


In this episode of The Daily Stoic, Ryan Holiday explores Stoic principles that can enhance leadership capabilities. Drawing on historical references from figures such as Seneca and Marcus Aurelius, Holiday outlines the pitfalls of leadership blindness and prescribes Stoic wisdom as a remedy.
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2:29You can't deny this. Seneca thought he knew Nero. He was confident in his ability to teach or contain or even control him. Other Stoics knew better. Thrasia, whose story we tell in Lives of the Stoic, opposed Nero from the start. Agrippinus, another fascinating Stoic in lives, wouldn't even attend Nero's parties because it was clear to him that the man was a tyrant. Surely these men and women communicated their concerns to Seneca. Surely people raised questions, but Seneca thought he knew better. He was also paid so handsomely by Nero, was so powerful as a result of his position as Nero's teacher and advisor, that it became hard for him to see what was there.
3:07It's a classic case of the problem outlined by Upton Sinclair many centuries later. It's very hard to get someone to see something that their salary or status or identity depends on them not seeing. We all have blind spots like this, and some are more forgivable than others. Marcus Aurelius with his stepbrother, Lucius Ferris, and recent presidents and their children. The reason we have trouble seeing what is so obvious to everyone isn't just that we're close to these people, it's that we don't want to admit we're wrong. We don't want to hear what we're being told because it will mean changing our minds, having tough conversations, making painful decisions.
3:44Yet even Marcus Aurelius would write in meditations that false friends should be avoided at all costs. He spoke of needing to understand the true character of those you're dealing with. And this doesn't mean we have to cut out everyone who isn't perfect from our lives. It doesn't mean we have to betray them, although in Seneca's case, Nero did need to be conspired against, and eventually Seneca did. But it does mean that we can't be naive. We can't deny what is obviously true, or that will cause us and others we love even more trouble. It's only delaying the inevitable, only deferring the painful choices and consequences will inevitably face.
4:22Ask yourself, who could I be if I was less tied to this thing, less sucked into this thing, and more present and focused with what's in front of me?
4:33For thousands of years, leaders have been turning to this secret weapon. They've been reading about it. They've been sharing it. They've been talking about it. They've been turning to stoic philosophy, to philosophy, to be better leaders. In meditations, Marx really says, no role is so well suited to philosophy as the one you're in right now. Not every reader is a leader, as Harry Truman famously said, but all leaders have to be readers. And I would say they have to be familiar with these ideas in stoic philosophy, dating back not just to Marcus Aurelius' time, but to the time of Frederick the Great, time of Admiral James Stockdale, to modern American presidents and sitting senators, head coaches of football teams, special forces operators.
5:16They've all been relying on this formula, these ideas from the ancient Stoics to be better at what they do, to be better at leading the people they've been put in charge of. I'm Ryan Holiday. I'm a leader in a handful of different ways, right? I run my own business and I'm a parent, right? And on this broad spectrum of different paths and roles that I have in life, I have to lead people. And just as a human, I have to lead myself. And I turn to Stoic philosophy to be better at that. I've written my books now about ancient philosophy. I've been lucky enough to talk about it to the NBA, the NFL, sitting senators and special forces leaders.
5:50And in today's episode, I want to give you some Stoic based leadership principles, some lessons, some best practices from the Stoics that will make you a better leader. And a lot of this, by the way, comes from the Daily Stoic Leadership Challenge, which you can check out at dailystoic.com slash lead. I'll talk more about that later. But if you want to be a better leader, stoicism can teach you so much. And that's what we go into in the challenge and what we're going to talk about in today's video.
6:20Things are changing all the time. In fact, this is the motto of Queen Elizabeth's household when she was queen. They would say, if things are going to stay the same, then things are going to have to change, right? It takes discipline to be strict about some things, flexible about others. In fact, this is the paradox. This the difficulty. This is the highest form of discipline. The 48 Laws of Power, Robert Greene's amazing book on power. The final law, the 48th law and the law of power, all these laws telling you do this, do this, don't do this, do this. The final law is throw that all out and assume a kind of formlessness and flexibility, right?
6:56Bruce Lee says, be like water, right? The ability to adjust and adapt, right? Even as you hold some things sacred is this sort of key expanding discipline. Everything is always in flux, but there are values that we hold fast to. We create calm within the storm throughout our discipline. We know what to cling to and we know what to let go to. We grab firm hold of our minds and our bodies while everyone else loses theirs, right? That's why this discipline is so important. So the more stressful things are, the tougher they are, or the more irrationally exuberant and exciting and fun and lucrative they are, We have the same opportunity to practice discipline, to get firm hold of ourselves, right?
7:38To adjust, but also to hold fast.
7:44There's that expression, and excuse the gendered nature of it, but it only works this way if you rhyme. Happy wife, happy life, right? How do you think about leadership and their personal life, applying being a leader at home, applying, having a balanced, happy home so that you're not bringing your garbage to the office and you're not bringing your garbage from the office home? So the first thing is your job as a leader is to make really fast transitions. Why that is you play many different roles in many different places. Your job is not to carry the last conversation. So forget about how happy things are.
8:18Your job is not to carry the last conversation to this conversation. If you're going to be entirely attentive to me, it's about our conversation. So even during the workday, You just had a conversation. We just we just did this this conversation. You can't you can't let that influence what's going to happen next by mood, by by focus, by lack of focus, wherever else. Your job is to make fast transitions. And so you've got it. If that means you need to settle yourself and sit out in your car for a couple of minutes before you walk in the house, you can now be dad. Then that's what you need to do.
8:46But your job is not to walk into that house and carry with you forward anything that came from before. And that's about conversation. It isn't about happy. It isn't about disappointment. and it's about conversation. And because all of those things reside in conversation. So your job is to make transitions, fast ones, from conversation to conversation on carrying the phone.
9:08To me, reading is the great, we're talking about books, reading is the way to not have to learn everything by trial and error. Right. General Mattis has talked about, you know, people have been fighting wars for five or 10 ,000 years. They've been writing books about it for about five or 10 ,000 years. And he goes, if you're a leader of troops in battle, he says, it's unconscionable for you to try to learn lessons by experience. Because that experience is paid for in the blood of other people, maybe even yourself, when someone else has been in more or less the same situation, not only learned a lesson, but then wrote a book about it.
9:47Or someone wrote a book about that experience. And so, you know, advice isn't just a nice to have thing. There's almost something selfish and reckless about not availing yourself of the fact that somebody, I like to say, somebody either smarter than you or much dumber than you has been in the same situation. And you should benefit from what either of them did or what both of them did.
10:16We think we're good at multitasking of switching back. Oh, I checked this, then I'm back. No, the scientists show that there's a residue. It takes us a considerable amount of time to go from one task to the other, to be fully locked in on that task. And so the fewer the interruptions, the more distance you have, the more locked in you have, the better your performance is going to be. When you look at your screen time, when it shows you how much time you spent on your phone, ask yourself, what could I have done with that time? Ask yourself, how is that fueling my ego? Who could I be if I was less tied to this thing, less sucked into this thing, and more present and focused with what's in front of me?
10:50The killer advantage in the information age, to go to Mattis' point, is uninterrupted focus. How good are you at concentrating? How locked in are you in a world where everyone else is distracted?
11:06So does the failure of the first business and having to sort of start over, were there any lessons you learned there that helped you in the Listeria crisis? I've got to imagine you were more resilient the second go around. Yeah, I mean, I think just anytime you have a crisis, it always helps. And I've had, I was going to say, unfortunately, but really fortunately, I've had a lot of crisis that I've been able to get through. And so, yeah, I mean, when we found a pint of ice cream with Listeria in it in 2015, March 2015, I mean, it was the call that we didn't want to get. Nobody wanted to get. And the bottom dropped out in a big way.
11:40So we really lost everything. We went from$100 million valuation literally three weeks before to less than zero. And so over the next year and actually several years, we had to climb back out of that hole, back up to where we are now. We learned a lot. I mean, I think that probably there was some resilience based on, you know, from past experiences. But, you know, really when that happened, it was like our first thing was prevent an outbreak, which we did. And then we looked around and we're like, oh, shit, now we have to like rebuild our entire company. And so then we just started working on that.
12:09But when you get to that place of nothing or you're just at the bottom, you are also kind of given the permission to fight like hell. You know what I mean? To fight in a way that you would never fight in a normal situation. So there is something kind of really great about it. You know, when you get into crisis, it really concentrates your values, your moral code or whatever. You know, it really like you shed all of your excess and get to the core in a way that you would never do in non-crisis times.
12:40My all-time favorite Marcus Aurelius story comes at the depths of the Antonine Plague, ravaged Rome. That's not even the only crisis that happens in his reign. There's a flood, there's a coup, there's an invasion. He's just like besieged on all sides. Rome's treasury is depleted. Things look very bleak. It's not clear even that the empire can continue. And so what does Marcus Aurelius do? He leads a two-month sale of the palace furnishings. He sells his robes and his jewels, his wife sells their furniture. They sell down the palace furnishings to raise money. The idea being that the leader takes the hit first, that the leader eats last as the expression goes.
13:18Like Marcus could have made this somebody else's problem. He could have denied that there was a problem. He could have kicked the can down the road. Instead, he stepped up and he did the hard thing. And he did the hard thing as a bit of demonstrative leadership. And to To me, that's what I love about Stoicism. It's an interior philosophy, but it's designed to shape your actions in the real world where the stakes are really high. Mark Stavilius wasn't a philosopher. He was a leader who happened to be a philosopher.
13:46People tend to have professional goals. I want to get to this rank. I want to make this amount of money. I want to have this kind of life. I think we're less likely, unfortunately, we're less prone to creating goals for us for our personal life. One of the other interesting parts in meditation is, as Marcus says, you're trying to be a better wrestler, but not a better friend. He says, not a better forgiver of faults, not a better friend in tight places. And so I think the idea of like, well, what are you working on? Are you working only on your professional development? Are you also working on your personal development?
14:19And I tend to find that when we're working on both, they help each other. And I probably argue that personal development helps you professionally more than and professional development transfers over personally.
14:33You have an interesting story in the book. You're talking about how collectively you and the men and women on the ship go, we're not going to lose our tempers at all. And you said you were sort of successful in that. I'm curious, how does one collectively manage the tempers of hundreds of people in very close quarters with each other? Number one, you set an example as the leader. And so job one is you don't lose your temper. And, you know, I know Albert Schweitzer. I'm no mother of Teresa. I'm like anybody else. I get frustrated and upset. But I have worked very, very hard over the course of my life not to allow my emotion to override my judgment.
15:11And I have found by observing other senior leaders who are prone to losing their temper, shall we say, that it never helps. It simply injects more chaos into what is already a frustrating situation. For me, you have to, as a leader, you have to try and let time slow down and understand what's happening. And that's in combat and it's in day-to-day operations. So number one, it's toned and set from the top. Number two, go to the most senior people on the ship and get their buy-in. So here you're talking about your number two called an executive officer on a Navy warship, the second in command, your command master chief, the senior enlisted sailor on the ship, and your department heads, typically four or five people who are the next oldest people in the crew.
15:58So you get their very specific buy-in and you are ruthless about enforcing it as a culture. You call out anybody who verges into that. And then third and finally, you indicate again and again and again to the sailors that we're not going to blow up. I expect you not to blow up. We're going to figure this out together. And that narrative is very, very important to solving the problem. Again, I found this works very well in the heat of combat, and it works very well in the day-to-day maintenance of the ship.
16:35I think the other key element here, if we're talking about discipline, is saying a magic word, very difficult word, right? One of the hardest words, which is no. This is a picture I have between two pictures of my kids in my office. That's Dr. Oliver Sacks in his office. A reminder that whoever is asking him to do something, he's got to say no to that person. I have a little memo from Truman's administration. It's an inter-office memo between him and his secretary. and she's saying, look, you've got all these requests. Should we tell him the president is too busy and I have to say no? And he underlines it and he says, the proper response is underlined.
17:09The idea is that the president has to say no. You have to say no to a lot of things.
17:17Meditations is filled with self-criticism, with pushing himself to be better, calling himself into account. Again, Marcus Riles is incredibly powerful. People told him how amazing he was. They worshipped him as a god. But the more successful, the more important, the more beloved you are, the more important it is to have this practice. Other people are going to hold you to account less. It's an opportunity for self-discipline. It has to be. No one could tell Marcus what he was doing wrong, what he needed to do better. He had to do that. The same is true in this world that we live in, where we have wonderful freedom, where we don't live under a tyrant, where there is no authority monitoring everything we do and say and think.
17:54But that doesn't mean we should do whatever we want to say and think or do. We have to hold ourselves accountable. we have to follow that process ourselves. When I wrote The Daily Stoic eight years ago, I had this crazy idea that I would just keep it going. The book was 366 meditations, but I'd write one more every single day and I'd give it away for free as an email. I thought maybe a few people would sign up. Couldn't have even comprehended a future in which three quarters of a million people would get this email every single day and would for almost a decade. If you want to get the email, if you want to be part of a community that is the largest group of Stoics ever assembled, in human history.
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Seneca thought he knew Nero. He was confident in his ability to teach or contain or even control him. Other Stoics knew better. Thrasea (whose story we tell in Lives of the Stoics) opposed him from the start. Agrippinus (another fascinating Stoic in Lives) wouldn’t even attend Nero’s parties, because it was clear to him that the man was a tyrant.
Surely these men (and women) communicated their concerns to Seneca. Surely people raised questions. But Seneca thought he knew better. He was also paid so handsomely by Nero, was so powerful as a result of his position as Nero’s teacher and advisor, that it became hard for him to see what was there. It was a classic case of that problem outlined by Upton Sinclair many centuries later: It’s very hard to get someone to see something that their salary (or status or identity) depends on them not seeing.
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