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The Daily Stoic

14 Sep 2026 · 13m · 4 chapters

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We All Need To Be Constrained

In short

The episode argues that success and autonomy remove “constraints,” which actually harms discipline, perspective, and social health. It claims we all need checks and balances: truth-telling partners, collaborators who cover weaknesses, governance like a board, and philosophy used as self-review (Marcus Aurelius resisting “Caesarification”). Guests connect this to real life: David Epstein’s Inside of the Box theme that constraints make people better; they discuss how excessive freedom hurt their second book and how self-publishing can become a “prison” of too many decisions. Notable examples include Marcus Aurelius, Zuckerberg’s metaverse pitch as a constraint-free mistake, and using fixed work windows (e.g., candle/hourglass) to prevent work swallowing family time.

Guests

David Epstein (author) and the host (Daily Stoic’s Ryan Holiday).

Written by AI. May contain mistakes.

Chapters

0:15

The Need for Constraints

Exploring the importance of constraints in our lives for maintaining sanity and decency.

“We'd like to think that we'd do fine if we were ever put in that position.”
3:54

The Paradox of Autonomy

Discussing how too much freedom can hinder productivity and creativity, and the value of constraints.

“Or if you had to truly earn selling this book in a way that your previous success wasn't exempting you from some of the stuff, you wouldn't work as hard.”
13:30

Constraints in Art and Life

Reflection on how constraints contribute to beauty in poetry and music, drawing from Stoic philosophy.

“So another problem I had with excessive autonomy was I said, gosh, a book is so consuming.”
14:00

The Power of Constraints in Creativity

Explore how constraints can enhance creativity and focus in life and art.

“one of the great things about being committed, if you're committed by choice, is you can stop wondering how to live and start living.”
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Transcript

Automatic transcript. May contain errors.

0:00Ryan 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.

0:14Ryan Holiday: We all need to be constrained. We'd like to think that we'd do fine if we were ever put in that position. If we were given real power, real wealth, real fame, it wouldn't change us, right? Of course it would. It changes everyone. It changed Marcus Aurelius too, or he wouldn't have needed to write in meditations about his struggle to resist being Caesarified or stained purple. It's just that Marcus Aurelius was so exceptional, he didn't change as much as everyone else who was emperor. He is, as we have said, the exception that proves the rule. The rest of us? No one should be king. And more practically, we all need checks and balances in our lives.

0:57Ryan Holiday: We need partners who tell us the truth. We need collaborators who balance out our weaknesses. We need a board of directors who can give us advice and help us resolve conflicts of interest. We need philosophy, as Marcus Aurelius used it, to put ourselves up for review and to challenge our impulses. We should not get to do everything we want. We should not be surrounded by yes-men and women. We should not think that we are superior to others or exempt from constraints. We need those constraints to keep us sane, to keep us decent, and they make us great. It's actually one of the themes in David Epstein's new book, Inside of the Box, How Constraints Make Us Better.

1:38Ryan Holiday: We actually had them on the podcast recently, and after the conversation, I was so inspired, I went back and wrote this email today. So I think they go well together. So I'm going to package them together, and let's get into it. I'm doing a bunch of dates for this Daily Stoic Live tour. Maybe you came and saw me on one of the previous ones. chances are it's probably wearing something from today's sponsor, Quince. They make great sweaters, they make great t-shirts, they make great button-ups, great pants. Just a great company. Their clothes are built to last, made with premium materials, and they're the kind of stuff you reach for every day.

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3:30Ryan Holiday: So when someone goes looking for your executive, Ironwall ensures they hit a dead end. So here's what you do. Go to ironwall.com slash Daily Stoic, fill out the quick form, request your free risk assessment and their team will show you just how exposed your executives are and how to lock it down before a threat reaches their front door. that's ironwall.com slash daily stoic learn how to stop online threats before they become real world attacks the link is in the show notes what success often does is obliterate constraints yeah and you would think that would be winning right just like you'd think that hey i have a full day to work on this project that's great that's actually not great yeah Because you'd probably do better if you only had an hour.

4:15Ryan Holiday: Or if you had to truly earn selling this book in a way that your previous success wasn't exempting you from some of the stuff, you wouldn't work as hard. Totally. I mean, it's actually given me some insight into why I think a lot of musicians, when they break out, they then make like a terrible second album, basically. And that kind of exactly happened to me. After my first book actually, you know, did pretty well, then I was given an offer to basically sign a. blank book contract, like without an idea. Right. Yes. And I almost did. And then I didn't thank goodness because it's a terrible thing.

4:51One reason I needed an extra year in my first book is because I hadn't done like enough research ahead of time because I hadn't been forced to because I was already a writer at Sports Illustrated and it was based on a long article I'd written. So I didn't really have anything forcing containment. Right. So I'd been so bad, even with range, which worked well. I was terrible at like drawing boundaries around my project, which was bad for my personal life, first of all, but also the book probably could have been a little more coherent in some respects. And this is actually not to go aside, but I just remembered we were at a writer's retreat together once after Range came out and we were asked, what are you optimizing for this year?

5:30And I said autonomy, because when I finished Range, I left my job. I was working at ProPublica as an investigative reporter at the time, but then I left that and for the first time had total freedom. And I said, I want to spend every minute of the day in a manner of my own choosing.

5:42Ryan Holiday: Yeah. Right. Fast forward two years. Definitely such a thing as too much autonomy. Now I've been reeling that back. Right. Containing my workday, joined a nonprofit board in my community, like inconveniencing myself to sync up my schedule with other people and to find ways to contain my workday. So it isn't just, you know, expanding into every nook and cranny. It's like I think about when Mark Zuckerberg first advertised the metaverse. Yeah. And he said, it's going to be amazing. Everyone is going to live in a universe totally tailored and individualized just to them. And I didn't think about it that much when he said it at the moment, but now I'm like, that sounds like hell.

6:17You know, that's like the path where I was going with so much freedom. It's like you're just living on your own. The irony is the metaverse was itself

6:24Ryan Holiday: a terrible idea. And that if Mark Zuckerberg had a different corporate governance structure around him, like he didn't control Facebook so much and he and Facebook wasn't so immensely profitable, that terrible idea would have been killed and because it's on its face, stupid and lame. If he'd had us as advisors, if only. Yeah. But I'm just saying like that ended up being like a 40 or 50 billion dollar like mistake that like I think most reasonable people, and I don't mean this in like sometimes there's groundbreaking ideas and you don't get it. It's just like you were solving a problem that no one asked you to solve, doing the thing that people don't want to do.

7:04Ryan Holiday: And probably even if it was an experiment could have been done much smaller and more effectively, gotten the feedback that you overwhelmingly got on this enormous experiment later, like maybe before you changed the entire name of the company to reflect this new thing. So again, you think you want total freedom. You think you want absolute power. You think you want no constraints. And I think you used the word contain there earlier. We tend to think of constraints as the bad thing, but the other side of constraints is containment. It contains the downside risk of you being catastrophically wrong or out of touch or whatever.

7:44I mean, even had the, you said, you know, most reasonable people could see that the metaverse was stupid. I think even had it worked, I think it would have been terrible for people. Because again, I was starting to do that in real life, going into a universe of my own creation, where I was on my own schedule and, you know, not inconveniencing myself. So I think maybe a lot of people actually would have gone for that, but it would have been terrible. Just like a lot of people would go for what I was going for and saying I can spend every moment in my own individualized world now because it seems so attractive.

8:11It feels like what you want, but it's actually bad for how humans, you know, a hyper-social species can thrive.

8:18Ryan Holiday: Again, this is a little inside baseball too, but I think you can see where it applies to other things. is like one of the reasons I don't like self-publishing is that, again, you think you want to get the final say on all things and be able to do it. I find most self-published books take longer than expected. They're not as good as they could have been. There's all these reasons they don't work that it turns out that the inefficiencies and the frustrating nature and the bureaucracy and the constraints of traditional publishing prevent from happening. I mean, I would say that I'm well aware that I don't want the final say.

8:54Like in book projects, so this is at least from the time of signing contract to turning in, I turned in a little early, but it was meant to be two years. And the first year I don't write. All just architect. Like the more experience I've gotten, the more I realize it's about the architect from one of the sentences. And there is a certain point where I realize I have completely lost perspective. There's stuff that's interesting to me that I just have no idea if it's interesting to other people anymore. And so that involves, you know, what journalists call drowning some of my kittens or killing your babies, where there are things that I think are really kill your darlings.

9:24Yeah. That I think are really painful. But I'm aware enough that I've just lost perspective and that you really need that other person.

9:30Ryan Holiday: Well, it's also just like, hey, like you throw off all the rules. You can do it. It can be as long as you want. It can come out whenever you want. The cover can be whatever you want. You don't have to compete with other titles. All that. Again, it seems like it'd be freedom. But in a way, it's kind of a prison because now you have to make all these decisions instead of going like, hey, this is how we do things here. And hey, you got to make this decision by this date and this is like also to go back to deadlines, which is where we started. If every deadline is movable because you're actually in charge, that's a real problem to be in.

9:59That's a real problematic space, too. When I signed this contract, I tell my agent he knows that I freak out as soon as I sign the contract. I'm like, what did I do? Can we get out? Did I sign it in pencil? Can we erase it? And his reaction this time was like, look, as you know, most people don't meet their book deadline. It's just a suggestion. I'm like, don't say that. Do not tell me that. I need to treat this thing as super real. It was like I was reading about Hayao Miyazaki, the great animated filmmaker, and he had a colleague who called him the never ending man because he was like, if we didn't say this is the day we're showing this in a theater.

10:28Yes. He would never stop. Right. He would never stop.

10:31Ryan Holiday: And as you get more successful and you have more leverage, all those things do become more flexible. And so the governance has to become a form of self-governance. Either you have to force yourself into things that you can't wiggle your way out of, or you have to say, no, no, no, no, this is the deadline and I'm holding myself to it, or this is the way it's going to go today. Yeah. Freedom within a framework. And I find that even within my days, like one of the things that once I became like not a daily employed journalist anymore, I would also say like my competitive advantage is going to be, I'm going to let this project swallow every moment of my life.

11:04Right. And so I found that I also had to start, you know, not being in an office anymore, containing my own workday. I sort of stole from Isabella Allende, who's a, I think one of the, not just I, a lot of people think is one of the greatest living writers, where she'll light a candle at the beginning of every workday and then blow it out at the end. And she's like, that's the end and closes the door and goes out. And I did not have that before. I was going to say like when the candle runs out, she's done, which would also be powerful. Yes. It's like you flip an hourglass and you're like, I have two hours or whatever it is.

11:30And I mean, I use electric candles because I'm not as brave as her and I have too much paper in my office. But it was the first time where like once I was out of office, I realized I needed a way to end the day, basically. Otherwise, it's like I'm thinking about it while I'm doing stuff with my son and all that kind of thing. So, yeah, just all the structures on you.

11:48Ryan Holiday: Well, people sometimes are worried, you know, like having kids or having getting married will sort of tie you down. And I go, yeah, to reality. Like it's a constraint in a good way in that there are suddenly other important demands on your time. There's this Philip Roth quote that I hate because he also sucks. But it was, you know, in my life, it's always – it was something like there's always an emergency and I'm the emergency. His point was it's all about him. Yeah, yeah. And because he's the center of gravity of this whole universe as this powerful, big writer person. And like, yeah, you actually don't want your work to consume your life.

12:33Ryan Holiday: You want it to be an important part of your life, but not the totality of your life. And having soccer practice or a kid that's sick or, you know, somebody who's going to be mad at you if you blow off dinner, whatever it is, it actually forces you to keep some semblance of regularity or normalcy, which turns out is actually very important. Totally. And that not only for your well-being, but also for kind of your rhythm. Yes. You know, like people need rhythm and like seasonality in their lives. And I don't think it impairs performance. Like, I don't think we're saying don't be ambitious or anything like that.

13:07Like, I think I'm better now than when I, in the past when I did let it totally swallow my life. It's the most important thing to me in that hour that I have. Or that two hours. But you only have the hour. You only have two hours. That's right. And I find that incredibly helpful. And like, I feel now like I could write more books too, because I have a better balance in that way. Like I have more constraints and structure. It's ultimately more sustainable. Absolutely. To your marriage point, by the way. So another problem I had with excessive autonomy was I said, gosh, a book is so consuming. I'm not going to write one until I find the perfect topic.

13:39So I spent all this time dipping my toes into topics and say, this is really interesting, but not perfect. I'm going to keep looking. And I spent like a long time doing that, you know, I mean, the pandemic was involved, but let's say two years. And then I come across this Mihaly Csikszentmihalyi quote, the psychologist who coined the term flow for the feeling of immersion in activity. And he's talking about marriage, but it could be applied to anything where he says, one of the great things about being committed, if you're committed by choice, is you can stop wondering how to live and start living.

14:08Like you don't spend that energy wondering, is there a next better thing? And that's what I immediately realized. That's what I was doing with topics. And you're never going to get the perfect one. So it was like that day I was like, I'm super interested in constraints. I obviously need them. I'm writing a proposal on this right then. And of course, you know, two weeks later, I'm five times as interested in it as I was before I started.

14:27Ryan Holiday: So when I think about the idea of constraints, the first thing in my mind is actually this quote from Cleanthes, who's one of the early Greek stoics. And he's talking about poetry. And he's talking about how the fetters of poetry, the constraints of the length, but also the rhythm and the rhyme structure is what creates the beauty of the poetry. And he says this is also true with a trumpet or a musical instrument. It's in sort of channeling and funneling the sound that you get anything. Now, obviously, in the centuries since, we've invented sort of freeform poetry and other forms of art, which I guess are great.

15:02Ryan Holiday: But there's a reason I think the haiku structure works or even just the rhythm and rhyme structure of poetry. Again, you'd think it would be constraining artistically, but in fact, it is what makes the art. Totally.

From the publisher

We should not get to do everything we want. We should not be surrounded by “yes” men and women. We should not think we are superior to others or exempt from constraints.


Watch the full conversation with David Epstein: https://www.youtube.com/watch?v=ngKTRs6ghQ8


David Epstein is the author of the #1 New York Times best seller Range: Why Generalists Triumph in a Specialized World. His book, Inside the Box: How Constraints Make Us Better, is out now!


📚 Grab signed copies of David Epstein Books at The Painted Porch:


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