Pod Insights The Daily Stoic | Wondery+ Why Struggling Is the Point | David Epstein About this episode The easier life gets, the less prepared we may be for what’s hard. In today’s episode, Ryan talks with David Epstein https://www.thepaintedporch.com/search?type=product&q=david+epstein* about “desirable difficulties,” the challenges that make learning slower and more frustrating in the moment but lead to greater growth over time.
David Epstein https://www.thepaintedporch.com/search?type=product&q=david+epstein* is the author of the #1 New York Times best seller Range: Why Generalists Triumph in a Specialized World https://www.thepaintedporch.com/products/range-why-generalists-triumph-in-a-specialized-world-signed?_pos=1&_sid=dc6c73241&_ss=r. His new book,Inside the Box: How Constraints Make Us Better https://www.thepaintedporch.com/products/inside-the-box-how-constraints-make-us-better?_pos=3&_sid=dc6c73241&_ss=r, is out now!
📚 Grabsigned copies https://www.thepaintedporch.com/search?type=product&q=david+epstein* of David Epstein's books https://www.thepaintedporch.com/search?type=product&q=david+epstein* atThe Painted Porch https://www.thepaintedporch.com/search?type=product&q=david+epstein*:
Range: Why Generalists Triumph in a Specialized World https://www.thepaintedporch.com/products/range-why-generalists-triumph-in-a-specialized-world-signed?_pos=1&_sid=dc6c73241&_ss=rInside the Box: How Constraints Make Us Better https://www.thepaintedporch.com/products/inside-the-box-how-constraints-make-us-better?_pos=3&_sid=dc6c73241&_ss=r
Connect with David Epstein https://davidepstein.com/ 👉Instagram https://www.instagram.com/davidepstein,YouTube https://www.youtube.com/@DavidEpsteinAuthor,X https://x.com/DavidEpstein,Substack https://davidepstein.substack.com/
🎟️DAILY STOIC LIVE https://www.dailystoiclive.com/| Ryan Holiday is coming to a city near you https://www.dailystoiclive.com/! Grab tickets here https://www.dailystoiclive.com/ | https://www.dailystoiclive.com/
🎙️AD-FREE https://dailystoic.supercast.com/| Support the podcast and go deeper into Stoicism by subscribing toThe Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content:https://dailystoic.supercast.com/
🎥 VIDEO EPISODES https://www.youtube.com/@DailyStoic/videos| Watch the video episodes onThe Daily Stoic YouTube channel https://www.youtube.com/@DailyStoic/videos:https://www.youtube.com/@DailyStoic/videos
✉️ FREE STOIC WISDOM https://dailystoic.com/dailyemail | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email athttps://dailystoic.com/dailyemail
See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.
Transcript Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 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.
0:15 Ryan Holiday? 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. But obviously, the 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,
1:00 Ryan Holiday? 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 at David Epstein. You can get signed copies of Range and Inside the Box. But let's get into this idea of desirable difficulties.
1:47 Ryan Holiday? What are desirable difficulties? That seems like an oxymoron.
1:50 Speaker 01 Yeah, it's a, that's a term psychologists use. First, the psychologist Robert Bjork to describe.
1:58 Speaker 01 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, 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, the more wrong you are actually, the more likely you are to retain the information. It's called the hypercorrection effect.
2:41 Ryan Holiday? Isn't there probably also something in just like, tests are stressful and getting comfortable being stressed and challenged has benefits too. Like, 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.
2:57 Speaker 01 Yes.
2:58 Ryan Holiday? And like, when people are like, oh, I'm just bad at taking a test. It's like, seems like you're gonna have a hard time just being a person then.
3:05 Speaker 01 Yeah.
3:05 Ryan Holiday? 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.
3:10 Speaker 01 For sure, for sure. 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 later will be.
3:22 Ryan Holiday? They had to come face to face with not knowing the thing and then they learned the thing after they learned that they didn't know it.
3:28 Speaker 01 Yeah, there's some priming of your brain that's like, I don't know this, I'm, 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. It's, 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 AAA,
4:13 Speaker 01 BBB, etc., 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 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 blocked-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.
4:55 Speaker 01 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.
5:21 Ryan Holiday? Your understanding that going into, you're going to have to understand it at a level that allows you to explain it to someone else. You can't just sort of, ah, yeah, yeah, I think I get it.
5:29 Speaker 01 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.
5:39 Ryan Holiday? Yeah.
5:40 Speaker 01 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.
5:47 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.
5:52 Speaker 01 Yeah.
5:53 Ryan Holiday? And, and the, 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.
6:21 Speaker 01 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, and it'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.
6:43 Ryan Holiday? They'd be like, hey, guys, I think we've got to 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.
6:56 Speaker 01 And he also lost a gold ring right by that bridge and put an ad in the newspaper. So there's like a, you know, a more than century old ad that's like president's gold ring lost reward and it's never been found. So.
7:07 Ryan Holiday? That's amazing. Could still be in there.
7:08 Speaker 01 Could, it's probably under, you know, however many meters of sediment now, but yeah.
7:12 Ryan Holiday? It just strikes me as 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 parent.
7:25 Speaker 01 Helicopter to snowplow, right? Just clear the road. I mean, I find this with, with my kid all the time. And 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.
7:48 Ryan Holiday? Sure, because they're doing dangerous things.
7:50 Speaker 01 On rocks or whatever it is. And so since then, I kind of, I'm not telling I like, I 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.
8:06 Ryan Holiday? Yes.
8:06 Speaker 01 And, you know, maybe get hurt. I'm like, I tell him like, as long as you don't break your head.
8:09 Ryan Holiday? Yes.
8:10 Speaker 01 It's okay. We'll fix anything else.
8:12 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.
8:19 Speaker 01 Maybe I should include neck also.
8:20 Ryan Holiday? He was on monkey bars without the, you know, the stuff at the bottom and then, and then the, you know, sure, no one was watching. And like, the idea that we were doing it well in the past is probably.
8:30 Speaker 01 Yes.
8:30 Ryan Holiday? A delusional, you know.
8:33 Speaker 01 Monkey bars over concrete that's like 20 feet high. Yeah.
8:35 Ryan Holiday? 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, um, you know, you can so easily specialize. It is 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 deal with.
9:07 Speaker 01 Everything is so convenient, right? It's like, if you're working from home too, right? As I do, it's like everything can be tailored to you and everything is super convenient. But I just don't think convenience as our regnant value is actually the way that people thrive.
9:21 Ryan Holiday? If you're going to eliminate inconvenience in one area, that ought to be with the idea that you are struggle, you are, you are finding other places more meaningful or significant ways to struggle elsewhere.
9:34 Speaker 01 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.
9:51 Ryan Holiday? Yes.
9:52 Speaker 01 So I started going places. I mean, I started going to these like dance meetups and, and class, you know, just to be somewhere with strangers again.
10:00 Ryan Holiday? Here's one I found, that's gonna sound a little humble braggy, but I was like, I found I was not going into rooms very often where I was not like a special person. Like it would 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 lacrosse. So it's like, I gotta do, go do that for him.
10:38 Speaker 01 Yeah.
10:39 Ryan Holiday? 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?
10:45 Speaker 01 Yeah.
10:45 Ryan Holiday? 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.
11:04 Speaker 01 Highly recommend some beginning dance classes, I have to say.
11:07 Ryan Holiday? That's not gonna happen.
11:07 Speaker 01 Go in there. Like, I went in, it's like, I probably single-handedly raised the average age by like five years.
11:12 Ryan Holiday? What is it, kids' dance class?
11:14 Speaker 01 Younger people, you know, twenties, most people in their twenties.
11:16 Ryan Holiday? I thought it'd all be old people who are retired and doing salsa or whatever.
11:19 Speaker 01 No, no, shuffling. So I got interested in it because I watched a documentary. I've, 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 in the same space. And so I showed up at these things and it's like, not only my 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?
11:48 Ryan Holiday? Yeah.
11:49 Speaker 01 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.
12:16 Ryan Holiday? Yeah.
12:16 Speaker 01 Right? Where nothing happy.
12:17 Ryan Holiday? Yeah.
12:18 Speaker 01 This happens between midnight and 10 a.m. 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 stakes practice for awkwardness.
12:34 Ryan Holiday? And low stakes, hey, we're going for a walk in the woods. And the rule is just gonna be, we're gonna go over the obstacles instead of finding the easy way.
12:42 Speaker 01 Yeah.
12:42 Ryan Holiday? 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.
12:50 Speaker 01 And if you're not, like, where are you, where do you expect somebody to learn how to get over obstacles?
12:54 Ryan Holiday? Yeah.
12:54 Speaker 01 If you're not taking those, you know, if you're doing the snowplow thing.
12:57 Ryan Holiday? Yes.
12:57 Speaker 01 Like, then don't be surprised when you're not there and they run straight into a snowbank.
13:03 Ryan Holiday? Well, it's like, I think that, one way I think about it is like, okay, it is inevitable that you are gonna experience difficulties and adversity and obstacles in life. Do you want, when that happens?
13:15 Ryan Holiday? 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.
13:32 Speaker 01 You just, you just reminded 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.
14:00 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. And like, 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, is a good place to be.
14:21 Speaker 01 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.
Previous The Stoic Mind Behind D-Day Next In The Resolute Urgency of Now | Finding The Right Mentors Page updated September 29, 2026 · transcript and summary are machine-generated
