more than century old ad that's like President's gold ring lost reward and it's never been found.

[Ryan Holiday]

So that's amazing. It could still be in there.

[David Epstein]

Could. It's probably under you know, however many meters of sediment now. But yeah, it just strikes me as

[Ryan Holiday]

so different than kind of what you can instinctively want to do as a parent and then sort of culturally we do as parents which is like how do I make things as easy as possible? Like they call them snowplow. Like that's the opposite of being a snowplow plan. Right.

[David Epstein]

You went from like helicopter to snowplow. Right. Just clear the road. I mean I find this with, with my kid all the time. You know I was interviewing Jonathan Haidt for, for the book and I remember one of the stats he was telling me was that a. I can't remember the exact age but I think it was like a 15 year old boy has about the same odds of breaking their arm now as a 50 year old man. Whereas a generation ago or two generations ago a 15 year old boy was way more likely because they're doing dangerous things or whatever it is. And so since then I kind of, I'm not telling. I like not like push my kid off a ledge or anything like that. But I've internalized. Okay. I accept the increased risk that he is going to break his arm or something bad is going to happen in return for kind of letting him wander some.

[Ryan Holiday]

Yes.

[David Epstein]

And you know, maybe get hurt. I'm like, I tell him like as long as you don't break your head, yes, it's okay. We'll fix anything else.

[Ryan Holiday]

And like look, some of it's for the best. I mean my dad broke his, his neck as a kid. Like that's what you don't want to happen like that. That's because maybe I should include neck. He was on monkey bars without the, you know, the stuff at the bottom and then, and then the, you know, I'm sure no one was watching and like the idea that we were doing it well in the past is probably.

[David Epstein]

Yes.

[Ryan Holiday]

A delusional, you know, monkey bars over

[David Epstein]

concrete that's like 20ft high.

[Ryan Holiday]

Yeah but, but yeah. Are your Kids experiencing discomfort and struggle. And then you can see it clearly how it's key in the. Your kids development. But what about you? Where, where, especially in a world where you can get everything delivered, you know, you can, you can, you know, you can so easily specialize all the ways that we just sort of naturally and almost gravitationally just remove the constraints and difficulties that, that by the way, you're struggling and getting better for having to

[David Epstein]

deal with everything is so convenient. Right. It's like if you're working from home too, right. As I do. It's like everything and everything is super convenient. But I just don't think convenience as our regnant value is actually the way that people thrive.

[Ryan Holiday]

If you're going to eliminate inconvenience in one area, that ought to be with the idea that you are struggling. You are, you are finding other places more meaningful or significant ways to struggle elsewhere.

[David Epstein]

Totally. Once again, once I got on my own individualized schedule, because I don't really have. I ceased to have colleagues when that happened. I didn't realize how much I would miss that. So one of my practices in reeling back my excessive autonomy, I guess you'd say, was I'm like, I am not having enough embodied experience with strangers.

[Ryan Holiday]

Yes.

[David Epstein]

So I started going places. I mean, I started going these like dance meetups and class, you know, just to be somewhere with strangers again.

[Ryan Holiday]

Here's one I found that's gonna sound a little humble, braggy, but I was like, found I was not going into rooms very often where I was not like a special person. Like, it'd be like, hey, I'm. I'm meeting this person. Like, this person is meeting me in the lobby to take me upstairs to the thing where everyone knows where I'm going to be and then I'm introduced. I wasn't like in a lot of. There's an awkwardness to that, to be sure, but I wasn't in a lot of like, awkward social situations where I was like, I come and I'm like, hey, I'm not sure what I'm supposed to do, you know, like. And so like, one of the reasons I like, okay, my kid just started to lacrosse, so it's like, I gotta go do that for him. And we're like, hey, we don't know what to do. Like, how do you. How are you in those situations where there's social discomfort and unfamiliarity and you're normal? You're the one that doesn't fit in. And then you have to figure out how to handle those situations and Then you become a person who can handle those situations. And if you don't do it, you become conversely the person who can't handle those kinds of situations. These are very unfamiliar and uncomfortable for you.

[David Epstein]

Highly recommend some beginning dance classes. I have to say, you go in there like I went in. It's like I probably single handedly raised the average age by like five years.

[Ryan Holiday]

Oh, this is a kids dance class.

[David Epstein]

Younger people, you know, 20s, most.

[Ryan Holiday]

I thought you would lower. I thought it'd all be old people who are retired and doing salsa or whatever.

[David Epstein]

No, no shuffling. So I got interested in it because I watched a documentary. I mean, I've always liked, I like dancing in general. But this kind of dancing was created in crowded clubs in Melbourne, Australia, because people wanted to be able to change directions and do stuff in a really small space. Which is probably why it's good for like Instagram because you're going back and forth the same space. And so I showed up these things and it's like, not only am I older, nobody cares what other stuff you've done. Right. Total beginner. And it's scary. Like I don't even know the etiquette, you know, warming. What do I. What do you wear? Yeah, but it's also kind of wonderful in that way. Right. Because it's so different and you get a chance to be a beginner again. And it's low stakes practice for awkwardness. Right. And I've always been a fan of that because when I started in journalism, I switched over from where I was training to be a scientist, got into writing and was certainly more introverted. Like I would pace around before I would interview somebody. Talking to strangers was not my thing. But then I. The only job I could get was being starting at midnight and going to the morning at a tabloid in New York City.

[Ryan Holiday]

Right.

[David Epstein]

Where nothing happy. Yeah, this happens between midnight and 10am going to the New York Daily News. So for low stakes practice, I would go in elevators and force myself to talk to people because it's over in 30 seconds to a minute, no matter what happens. Super awkward. But it's like great low stakes practice. So I'm a big fan of low

[Ryan Holiday]

stakes practice for awkwardness and low stakes. Hey, we're going for a walk in the woods. And the rule is just going to be we're going to go over the obstacles instead of finding the easy way. And then you go, hey, I'm confident in my ability, literally and figuratively to figure out how to deal with stuff that's in my way.

[David Epstein]

And if you're not, like, where are you? Where do you expect somebody to learn how to get over obstacles if you're not taking those? You know, if you're doing the snowplow thing.

[Ryan Holiday]

Yes.

[David Epstein]

Like, then don't be surprised when you're not there and they run straight into a snowbank.

[Ryan Holiday]

Well, it's like, I think that one way I think about it is like, okay, it is inevitable that you are going to experience difficulties and adversity and obstacles in life. Do you want, when that happens, for it to be the first time you are dealing with it in a serious way, or do you want to go, I deal with shit like this all the time. And so you're, you're developing reps, right? Like, you're, you're getting comfortable with an uncomfortable thing, and then when it happens in a big way, it's not unfamiliar to you.

[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, oh, 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. 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.

[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 bet and they would take the uncomfortable bet. The idea of exposing, forcing challenges on other people other than your kids is not your role in my view. Right. But the idea of, yeah, getting comfortable with cold and hard things is a good place to be.

[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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