#111 How To Build Self-Discipline (5 Step Routine) | Ryan Holiday

What is the simplest, smallest action that you could apply to have discipline in your life?

The problem is we tend to think of these ideas as like things you are or aren't. Aristotle specifically says, no, no, no, that's totally wrong. So if you want to be more courageous, you got to do stuff on a consistent basis that scares you. That's how you have courage. That's what discipline is. It's a habit or a practice that you build, not a thing that you are or aren't.

Today, bestselling author Ryan Holiday breaks down the exact frameworks he uses to stay calm when everything's on fire. Make sharper decisions under pressure, and most importantly, for you to get things done. So if you want to build a mind that doesn't crack when the stakes get high, this conversation is for you. How do you battle procrastination, and what have you learned through Stoicism on how the greats do this too?

Seneca says, uh, this is the one thing all fools have in common, is that they're always getting ready to start. You know, I'll do it in the morning is probably the most insidious lie there is, but it also presumes that there is a later.

Can Stoicism help with anxiety?

Of course. We know the Stoics experience anxiety. Marcus Aurelius talks about it in Meditations. He says—

You gave some advice that I thought was really prolific on what to do when you are panicking and you have no idea what to do next. So I wanted to ask you, you know, what do you do when you're in a moment of crisis? You're panicking, but you've got to break free.

So actually, this came from a talk I gave, uh, to the Los Angeles Rams. We were talking about this idea of panic rules, like what do you do when coverage gets blown, what do you do when things go crazy, like what are the sort of bedrock best practices that you go back to. Because I think we make a lot of things very complicated, and then when you're sort of in the shit, all that goes out the window. That's what I I feel like Stoicism as a philosophy is. And we tend to think of philosophy as like theoretical and abstract and very high-minded. But for the ancients, it was this kind of thing that you practiced and you went over, over, and over, and over again so that like in big moments, like when you have a big life decision or your life is on the line or your whole world is falling apart, like what do you do then? So that's what I think a panic rule is. And I guess, you know, if you're sort of distilling Stoicism down to some core practices, it's like focus on what you control, do the right thing, you know, don't let your emotions cloud your judgment about this. Just because they're simple doesn't mean they're easy.

That's so, so true. You know, it's interesting because I have read your book, I was telling you, for years, "The Daily Stoic." And why I love it is because Stoicism, you know, if I'm gonna go back and read Epictetus, or if I'm gonna go back and read even "Meditations," which I find like, a little bit more accessible. It's dense stuff. And what I think your books do such an incredible job of, and I want people to get today, is how to take these core ideas that lead to a disciplined and in some ways more beautiful life because of that discipline and get it simply. And so you had this great quote that I loved, which is, "When you're lacking motivation, remind yourself, discipline now, freedom later. The labor will pass and the rewards will last." Can you tell me more about that?

Yeah, there's a line from one of the great Stoic teachers. His name was Musonius Rufus, and he said, you know, when you do something in pursuit of pleasure or you're taking a shortcut, like, the benefit that you get from that passes quickly, but the shame or the consequence of it lasts. And he says, conversely, when you do something hard, the labor passes quickly, but like the good from that remains. Like when you work out, it's painful in the moment. When you get in a cold plunge, it's unpleasant at first. You know, when you get up early, you're tired. When you work an extra hour, you know, that's, that there's a cost to that. But the benefits, the benefits, they not just endure, in many cases, way off in the future, the pleasures or the benefits that you experience are a lagging indicator from that. And so if we wanna think of discipline, like discipline is, or self-discipline anyway, is about constraint. Do this, don't do that. That's hard, but it provides you the freedom down the road because you either have some financial security, you have strength, you have confidence, you have health, whatever the thing you're delaying gratification for. Well, at some point you do get that gratification, and it's a more sustainable, enduring, and stronger reward than whatever you would like to get in this moment.

Yeah. My husband's a former Navy SEAL, and he, I remember asking him once, like, why do you like to follow the rules so much? He actually likes to follow the rules.

Sure.

Often. I think you would agree with that classification. And I sort of don't. And so, and silly rules, like, I'm gonna walk across the street, not in the crosswalk. Like, very silly things. And he'll be like, "Let's just wait for the thing." And, you know, I was like, "How does that work? Like, you're a Navy SEAL." And his comment to me was like, the only reason that we could do the things that we did is because we had to operate inside of the rules. And like, the second that you lose the rules, there's actually all of this freedom within the constraints.

Yeah, there's an artist, I forget who it was, that said, you know, you wanna be orderly in your sort of personal life, in your space, in the studio, so that you could be radically transgressive in the art. And I think there's something to that. Like, it does require a certain amount of rule-breaking and independent thinking to be successful at anything. But if you question everything, if you're contrarian about everything, if you disregard everything, what you live in is chaos and dysfunction. And also it's exhausting because you have to think about everything. And so when we think about discipline, again, as a constraint, what it really is is freedom also from that chaos and dysfunction, and it's allowing you to channel your energy. One of the things I, I do talk about when I talk to military groups is, is sort of the tension you're talking about, which is like the whole system is about creating rule followers, creating cohesion, creating coherence, creating camaraderie, a sameness. And yet ultimately be successful at the end, there has to be independent thinking. There has to be the ability to in the moment do hard right things. And so, you know, from the entrepreneurial space, you can get so used to just doing your own thing that it makes it hard for you to function as part of a team or part of a group or just like simplify your existence. And then conversely, you can live in a very simple, straightforward existence, you know, You do what they tell you your whole life, and then comes some big moment where what they're telling you is wrong or incorrect or dangerous, and do you have the courage and strength to ignore those rules then? That's the tension every individual has to figure out.

Yeah, you know, you've read, I don't even know how many books and papers and research. You own a bookstore for, the love of God. And so, you know, what I think is interesting is if we take these like esoteric ideas, kind of like discipline, you do a great job of simplifying them to things that you can do. So if somebody's listening today and they're like, "All right, I'm buying in, I'm buying what you're selling, I'm buying this idea that a life that is more disciplined could actually be better," what is the simplest, smallest daily habit or action that you could apply to have discipline in your life?

The problem is we tend to think of these like virtues or these ideas as like things you are or aren't. That you have or don't have, right? Like, I'm a courageous person, I'm a creative person, I'm a disciplined person. And then we think it's this matter of identity, and then when we don't have it, we feel bad about ourselves. Actually, the ancients, Aristotle specifically, says, no, no, no, that's totally wrong. It's something you do or don't do, right? He says, like, to be a woodworker, you work with wood. That's how you develop the skill, the virtue of woodworking or playing the flute or whatever it is. So if you wanna be more courageous, you gotta do stuff on a consistent basis that scares you. That's how you have courage. You either are doing it or not. So it's that it's a verb and not a noun. And so like, if discipline, you're going into the new year, a lot of us are like, you know, I want to eat better. Maybe you're like, I want to be more disciplined. Well, that's a really hard thing to be generally. So you wanna pick some specific things and, you know, like, What time you wake up is a great one. Or conversely, what time do you go to bed? Like a lot of people are like, you gotta wake up early. Well, waking up early in isolation is not great if you stay up till 2 in the morning, right? 'Cause now you're actually being, you have what they would call in the military, poor sleep discipline, right? And so you, maybe it's like, hey, I'm gonna, in 2026, I'm gonna go to bed by 10:00 PM every night, right? Then you've just, by the way, made getting up earlier a lot easier. So I would pick it up, some core accessible, definable tasks or items that you're gonna be more disciplined about. Even like, I wanna eat better this year. That is a very hard, ill-defined thing to do. But if you say, I'm gonna quit sugar this year, or I'm gonna go vegan this year, whatever, it could be any across the spectrum of the thing. The point is, what is the, black and white line that you're drawing and then you're on one side of that line or not. That's what discipline is. It's a habit or a practice that you build, not a thing that you are or aren't.

Yeah, that's a good point. I also like this idea of, that you said, like, what is the one easier sort of snowball effect move that you could do that makes the others more simple? And so like, you're right, getting up early is harder than going to sleep earlier. Whereas like laying out your workout clothes, easier than just going to the gym. Sure. It's like, what is that preemptive move you could do that's 10x easier but leads to a higher likelihood of you doing the next step?

Yeah, like I want to use my phone less this year. Okay, so I'm going to delete social media apps from my phone or I'm not going to—

Do you actually do that?

I don't have any social media apps on my phone.

You're like my husband. He's the same. So that's—

I like, obviously I have to use it for my work. I mean, I have a team that helps me, but like if I have to check, it's on my wife's phone. So I go, hey, can I borrow your phone for a second? And then there's like, there's a ticking clock. She's like, give me my phone back, you know? But the point is like, how do you make it a little bit less tempting, right? Or maybe you go, I'm not going to sleep with my phone in the room, or I'm going to leave it in the car when I get home from work, right? And so you can, you can say, hey, generally I just want to do less of this thing, which means you're going to have to make Lots of individual choices throughout the day and the week and the month and the year. And you might be able to start strong with that, but as you go on, because you're tired, because you're hungry, because stuff's happening, you're gonna be able to make excuses. And so how can you make clearer, simpler things that have like a big cumulative impact? That's what you wanna think about.

We're just such good self-rationalizing machines too. Like I've realized that, you know, everybody's like, oh, that guy's bad, that guy's good. I'm like, we're all sort of bad and good. Varying degrees of good at self-rationalizing why we're bad or good.

Yes. Yeah. I mean, there is this insidious voice that's always sort of, well, it's okay this time, right? The ability to make excuses, the ability to make exceptions. This is like our superpower. And you want to sort of preempt that as much as you can.

I like this idea of no phones because you have another quote I love, which is the secret to success in almost all fields is large uninterrupted blocks of focused time.

Of course.

Which feels, one, impossible to get.

Yeah.

And so how do we get it? And why is that the key? What does history and your experience tell us?

You know, most of the big things in my life came from lots of thinking or concentration. I had an epiphany, I had an insight, I had an idea, I worked really hard on a problem. And then you go, well, if that's really the big mover, right? I mean, like even the number of ideas that I've had on vacation or on, I go, if I didn't have the discipline to put my work down and go for a hike, the last series I did, I had the idea on a hike with my kids. And so how are you setting the events in motion so that thing can happen, right? And I think people know that like, you know, creativity and problem solving requires focus. And then you go, okay, but when I look at your calendar, you were all meetings all day, all week. Of course you haven't been having ideas, right? Of course you haven't been having those conversations that unlock something. And also, of course you aren't happy. Like, this isn't what you're meant to do. You're not meant to be on Zoom calls all day. This sucks, right? And so I think like when I look at my calendar, I was just talking to my assistant about this, like, it— their job is to keep things out of the calendar, not put things in the calendar. Like, like the calendar should have large amounts of white space, in my opinion. And that, that's not because I'm not working. It's because I haven't scheduled interruptions to the work. Like, if there's a blank space in the calendar, I'm going to use that productively. That's who I am. But if there is podcasts and meetings and errands and phone calls, What I'm not— not only am I not doing the thing, now the thing I'm supposed to be doing is I'm trying to squeeze into the little cracks as opposed to it being the main thing. So, so like, how do we schedule the time when we're at our best is really important. And to me, and I think you find this with most creative people, it's usually the mornings when it's quietest. Toni Morrison, the The novelist, she was a single mom and she was an editor at Random House as she's working on her first novel. And she found like to get any writing done, she had to get up, she said, not just to get writing done, but to do her best writing, she liked to write as she saw the sunrise. And then she said it was, she found that she did her best writing before she heard the word mom for the first time. And so you're like, okay, so you know that that is from 4:30 AM to 6:00 AM. And so you've gotta orient your day around that, not, well, that's when I'm best, but I actually sit down finally to write at 2:00 PM, you know? And so when are you at your best? When can you concentrate the most? When are the fewest interruptions? And then how do you make some hard adult decisions to center everything around that?

I feel like you need to stop yelling at me. Sorry. 'Cause I feel very called out about this.

I'm yelling at myself as well. And these are things you learn the hard way. Like every time I sit down to work in the afternoon, I'm like, this is why I don't do this. Because like I'm at best 70% of my best, you know? And that's not what you wanna be doing.

But I love that line, like your job is to take things, keep things off the calendar, not put them on. That is not typically how we think. And it's like this inverse thinking, you know, the Charlie Mungerism, which is like, what is actually the goal? And so how can we think 2 or 3 steps forward? I like how your mind works like that. And so you have a couple of quotes that I love too on procrastination. Yeah. Which is something we all struggle with. But this one about to procrastinate is to be entitled. It is arrogant. It assumes there will be a later. It assumes you'll have the discipline to get it later despite not having the discipline now.

Yes.

And it's so beautiful. And so tell me, what— how do you battle procrastination and what have you learned through Stoicism on how the greats do this too?

Well, we all battle procrastination. Seneca says this is the one thing all fools have in common, is that they're always getting ready to start. We don't say we're never going to do it. We say tomorrow, we say next week, we say in the new year. We say, "Oh, when the kids start school." We make up a reason why it can't be now. And the problem with this, this connects to another really, I think, powerful Stoic practice. I have a Memento Mori ring on right now. The Stoics are meditating on our mortality. So like, it's not just like, hey, you're probably not gonna get to it later. That's a lie we tell ourselves. You know, I'll do it in the morning is probably the most insidious lie there is. But it also presumes that there is a later, right? Like, it presumes that you can call your mom, you know, when things settle down. It presumes that, next year is yours to take for granted. And it's not. We don't have forever. Not just that all of us are going to die at some point, but that point could be like right now or, or conversely, it could be someone else. I mean, it was a very life-changing experience for me. It's a— I feel guilty on some level that it came out of such a, you know, that it came at such a cost. But I remember when I was an editor at this newspaper, a friend of mine sent me this article. He was like, "Hey, here's my column." And I saw it, I remember I looked at the email, and I was like, "I'll get to this on Monday," you know? And he died on Sunday. He went out for a hike and he had a heart attack and he died. And I didn't even give him the courtesy of saying like, "Hey, I got this, thank you. I'll review it on Monday." I just, I left him on read, you know? And so, not only do you not have forever, not only could you go at any moment, but the person or the thing that you're taking for granted, could go away at any moment. And so it's not that it is for certain going to go, but it could. And this has to inform our procrastination, our tendency to procrastinate, because in light of it, it becomes extremely entitled and in some cases very reckless.

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Yeah.

But I think one of the things that it reminds me is this exactly this moment to more because I found for entrepreneurs, we're a little crazy. We always live in the future or like in the moment intensely. And so this idea of it could all end, it's not gonna matter, you don't matter, is actually kind of hard. And so I was curious from your take, for high achievers in particular, is living in the moment and this idea of analyzing death particularly hard?

Yeah, I mean, I think one of the things you see as high achievers or high performance people is this idea, we were talking about delayed gratification, that is what makes them great, right? Like, I'm gonna be really miserable now so that in the future I can be successful. And there's something to that, right? Like, as I say, all success is a lagging indicator. The problem is, and this isn't so much about Memento Mori, but it is an important thing. Like, the idea that the shit now is worth enduring because it will be amazing later is a dangerous thing to fool with, right? Not just because you might not get later, but because you don't actually control whether later happens. And by that, I don't mean you could die. I just mean, like the market could shift, the economy could crash, the government could nationalize your industry. So many things could happen, right? Like you can do everything right in life and get fucked. And so I do think we spend a lot of time doing things in the present and we're— but we're trading it for this future payoff. And again, this is partly rational and partly okay. But it can be, like, I've just learned that if, and I learned this the hard way over the many books that I've done, like, if the experience is miserable and painful and lonely and stressful, but the payoff is that it comes out and it hits the list and people say nice things about it, that's a big gamble because You can get screwed by the list. Your book could come out in the middle of a pandemic. You know, you could get canceled. Like, things can happen. And so I've tried to do a lot of work at getting better at not being miserable while I'm doing it, right? Like, how do I enjoy it while I'm doing it? That doesn't mean I don't work any less hard, but what I try to do is go like, this is the part that's up to me. And so enjoying it and getting rewarded for it is also up to me. And I'm not going to be a miserable fuck day to day so that in the future I feel good for 2 weeks when it comes out and then I start the whole thing again. That just, that seems like a bad trade is I guess what I'm saying. And I think a lot of, like whenever I talk to athletes, there's not a single athlete that you will ever talk to who's retired who doesn't say something like, I wish I enjoyed playing more. 'Cause at some point it just goes away and then, And then at that point, the winning and losing stops mattering. And all they think back is like, I was in the NBA and I was miserable because of winning or losing, instead of being able to just be grateful that I get to play professional basketball. Do you know what I mean?

Yeah, 100%. So how do you enjoy the journey while it is a miserable one?

Well, in the Bhagavad Gita, they say that, You know, you're entitled to the work, not the rewards of the work. And so you go, okay, this is the thing. There was a period in my life when I was younger when all I wanted was a chance to do a book, right? And here I am doing that, right? Like, this is the dream. This is what I signed up for. Like, you love real estate, you love managing people, you love training, you love practice, whatever the thing is, you have to love it. And not what maybe or maybe not comes out of the other side. And so I just try to put like the finishing touches on it each day and go like, I did my absolute best. I made a positive contribution. I got to do this thing. I gave my best. That's wonderful. And then I try to think of whatever rewards or success happens later, not as unimportant, but as extra. So I've said this before, but I remember on my first book, you know, I was probably 10% proud and happy that I got to do a book and 90%, that period where, so for people that don't know, your books come out on a Tuesday, sales are basically pre-orders, then Tuesday through Sunday. And then there's this period from Sunday to Wednesday, and then back a million years ago when I started, there was also Friday. You would find out on the, New York Times and The Wall Street Journal list. That week period where the book was done and there's nothing else I could do and I was waiting to hear how it did, that was 90% of the success for me on that first book, right? Like, I'm waiting to— I'm waiting for somebody else who I don't know, who is following arbitrary made-up rules and has a bias and an agenda. I'm waiting for them to tell me the vast majority— whether, uh, in the vast majority of cases, what I just worked for years of my life on was worth it or not. And that is crazy, right? Like, if, if waiting for the deal to close or the wire to come through or the, the article to hit the presses or whatever the thing is, right, the Grammy nomination to come in, the, the, the Oscars, whatever the thing is, if that's all of it for you, you better hope everything goes right and you're part of the in crowd and they accept you. And so I've tried steadily, and it's been a lot of work and there's been some ups and downs, but I've tried to flip that. Like 90%, I get to do my dream. I said what I wanted to say. I worked really hard on this. I know it's good. I grew as a person, all these things that are up to me. And then there's 10% where I'm like, Sweet, it debuted at number 1. That's really cool too. But like, I was already in the A range before that happened. Yeah.

You know, it's funny with creating online too. I've really found it the same way. I haven't been doing it as long as you, but let's say I started getting online 3.5, 4 years ago. And at first it's so easy to get sucked into this arbitrary number of people who engage or don't engage, like or don't like. And at some point you start realizing that, You hate the thing that you created to get the likes for other people to like it, but you don't like it. It is the most bizarre circle until finally, thankfully I was older when I started doing it, and I was like, this is a sick disease. Why are we playing this game? Let's create things we actually like and are proud of. And don't get me wrong, we stray away from it all the time, and all of a sudden I'm in a chicken suit on South Congress or something ludicrous. You're like, how did we get here? But that practice of coming back to, Did I create this thing because I'm really proud of it and I think it should exist in the world? And if everybody hates it, fuck me, but I don't care.

And also, how do you set up systems and a culture and make choices where it's enjoyable while you're doing it, right? So like, if you create so much stress and so much anxiety and so much pressure, and by the way, you're doing so many things at one time that, that like, you're just, your life sucks, you know, again, you're putting it all on the potential payoff, which, which if you talk to successful people, nobody ever gets. And I don't mean that they're never successful. I just mean nobody feels like they arrived, that they finally got, you know, more out of it than they put into it. That never happens. So you have to think like, how do you make your day-to-day life and system and career and the thing you do as close to a form of reward and enjoyment and a process that you appreciate. Um, and then here's the trick is like, if that's the case, you will do it a lot and you will probably make good stuff that works, right? If you hate it and it's the worst, like I know people who they haven't done this. And so like, they just don't do that much work. Like they're intimidated and reluctant to like, start again, right? Like, if you're an athlete who's dreading the start of the season, well, you're not gonna work that hard in the off-season. But if you're like someone who, I just fucking love playing, you're gonna play all the time, and you're always gonna be thinking about it, and you're just gonna put more into it. So weirdly, I found the less I think about what the Stoics would call the externals, the more I just do better work, and then paradoxically, the more I get the things.

Yeah, it is sort of funny, isn't it? You know, I wanna talk about, another paradox that I loved a story you wrote actually in the new book, Wisdom at Work, which is you tell the story of a Zen master and his beautifully prized cup and what happens, and then the story of Epictetus and his lamp. And one, I think it'd be interesting for you to tell the story if you remember it. And then two, I wanna talk about I can't sometimes reconcile the positive versus the negative of like manifesting or focusing on things.

Well, the Zen masters have a lot of stories about cups. I think the one you're talking about is the Zen master who has a cup. It's his prized possession, and he tells himself over and over again, "The cup is already broken. The cup is already broken." And one day the cup breaks, and he's not surprised by it. For the Stoics, although I'm sure they did appreciate positive visualization, they actually practiced negative visualization. So if the Stoics believed that the secret was real, they'd be getting themselves in some real trouble, right? Because they said that actually you should be thinking about the worst-case scenario, thinking about the cup being broken, thinking about the travel delays, thinking about getting canceled, thinking about the deal falling through, you know, thinking about negative media attention. And their point was not that this invites this to happen, because that's not how that works. It was that the unexpected lands the heaviest. Seneca said that the one thing a leader is never allowed to say is, "Wow, I didn't think that would happen." And you're right, he's right. That is the job of a leader is to be like, "Okay, we planned for this. Here's what we're gonna do." And you're talking about your husband, a Navy SEAL. They practice for the worst things the most. They don't go like, "And here's how it goes swimmingly, 'cause it always goes swimmingly." I mean, on the famous bin Laden raid, they had an extra helicopter because they planned that one might crash, right? And what you get, not only is it situations where one crashes and then you have the extra helicopter, but you've also developed this muscle of like, hey, shit goes wrong all the time and I don't freak out. I just go to the next option. And so that's what you want to cultivate, right? So like, people, The Stoics use this word indifferent a lot, and people think that indifference is like, that's a controversial word, right? Like indifference means you don't care, but the Stoics meant it in the sense like I'm indifferent to whether it is hot or cold. I'm indifferent to whether it is a bull market or a bear market, right? Like whether it's a time of peace or time of war, 'cause I'm gonna figure out what I'm gonna do.

Right?

That's what it's about. So I don't think it's like pessimistic. And I also don't think it's like tempting fate. What you're trying to do is think about what could happen so that if and when that does happen, you're like, okay, and then you do what you need to do.

So do you think most people visualize or manifest wrong?

Well, I think most people are afraid to think of bad things because they think they'll invite that into their life. And the problem is bad things are going to come into your life whether you think about them or not. And that's what they mean when they say the unexpected blow lands heaviest. Like, to be surprised is to add insult to injury, right? To, to think it's unfair, to think that it's, uh, devastating, to, to, to not know what to do. That's, that's how you take a bad thing and make it worse. So I don't think, you know, in a bull market or in a boom time to be going, what would I do if market dropped by 40%? You know, that's not gonna make the market go up or down, but it does put in, it puts in motion some thoughts that you might need to rely on at some point. Like Napoleon said that, his generals should say to themselves 3 times a day, "What would I do if the enemy appeared on my left? What would I do if the enemy appeared on my right? What would I do if the enemy appeared on me, behind me?" And this is to say, like, you don't know what the enemy's gonna do. They're precisely trying to come upon you as a surprise. But also, I think it's just a good mental exercise. Like, it's keeping your mind moving instead of being complacent and secure, which, you know, none of us are.

Do you think you have a photographic memory? Your one-liner recall is amazing.

This is my job. This is my job. I don't think I have a— actually, I know I don't have a photographic memory. What I have is a system by which when I find information that is interesting to me, I write it and organize it and return to it enough times that I develop a feel for it.

I wanna hear about that because, you know, you talk about Abraham Lincoln, you know, famously, I think people would call him a stubborn reader.

Yes.

And that he, you know, would have to, in order to get him to remember something, you would have to like etch it on steel, and steel is quite hard to etch on.

No, no, what he said was that his mind was like steel, that it's hard to scratch something into it, but once it's there, it's there forever.

So I wanna talk about that. So what is your process to do that?

Well, I read a lot. That's like, I see myself as like a professional reader. That's my job. And then I don't leave it there. Like, I read with a pen and I take notes and then I transfer those notes. I was just before this, I just read something for a book I'm writing and taking that and I'm transferring it to note cards by hand. And it's not quick and it is not scalable, but that is like the whole point. I think sometimes we look for technological solutions to make things easy. And the whole point is some things are supposed to be hard. Yeah. You know, it's supposed to be difficult and it is in the difficult part that you're scratching it into the steel and then it's there. So I, I do, I take advantage of all sorts of new tools, of course, AI being one of them, but My research method is as analog and as old school as it can be because I'm trying to actually understand what I'm dealing with.

You know, I love this because you talk a lot about knowledge. I mean, you could say your entire project in some way is that. And I think it was in Wisdom at Work, but I loved the line from the book. It's actually from Thomas Gray, I believe, where he said, you must love learning if you would possess it.

Yeah.

And, um, and I think that was applied to, to Lincoln in your book. But as a stubborn learner, somebody who wants to possess knowledge, how do we do that? How do you actually go and learn things? You've talked about reading books multiple times, you've talked about rereading them. Like, how does one go and really acquire deep knowledge and remember it?

Yeah, there's a magical thing that happens when you get a payoff for having, like, learned and studied something, right? Like, I think in school you're assigned a bunch of books and the payoff is like you do well on a test that you're not sure why you're having to do. But the first time you read a book and it changes your life, or it makes you a friend, or it makes you money, and you go, oh, there was like a return on this investment. Like, you think— like, Warren Buffett is told to read The Intelligent Investor by Ben Benjamin Graham. And you know, that's probably the single best investment in human history. You know, like he reads this one book and he makes $100 billion. But you know, my life was changed by a handful of books that I read. So it's a hard thing to explain until you've experienced it. But when you go, oh, this is for something, this isn't just like to impress random people, but like there is in these books, in these lectures, in these experiences, in these people out there, like priceless wisdom, things that can save, not just save you painful trial and error, but can make you money, can change the course of your life. That's like a really powerful thing. And it's sad to think like most people or many people have never experienced that. Like you talk to people when you're like, oh, I haven't read a book since high school. And you go, so you learned a lot of things the hard way. You know, like there's a lot of things that every phase of your life from then to now, everything you've done, a lot of people have done before you and made all the mistakes and made all the right choices and written books about it or made videos about it or talked about it or there's movies. Like, there's so many things you could have learned that you decided to learn on your own. That's crazy.

Yeah.

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And also I think books are really unique because you have to, if you're not listening to them but reading them, you really can't do anything else. There's no multitasking while reading a book, whereas a movie you could be thinking about other things. It's very passive. Like reading is so active. And again, to your point on hard things lead to the right outcome, it's harder. And so it probably does get that scratch and steal that, you know, Lincoln talks about. But I was curious for you, you're a big rereader of books from what I can see. So what are the 5, 10 books that Ryan Holiday says changed his life and that you go back to and reread over and over again?

Yeah, I think reading a book once is great, but when you read it again, you are reading a new book because you're a new person. The book is the same, but you are in a different place and you will take different things out of it. I think Marcus Aurelius' Meditations is one of the most incredible books ever written. You know, the private thoughts of the most powerful man in the world. You know, it's an amazing book. I think all of Robert Greene's books are amazing. You know, Mastery is worth reading and rereading, The 48 Laws of Power, The Laws of Human Nature. You know, like, Robert's stuff is designed to be layered and to take multiple things out of them. I think Thoreau and Emerson, you know, Civil Disobedience and Self-Reliance, also incredible. All of the Stoics, you have Seneca, you have Epictetus, I love. I read this book by Tolstoy almost every day called "The Calendar of Wisdom," which is like a collection of all of the reading he did in the course of his life, just like little passages every day. It's sort of, it's a similar book to "The Daily Stoic." You know, I think the idea is that to really understand something, you gotta spend a lot of time with it. It can't be— I think people are always looking for shortcuts, you know? And they're like, oh, I read this on 3x speed on audiobook. And you're like, I don't know if that's winning here. Like, I don't know if you're trying to get it done as fast as possible. I think you're trying to spend as much time as possible with it. And so, you know, I don't know anyone that reads a lot that's like trying to, to spend less time doing it.

No, that's definitely not the case. Is Tolstoy's book— is he just like tragically sad throughout it? I find all of his writing to be such a fiction—

is very much that way, but this is— it has more— it has more hope in it, and it's more spiritual than you would guess.

Interesting.

Yeah, it was bad. So he, he wrote it, he thought it was his, his greatest book, this thing called Calendar of Wisdom. And then, uh, you know, the Russian Revolution happens like almost right after his death, and so it's banned. And it's not really rediscovered until the late '80s. So it's just, it's a very popular book, but it's much, much less known than any of his fiction. And it's like a lovely little self-help book.

What, let's give like for a particular person. So you're a father. You have a son and a daughter?

I have two sons.

Two sons.

Yeah.

So, you know, for them coming into young men, let's say, what are the books that you will set, you know, on their desk as they come into being, you know, young men that you would want That's a good question.

I haven't come up with a reading list yet, 'cause they're still pretty young. But we spent a lot of time when they were young, you know, look, children's books are great, and they're all about pizza and monkeys and, you know, ridiculous shit. And I love that, right? There's nothing better than your kids, like, having fun reading. Like, Adam Rubin has this book called "The High Five Book." Have you seen this one? Where you're like smacking it? You know, like, they have this one right now that they love called like the, The Dumb Guide to All the Stupid Birds in the World, and it's just filled with cursing. I love all that stuff. But I think there's— that's not why we read to our kids, right? We read to our kids to instill them lessons and to teach them how to be a person in the world. And so we've spent a lot of time with the sort of myths and stories and fables. You know, like Aesop's Fables operate on these incredible multitude of levels, right? Like to them, it's a funny story about a fox and grapes. And to you, it's a lesson about not being jealous or abandoning what you have 'cause you want something else or writing off what someone else has. What I mean is that I try to go to the things that contain wisdom that maybe they don't fully understand in the moment, but I want that familiarity to be there, and I want it to be working on their brains. So we spent the last couple years, like, doing The Odyssey, and then we listened to podcasts about it, and then we read a graphic novel about it, and then we read the actual poetry, and then we went to Greece. And, like, what I'm trying to do is when there's that, like, flicker of interest, to fill it with all the possibilities of that thing. But I try to go mostly to stories of, like, great men and women from history that are going to inspire them to want to be like those people. So I don't want them to be like a monkey or whatever. Like, I want them to be, you know, like Cincinnatus or the 300 Spartans or George Washington. I want to pick those kind of stories that, you know, whether they're true or not is much less important to me than whether they have some kind of moral lesson that sticks with them that, by the way, when they get into situations in life, I can be like, "This is like that thing that we learned about." Yeah.

You know, you have a lot in here which I think is hard for people to do, but so important, which is about knowing oneself. And so, you know, there's a quote about so much knowledge is lost to us because we are ourselves lost and lost unto ourselves. The Oracle of Delphi sort of famously says, "Know thyself." Yeah, it's inscribed.

There's 3 things inscribed over the Temple of Apollo in Delphi where I was just this summer, and it's, "Know thyself, all things in moderation." And then this one I think has particular relevance to entrepreneurs, planners. It says, "Offer a guarantee and disaster threatens, which is basically Murphy's Law. You know, if you think it's going to go this way, just wait. But, but, you know, we tend to chase knowledge. You know, we want to learn about all these facts in the world. We want to learn about these systems, this history, how physics works, how the universe works. And then, yeah, we're strangers to ourselves. Like, I've met a lot of smart people I would say I've met many fewer people with what we would call self-awareness, right? And that self-knowledge and knowledge of our weaknesses, a knowledge of why we are the way we are, a knowledge of what we like, knowledge of what we don't like, knowledge of how and why we operate. By the way, also just knowledge of humanity too. That's why I think Robert Greene's book on human nature is so important. But just like knowing how we work, why we work, and some of this you get from reading, some of it you get from experience, some of it you get from therapy, some of it you get from close friends. But the idea of just knowing yourself is ultimately gonna be the knowledge I think you need most at difficult points in your life, because you're gonna wanna catch yourself from doing that thing that you might unconsciously do, or following that pattern again, or, reacting immaturely or irresponsibly. Like we all have, I would say, like an inner child, right? Like there's that part of us that's still a kid and you don't want a kid making adult decisions for you, right? And so if you don't know who that kid is and what they're triggered by and why they do the things they do, you're gonna make some real irresponsible, dangerous decisions in the moment. Moment, you're gonna think they make sense, but if you had a little more self-awareness, you'd be like, "No, no, that's that part of me that just instinctively, intuitively, you tell me to do this, I'm gonna do that." And it's like, sometimes that's a good thing to do, but maybe in this case, it's not. Yeah.

You wrote an entire book, "Ego Is the Enemy." You talk a lot about ego being bad, but can you tell us, the greats had to struggle. With ego.

Well, it is interesting, right? Like, I think we've all seen, whether in direct personal experience or, you know, culture, history, art, we can see what ego looks like in other people, and we can see how it holds them back. And it's not that egotistical people never become successful. Most of them, many of them do, right? Most successful people have big egos. But what you see up close is how this ego prevents them from being more successful. And then of course, what you don't see is all the times that ego destroyed someone before they became successful and you never heard about them. But I guess what I'm saying is that you can see how ego holds other people back so much, and then you're like, "But not me." And that's fucking ego right there. You know, like the idea that you don't have an ego is like the definition of ego, right? You're like, "I'm above this. It's different with me," is like, profoundly egotistical. But yeah, what ego does is it gets in the way of the feedback that we need to get, the relationships we need to have, the truth we need to see, the reality we need to understand, the weaknesses we have but can't see. And so if you're trying to do something that's really hard and the risks are high and the odds are low, ego is like a real dangerous thing to get in the mix. Oftentimes people go, "But isn't a little bit of ego important?" Right? Like, don't you have to have that part of you that wants to do stuff or that believes you can do stuff? I would say what you're probably talking about there is confidence. This person you're talking about, like, I think you probably very clearly see a distinction between confidence and ego. Ego is something toxic and much harder to deal with.

Oh yeah. I mean, what— What stories or moments made you even recognize this? You know how sometimes, I don't know about you, but I'll have to have a story break me through. And you could tell me something theoretical, and then unless you can kind of like, can you explain that to me or give me a case study or tell me a time where there's like, let me explain to you how ego destroyed a man or a woman.

Yes.

Or what we could learn from it.

Well, this is why reading and experience in the pursuit of wisdom are so important. Like you read about things and then you see it in real life and you go, "Oh, this is what that playwright from 2,000 years ago was talking about." Or conversely, you go out and you have a bunch of experiences and then you're watching Shakespeare or a movie, or you're listening to a song or a poem, you're reading a book and you're like, "Oh, this is that," right? Like there's this similarity there. And so I was thinking about doing this book about ego, so I wrote, "The Obstacle Is the Way," which is about the things that get in our way and how we can use them to our advantage. But I was like, well, but most obstacles are not external. It's not like, oh, this is a bear market, or oh, they just put a bunch of regulations in, or oh, this happened to this person and now they have to overcome. Most of the reasons that empires fall or people don't succeed, it has nothing to do with external stuff at all. It's in here, right? Like, the problem is you. Ego's like that big problem. So I was thinking about doing a book about ego, And I had been for many years the director of marketing at American Apparel, and I'd left when my book started to work. And I got called back when they famously fired the CEO and founder, and I was a consultant in what was a last-ditch attempt to save the company from him and the sort of downward spiral that he put it in. And watching someone who'd built basically a billion-dollar company that had 250 stores in 20 countries, that had revolutionized fashion, that had done a lot of good in the world too, and just also was this feat of logistical and business and creative genius. Watch them destroy it and then watch them not be able to handle the objective feedback that, hey, you fucked this up and we're firing you. And if you can just sit over here and be Be in timeout. Your shares will one day be worth a lot of money again. And instead engage in this sort of, this death wish. Like he destroyed it from the outside. He couldn't even allow it to be handed off to someone else. And it wasn't me that was doing it, but watching him then destroy it from the outside, double down on all the things that got him in trouble, and then, you know, lose all the shares and everyone lost their job. That was the sort of subtext of the book, is I was writing about ego historically, but I was watching it also happen in real time. And that's not an isolated incident, right? Like, there are so many stories like that in the history of business and politics. And there's this point where all the assets the person has turn into liabilities. And ego is usually like the swing vote. In that transition.

How do you tell if you're falling prey to ego? Is there like a practice you do?

Do you look in the mirror and you go, "Ryan, you good-looking son of a bitch, this is not it." When you find yourself saying like, "How dare you?" Or like, "Who are they?" "Who do they think they are?" "Do you have any idea?" Those are all things, like when you're saying like, "Oh, it's different this time," or "The rules don't apply." Or, "It's different with me," or, "You don't understand." I tend to find those kind of phrases or ideas to be very insightful little indicators. Oftentimes I find, and again, ego is there, it's always there. It's just, are you letting it make the decisions or not? When I send in one of my books and I get, I have in my inbox right now, a round of notes from my editor, and I've not looked at it for 3 weeks because I know my initial reaction is, "What the fuck? You know, how— like, who are you to tell me?" You know, like, I want to let this sit and I want to get in a better place. And then, you know, I find when I go through it, I go, "Okay, well, there's some stuff in here." And then, you know, maybe I'll do this one. You know, maybe I'll start with all the typos. I'll You know, and then after I've gone through it a couple times, I put in like 80% of what they said, right? But in the initial moment, you're like, "I handed you perfection and you gave me, you know, a marked up, underlined draft. How dare you?" You know? So it's like, I tend to find that the first reaction is emotional or egotistical, or, you know, that's where your insecurities come to light. But if you sort of sit and let it process a little bit, you can get something closer to more objective or rational.

Yeah. One of the other things I like about what you talk about is you have a lot of opinions, obviously, but which I think is a good thing. But I loved one of the lines you have from Marcus Aurelius, which is that you always have the power to have no opinion.

Sure.

So I was curious on you. Do you think everyone should have an opinion? And if so, why? If not, why?

Well, we all have opinions. It's just how often are these opinions serving us and how often do— did anyone ask? You know, understanding that you have the power to just not think about something, to not have an opinion, I think is very empowering, especially to go, Hey, like, I don't have to care about what you like, you know? I think that's it. Like, when you're young, you have a lot of opinions about like whether like music or art or comedy or whatever is like objectively good or not. And then you get older, you're like, who gives a shit? If you like this, you like it. You're not wrong. If you like it, you are not wrong, right? If you tell me I have to like it, That's different, but that's not what you're doing. But we, we just, we just tend to have opinions about so many things. That's what the media ecosystem is about, right? That's what social media is driven by. Hey, this happened. What do you think of this? Don't you want to leave a comment? You know, don't you want to get in an argument with a total fucking stranger about, about something that not only doesn't matter, but they might not even be a total stranger? You could be arguing with a bot right now. And so the ability to go, "That's what you think, cool," is really, really important. And what this should do ultimately is save you to have opinions or to feel strongly about the things that do matter and that you do have some semblance of a say.

Over.

And so I think just a lot of us are following too much in the sort of latest outrage cycle. We're following too much in real time as it's happening. Um, I even think about this as a parent, like the arguments I got in with my parents over things as a kid that in retrospect they don't care about and I don't care about anymore. And if they had just waited, I would have gotten over it, you know what I mean? Like, so I just try to think with my kids just like Do I need to have a thought on like how this— like, I'm making this as if it's some issue of character or if it's some something, you know, essential about the functioning of our lives. And it isn't, you know, like, uh, if you want to wear Crocs, wear Crocs. I don't care, you know, like, no, that's not allowed, you know, baseline. But, but so much of conflict, especially when your kids are older, is rooted in just your parents having the parents having opinions about things that they, that they don't, they don't need to have an opinion about.

That's very true. Have you ever left negative comments under somebody else's post on the internet?

I mean, every time I regret, like, there is not a single time I've ever posted anything on social media, like, in the moment that I later was like, I'm so glad I did that, you know.

I just always wonder who's out there, uh, comment, you know, like I'm having a breakfast and I really don't like yogurt, so no yogurt today. And somebody's like, "Fuck you, I love yogurt." You're like, "Why?

Can't you just love yogurt over there somewhere else?" I mean, for Daily Stoic, we were just doing this fundraising thing for Feeding America, and it was amazing to watch people have negative opinions about that.

Feeding America?

Yeah, it was just like, "Well, what about this?" Or whatever. Oh, right. What about this cause? I didn't see you talking about this also, or like, are you also gonna raise money for this? And it's like, I'm doing this right now. This is what the one I'm doing. You don't have to participate. No one asked, like, I didn't even ask you to participate. And by the way, what they're trying to do is denigrate the good that you are doing so they don't have to feel bad about the nothing they are generally doing. They're trying to go, if I cancel this out, then we're even, and then I don't have to feel, compelled to do something. That's something I think it took me a while to understand. But why do people gamble in casinos? Why do people smoke? Why do people do a lot of things that they shouldn't be doing? Is there some kind of biological urge or susceptibility that smart people or some kind of chemical or system has triggering— triggers or preys on, and they don't understand that that's what's happening. Do you know what I mean? Like, I think just realizing that like social media is dependent on your unpaid labor, emotional and otherwise, like it is designed to make you uncomfortable or provoke you into clicking, reading, or posting, or watching, or whatever it is. And that like, it's really good at that. And so I do have some sympathy for the people, right? Like the only way to win is not to play, right? And they've gotta understand that like, this thing is manipulating you. Like you're the product that's being sold here. Outrage that you're feeling, this fight that you're picking, that's the driving engine of this whole system, and you gotta not do it.

It's very true. Yeah, I've increasingly, now these days I'm like totally uninterested in discussing, for instance, politics. And so like, I think it's important as a civics, you know, person, a member of society to like do your civics duty and to participate in it, but I find like angrily yelling at people on the internet one way or the other is not that useful. And then what's fascinating is every time I have found somebody who might diabolically disagree with me. You know, I've had people on the podcast that are way to the left. I've had people on the podcast that are way to the right. Karl Rove. So, like, you know, I've got the full spectrum. And I actually loved Karl. And I loved the other, which I won't say because I don't know if she would classify herself that way, but way to the left, I loved too. Sure. And like, I learned lessons from both. And I know— well, I guess kind of where I wanted to go to this is like, I think we worry so much about what other people think about us, and we worry so much about what other people think or are allowed to think. And I was reading some of your pieces on, I believe it was Seneca. Is he the one that was like enslaved and imprisoned?

That's Epictetus.

Fuck, and I always call it Epictetus, but it's Epictetus. He's dead, he doesn't care. Anyway, I would be curious your take on like, you have so much from so many greats on what do you do when you feel like there are haters or people that don't like you?

Yeah. Well, haters existed in the ancient world. I mean, Seneca, who you were talking about, is not just a controversial political figure. He's not just a wealthy guy who has sort of, you know, people who don't like him for that reason. He's also Rome's greatest playwright at that time, so he would have written things and people would have said, "That sucks." You know, like, "I hate this." So, like, they got it from all angles. Marcus Aurelius is the emperor. The emperor of Rome. Like, there are statues of him, like people who are saying, "You're the greatest," like literally worshiping him as a god. And then there are people who are trying to kill him. And so, like, this is a timeless thing, right? He says in Meditations that for some reason, even though we all love ourselves more than other people, we care about other people's opinions more than our own. And one of the things I try to remind myself, a couple things, I go, number one, is it possible for everyone to like you? Like, is it possible that you could publish a book that 100% of the people think is good and appreciate? It's like, no, definitely not, right? Like, um, it's a, it's a percentage. Even, even a good percentage, there's still going to be a percentage of people that don't like it. And actually, the more successful you are, the bigger in raw terms that percentage will amount to. So, uh, I've been very fortunate. My books have sold millions of copies, which I take to mean there are millions of people who don't like me. Like, not just millions of people who saw the stuff and then decide— like, I would argue more people saw it and decided not to buy it than saw it and decided to buy it. And then of the 10 million people that have bought one of the books, I can't have 100% satisfaction guaranteed, right? So let's say 10% of people didn't like it. That's a million people. That's a major city in the United States that doesn't like me.

Just anti-Ryan signs.

But like, when you can do that math and you're like, okay, when I get a shitty email or I see a comment or a review in a newspaper is bad, what you're able to do is say to yourself, this is one of those people. Like, this person was statistically guaranteed to exist. There's no escaping it. Why am I surprised that I encountered one of them, right? Like, in fact, they are the tip of a larger iceberg that I'm not seeing. So let's leave it there. The other thing I try to tell myself is like, who is this person to tell me how to do what I'm doing? Like, I remember at one point this thought occurred to me. I was like, these people don't work hard enough for me to care about their opinion. Like, They don't know what I'm doing. They don't know what I'm trying to do. They don't know what success is to me. They don't know what I value. And also look at what they've done. You know, why am I letting them decide whether I succeeded or failed or not? And so when you kind of go, okay, certain percentage of people are not gonna like you, certain number of those people aren't worth thinking about at all. And then ultimately, like, success has to be self-defined. Or else it's not worth anything. That's kind of how I think about the haters thing. And then the other one that Mark Shreves does talk about a lot that I think is really interesting is he talks about people who want to leave a legacy, people who want to be remembered. And he just goes, "What good is that?" He's like, "The people in the future are gonna be just as dumb as the people who exist now, and you won't exist." So it won't do you any good whether they like you or not, right? Like, I think a lot of people, they spend all this time trying to create this, not just success now, but this monument that endures for all time, as if that's of value. Like, it isn't. It's not only something you don't control, even if it was guaranteed, it doesn't do Marcus Aurelius any good that I'm quoting from "Meditations" right now. It doesn't bring him back from the dead.

Also, if he walked on the street, we wouldn't even recognize him.

Yeah, sure.

So like, it's like there's no— and he's probably one of the most pervasive.

Yeah, that's, that's one of the most famous people who, who ever lived in their own life, and he's mostly forgotten. And if the movie Gladiator didn't exist, he'd be even more forgotten. It's like, it's just not something worth chasing.

Yeah, it's so good. Yeah, I, I always thought, uh, there was like a little, uh, Instagram line that I thought was funny, and it was like, you don't like me, you don't even have personality privileges. And I just I giggled because I think the Gen Z gets it right sometimes, you know? And a lot of these people, they say they don't like you, they know nothing about you. And how many people truly know you? Truly?

Well, the Stoics would also say, and this is from Epictetus, he says, "If they truly knew you, they'd probably say something worse." So like, just tell yourself you got off easy. Like, they're criticizing you for something that they read that you wrote or that they saw you do. Imagine if they could really peek inside. They could see your deepest thoughts, they could see what you do in private. You got off easy with this criticism, so, uh, take it and move on.

It's actually so good. There's also— my husband bought a little magnet that we kept in San Diego, and on it was a line from Marcus Aurelius, but it was something like, like, when you step outside your door, expect people to be terrible.

He opens meditations with this.

Yeah, how does that go?

Do you remember? It says that, you know, today the people you will meet will be angry and jealous and dishonest and stupid and noxious. And he just goes on down the list. And that, that is true. That's what the Stoics are saying. Don't be surprised. Like, don't expect to avoid this. But the second part of this is actually a little more hopeful than people give the Stoics credit for. He goes, but don't let them implicate you in ugliness. Don't let them drag you down to their level. And he says, it doesn't change the fact that we're all made to work with each other. And, and by the way, again, if, If there is a statistical necessity or certainty that some people are those things, then you should have sympathy for those people. You go, this is their job. They just like somebody has to pick up trash, somebody has to clean toilets, somebody, somebody has to do stuff, right? Somebody has to be that person too. And you're lucky that you're not that person and they're unlucky that they are that person. And that's, You go, okay, you're the 1 out of 100 that sucks, and that sucks.

Really important question. Yes. Should we all really get a donkey?

I think that donkeys are amazing. I actually asked Arnold Schwarzenegger that question, 'cause he has one too.

Get outta town.

And he said, I don't know if they're the best pets, but they're like big dumb dogs. Yeah, they're not smart. That take care of themselves. Well, they're very smart, but just like, big. I mean, dumb in that they're not as, like, coordinated as dogs, you know? Ours can open our fence, it can open the back door to our house. Like, they're very clever, um, and they all— like, people think they're stubborn, but it's more like they, um, they just don't do anything that they don't see a reason to do.

So you cuddle— do you cuddle their dog?

Yeah, they're very— they'll come up, and if you have carrots and stuff, they'll, they'll nuzzle against you. We have cows on our ranch, and so you need a donkey as, like, a livestock guarding animal. So we got one.

The donkey protects the cows?

Yeah, they'll, um, they'll chase off coyotes and mountain lions and dogs and stuff. Whoa. They're very, they're very, very protective. They just kind of just, they kind of hang out on the periphery of the herd and they just don't like anything messing up the vibe.

I like this. I knew I wanted donkeys on my Christmas list, so now we've moved that up.

Well, I'll, I'll give, if we have a So we have one, and then we had to get another one because they get lonely, and they have a baby every 13 or so months, and then it's a problem of what do we do? So I usually give them to people.

Oh my God, put me on the giveaway list, the Ryan Holiday donkey list. I would do some unhinged things for that, especially the baby donkeys. Okay, that was important. The other thing, this is, I didn't even know this about you. I had such a fun, you know how you follow somebody online for a long time, you read their books, and you have this parasocial relationship? Right? So you're like, I know what Ryan's all about. And then I went down a— just a rabbit hole of how long you have been on the internet and asked a bunch of your friends. But I came across like a lot of your marketing background, which I didn't know about.

Yeah.

And there was like a quote from a New York Times profile about you, by the way. The quote was amazing. I mean, the article was amazing.

Okay.

But the line was, Ryan Holiday runs his own marketing firm. Braschek, and has written boastfully about depraved publicity tactics he deployed on behalf of his clients. What a fucking line. I want to hear about some of these firsthand. What are these ridiculous marketing stunts?

You know, well, I mean, I wrote a whole book about sort of publicity stunts. And which one was that? It's called Trust Me, I'm Lying.

Oh, yeah.

And it's about sort of media manipulation and how the media system can be vulnerable to all of these things. I mean, I opened that book with a story about a movie I was working on, and it had a very small budget. And so, you know, we couldn't spend very much, so we took the relatively small bit of the budget and we bought some ads, which I then defaced. And then we took pictures of them, then we sent them around, and we created this sort of backlash against a campaign that, like, didn't exist really. And, you know, we got— like, it was banned by the Chicago Transit Authority. Like, we tried to buy, you know, like, ads in Chicago on all the trains, and then they rejected it, which is like what we wanted because we didn't have the money to spend on the thing. But then the media coverage around that got seen by many thousands of more people than would have ever seen the ad. So I did— I did a lot of stuff like— like that.

Do you do any of that anymore? Do you do it?

Not so much anymore. I mean, every once in a while I'll do something, uh, for fun. Uh, but, uh, my career there was fascinating and compelling. I wouldn't say it was, you know, exactly a positive contribution to society. And so I think I sort of grew out of it a little bit. But I was really interested in, like, how this system worked and what the vulnerabilities were in the system. And I sort of saw it as this challenge. I did a lot of stuff that was funny and interesting and provocative, but, you know, again, not really what I felt ultimately like I wanted to spend the rest of my life doing. What's funny, there's a quote in that New York Times profile you mentioned that is not haunted me, but some people try to throw in my face. I said, you know, she was like, maybe you're just writing about this to make money or something. And I was like, look, if you're good at marketing and you could sell anything. And I was like, especially if you don't have a conscience, right? I was like, you could sell cryptocurrency or this or that. You'd sell whatever you want, right? And I was like, Why would I choose this? That's what I was saying. But she sort of cut off the last part. So I was basically just saying like, if you're good enough and shameless enough, you can sell anything, which is why you always have to be careful about making sure your complete thought is untruncatable, right? Because the context of it can be stripped out of it. But my point was like, I just got tired. I was like, I'm— I don't want to— I don't want to spend my life selling other people's shit, you know? That's just not really what I wanted to do. And so I, I just— I was like, well, what do I care about? What am I interested in? And, and ultimately, like, my— even my marketing business, which I kept for many years, and I consulted mostly, but I just, I just thought, like, I just got tired of, like, giving advice that nobody listens to, even though they paid me for it. And I just thought, well, I know who will take my advice, me. So I just started to make my own things. And I think ultimately if you have like real marketing chops, that's what you should eventually evolve towards is your own stuff.

Yeah, I like on accident got invited by a friend who was the one getting the award to this kind of famous Advertising Association event in New York. And I went because I was in town and I adore her and she needed a buddy. And so I went with her and it was the most fascinating night actually, because it's an advertising event, right? And yet, if you were to hear the speeches—

Were they bad?

No, no, they were actually beautiful. And the videos were beautiful, but it was like, This is the most important room in the world with the people who are changing the world every day. And I'm like, am I in the cancer wing? Like, wait a second. Like, I feel like I'm in the wrong area. And so it was fascinating because person after person was talking about how advertising and marketing is like the cornerstone of humanity. And like, you could argue with that one way or the other. But what I kind of did like about it is like, whatever you're going to do—

Should be good at it.

Yeah, and you should maybe feel that way about it.

Yeah, although I remember when I was at American Apparel, every year I would go to this thing in New York called Adweek. Which is this like series of conferences and galas and award shows like that. And I remember the first time I went, you know, I was probably like 20, 21, and I'm like the kid there. I'm the only one not in a suit, you know, the only one not working at some big company with a huge budget. And then I went the next year, sort of same thing, and next year, and I always felt like an outsider. And I remember it occurring to me like the third or fourth year, if I keep coming to this, I'm gonna be a guy in a suit. Like, you can't do, you can't, you become like the people you spend time with, right? And actually, Epictetus has this line. He says, "If you live with a lame man, you will learn how to limp." And I just realized like, oh, this is an interesting period in my life and I'm learning a lot and I'm making good money and it's exciting and interesting, but like, there is, a point of no return that I am approaching, and I have to get out soon, or I have to commit to this thing. And so that was part of the reason that I ultimately, you know, sort of made the leap, which seemed crazy at the time. Like, wait, you're the director of marketing, a publicly traded company, you're gonna go write a book? Like, you don't even have a book deal for it, you're just gonna go write a book? Like, what's wrong with you, you know? But I just knew that wasn't, who I wanted to be and what I wanted to do. And again, to go to the idea of procrastination, everyone says, "At some point I'm gonna do it," and you're not, you know? And the longer you don't do it, the more and more likely it is that you will never do it because you've actually said over and over again who you actually are, which is the person you're currently being, not the person you think you could be.

It's so true. We call it the corner office phenomenon. And I'm like, basically, I've found this happens a lot with people that were in corporate spaces. It happened with me. I remember I had a moment like you where I literally, I looked down the hall at the guy who was in the corner office, who had the job that I would have if one day I achieved the highest of the heights in my profession. And I was like, oh my fucking God, no. He looks miserable. He had multiple wives. There were lots of cars in the garage. I don't care about garages. He was working nonstop. He wasn't healthy, vitamin D deprived. All of the things. And I think often we can just look at that and go, "Oh, when I'm there, I'm not gonna be like that. It'll be different when I'm there." But if instead you can really look down the hall and go, like, if I had lived that man's life, I would probably be that man. And so am I sure that that's what I want? If I can look into the future and see, is that the kind of suit that I want to wear?

Yeah, the system is shaping you every day that you are in it. And you are internalizing its values and its personality and its identity. And the idea that like, yeah, that you're going to go along to get along for 40 years and then be a visionary rule-breaking leader is extremely unlikely. Like, you, you just followed the rules for 40 years to get this thing that you're now terrified of losing, you're actually going to be less courageous, more risk-averse than you thought you would be. Like, you're like, "If I was in charge, it would be different." And it's like, no, it's going to be exactly the same because it was shaping you as you were in it.

Yeah. So do you think that humans are contagious?

I think examples are contagious. You know, I think culture is contagious. Values are contagious. Sure.

Like, I think we named the company Contemporaneous Thinking, obviously. And to your point, I kind of labored over that one. It's a terrible name. There's so many vowels and it's like A's and I's and I don't know where they're located. Nobody can spell it. Yeah, but maybe more important than that, I remember reading Letters to Young Contrarians back in the day, and I always really liked that book. It's kind of a ridiculous, short, cute book in some ways, but I liked the idea of like, you know, if you do not question things, then you will just assume everybody else is fake. You have to be careful to not be a contrarian for contrarian's sake. But at a base level, we do just kind of move along to get along, right? And so this pushback is hard. And with your books, I would say most of the stuff that you've created, and you do it now today, you'll post something about something politically you might think, and a lot of people hate it, and a lot of people love it. And I sometimes think maybe that's inoculation against caring. But How do you inoculate yourself against becoming somebody else's representation of you?

Yeah, it's a good question. I mean, I think— do you know what audience capture is?

No.

I think we work really hard as a creator, an artist, or writer, whatever, to build an audience. And then you think you have the audience, but actually the audience has you, 'cause now you're afraid of losing it, right? You're like, oh, when I talk about this, people don't like it. Or, you know, when I wrote about this, like, Substack subscriptions went down, or, you know, I got a lot of angry emails. And okay, so now what you've said is that you have a boss, right? Like, I became a writer and a creator to make what I wanted to make, not to make what you want me to make for you, right? And so, That's something I just think a lot about. Like, is this something that I think is important? Is this interesting to me? And then also I try to think like, what are my obligations? I have like a little note card on my desk and it just says like, are you being a good steward of Stoicism? And I think about that because, you know, I didn't invent this philosophy. It's a tradition that stretches back 25 centuries. I just happened to be publicly associated with it, and it's done me a lot of good. But if I'm only going to use it to tell people what they want to hear, or tell people the easy, obvious stuff, then I'm— then I'm exploiting it as opposed to contributing to it. And so I think there's a fine line, of course. Like, it's not about a giant middle finger to the audience all the time. That's not right. But you have to You have to do and say what you think is true and important. Because by the way, nobody was begging for me to talk about this 15 years ago when I started, right? If I asked for approval, I wouldn't have had the support to get going, right? So, like, you have to trust that instinct.

Yeah, yeah, it's a good point. I think it's a beautiful line because you get— you can become so selfish sometimes, I think, as a creator or as somebody with an audience or as somebody successful, because you can really surround yourself with sycophants, you know, and then you can create this weird world in which everything actually caters to you. Simultaneously, I think most people don't end up there. Maybe really successful people do. I think that's actually less normal. And it seems like most people let other people become the architects of the houses that they live in.

Yeah, and it's also, it's just more information and feedback than a human could possibly deal with. You know, like the Daily Stoic email goes out to a million people every day. Like even if 0.01% of them liked or didn't like what I said that day, that's, I can't allow, I have to have a boundary that that doesn't get in, you know?

Do you ever like read the really bad ones out loud like the Hollywood actors do sometimes?

Anytime I, come across, I go, why did I subject myself to this? This doesn't make me feel good. It doesn't make me feel bad. It just makes me confused. You know, like, it's like, I, you know what it is? It's like, you gotta have a compass and you gotta keep magnets away from the compass 'cause it fucks with it, right? And this is actually something Seneca talks about. He says, you know, you gotta know the path that you're on. And he says, not be distracted by the paths that crisscross yours. Or the footsteps from those who are hopelessly lost. And it's like, I'm doing what I'm trying to do. You might think you know what I'm trying to do, or you might think you know what I should do, but you don't. And conversely, other people doing their own thing, whether they're creators or writers or philosophers, they're doing their own thing. And if I take my eye off my paper to look at theirs, I'm gonna get myself into trouble. And so I try to keep kind of a narrow focus where like, this is what I'm doing, this is what I care about, and that's enough.

That's beautiful. Well, Ryan Holiday, I love your books. I've read "Ego Is the Enemy" and "The Obstacle Is the Way" and "The Daily Stoic" and now "Wisdom Takes Work." And now I have about 42 other books of yours to read, but those are some of my favorite. And truly, You know, there are a couple authors that, like Robert Greene, I was very nervous when I had him on the podcast.

He's the best.

He's amazing. And he's just as good in real life.

He's better.

And even after a stroke, you know, I was like, this man's horsepower is insane. But I was just such a fan of the way his brain worked. And I think it's the same with you. Like, you know, reading these books, these cannot be easy to put together, to take these complex ideas and make them simple. And so, you know, if you're watching, they're really, really worth it. Read, which is not always true for every book today. And so, well, thank you for writing them. Thank you for spending some time here with us.

Thanks for having me.