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

Episode Date: December 31, 2025

Most people think discipline is about willpower. Ryan Holiday knows better — it's about habit. After writing multiple bestselling books on Stoicism and spending decades studying history's highest performers, the author of The Obstacle Is The Way and Ego Is The Enemy has cracked the code on why the world's hardest workers aren't just talented or lucky. They've built systems that make discipline inevitable. In this raw conversation, Ryan breaks down the exact frameworks used by Marcus Aurelius, Seneca, and Epictetus to stay calm under fire, make sharper decisions under pressure, and most importantly — get things done. We dive into why discipline isn't something you are but something you do, how the Stoics battled procrastination (Seneca said all fools are always getting ready to start), and why negative visualization beats positive manifestation every time. Ryan reveals his actual research process (analog note cards, not AI shortcuts), why he reads the same books over and over, and how to inoculate yourself against audience capture when everyone's telling you what to create. But this isn't theory — it's applied philosophy. We get into why waking up early is useless if you stay up till 2 AM, how to make hard things black and white so you can't rationalize exceptions, and why your calendar should have large blocks of white space, not meetings. Ryan walks through his panic rules from coaching the LA Rams, why ego destroys more empires than external obstacles, and how he went from running publicity stunts and media manipulation campaigns to building one of the most disciplined creative practices in the world. If you've ever felt like discipline is this vague thing you either have or don't, or if you're tired of procrastinating on the life you know you should be building, this episode will change how you think about work, focus, and what it actually takes to win. Protect what you own. Next makes it fast, simple, and painless. Check it out: https://nextinsurance.com/codie ___________ 00:00:00 Introduction 00:01:06 Panic Rules: What To Do When Everything Falls Apart 00:03:05 Discipline Now, Freedom Later: The Labor Will Pass 00:07:37 The Simplest Daily Habit to Build Discipline 00:11:59 Large Uninterrupted Blocks of Time: The Secret to Success 00:16:09 Procrastination is Arrogant: It Assumes You Have Forever 00:22:39 Enjoying the Journey: Why the Work Matters More Than the Reward 00:28:22 Negative Visualization: Why the Stoics Planned for the Worst 00:33:10 The Note Card System: How Ryan Remembers Everything 00:34:52 You Must Love Learning If You Would Possess It 00:43:14 Know Thyself: The Oracle of Delphi's Most Important Command 00:46:05 Ego is the Enemy: How It Destroys Success 00:53:16 The Power to Have No Opinion 01:00:06 Haters, Criticism, and the Statistical Certainty of Dislike 01:18:04 Audience Capture: When Your Audience Has You 01:09:04 From Marketing Manipulator to Stoic Philosopher 01:15:17 The Corner Office Phenomenon: Looking Down the Hall 01:17:01 Are Humans Contagious? Culture, Values, and Becoming Who You Spend Time With 01:06:44 Should We All Get a Donkey? Life Lessons from the Ranch 01:21:15 Final Reflections: The Path That's Yours Alone ___________ MORE FROM BIGDEAL 🎥 YouTube: https://www.youtube.com/@podcastbigdeal 📸 Instagram: https://www.instagram.com/bigdeal.podcast 📽️ TikTok: https://www.tiktok.com/@big.deal.pod MORE FROM CODIE SANCHEZ 🎥 YouTube: https://www.youtube.com/@codiesanchezct 📸 Instagram: https://www.instagram.com/codiesanchez 📽️ TikTok: https://www.tiktok.com/@realcodiesanchez OTHER THINGS WE DO 🌐 Our community: https://contrarianthinking.typeform.com/to/WBztXXID 📰 Free newsletter: https://contrarianthinking.biz/3XWLlZp 📚 Biz buying course: https://contrarianthinking.biz/3NhjGgN 🏠 Resibrands: https://resibrands.com/ 💰 CT Capital: https://contrarianthinking.biz/4eRyGOk 🏦 Main St Hold Co: https://contrarianthinking.biz/3YfGa8u Learn more about your ad choices. Visit megaphone.fm/adchoices

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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've 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, best-selling 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, 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. It's probably the most insidious lie there is. But it also presumes that there is a later. Can stoicism help with anxiety? anxiety? Of course. We know the Stoics experience anxiety. Marksbrily 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 to Los Angeles Rams. We're 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 feel like stoicism as a philosophy is.

We tend to think of philosophy. It's 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 going to go back and read epictetus, or if I'm going to go back and read even meditations, which I find like a little bit more accessible, it's dense stuff.

Yes. 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 Stoke 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 want to think of discipline, like discipline is, or self-discipline anyway, is about constraint. Do this, don't do that.

Not, 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, you know, asking him once, like, why do you like to follow the rules so much? He actually likes to follow the rules. often. I think you would agree with that classification. And I, I sort of don't. And so, and silly rules,

like, I'm going to 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 want to be orderly in your sort of personal life, in your space, in your, 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're 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 do talk about when I talk to military groups, 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, to 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, you know, 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 come 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. Yeah. 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 the things that you can do. So if somebody's listening to 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 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, 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 of virtue of woodworking or playing the flute or whatever it is. So if you want to be more courageous, you've got to do stuff on a consistent basis that scares you. That's how you have courage. You either are doing it or not. So 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 want to 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 got to wake up early. Well, waking up early in isolation is not great if you stay up until 2 in the morning, right? Because now you're actually being, you have what they would call in the military, poor sleep discipline, right? And so maybe it's like, hey, in 2026, I'm going to go to bed by 10 p.m. every night.

Right? Then you've just, by the way, made getting up early a lot easier. So I would pick some core accessible, definable tasks or items that you're going to be more disciplined about. Even like, I want to eat better this year. That is a very hard, ill-defined thing to do. But if you say, I'm going to quit sugar this year or I'm going to 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. So 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 in my phone. I like my husband. He's the same. This is so... 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 the less of this. 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 going to 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 want to 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. We're just 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, blog.

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 walks with my family, 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, their job is to keep things out of the calendar, not put things in the calendar. Like, the calendar should have large amounts of white space, in my opinion. And 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, 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.

Tony Morrison, 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 a.m. to 6 a.m. And so you've got to orient your day around that, not, well, that's when I'm best, but I actually sit down finally to write at 2 p.m. 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. I'm sorry. Because I feel very called out about this. I'm yelling at myself as well. And these are things you learn the hard with. 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're. want to be doing. But I love that line, like your job is to take things, keep things off the calendar, not put that on, 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

two or three steps forward? I like how your mind works like that. And so you have a couple quotes that I love to on procrastination, 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, how do you battle procrastination? And what have you learned through stoicism on how the greats do this, too? Well, we all battle procrastination. This Seneca says, this is the one thing all fools have in common, is that they're always getting

ready to start, right? Like, we don't say we're never going to do it. We say tomorrow, we say next week, we say in the new year, right, we say, oh, when the kids start school, right, 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 Mento Mori ring on right now. The Stoics are meditating on our mortality. So, like, it's not just like, hey, you're probably not going to get to it later. That's a lie we tell ourselves. You know, I'll do it in the morning. It's 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 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 red, you know. And so you, 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, and

in some cases, very reckless. You just landed your first major client. Congrats. This is huge. But here's the thing. Big wins come with big exposure. One mistake, one mishap, one unexpected accident. And that dream contract could turn into a nightmare.

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And I'm not a big TV watcher, but I find it really useful because their lives are so hard and miserable and terrible and short. and, you know, it's the epitome of like nasty, brutish short. Yeah. But I think one of the things that it reminds me is this exactly this momentum 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 going to matter.

You don't matter. Yes. 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're talking about delayed gratification. That is what makes them great, right? Like, I'm going to be really miserable now so then 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 momentum more, 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? 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, 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 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, 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 two weeks when it comes out. And then I start the whole thing again. That seems like a bad trade, is I guess what I'm saying. I think a lot of, like, whenever I talk to athletes, there's not a single athlete that you've,

who will ever talk to who's retired, who doesn't say something like, I wish I enjoyed playing more. Because at some point, it just goes away. 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. 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.

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 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 don't know, your books come out on a Tuesday, sales are basically pre-orders and 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 Journalist. 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 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 article to him, 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 one. 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. It's, 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 three and a half four years ago. Yeah. 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, you know, 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? Yes. 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, you know, 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, like, you're just, your life sucks. You know, again, you're putting it all on the potential payoff, 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. 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 going to work that hard in the offseason. But if you're like someone who I just fucking love playing, you're going to play all the time, and you're always going to be thinking about it, and you're just going to put more into it. So weirdly, I found the less I think about what the Stokes would call the externals,

the more I just do better work. And then, paradoxically, the more I get the things. It is sort of funny, isn't it? You know, I want to 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 in 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 want to talk about, I can't sometimes reconcile the positive versus the negative of like manifesting or focusing on things.

Well, the Zen masters had 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, you know, one day the cup breaks, and he's not surprised by it.

For the Stoics, you know, although I'm sure they did appreciate positive visualization, they actually practiced negative visualization. So, like, 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, 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, right? 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 plan for this. Here's what we're going to do. Right. And you're talking about your husband and Navy Seal, they practice for the worst things the most, right? They don't go like, and here's how it goes swimmingly because it always goes swimmingly, right? It's like, I mean, on the famous Bin Laden raid,

they had an extra helicopter because they planned that one might crash, right? And what you what you get not only has a situation 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 time of peace or time of war, because I'm going to figure out what I'm going to 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 insults to injury, right? To think it's unfair, to think that it's devastating, to not know what to do. 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 percent? You know, that's not going to 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 three 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 is going to do.

They're precisely trying to come upon you as surprise. But also, I think it's just a good mental exercise. 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. it, I develop a feel for it. I want to 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 edge upon. No, no. What he said was that his mind was like steel. That it's hard, it's hard to scratch something into it.

Right. But once it's there, it's there forever. So I want to 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 was 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. 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 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 as 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 you said, you must. love learning, if you would, possess it. Yeah. And I think that was applied 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'd 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 Benjamin Graham. And, you know, that's probably a 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 experiences and these people out there, like priceless wisdom. Things that can say, not just

save you painful trial and air, 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, 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. 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 steel

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, what are the five, ten 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 Mark's Reelis's 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 Green's books are amazing.

You know, mastery is worth reading and rereading the 40 laws of power. The laws of human nature. You know, Reich Roberts' 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 are 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've got to spend a lot of time with it. It can't be, and 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, I don't know if that's winning here. Like, I don't, it's, 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. Oh, 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 hope in it, and it's more spiritual than you would guess. Interesting.

Yeah. It was, so he wrote it. He thought it was his greatest book, this thing called calendar of wisdom. And then, 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 them to raise? That's a good question. I haven't come up with the reading list yet because 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 dumb guy to all the stupid birds in the world. And it's just filled with like cursing. I love all that stuff. But I think there's, that's not why we read to our kids, right? Like, 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 because 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 wanted 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. Because I don't want them to be, like, a monkey or whatever.

Like, I want them to be, you know, like Cincinnati 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. 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 like 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. There's three things inscribed over the Temple of Apollo in Delphi where it was just this summer. And it's know they self, 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, 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, a 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, is why I think Robert Greene's book on human nature is so important.

But just like knowing like 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, you know, some of it you get from close friends. But the idea of just like knowing yourself is ultimately going to be the knowledge I think you need most at difficult points in your life. Because you're going to want to catch yourself from doing that thing that you might unconsciously do or following that pattern again or, you know, reacting immaturely or irretely. responsibly, 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 going to make some real irresponsible, dangerous decisions in the moment. You're going to

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 like instinctively, intuitively, like, you know, you tell me to do this, I'm going to do that. And it's like, sometimes that's a good thing to do, but maybe in this case, it's not. Yeah. You know, you wrote an entire book, Ego is the enemy. You talk about a lot about ego being bad. But can you tell us, like, 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. You're like, I'm above this. It's different with me. It's 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, you know, the odds are low, ego is like a real dangerous thing

to get in the mix. Now, 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 the believes you can do stuff? I would say what you're probably talking about there is confidence. This person you're talking about. I think you probably very clearly see a distinction between confidence and ego. It's, ego is something toxic and much harder to deal with. Oh, yeah. I mean, what, like, stories or moments made you even recognize this? You know how sometimes, I don't know about you, but like, 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 like, 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, like 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 Obstacles Away, 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 bare 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 think. seed. It has nothing to do with external stuff at all. It's in here, right? Like, the problem is you. Ego is 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 in 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 at 250 stores and 20 countries that had revolutionized fashion that had done a lot of good

in the world too, and 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 fuck this up and we're firing you. And if you can just sit over here and be in time out, your shares will one day be worth a lot of money again and instead engage in this sort of this death wish. He destroyed it from the outside. He couldn't even allow it to be handed off to someone else. 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, as 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 persons has turn into life. 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, good looking son of the bitch, this is not it. When you find yourself saying like, how dare you,

you know, or like, who are they? Who do they think they are? Yes. Do you have any idea? You know, those are all things like when you're saying like, oh, it's different this time or the rule. don't apply, or it's different with me, or you don't understand. I tend to find like those kind of phrases or ideas to be, to be very insightful little indicators, you know? Oftentimes, I find, and again, ego is there. It's always there. It's just, are you letting it make the decisions or not? Like, 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 three 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, which I think is a good thing. But I loved one of the lines you have for Marcus Aurelius, which is that you always have the power to have no opinion. 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 a, like, when you're young, you have a lot of opinions about, like, whether, like, music or art or comedy or whatever, it's 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 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? Don't you want to get in an argument with a total fucking stranger 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. 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 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 I that's not allowed You know, baseline. 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 need to have an opinion about. That's very true. Have you ever left negative comments under somebody else's posts on the internet? I mean, every time I regret. Like, there's 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. 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. You know, feeding America. Yeah, it was just like, well, what about this, you know, or whatever? Oh, right. Like, what about this cause? Or like, you know, I don't, I didn't see you talking about this also. Or like, are you also going to 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, like, I didn't even ask you to participate. And by the way, what they're trying to do is, 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, they're trying to go, if I cancel this out, then we're even. and then I don't have to feel, you know, like, compelled to do something.

That's something I think it took me a while to understand. But, like, why do people gamble in casinos? Like, why do people smoke? Like, 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, you know, some kind of chemical or system has triggering, like, triggers or, or, you know, praise on and they don't understand that that's what's happening. Do you know what I mean? 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 got to understand that like this thing is manipulating you. Like you're the product that's being sold here. This outrage that you're feeling, this fight that you're picking, that's the driving engine of this whole system. And you've got to 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 civic, you know, person, a member of society to, like, do your civic 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, Carl Rove. So like, you know, I've got the full spectrum.

And I actually loved Carl. 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. 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 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 in prison? That's Epictetus. And I always call it

epictetus, but it's epitetus. He's dead. He doesn't care. Anyway, I would be curious your take on like you have so much from so many grades on what do you do when you feel like there are haters or people that don't like you. Yeah. Well, the haters existed in the ancient world. I mean, Seneca, who we were talking about, is not just a controversial political figure. It'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 is 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, 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, it's a percentage, even a good percentage. There is 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 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 decided, 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, then 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 like, like, you're not. 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 going to like, you, a 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 Marks Rose does talk about a lot that I think is really interesting is he talks about, like, people who want to leave like a legacy, like people who want to be remembered. And he just goes, what good is that? You know, he's like, he's like, the people in the future, I mean, 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 to realize 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 it's like, there's no, and he's probably one of the most pervasive. Yeah, that's one of the most famous people 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 always thought there was like a little 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 giggled because I think the Gen Z gets it right sometime, you know? And a lot of these people, they say to they don't like you, they know nothing about you. And how many people truly know you, truly? Well, the Stokes would also say, and this is from Epictetus, he says, if they truly knew you, they'd probably say something.

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 and they could see what you do in private. You got off easy with this criticism. So take it and move on. That'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 when you step outside your door, expect people to be terrible. He opens meditations with this.

Yeah, how does that go? Do you remember? He says, 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 is true. That's what the Stokes 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 Stokes 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 by the way, again, 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 one out of a hundred that sucks and that sucks. Really important question. Yes.

Should we all really get a donkey? I think the donkeys are amazing. I actually asked Arnold Schwarzenegger that question because he has one too. Get out of town. And he said, I don't know if they're the best pets. But they're like big, dumb dogs that take care of themselves. Well, they're very smart, but just like big, I mean dumb and 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. And they all, like people think they're stubborn, but it's more like they just don't do anything that they don't see a reason to do. Do they cuddle? Do you cuddle their dogs? They'll come up and if you have carrots and stuff, 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 chase off coyotes and mountain lions and dogs and stuff. Whoa. They're very, very protective. They 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 to donkeys on my Christmas list. list. So now we've moved that up. Well, I'll give, if we have a, the problem, so we have one, then we had to get another one because they get lonely. And they have a, they have a baby every 13 or so

months. And then, then it's a problem of what do we do. So I usually give them, give them to people. Oh my God. Put me on the giveaway list, the riot 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, you follow somebody online. for a long time. You read their books and you have this parisocial relationship, right? So you're like, I know what Ryan's all about. And then I went down 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. 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, Brass Check. And and has written boastfully about the 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've done? Well, I mean, I wrote a whole book about sort of publicity stunts. 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. 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, 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 a lot of stuff like that.

Do you do any of that anymore? Do you do any crazy stuff? Not so much anymore. I mean, every once in all, I'll do something for fun. But 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 was a, there's a quote in that New York Times profile. You mentioned that it's not a 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, 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 I 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 untrunkatable, right?

Because the context of it can be stripped out of it. But my point was like, I just got time. I was like, I don't want to, I don't want to spend my life selling other people shit. You know, that's just not really what I wanted to do. And so I just, I was like, well, what do I care about? What am I interested in? 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 listened 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, this... Were they bad? No, no.

They're actually beautiful, and the videos are 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? 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 in American Apparel, every year I would go to this thing in New York called Ad Week, which is this like series of conferences and gala's and award shows like that. And I remember the first time I went, you know, it was probably 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 going to 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 says 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 sort of made the leap, which seems crazy at the time.

Like when you're the director of marketing and publicly trade company, you're going to write a book. Like you don't even have a book deal for you. You're just going to 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 going to 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 sent 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 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. You know, 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 going to 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 follow 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 were 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. I think we named the company Contrarian 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. 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's fate. You have to be careful to not. be a contrarian for contrarian's sake. But like 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, you know, most of the stuff that you've created, and you do it now today. Like 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 like, I sometimes think maybe that's like inoculation against caring. But like, 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. Because 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 a substact 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 it 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 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. Totally. You know, and then you can create this weird world in which everything actually caters to you. Yes. 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 stoke 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, 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've got to have a compass and you got to keep magnets away from the compass because it fucks with it, right?

And this is actually something Seneca talks about. He says, you know, you're going to know the past. 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 their own thing, there's, I'm going to 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 Holliday, 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 reads, but those are some of my favorite. And truly, you know, there are a couple authors that, like Robert Green, 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. 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 a read, which is not always true for every book today. Well, thank you. And so, well, thank you for writing them. Thank you for spending some time here with us. Thanks for having me.