The Keys to a Good Life | Ryan Holiday on Impact Theory

Think about this way. If you yell at your people every time something is wrong, they'll just be like, "Oh, Tom's a yeller. And if I just don't mind being yelled at, I can get away with anything." Do you know what I mean? And that's a very That happens in companies a lot. It's like, you have to be calcul- in some ways calculating and controlled and choose what you're going to get upset about. Otherwise, the people that you're projecting that to aren't going to be able to discern a minor mistake from a catastrophic mistake. It's very important that you're not the the boy who cried wolf. Everybody, welcome to Impact Theory. You are here, my friends, because you believe that human potential is nearly limitless, but you know that having potential is not the same as actually doing something with it. So, our goal with this show and company is to introduce you to the people and ideas that will help you actually execute on your dreams. All right. To paraphrase Steven Pressfield, today's guest is one of the greatest thinkers of our generation. He's a multiple-time best-selling author who's written a seemingly impossible six books in the last five years. His meditation on stoic philosophy, The Obstacle Is the Way, is not only a true perennial seller, it's been translated into more than 20 languages and has a devoted following of some of the most driven and successful people on the planet, including NFL coaches, world-class athletes, entrepreneurs, TV personalities, and even political leaders. By my estimation, it is one of the 10 most important books you must read if you want to develop a mindset for success. And even if this were his only book, I'd sit at his feet to learn. But every book he's written delivers a similar level of impact. This guy is without question my intellectual man crush Monday. The systematic and practical nature of his thinking is so powerful, it's nuts. Especially considering that he dropped out of college at 19 so he could apprentice with the master author Robert Greene. And by all accounts, my friends, he learned his lessons very well as he went on from there to not only become an amazing author in his own right, but in his early 20s became the director of marketing for the billion-dollar public company American Apparel, helping it achieve its astronomical levels of success and in the process becoming one of the most sought-after voices in the field of media strategy. His incredible marketing tactics, detailed in the book Trust Me, I'm Lying, not only became a best-seller, it helped him launch his own media consulting company Brass Check, which has advised companies like Google, Taser, and Complex, as well as world-renowned authors such as Neil Strauss, Tim Ferriss, and Tony Robbins. So, please help me in welcoming the best-selling author of Ego Is the Enemy and most recently perennial seller the modern-day philosopher king Ryan Holiday. Your reaction to that last part was amazing. Well, that was very kind. I I appreciate it. No, I've I've been effusive with my direct-to-your-face praise for quite some time now. So, hopefully you know that all of that is is truly sincere. That isn't hype for the show. Like reading your books, meeting you in person, the the way you think really does hit me like that. Well, no, that that means a lot. It's just a it's it's overwhelming to just stand there and watch you say Yes, that that I imagine. Yeah. But no, thank you. I appreciate it. Of course, dude. Yeah. So, where I want to start with you, you talk a lot about people only write the book that you couldn't not write. Um it's got to be something that really compels you, and I love that, and I totally agree. Sure. What drives you? I think what what drives me is is trying to figure out the things that I wish that I was taught, uh that I wish were part of what you're supposed to learn in elementary school and middle school and high school, you know, um philosophy was supposed to be historically this. It They would call it the guide to the good life, right? So, it's something we've been thinking about for a long time, but like where is this guide? You know, like what I no one gave it I read a lot of books in school. There were a lot of, you know, things that they made us look at and nowhere did I ever get this guide. And so, I think I I'm always sort of searching for for the answer to that question, you know, like how does one live? How is one supposed to live? What do you do in the morning? What do you do at night? You know, how do you find happiness? You know, the answers to these questions and and so, I'm looking for that personally and then I think professionally my job is to then share the answers to those questions as I've as I find them. That's really interesting. So, especially now that you're on the bandwagon of fatherhood Yes. which I'm very curious to hear more of your take on that. But like would you ever write like for somebody in grade school like that manual? I usually am writing to a younger version of myself when I'm writing. That's one of the I think you have to as a writer you have to have some idea who your audience is. Like you have to be able to envision that person and speak to them. And so, one of the people that I'm always trying to speak to is me whether it's 5 years ago or 10 years ago or 15 years ago. I don't know if I have enough insight into where I was at that age that I feel like I could really speak to to that exactly, but I do love really well done children's books. I mean like if you've ever read The Little Prince, there's tons of lessons in there. I think right now I'm I've still got enough to say to me just a couple years ago before I can go back in time quite that far. Right. What how had like the smile that you had in your face, I want to make sure we show that when I asked you about becoming a father. How has it changed the way that you think or approach life? So, my son is 13 months. So, I don't have a ton of experience yet. But I would say I'll give you three three lessons. I say So, number one is it much easier to say no to things because you realize we seem to have a a limitless capacity to steal time from ourselves, right? You know? And the Stoics talk about this all the time, you know, like we would you would be incensed if one of your neighbors encroached onto your physical property. But if one of your neighbors came over and just talked your ear off for an hour, you would find it rude to be like, "Get out of here. I don't want to speak with you." Right? Do you know what I mean? Like So we we protect our physical space much more than we protect our time, even though physical space can be regained and time can never be regained. And so one of the things that it's like even I've been married for a while and and I've been with my wife for a long time, I even found that I I was comfortable stealing time from her and from our relationship in a way that I'm not comfortable stealing time from a a child who I've promised as much of my time as I can to, right? So it becomes easier to say no to in essential things. That's number one. Number two, I would say is that especially when my son was first born, was sort of learning that like parenting is just actually just being there, right? Like just physically in the space. So almost nothing else in my life was would be like would sitting in a chair not doing anything be doing something, right? Right? And so it's it's really slowed me down in a very good way, right? That like my job is to sit here while he plays around on the floor doing whatever he wants. I don't need to be as purpose-oriented and that's been a really good lesson for me cuz I got Why is that a good lesson? Because if you think that action is the end-all be-all, you end up doing action for the sake of doing action, right? so I I feel like I should always be doing and doing and doing, but sometimes you're just supposed to be and often times just sort of being there and sitting there and being still is where their great insights come from. And this is also where happiness comes from. You know, it's hard to be happy and appreciate and feel gratitude when you're just moving all the time. It uh my therapist said to me one time, she was like, "You got to remember, it's it's human being, not human doing, right?" And and and the a kid is a really great reminder of the the the the being part because they're so always in the present moment, right? And then, I think the last lesson is just sort of watching someone experience sort of just complete joy and again presentness um is also a reminder that like things don't need to be as I I'm a very intense person. And although that intensity is responsible for a lot of my success, it's also responsible for my unpleasant moments, right? It's responsible for anguish that I feel or insecurity that I feel and that the need to be busy all the time. And so, I think just watching, you know, the simple pleasures that he can enjoy, I think uh lets me feel a bit more gratitude and and appreciation and then lets me focus on what's really essential. All right. Well, now let's ask a really interesting question, at least I'm deeply fascinated by this. So, now let's imagine you wake up tomorrow and you don't have kids. What of those things would actually carry forward as transformative elements for you? I would say in a way they're all I would carry forward all of them, but having this having this person, this living thing that you're responsible for, um keeps those lessons top of mind because there's real consequences for it, right? It's a reminder that you can't do everything all at once and you do have to prioritize. There's someone who will be upset, who will be hurt, who will suffer for this rather than you just deferring those costs into the future, which is what I did before I had a son and and what I think most people allow themselves to do all the time. You know, we know objectively that we're going to die. We don't have unlimited amounts of time, but we still spend it as if we have unlimited amounts of time because the consequences are so deferred into the future that we can get away with it. I also intellectually knew all those three things that I told you before, but it's been good. It's been the hardest thing that I've ever done and and I think it's good to challenge yourself that way. All right, so abstract it from kids for a second. You're you're you're a very methodical thinker. So, what is the matrix by which you make a decision for how to spend your time or even what to strive towards? Look, I struggled with the time thing before I had a kid. So, I'm all my instinct is I I heard a great line from Austin Kleon and I think he got it from somewhere else. He was saying, you know, that the job of the mindset of an entrepreneur or a creative person is that you basically say yes to everything until you can get to a position where you can say no. But, it's really hard to know that you've gotten to that position, right? Especially because you work yourself up into a state. I'll give you another actually analogy. A friend of mine, his name is Dr. Jonathan Fader. He's a sports psychologist. He works with the the New York Giants and the New York Mets. And he was saying that in baseball, uh particularly players from like the Dominican Republic, they have this saying. They said, "You don't walk off the island." So, basically, the only way you can get out of poverty or out of this place is by swinging, right? You can only hit your way off the island, right? And so, on the one hand, what that does is it creates really aggressive players. They swing at every pitch they can. But, then as soon as you make it in the major leagues, it's all about bat discipline, right? You can't swing at every pitch because the pitches are better uh because if you miss, it causes problems for your team. And so, it's this balance, right? Once you've arrived, the thing that got you there is now in some ways your worst enemy. And so, that's something that I have always struggled with is like I've always been the person that just said yes to everything. Early on in my career, you know, it was like, I can do all of it at the same time. I don't care if you think it's humanly impossible, I will outwork you. I will I will make it possible. And so, there was a time where I don't think I ever ended one of the opportunities that I had. So, I was just adding them on top and on top. And I never hit a wall. Like, I just never hit it. And so, always saying yes, always saying yes, that became who I was. And now, as I've as I've achieved a certain level of success, and what I've done is gotten harder and harder, now it's all about protecting the space that I need to do that work. I think just the idea of needing to make those hard choices, knowing what's important, what's not important, what I'm trying to accomplish, not only have I struggled with that already in my life, but then having a kid makes the stakes of that higher, but then it's also just a learning experience. Yeah. There's a concept in Perennial Seller which truly haunts me Okay. and is is clearly the sign of the thing that I struggle with along these lines, which was nothing is destroyed more great artists than the thought that they can do two mutually exclusive things at the same time. Yes. I butchered the quote, but no, right. the idea. And you've said that of your consulting business, you feel like all you do is untangle people's like mess of things that are often conflicting that they want to do. What what is it about that problem and how do you help people through it? Well, I think what I what I'm saying is that often times people go, "Okay, here's really what I want to do, and this is what I'm trying to accomplish." And then, they see all these other things that other people are doing, and then they they kind of see that as like a grab bag, and they're like, "I don't want a little of this, and a little of this, and a little of this, and I want it all at the same time." And that's not really possible, you know? You can't play five sports at the same time. You got to pick one, and you got to specialize. Maybe you can do two, but you probably can't do five, right? You can't be a classical musician and a rock star, you know, and this and this all at the same time. So, it's about sort of picking your lane and then knowing that some some goals are mutually exclusive. The question I ask clients the most is like, "What does success look like for you on this project?" And I get them to really describe it to me and let's say there's more than one thing in there. I go, "Now, if you can only pick one of those things and the other ones didn't happen, which one would you pick?" And I'm trying to get them to sift through some of that conflict so we can really hone in on what we're trying to do. And often times like where ego comes in is like we've got the things that impress other people and then the real meaningful impact that we're trying to have. And often times, I'm not saying that the the status things aren't nice and they're not they they're not impressive and they're not cool, but we've got to make sure that they're not coming at the expense of those other things. Right. I love that notion of, you know, asking yourself what success looks like for you and having that clarity. And how important is that clarity do you think for people that want to be successful? Like how much of this is you start with a goal that is abundantly clear and then you create a path? I think one of the things that has really helped me make some of the decisions we're talking about earlier is what does like an ideal day of your life look like? Like maybe not right now, but like what do you want a day in your life to look like? And so, if if that day is like, "Look, I'm the kind of person I love going to an office. I love lots of responsibility. I love lots of pressure. I thrive in that environment." Well, then great. You know that that's where you want to For me, when I think about like the high-powered executive who's who's who who an entire company is resting and falling on, I think, "How does that person have time to do any creative long-term thinking?" I don't think that they do. And so, I had to realize that, "Oh, these two paths" cuz I I was on two paths. I was a a writer and a researcher and then also I had I was at a big company that they were mutually exclusive that one was coming at the cost of the other and I tried to do both for a long time. I I at one point I stupidly uh doubled down on the one that I didn't want and I realized it occurred to me one day I was I was actually in LA. Um there there was some chaos at American Apparel and so I'd gotten called back in they were paying me great money and I it was like you know 9:00 a.m. I'd just gone for a run. I'm sitting down and I was writing. I looked at my watch and I was like, "Oh, I I have to be at the office. Like if I'm not at the office like people are going to be mad. They're going to wonder what they're paying." And I was like, "But my dream is not going into an office. The most important thing for me is to have the freedom to go where my day takes me especially creatively. I'm on a path that's taking me further away from what I want my ideal day to look like. That's not success, you know?" And so and Tim Ferriss has talked about this is you know some people it's like "My um dream life is being on a beach in Bali." Well, what does that actually cost? Could you have that now? Do you have to have a life that you don't like so that at the end of it potentially you're lucky enough to go there or could you find a way to get that now? I'm trying to think about this on a regular basis. Is my life resembling what those days are supposed to look like? And if I have too many days in a row that don't resemble what I want my day to look like, I go I'm I'm I'm having the opposite of success. You know what I mean? And what do you do very tactically in that moment? Is it journaling? What does that look like? So I I do journal uh every morning and every night. So part of my journaling is just like a detailing of events like not for history but just so I'm forced to recount what happened and actually think about it. You know the Stoics would say prepare for the day ahead and then you're supposed to reflect on the day that just passed. And so that sort of process of preparing in the morning and reviewing in the evening allows me to never get too far from where I I I want to be. You know what I mean? Like I'm never going to I'm never going to wake up 5 years from now, hopefully, 5 years from now and go, "This is just really not the life that I wanted." Because I'm I'm doing the a regular series of check-ins. So, going back to what you said about, you know, for a brief moment I actually doubled down in the thing that I didn't want, Yeah. which I totally get and understand in a way that I can't even convey to you. Why do you think people have a hard time identifying what they really want? And like what can people do to not find themselves in that situation? This is a very first-world problem, but I would say one of the hardest things to do in the world is to turn down money. Right? So, like I was in a conference room and someone said, you know, "Look, we need you to come back. Like we know you have this writing thing." This is when you're quitting. Yeah, or I'd already basically left. I was I was like sort of remote and and then and didn't have a day-to-day role. And they said, "Look, we we need you to come back. You know, this is going to be a tough, you know, series of months, but we think you can make a contribution. We need you to come back." And I said, "Well, look, you know, I've got all this stuff." And they they said, "Well, what would it cost to get you to come back?" And I threw out what I thought was a high number, and they said, "Done." And so, in that moment, I was like, "Well, that's a lot of money. If it would it would be irresponsible to say no to this, right?" And so, I was telling myself one that I could do it all at the same time. And then two that like, you know, I I wanted this money. You know, like, you know, and and it would it would seem dumb to say no to it. I deal with lots of successful like entrepreneurs and and athletes. And one of the things they're always talking about, they're like, "Oh, I just I love books. I love writing. I would love to be able to do that." And so, one of the things that struck me in that period where I was unhappy was it was like, "I get to do this thing that other people tell me they wish they could do. And here I am taking a bunch of money to do the thing that they say they don't like doing, you know? This is This doesn't make any sense at all. And so I had to back myself out of that situation. I you know, I left some money on the table as a result. And it was it wasn't a fun experience, but it was it was just I think in that moment I wasn't thinking, "What do I want my life to look like? What's the most important thing to me?" I was thinking, "How many zeros are in this check, right?" And that is not a great uh way to make decisions in your life. Because what do people do with their money? They buy freedom, right? But oftentimes they give up freedom to get money. And so that it was like, "Oh, I could just skip those steps and stay where I am and be very happy." God, that's so interesting, man. So yes, I think that that's a an eternal thing that people do with their their work they're giving up their freedom in order to buy some sort of future freedom, which may or may not ever come, by the way. Right. Um Cuz what if What if you do that and then you get hit by a bus? Yeah, or the money never comes. Sure, sure. Which is maybe even more likely, right? It just always slipping into the future, the eternal future. So my question is though, and there's there's two things really. So one, how did you deal with whatever the reverse of buyer's remorse is, right? Where you give the money back, and then that next time that you want to do something and realize I can't cuz I don't have the money, but oh if I just stuck it out and then yeah, we'll start there. It's not like I was choosing between, you know, the poorhouse and you know, paying for my groceries or something, right? Like this was this was extra. One of the pivotal conversations of my life was with Tim Ferriss when I was starting my company, and he said, "You know, Ryan, what do you do with your money?" And um I was like, "What do you mean?" He's like, "What do you What do you spend your money on?" And I was like, "Nothing. Like I just I like I just put it in a bank account and then I try to manage it responsibly. I live pretty reasonably and and uh I I I try to save my money and whatever. So, he's like, "Okay, so why are you going out and try to get more and more if you don't need it?" And And that was really helpful to me. So, now uh when I'm thinking about clients, uh like what what my test is at Brass Check is we go like, "Okay, is this work we're going to be proud of or is this giving us money that we need to do something we will be proud of?" That test is really, really important. A lot of times people are saying yes to money not because, "Hey, if I do this, then I can pour it into the movie project that everything depends on." It's like, "I need this so I can lease a nicer car." Right. One One concept I'm assuming it comes from Stoic philosophy and I can't remember if I read it in Perennial Seller or Ego Is the Enemy or both perhaps, but what would a person more humble than me learn from this moment? That's something I think is incredibly powerful. Walk people through what that means, what you're trying to get to, and what the result is of approaching things like that. Well, I think there's this cool exercise from Adam Smith, who was the economist. He He He wrote The Wealth of Nations, but he also wrote a book called The Theory of Moral Sentiments, which is this sort of brilliant book about philosophy and kind of like why we do the the right thing basically. And one of the things he he was talking about is he was like, "You should judge all your actions." He should You should subject it, he said, "to the indifferent spectator test." Which is like "What if there was a a totally impartial person who you didn't know who's just standing there watching you?" What would they think of this? You know, what How would they judge what's happening? And that's a way to sort of step out from your own logic, your own impulses, your own natural feelings, and sort of judge, you know, if you're not religious, you're not like, "What would Jesus do?" You're like, "What would some random guy think of this?" And if if If pass his test, it's probably not a good thing to do, right? And so, I think that's that's the test I go is like, what would a person who isn't so caught up in this, who whose identity isn't on the line, how would they react to this rude remark? Or how would they react to this lowball offer? They would not be nearly so caught up in it. It wouldn't threaten them the way that I'm feeling that right now. So, I'm going to borrow a little bit of their objectivity, and I'm going to try to I'm going to incorporate it into my reaction here. And the way that therapy is about questioning our thoughts, philosophy is giving us the tools to in the heat of the moment, you know, Victor Frankl would talk about how, you know, there's this between stimulus and response, there's like a a moment, and that's where we get to choose who we're going to be. And I think philosophy is about that moment, really. How often do you think about that moment for you, very specifically? Like, do you have a codified set of So, I think of my mind is a a Pachinko ball machine, if you know what those look like, right? You drop the ball on the top, and it bounces around over a lot of things. And those things that it's bouncing on is my um the code that I live by, right? My belief system. So, I take something negative, uh or, you know, there's nothing good or bad, but thinking makes it so. So, it's like, and I put it through all of that so that I get a a resulting outcome that is useful, which is how I think of it. Do you spend a lot of time building something like that? Yeah, yeah. You know, we're not robots, so we can't like, okay, I'm not going to react. This is like an intuitive almost an unconscious process, right? And and so, you're sort of you're trying to you're trying to put all this information in there. Uh you're trying to to to sort of put in those those little points that the thing is bouncing around on on the way down as a way of sort of slowing down the process. I think most people, your average person who who doesn't work on themselves, who's not reading, who doesn't care about any of this, they're just they're they're the time between stimulus and response is like nothing. Right. And the the more you work on it, the more you practice, the more you're able to question your own thoughts. So, what is that slowing it down? What does that practice process look like? Like, how do you practice that? That's a good question. I mean, it it'd be like how do they practice uh swinging a bat in baseball? I mean, they just swing it a lot and they they watch film of themselves, so they're stepping back and evaluating things after they happen. They're looking for cues. They're they've they've got other people around them who are giving them feedback. I think it's about a sort of cultivating an awareness and a process of continual reflection on the data that your life is creating all the time. Do you think most people do that, though? No, of course not. That's why it's such a huge competitive edge to start working on that. Do you know what I mean? And and the earlier you start working on it, the sooner you're going to start to see results, but the more those results are going to compound over time. There's nothing in let's say Stoic philosophy where we're saying, you know, the the idea that there's good or bad, there's just the interpretation that we have on things. So, I first learned that when I was 19 years old. I'm sitting in my apartment in college and I read this book and some person 2,000 years ago said that to me. So, I that was the first time I encountered it intellectually. A week later, that would have only a minuscule impact on my life, but every every time I've thought about it, every time I've studied it, every time I've tried to reflect on how in retrospect I could have done that better, I've accumulated slightly more know- more knowledge, more appreciation, more set more sense of that the truth of that and and the I've gotten better and better at it. I I might be only 20% better at it now, but I'm hoping that at 70 that that return will compound not unlike my retirement savings, right? Like, you're thinking about this and working on it and writing about it and talking to other people about it and and trying to evaluate your own behavior and then it's just this process of of reflection and miniscule improvement as you go. And you're not trying to get to perfection right now. You're just trying to get a little bit better than you were yesterday or an hour ago. Do you read Ray Dalio's Principles? I have not read it, but I've heard amazing things about it. Right. I I know his practice No, I know a bunch of the principles, but his practice is similar, right? He's like, "We're recording all our meetings. We're getting feedback from people in the office about how you're doing." One of my favorite stories about that uh Pete Carroll, the coach of the Seattle Seahawks, one of the best coaches in the NFL, he was talking about how, you know, coaches are constantly filming their players and they're forcing the players to break uh to break down game film. They're ruthless. Like it's like you could have a great game and then the next day you're you're back in the practice facility and, you know, the receivers coach is telling you what a horrible game you had and all the opportunities that you blew. And And so, uh obviously that's that's what makes these guys so great. And Coach Carroll was saying like, "I realized I don't do that to the coaches. Like the coaches never experience that." And so, he started filming his coaches and he would he would force them at the beginning of the season to look back at all the times that they blew it, right? That they lost their temper or that they missed something. And And so, I try to do that in my own life. I mean, one of the ways that I, you know, authors aren't supposed to read their own reviews, for instance. One of the reasons that I read most of the Amazon reviews, let's say, of my books is that I want to get feedback from people. So, I'm not reading them to feel like I'm awesome or to to sort of whip myself, but I want to see what people are responding to and I want to get unsolicited feedback on on I have a a filter that I put that information through, but I'm looking for as much feedback as I can about the things that I do so that I can incorporate that data and and get better. Uh so this is like my life's obsession, this moment right here. So one, I want to know what that filter is and we'll get to that in a second, but so you're you're incredibly successful, right? You've got your own company, it's doing well, working with the biggest companies ever, you're a multiple time best-selling author, and you have perennial sellers in the mix as well, which is sell sell sell sell sell. Why the hell do you subject yourself to the self-flagellation of an Amazon review? Like what what is that about? Well, I it's not self-flagellation. So you have to make that distinction. How do you prime yourself mentally for it not to become self-flagellation? I can't change what happened. So I'm looking for this feedback for tips and information that can help me improve so that that person who let's say they didn't like what I did, so that I can not let that happen again. They'd say, you know, Ryan, uh I really like this book, but I can't let my son read it because he uses the F-word a lot. And so it was like, okay, so some people don't like cursing. And then I noticed as I went through the the positive reviews, no one ever said, I really like how Ryan curses a lot. So this was a this wasn't something that was important to me, right? And here it was having a negative impact on some of the readers. And then let's say a marginal to no impact, no positive impact to the readers who were enjoying it. So to me, that's a pretty easy data point to go like, okay, in some cases, I think I need to drop an F-bomb here to catch people's attention, right? And I can see that when I talk, if the audience is you know, sort of drifting a little bit, I can call I can use it, you know? Um but there's no reason for me to do this in my and so in in The Daily Stoic there the there's no curse words and that was an improvement I think that I made the book better and I got that by going through this process. That makes a lot of sense. Now now talk to me you said you have like an installed filter that you use to know what to listen to and what not to listen to. Yeah, look at the feedback you're getting and then remember what you were trying to do. For instance, I'll get a criticism from let's call them stoic fundamentalists, right? People are really sort of nerds about philosophy who will say, you know, Ryan um you know, Ryan doesn't add anything new. He's just taking stoic principles and illustrating them with stories, right? So that'll be one criticism or they'll so they'll say you should read the originals. Don't read Ryan's book or other people will say, you know, Ryan is taking these timeless virtuous principles and then illustrating them with famous successful people and you know, that sort of cheapens it or you know, that's that's uh that's not what stoicism is about, let's say. Well, in both cases I was explicitly trying to do the thing they were criticizing me for, right? So I say in the book, if you're really interested in stoicism, go read the ancient stoic text. I cannot do better than them. What I was writing The Obstacle Is the Way and Ego Is the Enemy is for people who don't have time or interest in ancient philosophy but are trying to improve their life in some way. So I'm trying to meet them where they are. So when someone says that I didn't do this thing that I explicitly wasn't trying to do, my filter is going, okay, this person shouldn't have read the book. This wasn't for them. I don't need to take this personally, right? If you're trying to be everything for everyone and you read feedback, you're just going to get more lost cuz some one person's going to say this and another person's going to say that. But if you know, here's exactly what I was trying to accomplish and here's what that success looks like, then you can you can filter this information and go, "Okay, is this person's advice getting me closer to where I want to get or further from where I want to get?" And that has been really helpful to me. What I love about that, and I really hope people are listening to what you're saying, is you're doing it with an eye towards getting better. To me, there's an element, and this is why I brought up Principles by Ray Dalio, is his thing is all about like, "I'm just trying to get to truth." Yes. And one of the things that I wish on every human being is to one day, in some way, shape, or form, understand what it's like to be an entrepreneur in that if the company does well, fortune can be yours, and if it does poorly, you can lose everything. Sure. The amount of [ __ ] that cuts through is crazy. Like, it's not even necessarily that I don't want to have an ego. I would love to have a big, thriving ego, and people are always saying like, "How do you stay humble with the success?" Dude, because if I don't, I'm going to lose everything. No, the the reality of how low the margin for error is is like the ultimate recipe or sort of shortcut to humility. Like, let's say we're I'm fighting with um uh an editor or or someone or even just a friend who's reading one of my books about, you know, the use of this sentence or this paragraph or this stylistic or you know, something in a book. I don't have the room to be like, "You don't know what the [ __ ] you're talking about. Like, I'm the genius. Let me do this, right?" Because if I'm wrong, I don't feel so secure in uh what I do that I feel like I can afford to let ego make any of those decisions. I have to let truth make those decisions. So, you know, there's a a writing adage. It's like when when someone says that something's wrong, they're almost always right. And I think this is true in life. When someone says there's something wrong with what you're doing or, you know, how you're carrying yourself or what you're, you know, project or a product, um they're almost always right. When they explain why it's wrong or how to fix it, they're almost always wrong. So, it's like when someone's saying like, "I don't like chapter six." They're right. They don't like chapter six, right? When they say, "You should get rid of chapter six, or you should, you know, make chapter six the opposite of what it is, or get rid of this or they're probably wrong, but you should try to figure out why chapter six isn't working and improve it, and make sure that it's aligned with your vision, cuz maybe it's not. Or, if it's perfectly aligned with your vision, then you have to make the tough call and go, "Look, I'm not going to please this person." All right, so now the million-dollar question is, how the hell do you know the difference? First off, you should just go like, like, I'll give you an example. I I I I've talked about this before, too, but like, one of the dangers of entrepreneurship is, or making anything, is that like, people around you are going to be like, "That's not a good idea. Don't do it." And then, you don't listen, and you do it, and you end up being right. Well, you've kind of just learned a very dangerous lesson, which is like, just disregard what other people say. So, one of the reasons you tend to see people on the way up, take a company like Uber, they're just like blowing past conventional wisdom, business best practices. They're doing it their way over and over and over again, and they're going up and up and up. And that's creating a feedback loop, where it's like, "The rules don't matter. We do it our way. We do it our way." And they're being rewarded for it over and over again. And then, at some point, they cross a line, and now all of a sudden, they started to do things that are illegal, that are unethical, that their customers aren't going to like. But, there's a delay between doing that and being held responsible for that, and that's where the sort of catastrophic explosion and consequences inevitably come in. And so, whenever you feel yourself going, "I'm just going to blow past what everyone's saying. They're all idiots, you know, they don't know." That's a really bad sign that you're probably doing something out of ego. So, I think that certainty is something I'm always uh nervous about. Like, so, it's become sort of cliché in entrepreneur circles and and you've probably read this article. You know, the idea of like it's it's hell yes or hell no, right? Like you either you're either a thousand percent on it or you say no. But, all the difficult decisions I've ever made in my life were like you know, 51-49. So, so it's like in some ways I'm actually really skeptical. I I think that there's a great point in that article, which is like just don't do, you know, don't do stuff just cuz you're supposed to. But, it should be tough. And if it feels easy then I want to question that. I guess is is one of my answers. And then look, nobody said writing a book or being a leader or, you know, shepherding some vision and no one said it was going to be easy and clear and you were going to know. These are things that are going to keep you up at night and that you got to roll the dice on to a certain degree. And so, you just do it and then if you're wrong, you learn and you do it better next time. How do you keep your emotions out of the way? Like I I have a very simple formula, which is the thing that I want in this world I want so desperately that and it's not an ego thing. So, it's very I have an ego for sure, but it's very easy for me to set that aside cuz it's not the thing that I want most. Okay. And so, in those times of like emotionally I want to do this, but then I just check it against oh, does it actually help me get where I want to go? No, okay, cool. Then I'm going to go after that thing. What mechanism do you have for dealing with that? Well, what I think one of the best ways is just time, right? Abraham Lincoln famously, whenever he was like really mad at a subordinate, like, you know, one of the generals in the Civil War, he would write them like just a really nasty letter. Like he would just this is what you're doing wrong. This is, you know, he he would write everything that he wanted to say and then he'd put that letter in an envelope and then put it in his drawer and then wait, you know, a day or a week. And then most of the time he wouldn't send it. And so, one of the things I try to do is I go like do I really need to respond to this right now? Because that tends to be where that emotion The emotions are typically immediate, right? Like I'd find even the things that I'm really upset about, I'm most upset about them when I first find out about them. If I give it a weekend or if I sleep on it, I'm much less upset about them and I'm going to be more rational and I'm going to be more responsible with how I reply. So, I I just want to give it some time. I mean, one of the tests that I have I do this with emails a lot. Like if I'm fighting if I'm arguing with someone, I'll go like, "What if I just pretend I didn't get their response?" Like I'm not even going to read it. Like I know like I just said I just said my peace and then they sent me a response back like 5 minutes later. I'm just not going to I'm just going to delete it, right? And then I'll let them have to resend it to me or just let the issue drop. Right? So, I'm kind of just sticking my head in the sand, but I'm I'm really just creating space for there to be less cuz they're not going to resend the exact same thing. They're going to "Hey, we need to talk about that thing." I'll go, "Oh, what was it?" And then we'll You know what? We'll have a little bit a more reasonable of a dialogue. When I feel that impulse is like I got to do this right now, that's emotion and that's probably not going to get the best solution out of things. What are things that wind you up to use a nice British phrase? That get me pissed off? Yeah. You know, when people mess with my stuff. So, like if I like writing is about what I'm trying to accomplish, right? And so I did it the way I wanted it to be done and I'll get really upset like if something comes back to me even if it's small and like a change is made without just like I'm very open to taking criticism and feedback, but like I I caught something let's say with a copy editor recently on on a book I was working on where like they reworked something without They just assumed I would be okay with it and they reworked it and I caught it and that was very upsetting to me, right? Because if I hadn't caught it, something that I didn't sign off on could have gone out to the my readers. But you know, uh I was much more upset about it at 3:00 on a Tuesday than I was the following Thursday when I finally got to the bottom of what happened and I worked through it. It's just never that great to act out. Okay, actually I'll give you something cuz I think about this question a lot, too. And so I've asked some of the basketball coaches that I've that have worked with or have read my book. I was like, uh I was like, "Do you ever get like a technical on purpose?" Because like a coach, you know, the worst thing a coach could do is get so mad about something that they give the team the opposing team an extra point, right? So obviously you don't want to get a technical on accident like cuz you're just ripped around by your emotions, but sometimes you should get upset to send a message to your team, to send a message to the refs, you know, to get the crowd going, whatever it is. And so I'm I I was like that I'm I'm interested if I'm going to use my emotions, I want to be calm internally but projecting the emotional response that's going to be effective in that situation, but I don't want to be jerked around by those emotions unconsciously. Did that That's advanced class [ __ ] Yeah. So this is something I don't often talk to people about, but is is absolutely necessary, I think, to certainly be running a company is A, you've got to be able to control your emotions so that you're not getting whipped around as you said, but B, you have to understand that all of this, even emotions, expressed, suppressed, facial expressions, all of it is a performance meant to convey something. Yes. And once you understand that you can leverage outrage, intensity, anger, whatever the case may be, as a tool Yes. to move somebody down the road, then you can really start to become effective. Well, think about it this way. If you yell at your people every time something is wrong, they'll just be like, "Oh, Tom's a yeller." And if I just don't mind being yelled at, I can get away with anything. Do you know what I mean? And that's a very That happens in companies a lot. It's like you have to be calcu- in some ways calculating and controlled and choose what you're going to get upset about. Otherwise, the people that you're projecting that to aren't going to be able to discern a minor mistake from a catastrophic mistake. It's very important that you're not the the boy who cried wolf, you know, the the one who's who's uh screaming about inconsequential matters and then when someone messes something up when they cross that red line, they're not going to take it seriously cuz you're like, "Look, you yelled at me yesterday cuz the the coffee was cold." And you know, here you messed up something on my calendar or whatever it is. You've got to You've got to be able to use the Those are Those emotions, how you articulate what you're feeling or your you know, how you're going to act in a meeting or how you're going to you know, present a plan. That's a communication tool and you've got to be able to use that. You can't just be, "Oh, I'm not feeling it so I'm down today or I'm in a shitty mood so I'm going to be yelling today." That's not a good way to make those tough decisions. I think of Enemy and Perennial Seller somewhat as compendiums to each other. I don't know if you feel the same. Um What and I guess if you don't, I'll give you my reasons for that. If you want to create something great, Yeah. you need to get your ego out of the way, right? So that's the sort of the moral of the story for me, right? So the Perennial Seller addresses how to actually tactically create something that's great, but you can still feel the Ego's the Enemy elements in it where it's like you're ultimately the one that's going to stop you or propel you forward. Yes. So taking that concept of if you want to create something great, this is how you get out of your own way, what are like the three or four things that people need to do, think, believe, whatever in order to achieve greatness? Well, I So number one, like what are you actually trying to do? Cuz you can't do 15 things at the same time. So like here's what I'm making. That's the the main like do you actually know, right? Cuz sometimes people are trying to do too much at one time. And then who is this for? Cuz it can't be for you. You know, like obviously everything you work on should be fulfilling and exciting and interesting to you. But you're not the customer of your product by definition, right? You can't buy it from yourself. So like how is this going to provide value for the audience? That's like the most important thing and and that has to be the ruthless test that you check everything you're doing against. Number three is like who are the people that are helping you check whether you're doing that or not, right? And so I think you need to have that test even if you're self-funding an entrepreneurial venture. Like the fact that, you know, you were successful in the past so you don't have to get venture capital on your next project, that's great, but it's also a potential disadvantage because now you don't have this external objective feedback telling you where you can improve, where you can fall short. So that means you need to work extra hard to cultivate those people, whether it's a board of directors, whether it's trusted friends, whether it's a a focus group. Like who is interacting with this thing and giving you feedback? I think that's really important. And then I would say that fourth, and the most important one, and this is where ego I think kills a lot of projects, is people think like if I build it, they will come, right? If I just make something so good, it will automatically be successful. Or they go, "I'm a maker. Like I shouldn't have to also be a marketer." And and to me the creative process, the entrepreneurial process, is sort of two consecutive marathons. So you run this marathon, you you make a book, you know, you you have a movie in the can, you have a a prototype of an invention, whatever it is. You you know, you stagger across the finish line. You're like, "I did it." And like, you know, the race proctor, they grab you and you think they're taking you to the metal stand. They're like, "You know, you did it. You won." Uh but really they're just like taking you through a shoot to the starting line of the second marathon, which is now how the hell do we get this into people's hands, right? And so, with every book, it's like the first marathon is making it for me, and then the second marathon is like, "All right, now I have to be as creative, I have to work as hard, I have to throw as much energy into selling this thing to everyone that it's potentially for as humanly possible." And so, I tend to find that creatives are either or with books or movies or what whatever I'm working on is either they're only interested in the marketing marathon cuz they're great sales people and they think like, "Oh, I'll just slap something together." Or they're so creative and they so love that process that they want to they want to skip the second marathon. What does success look like for you? So, we started with that, you know, that you have to have that clarity. Like, in in life, what is success? For me, success is a couple things. I think it's to have the creative freedom to make the things that I feel compelled to make and produce, having the sort of lifestyle and personal freedom to set up my life how I how I want it to be, right? So, to not be, "Oh, I've got to go to Cleveland tomorrow for this thing that I don't want to go like I don't I want to have that freedom." And then, um, I think success is also getting better. Like, I I love books, I love writing, I've dedicated my life to this craft, and I want to be like one of the best people to do it. And so, success is, am I moving up in my abilities? Like, is every book, regardless of sales, is it better than the one that came before? That's it That's also one of my definitions of success. All right, and before I ask my last question, where can these guys find you? @ryanholiday on pretty much every social platform and then my website's ryanholiday.net and then the books are everywhere books are sold. Nice. Yeah. All right, so final question. What's the impact that you want to have on the world? This is part of my definition of success obviously is is to have impact. I think my impact is I I want to write things and come up with ideas and communicate sort of stories and connections from history that give people the that that that that answer that question that we started with talking about which is like how do you live? You know, what how do you get to the good life? I'm I'm trying to make the things that I wish that were there for me but that if they weren't there for me I can make them for other people. So like when someone says, you know, like this book changed my life or when someone says, I don't read but I read your book. That's the kind of impact. So I'm I'm trying to have impact with people that I feel like are maybe not well served by the existing things in the in the market. So I'm trying to You know, I'm trying to make books that that that help people with life, you know, that that's a that's a an easy thing to say it's a hard thing to do but I feel like I'm chipping away at it. I love it. Ryan, thank you so much. Yeah, yeah, yeah, man. All right. Guys, that to me is exactly what you're going to get as you dive into the world of Ryan Holiday is how do you get to the good life and that I don't think that there's a much better question anybody could be asking and answering themselves. So no matter what it is that you're trying to do, I'm telling you if you look at the the entire universe of the books that he puts out, there's this through line that I find incredibly important which is growth, learning, getting better, seeking truth and finding out the answers and even when you take Trust Me, I'm Lying, it it was the first really sort of naked raw look at what was going on and in that book, by the way, he thought that was going to end his career as a media strat a media strategist, not kick it off. And so, it was somebody who really wanted to say, "This is the truth of the way the world is." So, rather than dealing with the world the way that you want it to be, actually accept the way that it is. So, when you understand that book in context of somebody who's finally just saying, "Look, this is the reality. This is the world that we live in." And then you see him follow it up with stoic philosophy. And then you see him follow it up with um meditating on the ego and its dangers and perennial seller in the daily stoic and all the things that he's doing, it it really is all meant to be taken together as a gestalt. And when you do that, it really does become maybe the first movement in a grand book about how to find the good life. I I am obsessed with this guy in ways that you can't imagine. Uh I will leave it at that, guys. Dive into his world. It is incredible. It will help you become a better person. It has certainly helped me become a better version of myself. So, if you haven't already, be sure to subscribe, my friends. And until next time, be legendary. Take care. Ryan, thanks again, bro. What's up, Impactivists? If you've ever failed your New Year's resolutions, we've created a free guide just for you, the Resolution Reality Checklist. It teaches you how to write smarter resolutions that you will actually crush this year. You can download it today at info.impacttheory.com/resolutions.