The Daily Stoic - It’s Not Something You’re Born With. It’s Something You Earn. | 15 Stoic Strategies For Success

Episode Date: September 26, 2025

Just as one becomes strong through lifting weights, or skilled at woodworking through hours in the shop, we become wise through the same kind of effort. 📖 Preorder the final book in Ryan Holiday's The Stoic Virtues Series: "Wisdom Takes Work": https://store.dailystoic.com/pages/wisdom-takes-work📚 The Four Stoic Virtues: Justice, Temperance, Wisdom, Courage, are timeless keys to living your best life. The Daily Stoic is releasing a limited collector’s edition set of all four books signed and numbered, with a title page identifying these books as part of the only printing of this series. PLUS we're including one of the notecards Ryan used while writing the series. Pre-order the Limited Edition Stoic Virtues Series Today! | https://store.dailystoic.com/pages/stoic-virtues👉 Support the podcast and go deeper into Stoicism by subscribing to The Daily Stoic Premium - unlock ad-free listening, early access, and bonus content: https://dailystoic.supercast.com/🎙️ Follow The Daily Stoic Podcast on Instagram: https://www.instagram.com/dailystoicpodcast🎥 Watch top moments from The Daily Stoic Podcast on YouTube: https://www.youtube.com/@dailystoicpodcast✉️ Want Stoic wisdom delivered to your inbox daily? Sign up for the FREE Daily Stoic email at https://dailystoic.com/dailyemail🏛 Get Stoic inspired books, medallions, and prints to remember these lessons at the Daily Stoic Store: https://store.dailystoic.com/📱 Follow us:  Instagram, Twitter, YouTube, TikTok, and FacebookSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Welcome to the Daily Stoic Podcast, where each day we bring you a stoic-inspired meditation designed to help you find strength and insight and wisdom into everyday life. Each one of these episodes is based on the 2,000-year-old philosophy that has guided some of history's greatest men and women to help you learn from them. to follow in their example, and to start your day off with a little dose of courage and discipline and justice and wisdom. For more, visitdailystoic.com. Marcus Aurelius was not born wise. Neither was Seneca or Epictetus, Norcaito, or Xeno, or Cleanthes.

No one is born wise, ever. Though there are many forms of wisdom, one thing all wise people have in common is that they earned it. Wisdom is the result of an incredible amount of work, study, mentorship, experience, reflection. Just as one becomes strong through lifting weights or skill that woodworking through hours in the shop, we become wise. through the same kind of effort. As Seneca said, no man ever became wise by chance. And indeed, he said, much toil remains for all of us, no matter how brilliant or smart we naturally are.

More reading, more journaling, more asking questions, listening, debating, observing, learning from mistakes, seeking advice, questioning assumptions, more trying, more failing, more teachers, more long walks, more, more, more. Like the other virtues, wisdom is a byproduct of doing the right thing in the right way at the right time, not just once, but consistently over the course of a life. It is the result of a method. And yet, it is not actually ever possessed. That's because it is a method.

Not a groundbreaking one, but it's the same practices, the same questions that people have posed since we first started roaming the earth. And that's what the new book, Wisdom Takes Work, is about, the method, the timeless practices that help us get a little wiser each day, and the inspiration and the motivation we need to sustain that practice. It's questions we must keep asking habits and disciplines that, over a lifetime, bring us a little closer to wisdom. Hey, it's Ryan.

It's been my honor to do this Daily Stoke email over the last 10 years, and to have finally finished the Stoic Virtue series, which I've been working on for more than half of that time. If you've gotten anything out of the books over the years, it would mean so much to me if you could pre-order it. It's the most important and helpful thing you can do to support an author. It's how publishers decide how many copies to print, whether it appears in the bestseller list or not,

how many copies, bookstores order. All that comes from the pre-order numbers. So if you could pre-order it, it would mean so much to me. Dailystelic.com slash wisdom. I don't care what format, who you get it from, but this would be a huge help. So do that if you could. And I can't wait for you to hear the book. When you're busy, when you work hard, when you push yourself, one of the things that's really important is recovery.

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If you want to be better at what you do, you've got to put in more hours. If you want to achieve more, you have to push harder. If you want to beat the competition, you have to sacrifice more. You have to give up more. You have to be more single-minded than they are. You have to turn yourself into a machine, into a beast. You have to go all in. Isn't this what Marx really says in that famous passage in meditations

that people who love what they do wear themselves down doing it? Isn't that what Stoicism is, the discipline to push and push and push beyond any reasonable human expectation? In some ways, yes, but if that's your full understanding of Stoicism, you're going to get yourself in a lot of trouble, and you're going to burn yourself out. And that's what we're talking about in today's episode, not just Stoic strategies, for being successful, but Stoic Strategies for being successful, sustainable, for not burning yourself out. And so in today's episode, I'm going to give you Stoic strategies for not just working better and achieving more, but also living a better, more healthier, sustainable, and fulfilling life.

In Meditations, Mark Srula says, ambition is tying your success to what other people do or say, right if they select you if they approve you if they cheer for you says sanity is tying it to your own actions right that's the problem so much of what we want what we're aspiring to what our goals are are not in our control as epictetus would say but in fact they're the opposite they're handing over that control that judgment or evaluation to other people and so when your ambition shifts more internally towards what you control towards what you do to who you were while you did it you're empowered, right, and you're more self-sufficient. John Wooden said something like success is peace of mind, which is the direct result in knowing that you made the best effort to do your best

to become the best you're capable of becoming. And obviously John Wooden cares a lot about winning and he wins a lot. But you have this bigger, more encompassing definition of what your success is and who you're trying to be, how you judge yourself. So you can have a team that wins that you're disappointed in and you can have a team that loses that you couldn't be more proud of, right? And I try to get to a place, and I think I am at this place with my books where some of the books I'm most proud of have sold the fewest copies and the books that I'm, while proud of, I'm not changed by or puffed up by their success, right, because I've done better since. I'm more focused on other things in other projects. So you do your work, you focus on what you can

focus on, and, you know, you'll leave the rest of God, the gods, luck, the market, right? The whims of the universe, whatever you want to call it, you leave it there. Seneca says that life without design is erratic. The idea of having a routine, having structure, reducing the amount of variables and randomness in your life is a key part of performance. This is why athletes have routines. This is why practice is at a set time. This is why Lombardi would keep things on Lombardi time like punctuality.

Because you want to keep things contained. You want to keep chaos and disorder away. You want to get away from erraticness and you want to get towards purposefulness. This is why athletes have rituals that they do. This is why they have even superstitions. I think this is just a way of reinforcing structure of getting to a kind of routine, getting to the right head space. So think about all the ways in which your life is erratic and without design and focus on creating

structure and design there and you will see improvements in your performance as a result. There's a great story about Napoleon who famously wouldn't read his mail until three weeks after it arrived. He knew that most problems will resolve themselves. If you're so reachable, you will be inserting yourself into things that you don't need to be inserted on. You'll be spending time on things that will resolve themselves. We can imagine Marcus Reelius doing a similar strategy, Epictetus, or Seneca.

The idea of responding to everything in real time to being on top of everything in real time, Not only is this not a recipe for productivity, it's a recipe for misery too. You have to be willing not to know every single thing that's going on, to not be so reachable that anyone can interrupt you in your concentration at any time. Follow Napoleon's advice, sleep with your phone in the other room, leave your phone in the other room and you're going to do something important. Don't be so reachable. I have a little quote that I have framed in my office.

It's from Seneca. He says, too many people lack the fickle to live as they should and instead simply live as they have begun. We lack the ability to tweak and to change and to experiment to try to potentially find something better. So we just keep going down the path that we always went. Seneca says fickleness, but maybe in modern language we would say like adaptability. If you need things to be a certain way, then you're being held hostage by the situation.

You know, it's actually the, what's that quote? It's something like the oak tree fought against the storm and broke, but the willow tree bends and survived. It's like you need some amount of, you know, flexibility and adaptability. It's actually the flexible and supple things in life that survive, and it's the rigid and fixed things that break and are brittle. I think there's that line by Lao Zhu where he says, like, the way of the living is to bend and to adjust and the way of the dead is to, you know, be brittle and rigid. The secret to sanity and success is sleep. So I was a director of marketing and American Apparel for a long time. And there's a lot of reasons why that company failed. But I'll tell you one,

that I don't think enough outsiders understood. So Doug Charnney, the founder of American Apparel, had this open door policy. And when he said he had an open door that he was an accessible CEO, he meant it. Any employee at any level could call him or get in touch with him. And if you had a problem, he would listen to you. He was involved in all facets of the business. And this was positive in the sense that there was never a problem that he didn't know about. When there was an opportunity or a spark of something. He could really turn it into something that he didn't accept laziness. He had eyes and ears everywhere. He could jump on anything they needed to be jumped on and he could put out any fire. Now the downside of this was actually the same as the

upside. So you can imagine when the company was small, this work. But as it grew, suddenly it had a few stores, then it had more stores. Now it has 250 stores in 20 countries. What did that mean? it meant that no matter what time it was, someone somewhere had a problem. It meant that in some time zone, there was someone up who needed something. And I would say that slowly Dove's quality of sleep eroded to the point where by 2014, he was basically not sleeping at all. I remember he would call me sometimes and fall asleep on the phone, like sleep was something he was actively avoiding until the very last second that it grabbed him.

I remember there was this transition from one shipping facility to another. It was sort of impulsively and poorly planned out. It could have been done slower. He rushed into it. And at some point, he moves into the factory. It's kind of like with Elon Musk, where everyone sort of celebrating with the hands-on CEO sleeping on a cot in the factory.

But actually, this was a result of poor decision-making, I think, from sleep deprivation. And he exacerbated it, and it got worse and worse and worse. There was a famous scene where Dove is called in front of the board, sort of the lowest moment, the stock price is in the toilet. and he's mainlining Nescafe, like he's pouring Nescafe powder in cold water and drinking it to stay awake in front of the board. They were horrified, and ultimately they fired him, and his shares went to nothing. So there you have it. One of the fastest growing fashion brands in the

world, a company that was doing hundreds of millions of dollars in sales, it's not destroyed from the outside. It's not a competitor that came and destroyed it. Dove destroyed it. And Dove really destroyed himself in the process. He made a lot of mistakes. He did a lot of things he shouldn't be doing. But I think at the root of it was like he was out of his mind with sleep deprivation. He just wore himself to the bone. And he became someone very different than the person that was responsible for the success that had done the good things that were part of the company. This is obviously an extreme version of a story that happens all the time. Arianna Huffington, who actually carries a little note card with a quote from Marcus Aurelius with her,

She tells this horrifying story of waking up on the floor of her bathroom as she's building her business, covered in blood. She'd fallen and shattered her cheekbone on the bathtub as she'd passed out from sheer exhaustion. Now, look, Elon Musk seems to have been slightly more successful at balancing this than Dove has, or at least so far. But so many of the crises that he's working 23 hours a day to solve could have been resolved by a person who is actually not. so bleary-eyed, not taking uppers to stay awake and ambient to go to sleep. It's a vicious cycle where you make mistakes because you're cognitively impaired from sheer exhaustion and burnout and overwork. And then you have to work harder and harder and harder to stay afloom. I'm getting a little far from my point here, but what I'm trying to say is that working incredibly long hours,

working yourself to the bone, not taking care of yourself, neglecting sleep. It seems glamorous and cool, but it's actually destructive. It's actually a result of poor discipline. John Steinbeck talks about, he says, the undiscipline of overwork. He says it's the poorest of economies. You're trading sleep for working hours, but you're actually getting worse work out of it. I try to remind myself whenever I'm working late at the office, whenever I have some deadline I'm having to crush myself to hit, whenever I'm not taking care of myself because I've committed to too much, that I'm cheating myself. I'm cheating the work. I'm cheating my health. And I'm cheating my family. And that this isn't discipline. This is the result of a lack of discipline.

If you want more tranquility in your life, you have to do less. Marcus really says. And the magical thing when you do less, when you eliminate the inessential, when you stop saying yes to things that don't matter, when you stop getting caught up and busy work and nonsense, he says you get the double benefit of doing the essential things better, being with your kids, your creative work, getting outside, gratitude, all the things that matter in life you do better when you do less stuff. He says when you do less, you get the double satisfaction of doing the important things better. So much of what we do because we think we have to because other people are doing it because we're afraid to say no. No, you have to do less. When you do

less, you do more better. One of the things we have to strive for as Stoics is to have better boundaries. Stoics talk about being self-contained, about not being rattled by what's happening outside of managing your own crap, of controlling the inner citadel, your own soul, not vomiting your stuff onto other people, that's part of it, but also not allowing other people to vomit all over you, their problems, their issues, their lack of self-control, the things they want from you. You have to sort of keep up some defenses. You also have to be strong enough, confident enough, self-controlled enough, polite enough to say, I don't really want to do that. I'm not comfortable with that. I don't like that. I'm not okay with that. Here's what I am willing to do

instead. To me, boundaries are really about being a responsible, mature, communicative adult who sets the rules of engagement for your own life, for your interactions with other people. And if you can't do that, as they say, a country without borders is not a country. A person without boundaries isn't a person. It's hard to say no. You have to realize that when you're saying no to things, you're also saying yes is when you eliminate the inessential marks really says when you're really doing this saying yes to the essential you get the double benefit he says when you say no getting rid of the extraneous the extra the unnecessary and the double benefit is being able to do the essential the urgent the important to do it even better so i try to remind myself that every no is a yes and every yes

is also a no there's a book behind you i was just thinking about when i think of you one of my favorite books. Range. Have you read Range? I have not. Oh, so it's the subtitle is how generous triumph in a specialized world. What's interesting is like obviously to be great the NBA, any professional athlete, you have to be super specialized, right? Years and years, 10,000 hours of practice. At the same time, you're not one of those guys who, as Kobe was Kobe's all basketball. You were not all basketball. You had a range of interest and you explore those. I'm curious how guitar, music, language, reading, all the other things that you did, How did that make you a better basketball player and how is that sort of informed even now when you think about with your kids?

Yeah. I always had other things, you know, language, guitar and music came a little later. I had given up. I gave up on it in my mid-20s, early 20s. That's why I, you know, went back to it. But, like, I always wanted to do some things to take my mind off of basketball. Sure. Right?

It's a lot of flights, a lot of bus rides. So, you know, you need some hobbies. I didn't think of it this way. but I had a friend that told me your hobbies lead to greatness, you know, and I always thought that fascinating and just that made me look back on things. And I did these things just to kind of get my mind off of the game. Sure. Because, you know, I was all in the basketball.

That is all I did, but I also had other interests. And one of the things that I found was when I'm, like, so for instance, during the playoffs, I would cook the day before a game, I would cook dinner. because you have to concentrate on the meal or it's going to suck. Right. You know, so I'm looking at the time. I'm checking the meat. I'm making sure I don't burn, boil the water over.

It's a thing that I have to focus on. Sure. You know, because if I don't, my brain is going to start going, and then we're going to start thinking about tomorrow, and I'm going to be back in that rabbit hole. Right. It's fine. Sure.

You don't want to be there all the time. And one of the things I found is that once I start, relaxing in my cooking or in me playing the guitar or in me studying for something in language, I see some weird connection to where I think about basketball. But it would be like, oh, okay, I could put that to the side. It's like, it was this crazy thing of no, you know, no judgment. Wow, I never thought of that before. This is the move I'm going to do tomorrow.

I got it. Right. Yeah, sometimes when you're thinking about something else, you create room for your brain sort of, subconsciously solve some problem that we talked about willful will, you know, if you're, I got to solve this, I got to solve this, I got to solve, you're not going to make any progress. Yeah, yeah. And I think I read something somewhere, like Einstein played the violin.

If he ran into a problem, he just played violin for days, weeks, hours, whatever it took. So I always thought that pretty fascinating. And that's kind of what I started using my hobbies for. Because the grind will grind you down if you don't have anything to refresh. All the way down. You can stay in it and you can, you know, I was working with this, with a video game team in the Overwatch League. And it's these Korean kids, you know, living in L.A., competing.

And they weren't doing too good. They're supposed to be the best team in the world and they weren't doing too good. And their thing is to be like, okay, 18 hours a day. Playing video games. Playing video games. Like, hey, guys, you know what? Sometimes, you know what? Sometimes, you just stink.

Yeah, yeah. I've been there plenty of times. Sometimes you just need to go in there and be like, yeah, get out of here. Go for a walk. Go eat a delicious meal. Go do something else. Get out of here. You know, there is something to take from from just taking time off. That is, you know, you do need time to repair your brain and your body to be able to compete at maximum level. For some people, they lack discipline. This is why they can't get up off the couch. This is why they shove food in their mouth that they shouldn't do. It's why they don't do the hard work on themselves or whatever's in front of them. But then there's other people who have the exact opposite problem. They're too driven. They can't relax. They can't let up. They never know what enough is. Which is why at the Oracle of Delphi, their famous piece of advice, was moderation in all things. It's not good to have no discipline, to have no motivation and no drive. But conversely, it's not. not any better to have too much of these things. In the end, you wreck yourself. In the end, you don't become what you're capable of becoming. In the end, you hurt other people and you don't

fully realize the gifts that you have. So when we say that discipline is destiny, it's not any amount of discipline. It's the right amount of discipline that makes you who you are. Like a lot of people, I have a tendency to overwork, to overdue, to over commit, to take things too intensely marks a realist warns himself against this in meditations and it's stuck with me always he says in your actions don't procrastinate in your conversations don't confuse in your thoughts don't wander in your soul don't be passive or aggressive in your life don't be all about business don't be all about business there's a story about an ancient philosopher who wanted to prove that

philosophers were not motivated by and obsessed with money that they were indifferent to material things, but he didn't want that to come off as sour grapes, meaning it's not that the philosophers were incapable of making money, it's that they weren't consumed by the need to have a lot of it. To me, this is the idea of the preferred indifferent for the Stoics. That if making money is something you have the ability to do in your profession, why wouldn't you? Why would you do what you do for less than what it's worth? We shouldn't think of philosophy as being utterly indifferent to money. or that its relationship to money and the wealthy is spiteful.

No, a stoic should figure these things out. That's the discipline of wisdom. A stoic should be good at saving and investing. That's the discipline of temperance. But that doesn't mean your entire life is oriented around obsessed with getting more of it. Somebody once went up to the manager of Iron Maiden and said, you know, I really admire the work you're doing in the music business. and he said, the music business, I'm not in the music business, I'm in the iron fucking maiden

business. And this is actually a brilliant way of expressing it, right? I'm not in the publishing industry. I'm in the Ryan Holiday industry. You do what you do for the people that you do it for. Kevin Kelly talks about a thousand true fans and hopefully maybe it's way more than a thousand people. But those are the people that you're in business for and, of course, for your own artistic satisfaction and fulfillment. But you're not in the business. business as a whole, right? The business as a whole doesn't exist. The industry is not a real thing. It's just the label we've slapped on a group of independent individuals. And you've got to see it that way. You're doing what you do for the people that you do it for. And in fact, the lead singer

of Iron Maideness talked about this too. Bruce Dickinson, he said, you know, we've got our field and it makes no difference to us what neighboring farmers are doing, what people are doing in adjacent fields, because you can only plow one field. at a time. And that was such an important, huge breakthrough for me and how I think about my career, about how I think about what I do and how I live my life. Look, it's a bad use of your creativity. The time you're spending, imagining what might happen, the conversations you're making up in your head, the things that you think people are thinking about you. This is a bad way to deploy your creativity. You're using it to make

yourself miserable. You're imagining these terrible scenarios. Notice you're never imagining things going well, people liking you. You're putting your imagination to work on your anxiety, on your self-consciousness, on your doubt. And it's just not a good use of it. The Stokes would say our mind is this incredibly powerful thing. How are you going to deploy it? How are you going to use it? Are you going to use it to torture yourself or you're going to use it to move yourself forward to solve problems or create them? In one of his letters, Seneca talks about this man. He says he's a cautionary tale.

He said, this man has never seen the sunrise or the sunset. He was saying that this guy is just working himself to the bone. He said, it's so funny, right? We all fear death. We don't want to die. He says, but these people are burying themselves alive, burying themselves alive in triviality, in work, in bad boundaries. And it's that vicious cycle that's trapped so many successful and smart people.

This is so great. He says, let's lengthen our lives. He says, cut the night short, save some of the same. that for the day's business. Every day, I send out one stoic-inspired email to hundreds of thousands of people all over the world. If you want more stoic wisdom in your inbox, you can sign up at dailystoic.com slash email. It's totally free. Can unsubscribe at any time. We'd love to have you. Dailystoic.com slash email.

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