352 Overcome Your Ego with Ryan Holiday

"You've got to cultivate people around you who are not afraid to tell you the truth." - Ryan Holiday If you enjoyed this episode, check out show notes and more at http://lewishowes.com/352 Get more from Lewis! Get my New York Times Bestselling book, Make Money Easy! Get The Greatness Mindset audiobook on SpotifyText Lewis AIYouTubeInstagramWebsiteTiktokFacebookX

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Lewis Howes?

  Episode number 352 with bestselling author Ryan Holiday.

• 0:07Lewis Howes?

  Welcome to the School of Greatness. My name is Lewis Howes, a former pro athlete turned lifestyle entrepreneur. And each week, we bring you an inspiring person or message to help you discover how to unlock your inner greatness. Thanks for spending some time with me today. Now let the class begin.

• 0:33Lewis Howes?

  "When ego slips away, the best idea wins." That's a quote from my good friend and mentor, Chris Hawker. And this episode is all about ego and how in some ways ego can drive us to be an achievement of the things we want in our lives, but ultimately will leave us feeling broken, shattered, and hurting ourselves and others if we don't understand how to let it go. And Ryan is going to dissect this topic. He's got a new book out called "Ego is the Enemy." And Ryan Holiday is a media strategist and prominent writer on strategy and business. And after dropping out of college at 19, he went on to advise many bestselling authors

• 1:16Lewis Howes?

  and multi-platinum musicians. He served as Director of Marketing at American Apparel for many years, and he is also a bestselling author of "The Obstacle is the Way." Ryan and his partner Niels were also a key component in the strategy and the success of the School of Greatness book. They were a huge part of it for me, and it wouldn't have been a huge success, sold over 55,000 copies by now, and also hit New York Times Bestseller List. So I'm super grateful for his strategy, and I believe he's just a brilliant mind. And what we cover today are all things ego. And one of the main things is why Ryan says we should not be passionate in our lives,

• 1:59Lewis Howes?

  which I thought was interesting because I'm always talking about being passionate. So you get to hear both sides of the story there about why you should not be passionate, where Ryan has seen my ego get in the way of my life. If I ask him, what have I done where my ego has held me back from my greatness? So that kind of gets interesting at that moment. Also, how telling the truth can put you in a position of power, even when you know it's going to hurt someone's ego. The steps to finding your purpose and why purpose is more important than passion. And why thinking small is often the best way to start. I'm super excited for you guys to engage and hear this interview. Ryan's a brilliant guy and just such an incredible human being.

• 2:43Lewis Howes?

  So without further ado, let me introduce you the one, the only Ryan Holiday.

• 2:52Lewis Howes?

  Welcome everyone back to School of Greatness Podcast. Very excited about our guest. His name is Ryan Holiday. Ryan, good to see you, man.

• 2:58Ryan Holiday?

  Thanks for having me. This is a step up from when I first, when I first did your webinar like four years ago. What you've built is amazing. I mean, I think we just did it over Skype.

• 3:08Lewis Howes?

  Got you, got you. Yeah.

• 3:09Ryan Holiday?

  But what you've built has just been amazing.

• 3:11Lewis Howes?

  It's been fun, man.

• 3:12Ryan Holiday?

  It's been a hell of a ride.

• 3:14Lewis Howes?

  I'll tell you what, doing quality work consistently for four years, every week, you know, it does something.

• 3:19Ryan Holiday?

  Well, I think that's the thing that a lot of people miss, right? Like they see like someone has a huge podcast or a bestselling book and they think like, okay, how do I get that?

• 3:27Lewis Howes?

  Now.

• 3:28Ryan Holiday?

  Right now. Right. And so like they think it's like, okay, I need to spend this amount of money or I need to do this. And they don't realize that all those things were built iteratively.

• 3:36Lewis Howes?

  Time.

• 3:37Ryan Holiday?

  Yeah, like you didn't even, if I remember quickly, you weren't even starting a podcast.

• 3:41Lewis Howes?

  This was three and a half years ago I started the podcast. We just hit 350 episodes recently and you know, it's been three and a half years.

• 3:48Ryan Holiday?

  But I mean, you didn't even set out to build a podcast. You were just doing, you were doing something and you had this conversation with someone, which is a Robert Greene one, right? And you decided that that should be, yeah.

• 3:58Lewis Howes?

  That was the first interview, first episode, but I was doing a webinar with him.

• 4:00Ryan Holiday?

  Right.

• 4:01Lewis Howes?

  To promote his book.

• 4:02Lewis Howes?

  And then I was like, this is a great interview. Why don't I put this part of the podcast series?

• 4:06Ryan Holiday?

  Right.

• 4:07Lewis Howes?

  That I later decided I was gonna do.

• 4:09Ryan Holiday?

  Yeah. And so that's actually one of the things I talk about in Ego a little bit is that you you have to make sure that you don't make up stories about other people because it can seem like they set out to do this. So it's like, like you, it was somewhat accidental. It was about you took a chance, you did this thing, and then you started to see opportunities and you grew them versus like, I had a vision for a 350-episode podcast with millions of downloads, right? It's, it's, it's, it's less sexy than that, but more attainable. So it should be more inspiring, but people don't, people don't see that.

• 4:44Lewis Howes?

  Yeah. When I started the podcast originally, I remember I was moving to, I had just moved to LA and I was kind of going through a rough path through a relationship and just like, I just sold a company that I wasn't really that inspired with anymore. And I was kind of figuring out what was my next, you know, thing. What was my dream, my purpose, what was my meaning? And I remember I really enjoyed interviewing people at the time, or just connecting with people, conversations. And I was like, man, I've got pretty good relationships with some inspiring people. What if I share these with other people?

• 5:11Ryan Holiday?

  Right.

• 5:12Lewis Howes?

  And then I asked a few friends who, you know, Derek Halpern and John Lee Dumas was like, and Pat Flynn. I was like, how's the podcast going? And they were like, it's incredible. I don't know why Derek stopped his, but I was like, these guys can do it. I think I can figure it out.

• 5:25Ryan Holiday?

  Yeah.

• 5:25Lewis Howes?

  And I remember I set out the first year, I was like, I'm just gonna create some good content every single week and do it for a year and then see what happens.

• 5:31Ryan Holiday?

  Right.

• 5:32Lewis Howes?

  And I was like, I'm not gonna take any sponsors, like, I'm not gonna try any of that stuff.

• 5:35Ryan Holiday?

  Right.

• 5:36Lewis Howes?

  Just gonna build something like inspiring to me. And the sponsors came quickly because of that.

• 5:40Ryan Holiday?

  Sure.

• 5:41Lewis Howes?

  And it just kind of took off. It might have been the time of when I launched it, it might have been the...

• 5:45Ryan Holiday?

  But it's not like podcasts were even new then. They'd been around for years.

• 5:48Lewis Howes?

  Six, seven years, at least some of them. You know, Joe Rogan's been around for a long time, so.

• 5:52Ryan Holiday?

  I think what's also impressive about yours is how quickly you leveled up. Like, I'm, like, I feel awkward being on this show, being like the least important person on it. And it's the same thing with Tim Ferriss's show.

• 6:03Lewis Howes?

  Right, right, right. You've been on this show like 10 times, though.

• 6:05Ryan Holiday?

  No, just twice. But, but it's like... Then it's like Arnold and all these other people. And you, you've had all these enormous celebrities, which you would have had, like if you had thought you could have had them on your show when you're doing your first episode, you would have been crazy.

• 6:19Lewis Howes?

  Yeah.

• 6:19Ryan Holiday?

  But it was that you, you knew where you could grow it. It's like you did this thing, which gave you that opportunity like that.

• 6:25Lewis Howes?

  Yeah, they all build on each other. And it was, the vision was to be able to interview anyone I want.

• 6:30Ryan Holiday?

  Sure.

• 6:30Lewis Howes?

  And that's still the vision. I can't do it yet.

• 6:32Ryan Holiday?

  Right.

• 6:32Lewis Howes?

  It's still the goal. And, uh, you know, some of these interviews have taken a year to make happen of me following up and building relationship and, you know, donating to their foundations or whatever it takes.

• 6:42Ryan Holiday?

  Right.

• 6:42Lewis Howes?

  It's like, I want to be like-

• 6:43Ryan Holiday?

  And building your numbers.

• 6:44Lewis Howes?

  Exactly. Having the platform big enough that they're like, okay, now it makes sense for me to come on and give you my time.

• 6:50Ryan Holiday?

  Totally.

• 6:51Lewis Howes?

  So the goal is to keep getting bigger and, uh-

• 6:53Ryan Holiday?

  Of course.

• 6:54Lewis Howes?

  So that I can get anyone, you know, so that everyone comes to me and says, we need to get our message out there on the School of Greatness.

• 6:59Ryan Holiday?

  Sure.

• 7:00Lewis Howes?

  That's the vision.

• 7:00Ryan Holiday?

  Yeah.

• 7:01Lewis Howes?

  But it's been three and a half years and this is how long, this is how long it's taken to get me to get to this point.

• 7:05Ryan Holiday?

  Right.

• 7:06Lewis Howes?

  So we'll see how much longer it takes.

• 7:08Ryan Holiday?

  Or there, there is no, it doesn't take a certain amount of time because there's no endpoint.

• 7:13Lewis Howes?

  That's true. I'm not looking to stop at any time.

• 7:15Ryan Holiday?

  Right, right. It's not like, oh, if you get Oprah on, you're done. Although that would be a good note to go out on.

• 7:20Lewis Howes?

  Yeah. Yeah. It's funny. I was on my buddy Rob Bell's podcast and then the next interview he did was Oprah.

• 7:25Ryan Holiday?

  Wow.

• 7:26Lewis Howes?

  So it's my name and then Oprah's name in the podcast stream.

• 7:29Ryan Holiday?

  That's pretty good. Maybe they'll accidentally click you.

• 7:31Lewis Howes?

  It's close. Yeah, yeah, yeah. It's close. So, um, cool, man. Well, you got a, you got a new book out called Ego is the Enemy. And, uh, I'm curious, why, why ego? Why this topic and why now? And I, I watched the, uh, the video, which is really cool, the trailer.

• 7:46Ryan Holiday?

  Oh, thank you.

• 7:47Lewis Howes?

  Where you tell your whole story about it. Um, but why ego? What's the, why is this such an important topic to give two years of your life?

• 7:56Ryan Holiday?

  Yeah.

• 7:56Lewis Howes?

  Writing, thinking, promoting, and then more, obviously.

• 8:00Ryan Holiday?

  Yeah, that's a good question. I mean, so my last book was about- External obstacles. Mm hmm. And I feel like ego is the biggest internal obstacle. Or we are, in reality, the main thing that prevents people from being successful is not other people, it's not economic factors, it's themselves, right? And the main things that tears down success is definitely ego. When we start to think we're better than we are, that we're more, you know, we have it under control, that we don't need to work as hard. We know it all. Yeah, exactly. That's when, that's when we start to destroy what we've built. Or when we fail and then we feel like we can never come back, or that, you know, everyone hates us, or all these things. So what is ego? What's the definition?

• 8:45Ryan Holiday?

  So not Freudian ego, right? Not some complicated psychological definition. I'm using it in the very sort of common sense of like arrogance, entitlement, greed, selfishness, delusion. You know, when you see, when you see someone who's incredibly talented, but they just can't get out of their own way, and they can't stop making enemies, or causing problems for themselves. That's, to me, that's the ego that I'm talking about. Get out of their own way to do what? Achieve something, or to make an impact, or? Yeah, yeah, like they're working so hard on some problem, or they, think about like

• 9:27Ryan Holiday?

  someone like Kobe Bryant, incredibly talented, but he drives teammates away, right? And, and it's only, why can't he play, why couldn't he play with other people? Right? Could have won more championships with him, maybe. Totally, totally. And, and at the same time, why couldn't Shaquille O'Neal play with Kobe Bryant? It was in both of their, it was in both of their interests to get over what of those, whatever those differences were, but neither could do it. Why is it so hard for us to do that? I think, I think it's, it's a lot of things. I think, one, we don't know that it's there, right? I mean, the insidious part about ego is like, we think we're doing everything right, it's the other person that's causing the problem.

• 10:07Ryan Holiday?

  But, but I would say, I think it feels like, it feels like you're compromising on the most essential. Parts of you, right? Like, like you probably saw this with your book. When you let go of your ego. Yeah, like you get edits back from your editor. Right. And you're like, how dare you tell me about this, right? Yes. And in, in reality, they're just trying to help.

• 10:26Ryan Holiday?

  You don't know me. Yeah, you don't know me. What? This is so wrong. How dare you? Right, right, right. You know, so you get that reaction and, and you're, you feel like you're being attacked because ego is supposed to protect you. But really it's insulating you and blocking you from things that are actually good. So I, I think what ego is, is this, um, Cyril Connolly is one of my favorite writers. He was saying ego like cancer is the overproduction of cells. Right? And so ego is, ego is not, it's inherently a bad thing. It's that having too much of it is what creates. So I make the distinction between confidence, which is critical. Yes.

• 11:07Ryan Holiday?

  Like you have to believe you can do stuff. You have to know that you put in the work. You have to know what you're good at. That's essential, but ego is past confidence. Ego is when you have confidence in things that you shouldn't be confident of. Right. And so that's where you bite off more than you can chew. You say, screw them. I don't need them. I'm going to do this on my own, you know? You say everyone else is wrong. That's, that is the problem. You isolate yourself. Totally. Yeah. And you, it's like the amount of like, uh, there's this fascinating book about the history of Beanie Babies by Zach Beesonette. And he, like the famous moment in the Beanie Baby history is that he, he come up with this idea and everyone's like, that's horrible. You cannot do this. The Beanie Baby idea.

• 11:51Ryan Holiday?

  No, the Beanie Babies already existed. He had this like new one. I'm forgetting what it was, but, but the, his like assistant was like, do not announce this. Like, please do not do this. And he was like, I could put the tie logo on manure and people would buy it. Oh, my God. And of course they didn't, right? So it's like, it's that, but, but we've all been there. We've, it's like, we feel like we know better because we're so good at what we've done. And people have been wrong before. Like everyone told you all the things that you couldn't do and they were wrong. Yeah. And then now you think you have to prove everyone wrong all the time, but the reality is they're not wrong all the time. Sometimes they're right. And, and so balance and confidence is about knowing when to listen and when to respectfully not listen.

• 12:33Lewis Howes?

  That's a challenge.

• 12:34Ryan Holiday?

  It's so hard.

• 12:36Lewis Howes?

  I mean, but also look at the examples of, you know, the Muhammad Ali or Mayweather approach where it's over the top ego and they were and are the greatest essentially in one thing that they do.

• 12:45Ryan Holiday?

  Yeah. Well, there's that line from Muhammad Ali. He says, it's like, it's hard to be humble when you're as great as I am, which is true, but I think, I think you can actually take that quote in a way he didn't mean, which is yes, it is hard. That's why you have to work harder because.

• 12:59Lewis Howes?

  To be gracious and have humility and.

• 13:01Ryan Holiday?

  That, to be just a good person, but also, um, I feel like the, the trajectory of every single boxer ever is they become the greatest and then they over, they underestimate an opponent.

• 13:16Lewis Howes?

  And they fall.

• 13:17Ryan Holiday?

  And they fall and.

• 13:19Lewis Howes?

  Tyson, yeah, everyone.

• 13:20Ryan Holiday?

  Yeah, everybody and, and the saddest part about boxing is when they don't know when they should quit and then that's when they get hurt or, um, they do real damage to themselves. So it's like, you have to be humble, not only because you should be a good person.

• 13:35Lewis Howes?

  Hard to let go.

• 13:36Ryan Holiday?

  But it's hard to let go and, and, and you, the second you start to think you're better than you are, that's when an opponent seizes on that weakness and beats you with it.

• 13:47Lewis Howes?

  Do you think it was wise that Kobe retired now and he was like, I have nothing left and?

• 13:52Ryan Holiday?

  I mean, I think so. Uh, I think Jason Whitlock, uh, is right when he was saying that the sad part about the Kobe story is that he left the franchise in ruins, right? Like it's not like the, like it's, he didn't, if he left earlier or if he'd been able to.

• 14:07Lewis Howes?

  Left on top.

• 14:08Ryan Holiday?

  Left on top, or if he'd been able to help build a team that could survive after he left. And you could argue that's not his job, but, but you know, the Lakers are not going to be good for a few, the Clippers are better than the Lakers now. And so that, that has to like, you, when you look at like billionaires who can never retire and they can't pass the company on to anyone. To me, that tarnishes their legacy. It, it, it's a knock against their greatness that they were so selfish and could delegate so little that they, they built this thing, but then ultimately it couldn't outlast them because they couldn't share control.

• 14:44Lewis Howes?

  Wow. Hmm. Where's a moment in your life where ego really ruined you the most? Where there be a relationship or business or friendship or?

• 14:53Ryan Holiday?

  Um.

• 14:53Lewis Howes?

  Your health.

• 14:54Ryan Holiday?

  Yeah, I mean, obviously, I think there's lots of places. I think the big thing, like when I look back at my writing, the writing I did when I was like nineteen, twenty, twenty-one, it makes me so uncomfortable because it's, like, I cringe when I read what I wrote in the past because it's so certain. And you know what I mean?

• 15:11Lewis Howes?

  Like, matter of fact.

• 15:12Ryan Holiday?

  Yeah. And it's like, you realize at nineteen that you really didn't know anything about anything. And so I think, like, what I say in the book is that ego is different at every phase in your life. But I think it's, it's most embarrassing when you're young and you act like you know, you know way more than you do.

• 15:29Lewis Howes?

  Like every talky guy.

• 15:30Ryan Holiday?

  Yeah, you simplify really complex things and you feel like, you know, like, as you become more successful and you meet other successful people, and maybe you even meet people that you've like, read about in the news that you've made like snap judgments about.

• 15:44Lewis Howes?

  Right.

• 15:44Ryan Holiday?

  You realize like, oh, like, you know, it's more complicated than I thought, or they're actually a good person, or they have multiple sides to them, or that this issue, there really is no like, black and white to it, you know? And I think when I look back, like, I wonder all the things that I missed, or that I didn't pick up on, or that I couldn't have learned because I thought I already knew. Like, there's this epic, epic Tetus quote, he's a famous Stoic, and he says, "One cannot learn that which they think they already know." And I think my youth, and maybe yours is the same way, but definitely for a lot of people, is defined by thinking we already know everything. And that's when we should be learning the most.

• 16:24Lewis Howes?

  Yeah. Interesting. What's a, what's a specific example you have where you feel like, wow, this really, this ego consumed me so much that I just destructed some part of me? Or a relationship, or like, your life changed because of this experience?

• 16:41Ryan Holiday?

  Well, so one, one of the things I talk about in the book a little bit, I call them these sort of Fight Club moments. And then these moments where you're like, you're, you just get destroyed. And you have to, you have to like, look at yourself and who you were. And I remember I was working, I, I worked for Tucker Maxx when I was in college. And I made some, like, we were talking about some- Then we had this like message board where we talked and we're talking about something and I made some smart ass. Or chat. Yeah, like we were chatting on this message board, like all the employees that were at First Company and we were like chatting about some uh some like throwaway thing. And and I was acting like I knew what I was talking about and I didn't and he just like tore me a new one, just like so like in front of everyone.

• 17:24Ryan Holiday?

  Yeah, in front of all the other employees and I like I had a panic attack, like I had to go to the hospital. And like in retrospect, I don't think it was good leadership on his part. Like I don't think like I wouldn't do that. I would never publicly. Eviscerate someone, but there are those moments where you're like, wait, what was I do? Like, why did I think that I needed to even be involved in this conversation? Like, I remember another one I was working, I worked not far from here in Beverly Hills at this talent management agency and we had this some big meeting and a bunch of people were talking and I was like the assistant who was like supposed to sort of like sit on the side and I remember like they they were talking about something that I kind of knew about and I like interrupted and I said something.

• 18:04Ryan Holiday?

  And then after my boss was like, why did you say that? He was like, did you say it because um you had something to say? Or you just wanted people to like acknowledge you existed? He's like, did you really, did that really needed to be said? Or you just wanted to say something? And I was like, fuck, you know, you're totally right. Like I was just, I had, that had no purpose whatsoever. Except for my own ego and those are like, you know, those are the moments where people make important people. Don't give you a second chance. They're like, okay, that kid, he doesn't know what he's talking about or you know, like, don't invite him to any more meetings. Right, right.

• 18:42Ryan Holiday?

  And I like, I obviously I didn't like ruin anything for myself, but you realize just the wrong, the wrong remark at the wrong time can be the end. Or you know, you treat the wrong person the wrong way and that's the end for you, you know?

• 18:58Ryan Holiday?

  When is uh?

• 18:59Lewis Howes?

  Confidence crosses the line into ego because you've got to be confident in your work and your skills and your ability when you go into a job interview, when you go into whatever, playing a big game in sports, your relationship. If you don't have confidence, people aren't going to want to keep you around.

• 19:14Ryan Holiday?

  Yes.

• 19:15Lewis Howes?

  In any area of your life, after a certain time, they're like, okay, it's time to believe in yourself.

• 19:19Ryan Holiday?

  Yes.

• 19:19Lewis Howes?

  So what is the difference between believing yourself with 100% certainty that I'm going to win this game and give my all to you're just a cocky egotistical maniac?

• 19:30Ryan Holiday?

  No, that's a good point. I mean, so I think Aristotle says that it's a spectrum. So like he would say like courage and, or sorry, he would say like recklessness and cowardice are the extremes and like courage is in the middle. Right? Or it's it's above. So it's like a triangle. And I think it's like that. So confidence, like ego is, you know, on the greatest who ever lived, I'm perfect, you know, I've got it all handled. Nobody knows better than me. Yeah. And then like, I'm worthless. I don't know anything. Why would anyone listen to me? Those are, in a weird way, those are both sort of self-absorbed.

• 20:06Lewis Howes?

  Yes.

• 20:07Ryan Holiday?

  Positions, right? You're just all you're just thinking about yourself.

• 20:09Lewis Howes?

  Denial on the either.

• 20:10Ryan Holiday?

  Yeah. Yeah. And you're just over here, you're just not thinking well of yourself and over here, you're thinking too well of yourself. So confidence is in the middle, but I think, I think.

• 20:21Ryan Holiday?

  It's interesting, like confidence has to be based, Frank Shamrock, an MMA fighter, he was saying like, confidence is earned, right? And that's the, if your confidence is on, I did the work, or that I'm a fast learner, or that I'm like, I'm a fast learner, so I'm going to be able to figure this out. Or like, I studied harder than anyone else, or, you know, I've like, I know I can do this because like, you know, about how much weight you can lift. Because you go to the gym and you've done it before. You're not, you don't just, you might know, you might have a. An inkling that you're capable of a lot more, but you're confident based on what you've

• 21:04Ryan Holiday?

  done or done in a sort of a reasonable circle. So I think that's where the confidence is. It's like, okay, I know, I know that I can write a book because I've studied harder. I've written long things before. I've worked with other authors, you know, those, it's not like, oh, sure, I should have a book, you know, like that, that's the difference.

• 21:24Lewis Howes?

  Yeah, interesting. Okay. And you also talk about in the book, you say humility and reality are the cure for symptoms of ego.

• 21:31Ryan Holiday?

  Yeah.

• 21:32Lewis Howes?

  Why is that? What do you mean by that?

• 21:34Ryan Holiday?

  Well, so if, if, if ego is being confident in things that you shouldn't be confident in, reality is like, oh, wait, okay, I was, I, I got too far over my skis. You know what I mean? Like I, I went too far in the other direction. I needed like a little bit of a wake up call. And so sometimes that's why failure can be good, or not catastrophic failure, but like little things, right? Like you, you're confident. So, you know, you put something out there and someone's like, hey, this is wrong for the following reasons. You gotta listen to that stuff, or you keep investing and you go further and further. And then when you do fall and when you do fail, it's like really painful.

• 22:10Lewis Howes?

  Yeah, interesting.

• 22:11Ryan Holiday?

  So I think you gotta cultivate people around you who are not afraid to tell you the truth. That's the hard part is like, I mean, especially as you become successful, I'm sure you've seen this.

• 22:22Lewis Howes?

  I think you've gotta be willing to have people tell you the truth.

• 22:24Ryan Holiday?

  Yes.

• 22:25Lewis Howes?

  Cause most people don't wanna hear the truth.

• 22:26Ryan Holiday?

  Yes, right.

• 22:27Lewis Howes?

  Even if they say it, they're like, they don't wanna hear it, right?

• 22:29Ryan Holiday?

  Right. You have to make sure you don't punish people for telling you the truth, like by not talking to them or fighting them. Even if you disagree, you have to hear them. But it's like, it's like, you can realize like, man, I only talk to people who worked for me today, right? Like who are in some sense not super motivated to tell me the truth. Like I've been around a lot of really, really successful, wealthy people and you realize like, if I were to tell this person, like the only way I could deliver the truth to this person would be like a kamikaze mission. Like, like they, we would not be friends after. Like they've gotten so far that like, I'm gonna have to, I'm gonna have to go in and say all this unpleasant stuff and.

• 23:11Ryan Holiday?

  That's going to be the end of it. And then you realize like, and then you usually don't do it. Right? Like, you know, it's like if, if I'd gotten to a point where like you, you follow me on social media and you, you, you thought I would like, you knew, you know what my life is like, but the pictures I was posting were not at all representative. You knew maybe I was inflating numbers about what I've done. Or like, you know, look at this photo with me and this celebrity, but you knew like I paid to meet that person, you know, all the things. And, and like, you might know like, hey, Ryan, like, you might want to say like, hey, Ryan, like, people are starting to think you're full of it. Like you're not, you don't, you're not coming off well. You should change, but like, you might not do it because you would be worried that I'm gonna, I'm gonna shoot the messenger essentially, right?

• 23:55Ryan Holiday?

  And so that's the difficult thing is like, if you don't have that realism in your life and you don't cultivate it, you're not checking in all the time. You get to a point where it's like, people realize that it's not in their interest to tell you the truth.

• 24:07Lewis Howes?

  What's a good way to approach someone that you want to tell the truth to who has an overwhelming sense of ego or

• 24:15Lewis Howes?

  that don't have reality?

• 24:16Ryan Holiday?

  Yeah, that's well.

• 24:17Lewis Howes?

  How do you approach that person?

• 24:18Ryan Holiday?

  First off, I would say that it's weird, but actually you can, if everyone else is lying, like if everyone else in that organization is not telling the truth. Oftentimes being the person that tells the uncomfortable truths is us, is a position of power, right? Because, because you're the only one that's not like everyone else.

• 24:37Lewis Howes?

  They'll start to trust your opinion more.

• 24:39Ryan Holiday?

  And I think, so the big thing I found is that it's not about, it's not about showing that you're smarter. And it's not about making them feel stupid. It's often, I find it's, hey, here's my opinion about this thing. Like, like, let's say, uh, someone's making some important business decision and you think they're making the wrong decision. You say, look, I think this is the wrong decision for these reasons. But you're the boss, so you've got to make the call. And then. Whatever they decide, if they decide not to go with you, you still have to support them in whatever they're doing. And then you have to let the results speak for themselves. Cause they'll, if they're not insane, they'll remember, hey, Louis told me when I was thinking about like,

• 25:22Ryan Holiday?

  hey, I was thinking about, you know, investing in this company. And Louis said, that's a bad idea. And I did it anyway. And then I lost all my money. As long, as long as you, as long as you weren't a jerk to them and you didn't rub it in along the way. And then, you know, I, I like to even pretend that I didn't do, like, I, I don't, I don't, I not only don't want to do, I told you so. I want to like.

• 25:48Lewis Howes?

  Well, your ego wants to say that.

• 25:50Ryan Holiday?

  Sure, sure. Yeah. But, but I'm saying like politically and relationship wise, you not only don't say you told you so, you don't even mention it, right?

• 25:57Lewis Howes?

  Let it go.

• 25:58Ryan Holiday?

  Let it go and let, let them say, let them remember, hey, at that critical moment, Louis was right and he was big enough about being right that he didn't rub it in. He's the kind of person that I should go to for advice in the future. Or he's a voice that I know is, is.

• 26:17Lewis Howes?

  Reasonable.

• 26:17Ryan Holiday?

  Is reasonable and speaking the truth and not selfish and just not, not about him. It's about the truth.

• 26:25Lewis Howes?

  Yeah. Here's something you say that most people say, find your passion and follow it. But you say, don't be passionate. Why is that?

• 26:32Ryan Holiday?

  Well, I think passion, I think passion is dangerous, right? So the, throughout philosophy, especially in Stoic philosophy, they warn against the passions. Like lust, greed, anger, fear. This is what, historically, passion has meant extreme emotions.

• 26:50Lewis Howes?

  Yes.

• 26:50Ryan Holiday?

  And so I, I tend, I, I tend to gravitate towards that definition. But I think purpose is better than passion, right? Because passion is.

• 27:00Lewis Howes?

  It's like a mission.

• 27:01Ryan Holiday?

  Yeah. Passion is like, I like this, it feels good. I want to do this. Purpose is, here's what I'm trying to accomplish. Here's why it's important and.

• 27:12Ryan Holiday?

  And I'm not going to stop until it's done. Like, who would you rather have work for you? The guy that just really loves writing? Or the person who's like trying to write for a reason? You know? And so that passion can be blinding and it can get you like, it's not enough just to love something or else everyone would do what they love. You also have to be good at it. And you also have to know how to make smart decisions and how to plan.

• 27:39Lewis Howes?

  Is it possible for us to always have a purpose?

• 27:41Ryan Holiday?

  What do you mean?

• 27:43Lewis Howes?

  I mean, a lot of people, I think, don't know what their purpose is.

• 27:45Ryan Holiday?

  Sure.

• 27:46Lewis Howes?

  They don't know how to discover it. They don't even know what they're passionate about. So how do you find a purpose? Period. How do you even go about saying, oh, this is my purpose at this point in my life?

• 27:56Ryan Holiday?

  Yeah, well, I think one of the reasons that people like to say, find your passion, is that sounds really smart. And you don't like, no one's like, okay, then what? Right? Like, it's just, it's just like, it's like, do what you love. You know, it's okay. Then how? You know, so when I, when I'm saying purpose, I think it's about defining your goals, defining what the life you're trying to build is. And, and having a real model for what you're doing.

• 28:25Lewis Howes?

  Yeah.

• 28:25Ryan Holiday?

  And for me, I've tried to, I've tried to be very clear about what I'm trying to accomplish to myself. So that I'm not getting distracted by all these, like, I like to do lots of things.

• 28:39Lewis Howes?

  Me too.

• 28:40Ryan Holiday?

  But I, you gotta pick one to really get good at it, you know? And it's also, it's like, if you're doing this thing because it means something to you and you know exactly what success looks like for you, it's nice because then you're not as distracted by the fact that so and so is posting photos of them surrounded by hundred dollar bills on Instagram or on a yacht in a visa or whatever. You know, you, you want to make sure that you're not comparing yourself to other people. You want to compare yourself against the progress you've made to, for whatever your purpose is.

• 29:13Lewis Howes?

  Most people never do that. That's the best way to compare yourself as to how far you've come and what you've created as opposed to what everyone else has created around you.

• 29:20Ryan Holiday?

  Well, you probably learned that in sports, right? Where it's like, it's not about what other players are doing. It's about whatever you, whatever you're capable of.

• 29:28Lewis Howes?

  The progress from the previous game or the previous week or what we've done.

• 29:30Ryan Holiday?

  Right.

• 29:31Lewis Howes?

  Getting closer to our goal or to our vision.

• 29:33Ryan Holiday?

  Yeah, because like, look, some people are freaks. You know what I mean? Like, some people are just way better than you. And they're always gonna be better than you, and they're not gonna have to work as hard as you. So it's like, if you're comparing yourself to them or just mimicking them, you're not, it's, that's not the right, that's not the right approach.

• 29:51Lewis Howes?

  But everyone has their demons in battles.

• 29:53Ryan Holiday?

  Of course.

• 29:53Lewis Howes?

  It doesn't matter if they're like the richest person or the most successful, the most good looking, the most athletic. There's some battle I feel like we're always facing.

• 30:03Ryan Holiday?

  Yeah.

• 30:03Lewis Howes?

  It's hard to just be like, I've got it all figured out in all areas of my life. I don't know. Have you met anyone who's just like, everything's figured out? Like, I don't have any challenges.

• 30:12Ryan Holiday?

  I would say the people who you feel like have it most figured out are probably struggling the deepest.

• 30:18Lewis Howes?

  The most.

• 30:18Ryan Holiday?

  There's this, uh, James Baldwin, um, has, his, his, his father was sort of like an abusive, uh, bad person. Not a bad person. He didn't have a great father. And I remember I was reading one of his essays and he quoted the eulogy that his pastor gave his father. And it, the, the, the pastor said, thou knowest the man, thou knowest not his wrestling. Like, you, cause you don't know what each person is wrestling with inside. You don't know if that beautiful celebrity is wrestling with an eating disorder. You don't know if that guy.

• 30:51Lewis Howes?

  Or a weight loss or whatever.

• 30:52Ryan Holiday?

  Yeah, you don't know if that guy who seems like he has a happy family is miserable and cheats on his wife. You know, you don't know if that person who has complete, who sold millions of albums feels like a failure because their parents never told them they loved them. You know, you don't know what people are struggling with and it's like, so it's like, you can't, you can't compare yourself to them because you don't know what the, you don't know whatever they have, you don't know what they have, you don't know what it costs them. Do you know what I mean? You don't know what's inside.

• 31:24Lewis Howes?

  Yeah. Why do you think we have so many obstacles?

• 31:27Ryan Holiday?

  In life? Well, I mean, look, the world is indifferent to you and I, right? Like, the world is not, oh, Lewis wants to be a professional baseball player. Like, how do I make that happen? You know, like, or, you know, Ryan wants to be an Olympic skier? How can I make that happen? Right? Like, the world is, the world is not only indifferent to like our personal goals. Like, the world doesn't even care about the human race, right? Like, we could all be wiped out by like a volcano tomorrow, right? So, it's, it's that we are a very small piece of like a complex universe. And the result is that things don't go the way we want them to go. So I think those are the external obstacles. And if that wasn't hard enough.

• 32:10Lewis Howes?

  The internal.

• 32:10Ryan Holiday?

  Yeah, then we put on top of that, you know, struggles with addiction, or struggles with self-worth, or struggles with other people. You know, we, we add to that things that make an extraordinarily difficult thing like even more difficult.

• 32:29Lewis Howes?

  Yeah.

• 32:30Ryan Holiday?

  And we don't even know it, right? We don't know the people that we've alienated, or we don't know how we've, you know, like, you think like, you know, your journey was from point A to point B, but you don't actually, like, it could have been shorter if you had done this differently. You never know.

• 32:46Lewis Howes?

  If you had a unlimited amount of money that I gave you right now to solve one challenge in the world, whether it be an internal challenge that humans face, or some type of external challenge, and snap your fingers, it's solved. And we never longer had that challenge in the world or internally, what would that be?

• 33:05Ryan Holiday?

  Man, that is a, that is a crazy question.

• 33:09Ryan Holiday?

  We talked about William McGaskell a while ago, right? Who does effective altruism. And I think what's interesting about his work is he's saying it's like, we all try to pick causes that are like close to us, right? It's like, I like reading, so like, you would think like, I would go like, well, how can I, you know, give money to a charity that helps kids read? And that's like a good cause, but what we never think is like, there are millions of people who are just flat out starving or dying of some disease. So I feel like if you give me an unlimited. Limited money, amount of money, the rational thing to do would be to say, okay, what would, what would help objectively save the most amount of lives? Right? Like, there's people out there, and I think these are real heroes,

• 33:50Ryan Holiday?

  who go like, okay, you know, I work on Wall Street, I make $500,000 a year. I only need 70,000 to live. I'm gonna give the rest of that money to a charity and I'm gonna save 30,000 people a year. Or like, people do that. And that's like, to me, that's like real heroism because it, in a weird way, it's taking the ego out of it. It's not like, I would love to see my name on the side of a library at Harvard, or I would love, I would love an art gallery downtown that houses my collection. In those ways, obviously, those are still good things to do with your money. And it's better than buying yourself a yacht or whatever. But it is ego, right? Like-

• 34:27Lewis Howes?

  Doesn't he talk about actually putting your name out there when making the donations, though? Doesn't he say that? Like, you should not make it anonymous in order to inspire others to-

• 34:36Ryan Holiday?

  I think he's saying that. Yeah, I think he does, but-

• 34:39Lewis Howes?

  You shouldn't try to be Donald Trump with your name everywhere.

• 34:41Ryan Holiday?

  Yes, but, but it's not like, people go, it's like, oh, I, some, some, some guy just gave like a hundred million dollars to Central Park. Right? Some big hedge fund manager in New York. And it's like, Central Park is one of the wealthiest, most protected, like, best parks in the world. It doesn't need a hundred million dollars. Like, nothing bad is happening to-

• 35:02Lewis Howes?

  Right. Whereas Mark Zuckerberg gave it to like, the school system in New Jersey or something, right?

• 35:06Ryan Holiday?

  Yes.

• 35:07Lewis Howes?

  A hundred million dollars to schools.

• 35:08Ryan Holiday?

  Yeah, you wanna, but you wanna do the math on like, what is actually gonna help objectively the most amount of people?

• 35:16Lewis Howes?

  So how do we get out of our own head, then? You know, when we don't even know we're in our head?

• 35:20Ryan Holiday?

  Sure.

• 35:21Lewis Howes?

  Cause we don't think anything's wrong with us.

• 35:22Ryan Holiday?

  Yeah.

• 35:24Lewis Howes?

  How do we get out of it?

• 35:26Ryan Holiday?

  Well, right, right. Well, and it's interesting because being in your head can be really great and really miserable at the same time. Anne Lamott, she wrote this amazing book called Bird by Bird. And she talks about, she says, in every writer's head, they're listening to this radio station called KFKD. So K-F, and in one ear, it's saying like, you're the best, you're amazing. It's like, she's like, it's blaring rap music about how awesome you are. And in the other, it's like playing like the saddest, most depressing songs about how worthless you are. So you wanna get out of your own head, cause you, as nice as the good one feels, the bad one is terrible. To me, I would say, like, you're not far from Runyon Canyon. When you walk up that canyon,

• 36:08Ryan Holiday?

  or you're in the wilderness, or you're standing next to the ocean, and you're just experiencing the present moment, you're not thinking about how amazing you are, and you're not thinking about how worthless you are either. So to me, I think nature's a big one. I think, uh, asking yourself questions, like, um, I, in a weird way, it's sort of kind of going back in your head to get out of your head, but I think asking yourself tough questions. Who am I? What kind of person do I want to be? You know, is this the right thing to do? Pausing for a second, instead of just reacting emotionally all the time, is a way to kind of get out of that self-absorbed cycle.

• 36:46Lewis Howes?

  Right. You'd said that though we think big, we must act and live small in order to accomplish what we seek. Why live small?

• 36:57Ryan Holiday?

  Isn't that almost exactly what we're talking about with your podcast, though? It's like-

• 37:00Lewis Howes?

  Small steps every day.

• 37:01Ryan Holiday?

  Yeah, yeah. Um, Paul Graham talks about this. He's like, the way to change the world is to start by changing some tiny thing.

• 37:10Lewis Howes?

  Yeah, take it one step.

• 37:11Ryan Holiday?

  Yeah, right. It's not, it's not having this frighteningly ambitious, world-changing idea. Like, that's great. Like, I gave a talk at Google a few weeks ago, and there's this quote from Larry Page, uh, where he's saying, like, "The way I pick startups to invest in is I ask themselves, like, is what you're working on going to change the world?" And that sounds really inspiring. Except for YouTube wa- or sorry, Google was, uh, his thesis that he was writing. And it was like a research project, and it became Google. YouTube started as a dating site, right? Like, Gmail was like an internal project, um, that, you know, they thought, hey, maybe we could make this email thing. Like, maybe it'll work, maybe it won't.

• 37:54Ryan Holiday?

  Meanwhile, these sort of big, huge projects, they fail all the time because we can be wrong. And, and because we've, like, you have flex- like, you're, let's say the, the podcast episode didn't work, right? You could have pivoted into any number of other things.

• 38:10Lewis Howes?

  But if I was like, this is the thing.

• 38:11Ryan Holiday?

  Yeah, I have to do this.

• 38:13Lewis Howes?

  This is gonna happen. It's gonna be huge.

• 38:15Ryan Holiday?

  Right, then-

• 38:15Lewis Howes?

  Which a lot of podcasters say when they start out.

• 38:17Ryan Holiday?

  Yeah, and they, so they over-invest in it, they over-commit. And then they can't see, they can't, they can't.

• 38:26Lewis Howes?

  Get out of their own way when it's not working.

• 38:27Ryan Holiday?

  Yeah, they can't, they can't see what the problems are. They, they, they start too big.

• 38:32Lewis Howes?

  Interesting. I like that. Who would you say is the best example of someone, either you know or you don't know, who is like, man, they just don't have any ego, or they have the right amount at the right times, or they're flexible with it, and they're so aware of it. And they're just like, you know, taking command of whatever their vision is in the world and making things happen.

• 38:54Ryan Holiday?

  My favorite story, or my favorite person in the book is George Marshall, the, the World War II general. The Marshall Plan is named after him. He was this amazing man. His, there's this famous story about him where, or his famous encounter with his wife, and someone said like, oh, he had no ego. And, and she was like, no, you don't understand. He had an ego like everyone else. He just believed in what he was doing so much that he never let it get in the way. And so, like, for instance, right before the, the D-Day invasion,

• 39:25Ryan Holiday?

  FDR, he asked Marshall, he was like, look, you're very important to me here in Washington, but I realize like, this is like, an opportunity of a lifetime. Do you, do you want to command the troops at D-Day? And George Marshall, like, he wanted it more than anything in the world. And he said, I don't want my personal feelings to impact your decision at all. You decide. And so FDR chooses Eisenhower, who does an amazing job. Obviously, that we win World War II. But it, in a way, that, that, what Marshall was doing was choosing the mission over himself.

• 40:02Lewis Howes?

  Yeah.

• 40:03Ryan Holiday?

  And that's so hard to do. And we think in that moment, like, if I don't do that, no one will ever remember me. I'll be a loser. Right? But that's not true. Like, in fact, it, it made him essential. It, it, it helped win the war. He, he goes on to do all these other amazing things. He's a, he accomplished more than you and I could ever dream of. But there, and there's a quote from Truman where he says, like, never did George Marshall think about himself. And it was, it was in repeatedly doing that, that he was able to accomplish all these things that will outlast him far more than any selfish marketing or decisions were at the time.

• 40:41Lewis Howes?

  It's interesting, a mentor, early mentor, now friend of mine, Chris Hawker, he's, I believe the quote that he has on his office, he's a famous inventor, invented many products, is when ego slips away, the best idea wins.

• 40:53Ryan Holiday?

  That's great.

• 40:54Lewis Howes?

  And he, I think it's on his wall, because he does lots of, he's taken like seventy-five products to market, inventions, but he's constantly brainstorming with his team.

• 41:03Ryan Holiday?

  Yeah.

• 41:03Lewis Howes?

  And you would think that a guy who's invented a lot and, you know, patented and everything and knows everything about it, that he'd be like, no, this is the way it's going to be, but he lets his ego go and says the best idea needs to win, otherwise it's going to fail. If it's just my idea and it's like, has to be my way. So when ego slips away, the best idea wins.

• 41:20Ryan Holiday?

  There's a, there's a quote from Tony Adams, who's a soccer coach, famous soccer coach, and it's pretty cheesy, but it's totally true. He says, um, when you play for the name on the front of the jersey, they'll remember the name on the back. But we're so, Pat Riley calls this the disease of me. We think in the short term, like, I'm not getting enough attention, I'm not being appreciated, I'm not getting paid enough. We think about all these minor concerns because we're worried it's going to hurt us in the long term. And really, that's just distracting us from doing the work that is ultimately the only reason anyone is remembered for anything. Like, like, I mean, you've experienced this with your book, it's like, you, and you've got the bestseller list like right there on the wall.

• 42:01Ryan Holiday?

  And you want to win in the short term, but really, no, I don't remember how many, how many copies of The Great Gatsby sell in its first week? Nobody knows, right? Like, no, any book that's like, good to great, how, how, how was its first week's sales? Like, nobody knows, right? What matters is, did you make something that stands the test of time? And did you keep working at it past when everyone else would have given up and said like, it's on to the next thing? Or, you know, I'll do this other thing because I can make more money or whatever. Like, you've got to, you've got to stay at it and stay at it and stay at it long past whenever the ego gets bored.

• 42:38Lewis Howes?

  Hmm. I got a few questions left.

• 42:40Ryan Holiday?

  All right.

• 42:41Lewis Howes?

  This came to me, what do you, I'll ask you a personal question.

• 42:44Ryan Holiday?

  All right.

• 42:44Lewis Howes?

  Where do you see that my ego gets in the way of my, any area of my business, life, relationships? Where have you seen?

• 42:54Ryan Holiday?

  Well.

• 42:54Lewis Howes?

  Feel free to be truthful with me.

• 42:56Ryan Holiday?

  Is this a kamikaze mission?

• 42:59Lewis Howes?

  No, no, no. This just came to me because I'm like, let's see what comes up.

• 43:04Ryan Holiday?

  You know, I'll give you a good one. I don't know if this is necessarily ego, but it's gonna sound weird. So I was really interested in Brazilian Jiu Jitsu for a while. I've stopped doing it, so I don't want to act like I'm some genius about it. Yeah, but I remember my, I was talking to, I guess, my professor, whatever you call them, and he was saying, what happens for big guys is that they don't get as good at the fundamentals and the skills because they can just put weight on people. Like, they could beat someone like, like you could beat me.

• 43:36Lewis Howes?

  With strength.

• 43:36Ryan Holiday?

  Yeah, with strength, and you wouldn't learn the skill. I would say, well, you have some things going for you that not everyone in the writing and podcasting spaces, which is, you're handsome, you're tall, you're very charismatic, right? And so I think we all have strengths, and those strengths sometimes compensate for weaknesses. So like, I think, maybe, I'm not saying it is a problem for you, but it could be, which is you can get used to skating by on those things, and then the substance can start to suffer. And so you always want to be the harshest critic of your own work, right? Like, is this good enough? Am I saying something new enough? Is this original enough?

• 44:20Ryan Holiday?

  You know, and am I pushing myself to be real and vulnerable and honest? Like, when James Altucher says you gotta say the thing that you're afraid to say, no one else can hold you to that stand. Like, no one else can be like, oh, you're afraid to say that because only you know what you're afraid of, right? And so, in the sense that like, as a writer, I have to work harder than you, right? Because I don't have some of the things that you have. You want to make sure that you're holding yourself to those things, even though you don't need to.

• 44:52Lewis Howes?

  Right. Yeah. Okay. I like that. That's good.

• 44:56Ryan Holiday?

  Do I have to leave now?

• 44:56Lewis Howes?

  No, no. It's time to beat you up. No, I was kidding. Interesting. What is your biggest fear?

• 45:03Ryan Holiday?

  As a human being, or?

• 45:04Lewis Howes?

  Yeah.

• 45:05Ryan Holiday?

  My wife's expecting, so I'm worried that, I'm worried that I'm so, like, my work is so important to me, and my identity is so tied up in it, that I'll make. A lot of really decisions that seem important at the time that in retrospect don't matter at all. Like it's like, oh, you know, somebody, some random person emailed me and I have to respond, you know, and I'm gonna miss some moment and I'll never be, it's not that I'll never be able to get it back. It's that I stole that from someone. Do you know what I mean? And I'm worried that I have selfishness on the one hand, but also just like,

• 45:50Ryan Holiday?

  and it comes from a place of insecurity, like feeling like if you let up for a second, you'll lose what you have.

• 45:55Lewis Howes?

  Relevant or you're not gonna build momentum or whatever. Yeah.

• 45:58Ryan Holiday?

  Yeah. So that, that I had that actual fear of losing the momentum. And then I have a fear on top of that fear that in giving into it, I'll do something that will hurt other people. Like it's like, I can choose to live with whatever fears I want. But I've made a decision now to have a kid and that is, they don't like, they didn't sign up for that. Do you know what I mean?

• 46:21Lewis Howes?

  Yeah. Interesting. And what do you feel like your purpose is right now?

• 46:24Ryan Holiday?

  I really, I really love writing. Like I really, I really love writing and I feel like I've been lucky enough to write things that other people haven't like, like I've actually seen this, like, so I write a lot about ancient philosophy and some of the people in that community have started to become like resentful of that writing because it's become popular. And so on one hand, the egotistical reaction is-

• 46:48Lewis Howes?

  It's not just like academic anymore or whatever.

• 46:50Ryan Holiday?

  Yeah. Yeah. And, and you know where it is. Like, you know, people, when, when you start to become successful, people resent you for that success. And so on the one hand, the egotistical reaction is just to dismiss that. And you're like, you know, they're haters. Don't listen. But it's more, it's like, oh, actually like, of all the people who get to talk about this, like I somehow I'm the one, right? And I think, um, my purpose is that I have, I have the ability to talk about this stuff at a scale that other people haven't been able to get. And now I have to make sure that I'm doing that well. And then I'm working hard and then I'm producing things that matter.

• 47:29Lewis Howes?

  If you could achieve anything you wanted to achieve, what would you want?

• 47:33Ryan Holiday?

  I don't think there's anything, and I hope this doesn't sound weird, but like there's nothing that like-

• 47:39Ryan Holiday?

  There's like all I, starting from about when I was like nineteen or twenty years old, I really wanted to be a writer and I wanted to write books. And I don't know, I just thought, I thought that that, that people, I, cause I love books and I love. Did your parents give you books as a kid? Did you? They did, they did not like good books, but you know what I mean? Like I was always reading, but they were like adventure novels. So like they instilled to me the, the joy of reading, but not, not the right direction yet. That came from mentors, but I just, I just, the idea that you get to research and teach people and talk about these things for a living is like amazing to me. And it's this tradition that goes back literally thousands of years. Like that has a lot of meaning to me.

• 48:24Ryan Holiday?

  And so I, I, I kind of forget the question, but. Or the achievement, achieving you. Oh, what can, so like, I think one of the hard things about life is that you probably, do you get people go like, so what's next? All the time, all the time. And they, if you're like, no, this, like this, like that. I would say this is what's now. Yeah. I'm talking about this one. That's a great answer. I say this, right now is what I'm working on next. Yeah. And, and like, I think, but the pressure is that you should say, well, and now I'm gonna become a billionaire. Right, right. The next bigger thing. Yes. And, and I think that puts people on a path that eventually makes them very unhappy because like,

• 49:04Ryan Holiday?

  this is what I wanted to do. So why would I, just because I've done it and I got to do it earlier than I expected. I'm gonna go do something I, I just came up with in my head, right? Like I've seen a lot of people that are like, everyone else is starting companies, I should start a company. Well, maybe I don't like that. And so why should I do it just because everyone else is doing it? So I've tried to, for me, I'm trying to be very disciplined and not, people will throw oppor, I think the myth is that opportunities are hard to come by. They are early on, but then you get a lot of them and you have to learn which ones to say no to. Yeah. It's really challenging. I want to say yes to it all. Of course. And, and like, the reason you are successful is because at some point in your life, you said yes to everything. Right. And then I learned how to say no to everything.

• 49:49Ryan Holiday?

  Yeah, Jonathan Fader, he wrote this book called Life is Sport. He's the team psychologist for the Mets. I told you about him. He had, he was telling me this thing. He was like, in the Dominican Republic, they have this saying, and I forget what it is in Spanish, but it's you don't walk off the island, right? You have to hit your way off the island. So you have to swing at every pitch. But as you become more successful, like he's saying, then what happens is these guys, they come to the major leagues. And now, all of a sudden, they have to choose which pitches to swing. If they swing at everything, they're not any, like pitchers know.

• 50:25Lewis Howes?

  They strike them out.

• 50:26Ryan Holiday?

  They strike them out and then they hurt the whole team. And so it's like, wait, so you used to have to swing at everything. And now, all of a sudden, you have to learn when, when to not swing and when to swing.

• 50:36Lewis Howes?

  Right.

• 50:36Ryan Holiday?

  And I think success is, it's the same for all of us. You do something and now, all of a sudden, hey, do you want to appear on this podcast? You want to do this TV show? Do you want to write this thing? And you have to know what projects to say yes to. And I'll give you an example. You could have written a book much earlier than you wrote a book.

• 50:52Lewis Howes?

  Yeah.

• 50:52Ryan Holiday?

  And, because I remember, actually.

• 50:55Lewis Howes?

  I wrote a proposal four years before the book came out.

• 50:57Ryan Holiday?

  Well, I was going to say, the day I sold my book, I was in New York City and we had lunch with Steve Hanselman. And you were like, I'm thinking about doing a book.

• 51:04Lewis Howes?

  The barbecue place we talked to.

• 51:05Ryan Holiday?

  Yes.

• 51:05Lewis Howes?

  Maybe that was afterwards.

• 51:07Ryan Holiday?

  Yeah, oh, at Hill Country?

• 51:09Lewis Howes?

  Yes.

• 51:09Ryan Holiday?

  Yes, but this was at some sushi restaurant.

• 51:11Lewis Howes?

  Okay.

• 51:11Ryan Holiday?

  And you were, you were thinking about doing a book. And you, you waited four years. I find, I find very impressive. Because you knew about how much you wanted to sell it for.

• 51:22Lewis Howes?

  It didn't feel right to me. Didn't feel right at that time.

• 51:25Ryan Holiday?

  That, but that's one of the hardest things in the world. You turned, you turned down, although you didn't really have offers, because you didn't go out with it. But like, you could have made six figures and then more in six figures. Until you, by, by having discipline, you made the most money and you wrote the best book you could have written.

• 51:42Lewis Howes?

  Yeah. I had a whole nother book proposal that was. More about like business and lifestyle. And I was just like, we have wrote the whole thing. And Steve was like, all right, let's go shopping around. It's like, uh, the last minute, I was like, this doesn't feel right to me. And I remember being so terrified to tell him, cause like, we just spent two years on this.

• 51:58Ryan Holiday?

  Right.

• 51:58Lewis Howes?

  You know?

• 51:59Ryan Holiday?

  Yeah, yeah. And, and it's like, you, he's pressuring, I mean, Steve is great. He's done, would never pressure anyone. But he has a real interest, being your agent to go out and you have to say, actually, this isn't right. Right? Or, or people go, well, this person offered me 10% more money, but it's like, they don't believe in what you're doing at all.

• 52:18Lewis Howes?

  Yeah.

• 52:18Ryan Holiday?

  So are you gonna, are you gonna jeopardize everything that you're working for to make 10% more in the short term?

• 52:24Lewis Howes?

  Yeah.

• 52:25Ryan Holiday?

  Or do you have the discipline not to swing at that pitch?

• 52:27Lewis Howes?

  And wait a whole college experience until you come out with it.

• 52:30Ryan Holiday?

  I mean, four years is so long.

• 52:32Lewis Howes?

  It's a long time, man. It was worth it though.

• 52:34Ryan Holiday?

  But, and, and this is why you can't compare yourself to other people. How many people came out with books that you knew in that four year period?

• 52:41Lewis Howes?

  A lot of people, man.

• 52:42Ryan Holiday?

  And that if you don't have confidence and you don't have a belief in what you're doing, that's where you doubt yourself and that's where you go, fine, I'll just copy them.

• 52:50Lewis Howes?

  Right. And then it's just an average work, piece of work.

• 52:53Ryan Holiday?

  And won't last.

• 52:53Lewis Howes?

  Yeah, exactly. Who was more influential to you growing up, your mom or your dad?

• 52:58Ryan Holiday?

  That's a good question. Uh, definitely my dad.

• 53:00Lewis Howes?

  Why?

• 53:01Ryan Holiday?

  Um, my dad was just like a strong, so my dad was a police officer, but became very financially successful. Not from being a police officer, like he invested in real estate and he's, he invented this, uh, this arm that could pick up explosive devices. And he did all this cool stuff. And I, the idea that like, you didn't have to be defined by that one thing that you do. And that you could understand things that were related to it and work really hard. That was very influential to me.

• 53:33Lewis Howes?

  That's cool.

• 53:33Ryan Holiday?

  Yeah.

• 53:34Lewis Howes?

  And what are you most grateful for in your life recently?

• 53:37Ryan Holiday?

  Um, so I, my wife and I, we, we live on this farm and

• 53:42Lewis Howes?

  With donkeys and goats.

• 53:43Ryan Holiday?

  With donkeys, like it's like, I live in my dream house, like my dream house, my dream life.

• 53:50Lewis Howes?

  Except for the rattlesnakes.

• 53:51Ryan Holiday?

  I did kill a rattlesnake two days ago, although that was fun. Uh, but, but it's like, I think this is the other reason why you have to be present and actually enjoy the, the moment is that it's like, this is everything that I want. And I have to remind myself that it's everything I want and that that's freeing and not get distracted by like, oh, and it would be nice to have like,

• 54:12Lewis Howes?

  The bigger and better thing.

• 54:12Ryan Holiday?

  Right. Like as soon as you buy a house, you're like, in an apartment, you're never like, I'd really like to redo this bathroom. But as soon as you own a house, you're like, I don't like these floors, you know? And trying to, trying to actually be grateful for what you have, things that you would have killed like a year earlier to have. As soon as you have them, all of a sudden you think about how they could be better. And I think you've, you've written about this a lot, but gratitude is incredibly important. Not just because it's what you owe other people, but it makes you appreciate what you have versus focusing on what you could have or don't have, which are egotistical things and also recipes for misery.

• 54:50Lewis Howes?

  Mm hmm. Yeah, I like that. A couple of final questions before I ask him, I want to make sure everyone gets the book. Ego is the Enemy. Go pick it up right now. I'll put it in the, the show notes as well. But go check it out. It's a great book. It's a, a short read too, compared to most big books. It's a smaller book, but it's a lot of great information there.

• 55:08Ryan Holiday?

  You ask very moving questions. You asked me one, you said something like, is it better to be smart or kind? Was that the question?

• 55:15Lewis Howes?

  Was this the last time?

• 55:16Ryan Holiday?

  Yeah, this is the first time. You asked me something like that and I just thought it was an amazing question. I think about it a lot.

• 55:21Lewis Howes?

  Really? Is it better to be smart or kind?

• 55:23Ryan Holiday?

  Uh, it's definitely better to be kind, I think.

• 55:27Lewis Howes?

  You think?

• 55:28Ryan Holiday?

  I mean, yeah, yeah, yeah, it's definitely.

• 55:31Lewis Howes?

  One is more rare.

• 55:32Ryan Holiday?

  One is more rare.

• 55:33Lewis Howes?

  Yeah. Kind is more rare?

• 55:35Ryan Holiday?

  I would say kind is more rare.

• 55:36Lewis Howes?

  Really?

• 55:36Ryan Holiday?

  Yeah.

• 55:37Lewis Howes?

  Do people aren't kind?

• 55:38Ryan Holiday?

  Yeah, I think so. There's lots of smart people. Would the world be better with more smart people or more kind people?

• 55:44Lewis Howes?

  I think kind.

• 55:45Ryan Holiday?

  Probably, yeah.

• 55:46Lewis Howes?

  I mean, the wars that are happening are based on people who think they're smart.

• 55:50Ryan Holiday?

  Yes, right.

• 55:51Lewis Howes?

  Not kind people are creating wars.

• 55:53Ryan Holiday?

  Well, that's the thing is Socrates says, no one does wrong on purpose, right? So the smart people all think they are doing the smart thing.

• 56:01Lewis Howes?

  And I think if, you know, if people led more with their heart, as cheesy as that sounds, ego would drop.

• 56:07Ryan Holiday?

  Sure.

• 56:08Lewis Howes?

  And the heart would lead. When the head is away,

• 56:11Ryan Holiday?

  Yeah.

• 56:11Lewis Howes?

  the heart will lead, right?

• 56:12Ryan Holiday?

  Yeah, yeah, sure.

• 56:14Lewis Howes?

  Cool. I'm glad you brought it up. Okay, this is a question I asked at the end for everyone. It's called the three truths.

• 56:19Ryan Holiday?

  Okay.

• 56:20Lewis Howes?

  And you're a writer, so you're going to create many works of art for the rest of your life, and you've already got great books. You've helped a lot of people, a lot of smart people, write incredible books, including myself. You helped me with School of Greatness. And it's the last day for you, many years from now, and all your friends and family, everything you've ever wanted, you've achieved.

• 56:41Ryan Holiday?

  Okay.

• 56:42Lewis Howes?

  You've got the dream family, you've got the dream home,

• 56:45Ryan Holiday?

  Yeah.

• 56:45Lewis Howes?

  thousands of donkeys, whatever you want.

• 56:47Ryan Holiday?

  No more donkeys.

• 56:48Lewis Howes?

  You've got it all.

• 56:49Ryan Holiday?

  Yeah.

• 56:49Lewis Howes?

  And, but all of your work is erased.

• 56:52Ryan Holiday?

  Okay.

• 56:53Lewis Howes?

  And you have a piece of paper and a pen, and you get to write down three truths, things you know to be true about all of your experiences in life that you would pass on to people.

• 57:00Ryan Holiday?

  Sure.

• 57:01Lewis Howes?

  As your bible, essentially, for how to live life.

• 57:04Ryan Holiday?

  Okay.

• 57:05Lewis Howes?

  What would be your three truths?

• 57:06Ryan Holiday?

  That's great. Well, first off, I think you should live your life as though your works are going to be erased, because when you're dead, they are erased to you, right? But, okay, so the first one would be, and this is the essence of Stoic philosophy, I think, it says, you don't control what happens to you, you control how you respond. So that'd be truth number one. Truth number two would be what we talked about earlier, where you can't learn that which you think you already know. I think that's an essential, an essential truth that puts you in a mindset to learn your entire life.

• 57:41Ryan Holiday?

  Uh, you know what? I'll give you one more stoic quote. We'll make this all stoic. There's a line from Seneca where he's saying, "Some people lack the courage." What's he saying? "Some people lack the courage to live the life they want and live only as they have begun." Right? So that's the, that people lack the courage to change, to make, to, to do abrupt changes, especially as they get later on in life. And I would say, most of the big decisions in my life, you know, deciding to leave college, which was going well, the decision to leave American Apparel and become a writer, you know, the decision to not write marketing books, but to write about other things. These were dramatic changes that cost money, you know, or meant closing the door on big things,

• 58:25Ryan Holiday?

  but opened up enormous upside. And so I think, I think you have, you can't, just because you're good at something, or just because you've done it for a long time, is not necessarily a reason to continue that thing.

• 58:40Lewis Howes?

  I like that.

• 58:41Ryan Holiday?

  What are yours?

• 58:42Lewis Howes?

  When you get a podcast, you ask me that.

• 58:44Ryan Holiday?

  Okay. All right.

• 58:47Lewis Howes?

  I've actually said them on here before, so I'll have to go back and let you know what I said. But what do you think the world needs more of?

• 58:56Ryan Holiday?

  I would say, right now, I mean, one of the things that stresses me out is, is a lack of tolerance. Both, I think we've become increasingly less tolerant, I mean, in this campaign, a less tolerance to, like, for instance, this backlash against immigrants, both in the United States and internationally. I mean, we're here in Los Angeles. Los Angeles is awesome because it's filled with immigrants. New York is awesome because it's filled with immigrants. And the idea that immigrants make things worse is just not only economically false, but it's culturally false. And it's ethically bankrupt as well, right? Just because you're born here does not give you some special claim to this land over the rest of the world, right?

• 59:39Ryan Holiday?

  And so I think, I think a lack of tolerance of other people and their hopes and dreams is a big one that alarms me, but I think more, like if we're more just talking about like America. I think our lack of tolerance of conflicting or unpleasant ideas is equally problematic. Right? So I don't like the idea of safe spaces and, you know, calling people racists or bigots because you don't like what they're saying. I, I think you, you need to get to a point where you can deal with uncomfortable, unpleasant truths. There's a line from Epictetus where he says, "When you're offended, your mind is complicit in the offense."

• 1:00:20Ryan Holiday?

  Right? So if you say something mean to me, I choose whether I'm mad at, like, I choose whether that offends me or whether I'm going to hold it against you, right? That part is on me. And so I think we need to become tolerant of, tolerant of unpleasant ideas, incorrect ideas, poorly articulated ideas, because it's, life is too short to be outraged about things, especially things that people have just said. Like, I'd rather we focus on what people do.

• 1:00:53Lewis Howes?

  I like that. I like that. Is it more important to do or be?

• 1:00:58Ryan Holiday?

  You know, there's actually, I, I think I know the question you're, you're saying, and I would say it's more important to be, like, to be true to what you're saying than, you know, to sort of be a good person rather than, you know, but I have a chapter in the book, there's this famous speech from, from John Boyd, and he would, he would say this to every one of his young proteges, he would say, "To do or to be," that was called his "To Do or To Be" speech. And basically what he was saying is that being promoted and, you know, rising to responsibility and power and being recognized is not the same and is not as important as doing great work.

• 1:01:40Ryan Holiday?

  Affecting change behind the scenes. So it's like, we've become so obsessed with, you know, being promoted, or being recognized, or getting credit. Yes, right. It's like, people would rather be a bestseller than write an amazing book.

• 1:01:53Lewis Howes?

  Right.

• 1:01:53Ryan Holiday?

  And that is totally wrong.

• 1:01:55Lewis Howes?

  People do that. They hack the system to just buy their way on.

• 1:01:58Ryan Holiday?

  Absolutely. And that, so it's, it's, do you want, like, just because the rules are crooked, and they are, for the bestseller list, they're crooked as hell, they're worthless. But people spend hours and hours and hundreds of thousands of dollars trying to game that system, instead of spending that time making something that is, transcends that system, and will outlast it and matter. So I think, in John Boyd, even he's saying to do or to be, he's saying, doing is more important than whether you get the credit for it or not.

• 1:02:31Lewis Howes?

  Gotcha, gotcha. Before I ask the final question, I want to take a moment to acknowledge you, Ryan.

• 1:02:35Ryan Holiday?

  Okay.

• 1:02:36Lewis Howes?

  I acknowledge you for your, your brilliance, and your creativity, and your ability to take major risks in your life, when they are uncomfortable for you. Because I think there are so many people that are brilliant and creative, that stay in the same game, just to be more recognized and make more money. And you continue to, to follow your purpose, as opposed to following the money. And, and in the process, you help so many people, along the way, you've helped guide me, and my journey, with my book and my work. You're always someone I can lean on with some great brilliance, and you've helped so many people. So I want to acknowledge you for constantly learning, and realizing that

• 1:03:21Lewis Howes?

  you get to continue to learn while your journey.

• 1:03:23Ryan Holiday?

  Yeah.

• 1:03:24Lewis Howes?

  And giving to so many people with the work you create. So I want to acknowledge you for that, yeah. And the final question I have is, what's your definition of greatness?

• 1:03:33Ryan Holiday?

  Trying to remember what I said last time. No, no, so I could not say not say that. I think the definition of greatness is fulfilling, fulfilling whatever potential you have and then some, right? So, because people in your life, they see you and they recognize that you've got some potential and they sort of, you often, you have a sense of where someone's going to go almost better than they do. But then I think, I think true greatness is the wow, where did that come from? Like little element right on top, right? Like, everyone knew Michael Jordan was a great basketball player, but that game where he played, where he had the flu and he could barely stand up,

• 1:04:15Ryan Holiday?

  that's like a, where did that, like where is that? Do you know what I mean? And I love, I love stories like that.

• 1:04:22Lewis Howes?

  Yeah, there you go. Ryan Holiday.

• 1:04:24Ryan Holiday?

  Thanks, man.

• 1:04:25Lewis Howes?

  Appreciate it.

• 1:04:28Lewis Howes?

  And there you have it. I hope you enjoyed this episode as much as I did. And let me ask you a question. Are you letting your ego get in the way? Are you even aware that your ego is holding you back? Or are you completely aware when your ego comes up and holds you back? Feel free to tweet me right now, at Lewis Howes and at Ryan Holiday. And let me know if your ego has ever held you back in a situation and tweet me what that is. This episode is lewishouse.com/352. If you enjoyed it, please share it with your friends. Let your friends know about this as I think it's an important topic for us to think about and discuss

• 1:05:09Lewis Howes?

  and bring to light, because the more we hold on to our ego and needing to be right and needing to be heard and needing to be acknowledged all the time and having it be our idea and get us getting the credit, the more chances we have for suffering, depression, anger, frustration, resentment, all these things come up. So it's important that we understand how to manage this thing called ego, because in some ways it can move us forward and other ways it can hold us down and leave us crippled. So please share this with your friends, lewishouse.com/352. Also, leave a comment on the blog. And let me know what you thought. I'm super excited for you to get this one out there to your friends. And if this is your first time here on the podcast, please subscribe

• 1:05:51Lewis Howes?

  over on iTunes and leave a review. We have over a thousand five-star reviews. I'm super grateful for every one of them. And the reason we continue to grow this podcast is because people subscribe, they listen, they share, and they leave reviews. So if you have been listening for a while, you have not yet left a review, then now's the time. I'm asking you, please, to leave a review. If this has brought any value to you in any way, let me know what you think. I'd love to get your feedback to continue to make this a better and better podcast to serve you. And last but not least, you guys know what to do. It's time to go out there and do something great.