The Stoic Secrets Great Leaders Use | Daniel Coyle

The more you control, the worse you lead. In this conversation, Ryan talks with leadership expert Daniel Coyle about why the best teams aren’t run like machines, why connection matters more than control, and what Marcus Aurelius can teach us about leadership that endures. Daniel Coyle is the award-winning author of the New York Times bestsellers The Culture Code, The Talent Code, and his NEW book Flourish: The Art of Building Meaning, Joy, and Fulfillment. Check out more of Dan’s work on his website https://danielcoyle.com/📚 Grab signed copies of Daniel’s books at The Painted Porch: The Culture CodeThe Talent CodeFlourish: The Art of Building Meaning, Joy, and Fulfillment💡 We designed The Daily Stoic Leadership Challenge: Ancient Wisdom For Modern Leaders to mirror the kind of education that produced historically great leaders like Marcus Aurelius. Check it out at store.dailystoic.comGet The Daily Stoic Leadership Challenge: Ancient Wisdom For Modern Leaders & all other Daily Stoic courses for FREE when you join Daily Stoic Life | dailystoic.com/life🎥 VIDEO EPISODES| Watch the video episodes on The Daily Stoic YouTube channel: https://www.youtube.com/@DailyStoic/videos✉️ FREE STOIC WISDOM | Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail 📢 Share | ⚙️ Manage Subscription

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.

• 0:14Ryan Holiday?

  Hey, it's Ryan and welcome to another episode of the Daily Stoic Podcast. Today, we're going to be talking about leadership. Right? When we think of leaders, we picture that lone figure at the top, the emperor, the CEO, the head coach, the self-made billionaire, that the person who got themselves there out of sheer willpower and strength and brilliance and superiority. But that's not how the Stoics saw it. That's not how it is. And that's not what we're going to be talking about today. Dan Coyle has spent years studying what actually makes great teams and organizations work. I was just down speaking to the Chicago Cubs and I was talking to the GM,

• 0:59Ryan Holiday?

  actually, his name's Carter Hawkins. And he had previously been with the Cleveland Guardians. And I asked him if he knew Dan Coyle. And he just went and raved about Dan, who happened to have stopped by the studio not too long ago. You might know some of his books. He wrote The Culture Code, The Talent Code, The Little Book of Talent. He has this new book called Flourish. But basically, his sort of thinking and writing on leadership has taken him inside some of the most successful groups in the world. As I said, elite sports teams, military units, companies, hedge funds. We're all trying to create leaders and cultivate leadership. And so what we're going to focus on in today's episode is something that he and I talked about.

• 1:44Ryan Holiday?

  Because leadership isn't about pulling levers and controlling outcomes. It's not about genius or superiority. It's actually about relationships. It's about meaning. It's about building environments where people feel safe, feel connected, like their contribution matters. These are the conditions. Where teams and groups and countries and communities flourish. So let's get into some of that.

• 2:10Speaker 01

  When we talk about leader, there's a mental model that comes in all of our minds that we're kind of entrained on, which is like captain of the ship, right? I'm steering, I'm controlling, I'm in charge of things. And I think a lot of us start out with that model and a lot of our systems are built with that model.

• 2:25Ryan Holiday?

  Yes.

• 2:25Speaker 01

  And what happens, at least as I've experienced it in the three books that I've written that connect with this, is that most leaders go through this process where they do that for a while. Then they reach kind of a turning point and all of a sudden that they realize they have some insight, some road to Damascus.

• 2:41Ryan Holiday?

  Yeah.

• 2:42Speaker 01

  Is that the correct road?

• 2:43Ryan Holiday?

  Sure.

• 2:43Speaker 01

  Some road to Damascus moment where it's like, this is not working. I'm running it like it's a machine. I'm trying to put levers and get instructions and have measurable outcomes and absolutely push, push, push. And what they do is they let go of the reins a little bit. And that's the time when they start cluing into how, I would argue, the world actually works, which is that it's not a machine.

• 3:01Ryan Holiday?

  Yeah.

• 3:02Speaker 01

  It's more like a garden that you can grow and cultivate and have move in a certain way. And all the good organizations.

• 3:08Ryan Holiday?

  The organization is not a machine.

• 3:09Speaker 01

  An organization, ultimately, it has machine-like functions, but ultimately, like down super deep, it's a living thing, right? And if you're going to beat entropy.

• 3:18Ryan Holiday?

  Yeah.

• 3:18Speaker 01

  If you're going to like, keep surviving and adapting in this changing world, if you operate like it's a machine you can steer, you'll reach the end. Like it will stop working. So what these leaders do is they realize a couple of things. The first is that they need to create a sense of meaning and mattering. They need to really have people connect and build relationships. That ends up being area number one. Area number two is they need to design space for agency. They need to create spaces. Organizations aren't machines. They're functioning more like rivers. Like you need to have clear boundaries. What we're not going to do.

• 3:50Ryan Holiday?

  Yes.

• 3:51Speaker 01

  Riverbank's going to just stand strong. It's not going to do anything. What we're not going to do. We need to have a gradient, like a horizon we're going toward, right? We're going that direction. And anything you do in that space, go do it. Have some agency. And the good organization, when you look at the SEALs, when you look at Pixar, when you look at top performing organizations, what their leaders do inevitably, I think, is they create that sense of mattering and meaning, which you can think of as almost like, that's the connective energy. Like that's the cells that are alive, that are connected. And now, we're going to channel that energy into this direction, not here, not here, in this space. And now it's up to you guys, go do it.

• 4:28Ryan Holiday?

  We think of the leader as being the sort of the solitary figure.

• 4:32Speaker 01

  Yeah.

• 4:32Ryan Holiday?

  As though the leader is not themselves being led and taught and coached.

• 4:38Speaker 01

  Hmm. Yeah.

• 4:39Ryan Holiday?

  How do you think about that?

• 4:40Speaker 01

  I think it's changing.

• 4:41Ryan Holiday?

  Yeah.

• 4:41Speaker 01

  Now it's, you know, I work with the Cleveland Guardians a little bit and.

• 4:44Ryan Holiday?

  A little bit. I mean, you've been there a long time.

• 4:45Speaker 01

  12 years, 12 years. Yeah. Yeah. And um, we have, we have a coach, Stephen Vogt. He's the best coach in baseball and somebody asked him that in a call, like, who do you go to for advice? And he goes, well, I have a coach.

• 4:54Ryan Holiday?

  Yeah.

• 4:54Speaker 01

  Right? We think, oh, you need a coach to a certain point in life. But as Dave Epstein has pointed out, like, that point never stops, does it? Like, the best leaders are always trying to, because it's a challenging job and because you've got to create a space where you can get insight.

• 5:10Ryan Holiday?

  Yes.

• 5:11Speaker 01

  So they're intentionally, and I guess this goes back to the basic principles we're talking about. They're intentionally creating space where they can connect to that meaning and also experiment in directions, it's kind of rivering their way toward an insight. Like, oh, wow, that works. I didn't think that would work, but that does work.

• 5:26Ryan Holiday?

  And also just someone who's, who has more reps than you in the thing. Not that they, not even necessarily that they've done it, because some of the coaches aren't actually good at the thing they're doing.

• 5:37Speaker 01

  Yes.

• 5:37Ryan Holiday?

  Right? Like, your swing coach might not actually be a great golfer.

• 5:40Speaker 01

  Oh, man.

• 5:41Ryan Holiday?

  But they've worked with hundreds and hundreds of other people. So they've seen all the different swings and they've studied it a thousand. You need, your own experience does not have enough breadth to, to sustain and help you in all the different contingencies that you're going to bump into.

• 5:58Speaker 01

  One of the big unlocks for me with this, with looking at this stuff, has been the difference between complicated and complex. We use that as the synonyms, right?

• 6:06Ryan Holiday?

  Sure.

• 6:07Speaker 01

  It ain't. Complicated things come together the same way every time. A set of Legos, instructions to build a Ferrari.

• 6:12Ryan Holiday?

  A watch.

• 6:13Speaker 01

  A watch. Same every single time, right? You put it together, you'll get a watch. Complex things change as you interact with them. So the question asked, is it more like building a watch? Is it more like raising a teenager?

• 6:24Ryan Holiday?

  Yeah.

• 6:25Speaker 01

  There's no set of instructions. There's no one, two, three, four, five.

• 6:27Ryan Holiday?

  Right.

• 6:28Speaker 01

  And so, yet, we walk through life, because of the way our brains are built, always sort of seeing machines and the way we're also kind of trained.

• 6:36Ryan Holiday?

  Yeah.

• 6:36Speaker 01

  I think. We're always looking for machines, always. Assuming things are machines, we're always looking for that straight line solution.

• 6:42Ryan Holiday?

  Yeah.

• 6:42Speaker 01

  That will fix it, like that will allow us that sense of control that we want. And I think leaders especially who realize it's not complicated. It's actually complex. We're on this journey of experimenting that's going to take us left and right and around. And there'll be new stuff. And when that new stuff appears, I need to be ready for it.

• 7:01Ryan Holiday?

  If it's complex, you want as much information as you could possibly have.

• 7:06Speaker 01

  And you want to learn by experience. The best, what a mathematician would say is, and complex systems dynamic theory would say is the best way to learn when it's complicated is find the expert. Like find the expert who's a watchmaker. When it's complex, you actually have to learn through experience. Probe is the word. So do an experiment, do an experiment, see what happens. And then you'll get what they would call attractors, like patterns will come up that you notice. And you're like, oh, that's cool or oh, that sucks. And then you kind of follow where that takes you.

• 7:34Ryan Holiday?

  Yeah.

• 7:35Speaker 01

  And that's kind of how we live our lives, actually, when you zoom way out.

• 7:38Ryan Holiday?

  Well, it's funny, maybe where some of this stuff intersects with what I write about. I'm fascinated by this sort of brief period of Roman history where Hadrian's the emperor. And he is having to choose a successor. There's a handful of Roman emperors who don't have sons and they have to choose their successor. So he's having to choose, you know, somebody for a job that only like 15 other people have ever had. And so, you know, who does he pick? And for some reason, he picks this kid who would become Marcus Aurelius. You know, a privileged, but otherwise, you know, unremarkable person. And he decides to groom him for power, but he understands he doesn't have enough time left. So he adopts this older Roman senator named Antoninus.

• 8:22Ryan Holiday?

  On the condition that Antoninus in turn adopt Marcus Aurelius. So this sort of, he's not just choosing his successor, he's choosing his successor's successor. And he probably thinks that Antoninus is going to live for, I don't know, five years or something. Or maybe he even thinks like at some point Marcus will kill him and then he'll take over. Like just the brutality of the, of the, the ancient world is going to handle this problem. But instead Antoninus lives for two. Decades. And these two men, Marcus Rilis and Antoninus, who have no affiliation, other than they were just thrown together by this guy who they're also not related to. They develop an incredible affinity for each other. So, so Antoninus rules, he takes

• 9:02Ryan Holiday?

  seriously that he's gonna tutor this kid. And at some point, Marcus becomes co-Emperor. Again, like this has never happened before in human history. So Antoninus ruling and teaching, then, then they're co-ruling together. But it's basically this, this two-decade apprenticeship. And then eventually Marcus Rilis becomes Emperor. And then, this is where the story gets interesting. He has a son. His son is Commodus. So you, one version is Commodus gets a 15-year head start of on the job training. But instead, it actually goes horrendous. Like, it's, it's as bad as Joaquin Phoenix's character portrays it in Gladiator. And so, you know, what goes wrong?

• 9:44Ryan Holiday?

  So it's, it's rare that you get, because history is not a science experiment. You don't get to control for your variables. But here, you have like this sort of compare and contrast. It works in one case, and then it doesn't work in this other case. I'm just endlessly fascinated with, first off, the idea of like actually saying like, hey, I want to learn everything I can about this job I'm about to take. And then, you know, how somebody else who decides not to do it, it goes so terribly.

• 10:10Speaker 01

  It makes me think of so much the NFL coaching trees, right? Though sometimes it'll go really well. Sometimes they do not, right? And the apprenticeships of the Renaissance, right? These long periods where it was just, this is craft. You might be painting the Sistine Chapel, but you know what? You gotta get your reps.

• 10:25Ryan Holiday?

  You think you're ready, you're not even close. Come back to me in 20 years.

• 10:28Speaker 01

  Yeah, let's hang out. You're gonna mix some paints for a while, right? It's that. And so that ends up being, I think it gives you a clear vision on how talent is actually grown. And also, especially that motivational piece. You know, the kid who's born into, hey, I've got this great mentor and I'm gonna spend 20 years with him, versus the kid who's just born thinking, hey, silver spoon, I've got it. I'm next in line. I'm good.

• 10:49Ryan Holiday?

  It's like, potential could be biological or genetic, because you're, you're born in this position or not, you're this height or this height, you have this fast twitch muscle fiber, or you don't. But then everything from there, the swing vote is, do you cultivate it? Do you do the work? Do you have the teachers?

• 11:05Speaker 01

  Right.

• 11:05Ryan Holiday?

  Do you follow the tradition?

• 11:08Speaker 01

  Which ends up looking not like a machine, but like an ecosystem. And that you have to have a source of energy for it.

• 11:12Ryan Holiday?

  Yes.

• 11:12Speaker 01

  Commodus maybe wasn't psyched to do that role. Maybe he was psyched about something else.

• 11:17Ryan Holiday?

  Well, we're told by this one ancient historian that, that Marcus is sort of aware of this. One of the interesting things about Marcus Rilus's Meditations is the first like 10 pages are just him thanking all his teachers and mentors. And he says, one of the things he learns from Antoninus is to always seed the Florida experts, to learn from other people. We're told by a historian who lives through Commodus's reign that Marcus selects a group of people, not just one senator, but he says, the best men in the empire to teach this person. And that at some point, very early on, Commodus goes, nah, you know, I don't want to listen to the old guys anymore. And that is, to me, probably that, that's the critical divergence.

• 11:57Speaker 01

  Isn't that crazy to think about? Like one morning he gets up and he's kind of sick of it. And that emotion ends up changing the course.

• 12:04Ryan Holiday?

  Of human history. I mean, that is the decline and fall of Rome begins there.

• 12:08Speaker 01

  Begins with that morning.

• 12:09Ryan Holiday?

  Pax Romana ends with Commodus.

• 12:10Speaker 01

  Yep.

• 12:10Ryan Holiday?

  And, you know, the end of the empire, you could argue, ends with him too. Because, yeah, you know, one guy decides he's a know it all and therefore knows all there is to know.

• 12:24Ryan Holiday?

  One of the things that, that Dan and I were talking about is how Marcus Rilius thanks his mentors in Meditations. But let's actually read what some of Marcus thanks those mentors for. I'm getting out, this is my leather bound copy of Meditations. It's actually the one, if you've ever seen me do my talks, is the one I tend to bring on stage. Here's what Marcus Rilus thanks Rusticus for. The recognition that I needed to train and discipline my character, not to be sidetracked by my interest in rhetoric. He says, to read attentively and not be satisfied with just getting the gist of things and to not fall for every smooth talker. Here's what he thanks Apollonius for.

• 13:03Ryan Holiday?

  Independence and unvarying reliability, to pay attention to nothing, no matter how fleeting, except the logos. And to be the same in all circumstances, intense pain, loss of a child, chronic illness. And to see clearly from his example that a man can show both strength and flexibility. He thanks Sextus for teaching him kindness, to display gravity without errors. He thanks his rhetoric teacher, Fronto, for teaching him how to recognize the malice, cunning, and hypocrisy that power produces. And of course, from Antoninus, his greatest teacher, he learns compassion, unwavering adherence to decisions, indifference to superficial honors, hard work, persistence, listening to anyone who could contribute

• 13:47Ryan Holiday?

  to the public good, a sense of when to push and when to back off, his search in questions at meetings, kind of single-mindedness, almost never content with first impressions or breaking off the discussion prematurely, his constancy to his friends, never getting fed up with them or playing favorites, self-reliance always, and cheerfulness, his constant devotion to the empire's needs, his stewardship of the treasury, his willingness to take responsibility and blame, the way he handled the material comforts that fortune supplied to him in such abundance, without arrogance and without apology. If they were there, he took advantage of them. If not, he didn't miss them. But most of all,

• 14:29Ryan Holiday?

  I am struck by what he learns from Maximus. I actually just read this one onstage the other day. It says, "From Maximus, he learned self-control and resistance to distractions, optimism in adversity, especially illness, a personality in balance, dignity and grace together, doing your job without whining, other people's certainty that what he said was what he thought and that what he did was done without malice, never taken aback or apprehensive, neither rash nor hesitant or bewildered or at a loss, not obsequious, but not aggressive or paranoid either, generosity, charity, honesty, the sense he gave of staying on the path rather than being kept on it." And those are just a couple

• 15:14Ryan Holiday?

  of the things he thanks. But back to me and Dan.

• 15:19Speaker 01

  Springsteen's been in the news lately and it's like, he talks about the moment he saw Elvis on the television.

• 15:24Ryan Holiday?

  Yeah.

• 15:25Speaker 01

  Like the moment, right? These moments of ignition and they're not about information. They're not about like learning some fact or seeing some person. It is about this energized relationship where you are, you find yourself mattering. You find this sense you that you're, you're seeing some immense value, some enchanted circle. And those moments, I think they happen all the time and they end up driving these big things that happen both in history and in our lives individually. And cluing into them as a parent, I think about that a lot. As a community member, I think about that a lot. As somebody who's in, in a high performing organization, it's like, how do we cultivate those? Like, where did that happen? I can't help but wonder, like, where did that happen for you? Cause you got lit up at a pretty young age.

• 16:07Ryan Holiday?

  I did, I mean, someone handed me the ideas from the Stoics and I was like, oh, where's this been?

• 16:11Speaker 01

  I'm in.

• 16:11Ryan Holiday?

  I'm in.

• 16:12Speaker 01

  Go back an inch, but like, what led you to be in?

• 16:15Ryan Holiday?

  What led me to see it or what led me to be excited?

• 16:18Speaker 01

  Why were you craving? What itch did it scratch for you or where did it, where did it resonate?

• 16:22Ryan Holiday?

  Why one thing lights us up and another doesn't? I think there is, I do think there's something sort of otherworldly about. I don't know how much choice we have over that.

• 16:31Speaker 01

  You saw Elvis through the TV.

• 16:33Ryan Holiday?

  Yeah, I think, yeah, there's just some, sometimes it lines up. Like why this person loves physics and this person loves, you know, physical education, you know, who knows? But like the decision to me that's interesting is what do you do next? Like, cause how many people go, oh, well, that's impossible. Or, oh, but that seems like a lot of work or that's not for people like me. Or, you know, it's what do you, what do you do with it? That that's what ultimately matters.

• 17:00Speaker 01

  Right, right. It's true. You get your reps, right?

• 17:03Ryan Holiday?

  Or do you do the reps or not?

• 17:05Speaker 01

  Yeah, right.

• 17:05Ryan Holiday?

  I bet you see this a lot with athletes that you've seen come in through the organizations or you see someone who has all the raw materials.

• 17:13Speaker 01

  Oh, man.

• 17:13Ryan Holiday?

  But it just doesn't happen.

• 17:14Speaker 01

  And the reverse, someone who's like, yeah, they're too short, they're too slow, da, da, da, da, but they can absolutely do it. And it is this, you know, it's a combination of things, but it is, an ecosystem is a good way to look at it. Because look, you're going to need to be plugged into some big source of energy.

• 17:27Ryan Holiday?

  Yeah.

• 17:28Speaker 01

  Favorite example of this is Jose Ramirez. He's five foot seven. He was signed for $50,000. He walks like, do you ever watch the Jeffersons? George Jefferson is, he's the most swagger walk, he's the most swaggy guy on the planet. Jose is. And when he got to the major leagues, there was another player who, who was brought up with him. And the other player was getting autographs of the other major leaguers in the clubhouse. And they were, and Jose, he said, Jose, should I, you want to get some autographs? And he goes, they should ask me for my autograph. Like, I'm Jose Ramirez.

• 17:58Ryan Holiday?

  Is that confidence or is that ego?

• 18:00Speaker 01

  I think it's earned at some level. It's, it's deeply earned. But in a sport, it's a unique context. It's a sport where you fail a lot and having that kind of crazy self-belief can be helpful to a point. And then, man, that guy gets his reps. That guy pays every swing matters. He knows what he is up to with every rep. And he gets more out of each rep. So from the distance, oh yeah, he's just super confident and that helped. From, from depth, he's, he's absolutely, it's based deeply on something.

• 18:40Ryan Holiday?

  So it's actually funny, right after Dan left, we had a great little chat and then we walked around the bookstore. He sent a note and he said, he felt like there was something he wanted to add about a story he was telling about the Cleveland Guardian star, Jose Ramirez, that, that he thought would explain him as the leader he is today. So let me put that in here.

• 18:59Speaker 01

  How fearless he was, how he walked in and felt like instantly he was not intimidated by the major league environment. And the question is, when you dig into that, it's like, where does that fearlessness come from? Where does that confidence come from? And when you look into that, you go back to when he was 13 years old in Bani, in the Dominican Republic, and Jose was playing for an adult league. And it was some tough guys and there was some gambling. And he has said that behind home plate, they kept a machete. Kind of for, I guess, inspiration, you might say. So that's the kind of background that he came out. And when you come out playing game after game with that kind of pressure,

• 19:41Speaker 01

  the big leagues maybe isn't as intimidating to him as it would be to some other folks.

• 19:45Ryan Holiday?

  Okay, back to, to Dan and I chatting in the studio. I bet you see people who, who everyone is trying to get to put in the work, trying to give them the things they need to realize that potential. And it's just not getting through. And I suspect that at some level, that's the story of communists. There's also this fascinating statue of Seneca and Nero. And, um, you know, Seneca is like trying to teach Nero and Nero is just kind of just your classic.

• 20:14Speaker 01

  No way.

• 20:15Ryan Holiday?

  Sullen, petulant teenager that could not give two shits less, you know? That unreachable ability is probably what keeps coaches up at night. Like, I know if I could reach this kid, they could do it.

• 20:28Speaker 01

  Absolutely. They're so defended.

• 20:30Ryan Holiday?

  Yeah.

• 20:30Speaker 01

  And they're so defended by what got them there.

• 20:32Ryan Holiday?

  Yeah.

• 20:32Speaker 01

  They've always been the best player. They're very well defended. And what ends up working in some cases is, well, it works in every, every case really, is a moment of vulnerability, sometimes with an injury, sometimes with getting sent down. You'll have a window where they're kind of reachable, where it opens. And vulnerability, I think we often, we sometimes think of vulnerability the wrong way. Like moments of shared vulnerability are what create relationships. They're not, you don't have to like build up trust before you can be vulnerable. Like it's the vulnerability that, that makes it happen. And so having conversations during that time and creating a space where they can reflect and maybe find some new mental models and some new meaning and a new type of strength. Like there's the brittle strength. I'll show you I'm the best player. I've always been the best player. That's, that's brittle in the end.

• 21:16Speaker 01

  But then you've got something softer, something stronger, something that's more oriented often around service, around being a good teammate.

• 21:25Ryan Holiday?

  Yes.

• 21:26Speaker 01

  Around realizing that, hey, if you go 0 for 4 and the team wins, that's a good day.

• 21:31Ryan Holiday?

  Yeah.

• 21:31Speaker 01

  Right? So finding that, that level of, it's sort of a growing up process for them many times. And, and these days, if you're 19, you're a great athlete, you haven't had that many reps at growing up.

• 21:42Ryan Holiday?

  Yes.

• 21:43Speaker 01

  So approaching them with a ton of patience and understanding, because the easiest thing to do is to say, kids are tool.

• 21:49Ryan Holiday?

  Right, right.

• 21:50Speaker 01

  It's really, really tempting and easy. And that's true to a point.

• 21:53Ryan Holiday?

  Yeah.

• 21:54Speaker 01

  But if you continue to create that space and continue to give them opportunities to get those reps at growing up, you end up with a better outcome, actual, actual growth, which is painful, but worth it.

• 22:04Ryan Holiday?

  Yeah. The coach that's able to sort of wait for the opportunity or the way in, like they know this person needs to hear this thing, but they also know they're not ready to hear that thing.

• 22:15Speaker 01

  Yep.

• 22:15Ryan Holiday?

  And they're willing to. Give them the latitude.

• 22:20Speaker 01

  Yep.

• 22:20Ryan Holiday?

  And the time till they're ready to come around.

• 22:23Speaker 01

  Grace is not a bad word for that.

• 22:24Ryan Holiday?

  Sure.

• 22:25Speaker 01

  In a way, like it is, because that's what it kind of takes. It's a gift. It's like, give them, give them that space.

• 22:31Ryan Holiday?

  Especially, yeah, you're thinking about it's that 20 years of day to day instruction. Right? Like you think about, that's why you need that time. And you could argue that I think a lot of organizations and industries fail. I mean, even our industry, like in publishing, like, how many authors do more than one book with the same publisher?

• 22:47Speaker 01

  Yeah.

• 22:47Ryan Holiday?

  Is extremely rare. And then publishers wonder why, you know, they have to miss so many times. It's because you don't cultivate or develop talent. You've decided to be a one off transactional relationship industry. And then you don't cultivate talent. How many coaches stay with the same team? How many players, you know, get shipped it? Like, because, because everyone is looking, you have to have that short term success. It prevents you from developing long term leaders and long term talent.

• 23:18Speaker 01

  It's so true. And then the deeper irony of that is we're so terrible at predicting who's going to be good.

• 23:23Ryan Holiday?

  Yes. You'd think we'd have some humility about it.

• 23:25Speaker 01

  You'd think we would. You think, well, give that person another chance. Like, like, really, people, there is.

• 23:29Ryan Holiday?

  I mean, Sam Darnold.

• 23:30Speaker 01

  Yeah. Oh, my God. You're right. Right. That's perfect.

• 23:33Ryan Holiday?

  Yes.

• 23:33Speaker 01

  That's perfect. Right. Yeah.

• 23:35Ryan Holiday?

  Here he is. And weirdly, that story is more common than Drake May, who's leading a team to a Super Bowl, like in his first season or second season or whatever. Like, it's much more common that people struggle and fail and eventually come around and then surprise us somehow. That's surprising.

• 23:51Speaker 01

  Right.

• 23:51Ryan Holiday?

  Even though it's the most common story. But instead, we go number one draft pick should be good out of the gate. And then they're not, and we get rid of them.

• 24:00Speaker 01

  Get rid of them. Right. And then you go, you know, even one layer deeper there. And you always find that community of people. There's so many, you know, there's a lot of science on this too. But it's just like, it's, you know, Darnold is not an individual, actually.

• 24:13Ryan Holiday?

  Sure.

• 24:13Speaker 01

  Right? There is this whole dance that's going on with information and with movement on the field. And he's a part of that. And as a whole, they're quite effective. And you could pull him out of that and he would stop being effective. But we can't stop focusing on the individual and celebrating the individual. Every time, especially with this latest project, it's just like, man, the power of community. It's like, you always see the solitary genius and the lone hero, and then you go, well, kinda. Let's go a little deeper there. What about that moment when, you know, they had the mentor? And so in my life, anyway, learning to, even though I'm singling out those individuals, learning to like actually squint my eyes a little bit and look for the lattice work of relationships and those moments that helped form them through time.

• 24:56Speaker 01

  And those reps where nothing happened and then finally things came together. It's like, it's always way more complex than you think.

• 25:02Ryan Holiday?

  Yeah, it's like a successful president has a cabinet, which is the official relationships. Then they have what we call the kitchen cabinet, which is the unofficial advisors and teachers. And then maybe they have a spouse and, you know, like there's, there's this huge network of people that are involved. And if they don't have it, if they are the solitary figures, those are usually not just the most miserable of the leaders. But ultimately, they make some catastrophic, unforced error.

• 25:29Speaker 01

  Right.

• 25:30Ryan Holiday?

  You know, I'm sure there are a lot of people that could have told Putin exactly how invading Ukraine would go.

• 25:35Speaker 01

  Yeah, right, right. Not a secret.

• 25:37Ryan Holiday?

  Except for there are no people who could tell them that because that is a kamikaze mission.

• 25:41Speaker 01

  That's right.

• 25:41Ryan Holiday?

  And that is the sort of trap that dictators and sort of imperial CEOs and whatever, you know, whatever the, the less sort of violent authoritarian version of it is, is the more isolated you are, the worse you are because you're just getting less information and insights.

• 25:59Speaker 01

  The group brains are really pretty good, right?

• 26:01Ryan Holiday?

  Yeah, we call it group think, but like sometimes, yeah, that can hold you back. But most of the time, it also holds you back from plunging off a cliff.

• 26:08Speaker 01

  Yes, with genuine curiosity. And I keep seeing, you know, I talked to a guy named Dave Cooper one time who headed up the people who got Bin Laden, Navy SEAL Team Six commander. And he said, the most foremost important words that a leader can say are, I screwed that up. Right? And they go, it goes two directions. You are fallible. You have wrong instincts. You screw things up.

• 26:29Ryan Holiday?

  Sure.

• 26:29Speaker 01

  But to everybody around you, it creates that space where they can step in and say.

• 26:34Ryan Holiday?

  Yeah, next time they can help you, they can help you before you screw it up because they know you're interested in, you're okay with being wrong.

• 26:40Speaker 01

  You gotta talk to me.

• 26:41Ryan Holiday?

  Yeah.

• 26:41Speaker 01

  He would stand next to a window and kind of do it on purpose. And then there'd be someone new in the room. He would say, hey, you gotta tell me to move away from the window. I didn't realize I was standing by the window. That's a dangerous place for me to stand. Grab me, if you have to grab me, grab me. Creating that space where you're saying, you know, hey, you have a voice. This is not just safe for you to speak up, but it's you have a role here. It's really important that you speak up.

• 27:04Ryan Holiday?

  Yeah, there's a story about Hadrian, who was actually not that great of a leader. He was a problematic, not ironically, not the model that Marcus really wants to model himself after. It's ultimately Antoninus. But there's a story about Hadrian arguing with one of his advisors over some philosophical question or mathematical questions, some, some thing that they're arguing over. And, and they go back and forth. And eventually the advisor says, you know, actually, you know what? You're right. I'm wrong, you're right. And a friend comes, why did you, why did you do that? You're like objectively right here. There's no, let me show you, you know, why you're actually correct. And the advisor goes, I think you're mistaken. He says, the man who commands 40 legions is always correct.

• 27:46Ryan Holiday?

  And that is the problem with being the, the leader or the, the person in charge, especially if you are intimidating or vindictive or, you know, withholding or any of those things that can serve as a sort of, not just a deterrent, but then also a punishment to people who, uh, correct you. Or you, you end up not getting the thing you desperately want.

• 28:09Speaker 01

  And so to do that, that jujitsu that is required of do that, of constantly humbling yourself, but constantly asking the least powerful person what they think, of constantly invoking stories where you screwed up.

• 28:19Ryan Holiday?

  Yes.

• 28:20Speaker 01

  Is like, ends up being like the stoic practice, maybe of like, this sucks. But God, it creates conditions for this, for this group brain to light up a little bit and, and knocks us out of our reflexive hierarchical kind of wince that we all do around power. And so these, the leaders that I've been around have got those jujitsu moves down. They always are saying, I'm probably off on this. I don't know. What, what do you think, Bob? And they're constantly deflecting. They're constantly walking around and saying, hey, if you could. Change one thing about what we do here. What would it be?

• 28:52Ryan Holiday?

  Yeah.

• 28:53Speaker 01

  One thing, change one thing. They're like a little fire hose of little signals that are like, I'm, I'm an idiot. It's kind of what all of them say, you know, help me out.

• 29:00Ryan Holiday?

  What they're, what they're not doing is what leaders think works. They go like, my door is always open.

• 29:04Speaker 01

  Nope.

• 29:05Ryan Holiday?

  And, and then they think that's what's going to create a culture of feedback and criticism and, you know, sharing.

• 29:13Speaker 01

  No, right. Exactly. It doesn't come close. You have to actually build spaces, platforms, support people to get in that room and say those things because we don't typically want to.

• 29:23Ryan Holiday?

  There's a story, I think I told it in Wisdom Takes Work about Elon Musk, where someone, he just shared something horrendously offensive and stupid on, on Twitter. And one of his employees was like, hey, like I genuinely worried that you shared this, you know, like 1% of the population would fall for this thing and you fell for, you know, he's like, sort of laying into him.

• 29:40Speaker 01

  Right.

• 29:40Ryan Holiday?

  And, and Elon Musk, like, you're fucking fired. You know, he fires him, kicks him out of the room. And then, um, later in that same meeting, he, he says like, why isn't anyone else talking? You know, it's like, because you just executed someone in front of them.

• 29:54Speaker 01

  Yeah.

• 29:54Ryan Holiday?

  Like they're not only not going to share in this meeting, they're not going to share some safety concern or some legal concern nine months from now or nine years from now that could prove catastrophic because you just gave them a very powerful demonstration of what you do when people criticize you to your face.

• 30:15Speaker 01

  It's unbelievable. The lack of awareness of some of that stuff is almost hard to believe. Our propensity for self-deception is.

• 30:21Ryan Holiday?

  And the timelessness of it, right? This is, this is what.

• 30:24Speaker 01

  This is mythic.

• 30:24Ryan Holiday?

  Kings were doing 10,000 years ago. And, you know, it's also what, you know, parents do. We go like, I want you to come to me with anything.

• 30:33Speaker 01

  Right.

• 30:33Ryan Holiday?

  And then, and then the last time they came to you, you grounded them. And then you wondered why they, they're not opening up to you.

• 30:40Speaker 01

  And underneath it all, like I'm, I'm so fascinated by that moment, those moments, because another sort of big unlock for me, this idea that we've got two attention systems, like we have kind of a task attention system that likes to do that kind of stuff, that likes control, that is able to get, well, no one rid me of this priest. You know, that says bold things and that sees the world. Through a very, very narrow tube.

• 31:04Ryan Holiday?

  Yeah.

• 31:05Speaker 01

  And that is built, the evolutionary part is fascinating to me, that is built to grab food, is built to spot something valuable, control it.

• 31:13Ryan Holiday?

  Yeah. Win the

• 31:14Speaker 01

  Quickly.

• 31:14Ryan Holiday?

  Win the interaction you're currently in.

• 31:16Speaker 01

  Task attention, win it, right? And then there's this other form of attention, you know, relational attention, where it's like, oh, evolutionarily, I need to pay attention to the sky, to the social fabric. I need to be nuanced. I need to really connect to what's going on.

• 31:31Ryan Holiday?

  Right.

• 31:31Speaker 01

  And the unlock was that they compete. You can't have both on at the same time.

• 31:35Ryan Holiday?

  Sure.

• 31:36Speaker 01

  And in all these moments, they're all like examples of people who are feeling super strong. Cause that's how you feel when you're controlling. It feels great to say that. Musk felt awesome when he said that.

• 31:46Ryan Holiday?

  Yeah, yeah. He was reveling in his power.

• 31:48Speaker 01

  So much control.

• 31:49Ryan Holiday?

  Yeah.

• 31:50Speaker 01

  And the move, over and over again, is to like surrender that and say, well, wait a minute. Wait a minute. I really can't control it. I'm really not the center of everything. I can't control everything. I'm just a person in this space. What's going, what is this? What's actually going on here? And the leaders who have the ability to make that move.

• 32:06Ryan Holiday?

  Yeah.

• 32:07Speaker 01

  Where they got to be a leader, some because they like control a lot of times. But to have that move where they can actually sort of let go, or parents who can have that move and actually sort of let go, it's like endlessly powerful.

• 32:18Ryan Holiday?

  The flipping between short term, long term. Do I want to be right about the couch or do I want to stay married?

• 32:22Speaker 01

  Yeah.

• 32:23Ryan Holiday?

  You know, do I want to decide my kids' major? Or do I want them to bring their grandkids around 20 years? You know, like, like, how do you think about the, are you in the trap of the present moment?

• 32:35Speaker 01

  Right.

• 32:36Ryan Holiday?

  Or can, it's funny because we think like, we go, they're philosophical. It's not like they know Aristotle.

• 32:41Speaker 01

  Right.

• 32:41Ryan Holiday?

  It's like the lowercase philosophical, I think to me, it's like, can you see the big picture? Can you go to what really matters?

• 32:47Speaker 01

  Right.

• 32:48Ryan Holiday?

  And so often you're in these exchanges where the thing you're trying to win doesn't fucking matter at all.

• 32:54Speaker 01

  Right. And our society is sort of increasingly built around those types of exchanges.

• 33:00Ryan Holiday?

  And as we wrap up here, one thing that stands out to me from this conversation is how simple some of these ideas are, but how easy they are to overlook. And of course, how difficult they are to put into practice. Culture isn't built through big speeches or strategies. Leadership isn't this performative thing. It's built through small signals repeated over and over again. And I think that's what Dan's work reminds us of. If leadership is more like tending a garden than running a machine, and the job isn't control, it's about creating the conditions, making the example, so that people feel safe enough to contribute, to grow, and ultimately to flourish. Thanks again to Dan for coming out to the Paint and Porch to have this conversation in person.

• 33:44Ryan Holiday?

  If you're looking to become a better leader in your personal or professional life, I think you should check out The Culture Code, The Talent Code, The Little Book of Talent. Of course, his new book Flourish. I'll link to those in today's show notes. You can go to his website, danielcoyle.com. And then we also have a big course we did here at Daily Stoic, all about leadership that I think you'll like, the Daily Stoic Leadership Challenge. It's our longest course, it's our most involved course. You have a bunch of in-depth interviews like this one in there, and you can find all that at dailystoic.com/leadership. Or if you join us in Daily Stoic Life at dailystoiclife.com, you get that course and all of our courses for free as part of it.

• 34:22Ryan Holiday?

  Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us, and it would really help the show. We appreciate it, and I'll see you next episode.