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

24:39And then back a million years ago,

24:41Ryan Holiday: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. 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 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 waiting for the deal to close or the wire to come through or the article to hit the presses or whatever the thing is, right, the Grammy nomination to come in, 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.

25:43Ryan Holiday: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 I was already in the A range before that happened. Yeah. 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 three and a half, four years ago.

26:20And 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.

26:53You'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.

27:02Ryan Holiday: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, 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?

27:55Ryan Holiday:And then here's the trick is 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 off season. 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.

28:31Ryan Holiday: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. Yeah, it is sort of funny, isn't it? 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 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 want to talk about, I can't sometimes reconcile the positive versus the negative of like manifesting or focusing on things.

29:14Ryan Holiday: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.

30:00Ryan Holiday: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 planned 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?

30:46Ryan Holiday:And what you get, not only is the 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?

31:25Ryan Holiday: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 pessimistic, and I also don't think it's 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.

32:09And 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.

32:28Ryan Holiday:So I don't think 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 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 with a surprise.

33:08Ryan Holiday: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 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.

33:53Yes. 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 upon. No, no.

34:01Ryan Holiday:What he said was that his mind was like steel, that 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. I see myself as a professional reader. That's my job. And then I don't leave it there. 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.

34:48And the whole point is some things are supposed to be hard. 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 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.

35:42And 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. 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 learned and studied something, right? I think in school, you're assigned a bunch of books, and the payoff is 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.

36:31Like Warren Buffett is told to read The Intelligent Investor by Benjamin Graham. And that's probably the single best investment in human history. Like he reads this one book and he makes$100 billion. But my life was changed by a handful of books that I read. 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 can change the course of your life.

37:16That'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 and 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. 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 score more with the college branded venmo debit card and earn up to five percent cash back with venmo stash got paid back with the venmo debit card you can instantly access your balance and spend on what you want like game day snacks, gear, tickets, and more.

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39:14And 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 Lincoln talks about. But I was curious for you, you're a big re-reader of books from what I can see. So what are the five, ten books that Ryan Holiday says changed his life and that you go back to and re-read over and over again?

39:50Yeah, 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 Suleis' Meditations is one of the most incredible books ever written. The Private Thoughts are the most powerful man in the world. It's an amazing book. I think all of Robert Greene's books are amazing. Mastery is worth reading and rereading The 48 Laws of Power, The Laws of Human Nature. Like Robert's stuff is designed to be layered and to take multiple things out of them.

40:30I 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 got to spend a lot of time with it 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 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.

41:23I 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 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 - His 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. So he wrote it. He thought it was his greatest book, this thing called Calendar of Wisdom. And then the Russian Revolution happens like almost right after his death.

41:58And so it's banned. And it's not really rediscovered until the late 80s. So 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 That's a good question. I haven't come up with the reading list yet because they're still pretty young.

42:36But 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 Guide 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?

43:11Like 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 want it to be working on their brains.

43:58So we spent the last couple of 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 what I'm trying to do is when there's that flicker of interest to fill it with all the possibilities of that thing. But I try to go mostly to stories of 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. I want them to be like Cincinnatus or the 300 Spartans or George Washington. And 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.

44:50By 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 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.

45:36it says, offer a guarantee and disaster threatens, which is basically Murphy's law. If you think it's going to go this way, just wait. But we tend to chase knowledge. 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. 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.

46:25By the way, also just knowledge of humanity, too, is why I think Robert Greene's book on human nature is so important. But just 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 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 reacting immaturely or irresponsibly.

47:02We all have, I would say, an inner child. There's that part of us that's still a kid, and you don't want a kid making adult decisions for you. And so if you don't know who that kid is and what they're triggered by 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.

47:43Yeah. 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, the greats had to struggle with ego? Well, it is interesting, right? I think we've all seen, whether in direct personal experience or 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. 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.

48:28But 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. It's like, you know, 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.

49:13Now, 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, 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 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?

49:54Or tell me a time where there's like, Let me explain to you how ego destroyed a man or a woman or what we could learn from it. Well, this is why reading and experience in The Pursuit of Wisdom are so important. 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? There's a similarity there. And so I was thinking about doing this book about ego.

50:36So 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 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? 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 at American Apparel and I'd left when my book started to work.

51:13And 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, 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 in timeout, your shares will one day be worth a lot of money again and instead engage in this death wish.

52:07He 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 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.

52:51And 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? 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. And I tend to find those kind of phrases or ideas to be very insightful little indicators. Oftentimes, I find—and again, ego is there.

53:40It'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? Who are you to tell me? I want to let this sit and I want to get in a better place. And then I find when I go through it, I go, okay, well, there's some stuff in here. And then maybe I'll do this one. Maybe I'll start with all the typos. And then after I've gone through it a couple of times, I put in like 80 % of what they said, right?

54:21But in the initial moment, you're like, I handed you perfection and you gave me a marked up underlined draft, how dare you? So it's like, I tend to find that the first reaction is emotional or egotistical or 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 from Marcus Aurelius, which is that you always have the power to have no opinion.

55:06Sure. 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 did anyone ask? 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, 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 uh 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?

56:10That'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, oh, 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.

56:57We'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 does it like, I'm making this as if it's some issue of character or if it's something essential about the functioning of our lives, and it isn't. If you want to wear Crocs, wear Crocs. I don't care.

57:36No, that's not allowed. Baseline. But so much of conflict, especially when your kids are older, is rooted in just the parents having opinions about things that 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'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.

58:15And 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. For Feeding America? Yeah, it was just like, well, what about this? You know, or whatever. Oh, right.

59:06you 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 praise on, and they don't understand that that's what's happening. Do you know what I mean? I think just realizing that social media is dependent on your unpaid labor, emotional and otherwise, it is designed to make you uncomfortable or provoke you into clicking, reading, or posting or watching or whatever it is, and that it's really good at that.

1:00:08And so I do have some sympathy for the people, right? The only way to win is not to play, right? And they've got to understand that this thing is manipulating you. 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 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 civics, you know, person, a member of society to like do your civics duty and to participate in it.

1:00:54But 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. 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.

1:01:30And we worry so much about what other people think or 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. 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, the haters existed in the ancient world. I mean, Seneca, who you were talking about, is not just a controversial political figure.

1:02:04It'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. Like, I hate this. So they got it from all angles. Marcus Rios is the emperor of Rome. There are statues of him, people who are saying you're the greatest, literally worshiping him as a god. And then there are people who are trying to kill him. And so 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.

1:02:45And 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, 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.

1:03:26Not just millions of people who saw the stuff and then decided, 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 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.

1:04:06Like 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.

1:04:41And 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, a 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, 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 Schroes 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?

1:05:19He'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? 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. 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.

1:05:58Yeah, 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 they don't like you.

1:06:33They 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 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.

1:07:10And 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 obnoxious. And he just goes on down the list. And 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.

1:07:44Don'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. Just like somebody has to pick up trash, somebody has to clean toilets, 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.

1:08:24Really 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 in that they're not as coordinated as dogs. Ours can open our fence. It can open the back door to our house. They're very clever. And 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.

1:09:07Do they cuddle? to cuddle their donkey? Yeah, 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 a donkey. It's on my Christmas list. So now we've moved that up. Well, I'll give, if we have the problem, so we have one and we had to get another one because they get lonely and they have a baby every 13 or so months.

1:09:49And 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 just a rabbit hole of how long you have been on the internet and asked a bunch of your friends.

1:10:21But 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 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've done? Well, I mean, I wrote a whole book about sort of publicity stunts. Which one was that?

1:10:55It'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, and 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.

1:11:33Like 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 a while 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.

1:12:19But 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 quote in that New York Times profile. You mentioned that it's not that it 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.

1:12:54And 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. 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 don't want to spend my life selling other people shit.

1:13:34That's just not really what I wanted to do. And so I was like, well, what do I care about? What am I interested in? And ultimately, even my marketing business, which I kept for many years, and I consulted mostly, but 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.

1:14:24And 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.

1:15:04And 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. You 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 Ad Week, which is this series of conferences and galas and award shows like that. And I remember the first time I went, I was probably 20, 21, and I'm like the kid there. I'm the only one not in a suit, 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.

1:15:35And 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 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 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.

1:16:18And so that was part of the reason that I ultimately sort of made the leap, which seemed crazy at the time. When you're the director of marketing and publicly traded company, you're gonna go write a book. You don't even have a book deal for it. You're just gonna go write a book. What's wrong with you? 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. 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.

1:17:02It'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. 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.

1:17:34All 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 you're going to go along to get along for 40 years and then be a visionary, rule-breaking leader is extremely unlikely.

1:18:18Yeah. 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. 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 Conterent Thinking, obviously. And to your point, I kind of labored over that.

1:18:59One, 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's fate. 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.

1:19:31And 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 like 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.

1:20:09Because 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, sub stack 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?

1:20:48I have a little note card on my desk, and it just says, are you being a good steward of Stoicism? And I think about that because I didn't invent this philosophy. It's a tradition that stretches back 25 centuries. I just happen 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 exploiting it as opposed to contributing to it. And so I think there's a fine line, of course. 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.

1:21:40because, 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, you have to trust that instinct. Yeah. Yeah, it's a good point. I think it's a beautiful line because 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.

1:22:19Maybe 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 uh 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 um do you ever like read the really bad ones out loud like the hollywood actors do sometimes anytime i i come across i go why did i subject myself to this doesn't make me feel good it doesn't make me feel bad it just makes me confused you know like Like, it's like I, you know what it is?

1:23:04It's like, you 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 got to 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.

1:23:42And if I take my eye off my paper to look at theirs, 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 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. 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.

1:24:19And 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 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.

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