We All Need To Be Constrained

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 https://www.youtube.com/watch?v=ngKTRs6ghQ8 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 https://www.thepaintedporch.com/products/range-why-generalists-triumph-in-a-specialized-world-signed?_pos=1&_sid=dc6c73241&_ss=r. His 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 Books 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 🎟️ 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 to The Daily Stoic Premium https://dailystoic.supercast.com/ - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/ https://dailystoic.supercast.com/ ✉️ FREE STOIC WISDOM https://dailystoic.com/dailyemail | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail https://dailystoic.com/dailyemail -- Stop online threats before they become real-world attacks. Visit ironwall.com/DAILYSTOIC and request a free Risk Assessment to see exactly how exposed your executives are. -- Wealthfront’s high-yield cash account: https://www.wealthfront.com/stoic This experience may not be representative of other Wealthfront clients, and there is no guarantee of future performance or success. Experiences will vary. Ryan Holiday, who’s a client of Wealthfront, receives cash compensation from Wealthfront Brokerage for paid testimonials in his podcast, creating a conflict of interest. More details available via the referral link. The Direct Deposit Plus Investing Program from Wealthfront Advisers LLC and Wealthfront Brokerage LLC provides eligible clients a 0.25% APY increase above the base APY on eligible Cash Account balances (up to an overall boosted rate of 4.30% for a limited time when including the three month 0.75% APY boost for new clients) when you direct deposit $1,000 a month, plus open, fund, and maintain an investing account. Wealthfront may change or end the program at any time and determine eligibility at its discretion. Terms apply. Full details at wealthfront.com/promo-terms. The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC ("Wealthfront Brokerage"), Member FINRA/SIPC. Wealthfront Brokerage is not a bank. The Annual Percentage Yield ("APY") on cash deposits as of January 30, 2026, is representative, requires no minimum, and may change at any time. References to the APY for the Wealthfront Cash Account, including any APY increase, are to the APY paid by insured depository institutions that participate in our cash sweep program (the "Program Banks”). Wealthfront Brokerage does not pay interest. Wealthfront Brokerage sweeps cash balances to Program Banks, where they earn the variable APY. Instant and same-day withdrawals use the Real-Time Payments (RTP) network or FedNow service. Transfers may be limited by your receiving institution, daily caps, or participating entities. New Cash Account deposits have a 2–4 day hold before transfer. Wealthfront does not charge fees for these services, but receiving institutions may impose an RTP or FedNow Fee. Processing times may vary.. Fees & Eligibility requirements may apply to certain checking features. Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Investing involves risk, including the possible loss of principal. Securities investments are not bank deposits, bank-guaranteed or FDIC-insured, and may lose value. See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 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.

• 0:15Ryan Holiday?

  We all need to be constrained. We'd like to think that we 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.

• 0:51Ryan Holiday?

  The rest of us? No one should be king. And more practically, we all need checks and balances in our lives. 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. There's actually one of the themes in David Epstein's new book,

• 1:35Ryan Holiday?

  Inside of the Box: How Constraints Make Us Better. We actually had him 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.

• 1:51Ryan Holiday?

  What success often does is obliterate constraints.

• 1:54Speaker 01

  Yeah.

• 1:55Ryan Holiday?

  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.

• 2:05Speaker 01

  Yeah.

• 2:05Ryan Holiday?

  Because you'd probably do better if you only had an hour. 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 do as, you wouldn't work as hard.

• 2:18Speaker 01

  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, 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?

• 2:38Ryan Holiday?

  Yes.

• 2:39Speaker 01

  And I almost did, and then I didn't, thank goodness, because it's a terrible thing to do. One 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? And I said autonomy.

• 3:24Speaker 01

  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.

• 3:34Ryan Holiday?

  Yeah.

• 3:35Speaker 01

  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.

• 3:58Ryan Holiday?

  Yes.

• 3:58Speaker 01

  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. You know, that's like the path where I was going with so much freedom. It's like you're just living on your own.

• 4:15Ryan Holiday?

  The irony is the metaverse was itself a terrible idea. And 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.

• 4:35Speaker 01

  If he'd had us as advisors, if only.

• 4:37Ryan Holiday?

  Yeah. But I'm just saying like, that ended up being like a $40 or $50 billion, like mistake.

• 4:44Speaker 01

  Yeah.

• 4:44Ryan Holiday?

  That, that like, I think most reasonable people, and I don't mean this in like, sometimes there's groundbreaking ideas, 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.

• 4:57Speaker 01

  Yeah.

• 4:57Ryan Holiday?

  And probably, even if it wasn't 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. Like, so again, you think you want total freedom. You think you want absolute power. You think you want no constraints. And, 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.

• 5:36Speaker 01

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

• 6:10Ryan Holiday?

  Again, this is a little inside baseball too, but I think if 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 be, 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, but it turns out that the inefficiencies and the frustrating nature and the bureaucracy and the constraints of traditional publishing prevent from happening.

• 6:43Speaker 01

  I mean, I would say that I'm well aware that I don't want the final say. Like 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 experienced 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, yeah, that I think are really painful. But I'm aware enough that I've just lost perspective and that you really need that, that other person.

• 7:23Ryan 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 type. All, 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. 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, that's a real problematic space too.

• 7:54Speaker 01

  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, 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.

• 8:08Ryan Holiday?

  Yes.

• 8:08Speaker 01

  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.

• 8:21Ryan Holiday?

  Yes.

• 8:21Speaker 01

  He would never stop tweaking. He would never stop.

• 8:24Ryan Holiday?

  And, 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.

• 8:44Speaker 01

  Yeah. Freedom within a framework. And I, 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, right? 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 Isabel 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.

• 9:16Ryan Holiday?

  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.

• 9:23Speaker 01

  And 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 an office, I realized I needed a way to end the day, basically. Otherwise, it's like, I'm thinking about it. Well, my, I'm doing stuff with my son and all that kind of thing. So you're just, all the structure's on you.

• 9:40Ryan Holiday?

  Well, people sometimes are worried, you know, like having kids or having, getting married will like sort of tie you down. And I go, yeah, to reality. Like it's a, it's a constraint in a good way in that it, there are suddenly other important demands on your time. There's this Philip Roth quote that I hate.

• 9:58Ryan Holiday?

  Because he's, well, he also sucks. But, but, but it was, you know, in my life, it's always in, it was something like, there's always an emergency and I'm the emergency. Or like his, his point was, it's all about him.

• 10:12Speaker 01

  Yeah.

• 10:12Ryan Holiday?

  And, and because he's the center of gravity of this whole universe as this powerful, big writer person. And like, um, yeah, you actually don't want your work to consume your life. 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, if you blow off dinner, whatever it is. It actually forces you to keep some semblance of regularity or normalcy, which is, turns out is actually very important.

• 10:47Speaker 01

  Totally. And that not only for your wellbeing, but also for kind of your, your rhythm.

• 10:50Ryan Holiday?

  Yes.

• 10:51Speaker 01

  You know, like people need rhythm and like seasonal, seasonality in their lives. And I don't think it impairs perform, like I don't think we're saying, don't be ambitious or anything like that. Like 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.

• 11:08Ryan Holiday?

  But you only have the hour, you only have two hours.

• 11:11Speaker 01

  That's right. And I find that incredibly helpful. And, 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.

• 11:20Ryan Holiday?

  Ultimately more sustainable.

• 11:21Speaker 01

  Absolutely. To your, 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. So I spent all this time dipping my toes into topics and saying, 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 and inactivity. 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. Like you don't spend that energy wondering, is there a next better thing?

• 12:03Ryan Holiday?

  Right.

• 12:04Speaker 01

  And that's, I immediately realized that's what I was doing with topics. And you're never going to get the perfect one.

• 12:08Ryan Holiday?

  Right.

• 12:09Speaker 01

  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.

• 12:19Ryan Holiday?

  So when I think about the idea of constraints, the, the first thing in my mind is actually this quote from Klianthis, who's one of the early Greek Stoics. And he is 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 the trumpet or a musical instrument. It's, 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 free form poetry and other forms of art, which I guess are great. But there's a reason, I think, the haiku structure works or even just the rhythm and rhyme structure of poetry.

• 13:02Ryan Holiday?

  Again, you'd think it would be constraining artistically, but in fact, it is what makes the art.

• 13:09Speaker 01

  Totally.