The School of Greatness - 64 Ryan Holiday: Using Practical Ancient Philosophy as a Guide to Achieving Mastery

Episode Date: May 1, 2014

Would you like to learn philosophy in a way that is actually practical? Ryan Holiday comes on the School of Greatness to share his wealth of knowledge on how to integrate stoic philosophy into succeeding in our modern day world. To get all the show notes, links and much, much, more; head over to www.LewisHowes.com/64

This is episode number 64 with Ryan Holiday. 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. What is up, greats?

Thanks so much for checking out this episode today. I've got a very special one. It's with my good friend, Ryan Holiday, who is probably one of the youngest geniuses you'll ever meet when it comes to building a business, marketing, advertising, and just being creative in general. And he is most well known for being the director of marketing at American Apparel. And I think he got the job when he was like 21, which is just ridiculous by itself. But he has some pretty big-time clients as well that he worked with on the side while he's been working with American Apparel, people like Tucker Max, Robert Greene, Tim Ferriss, and a number of other people.

But he's done some incredible things. He's considered a media manipulator. He's got a book called Trust Me, I'm Lying, Confessions of a Media Manipulator that was a Wall Street Journal bestseller. And he's just done some amazing things online when it comes to marketing. But this is all about something a little different. And it's something that I'm really in tune with. And it's all about adversity and obstacles. tune with. And it's all about adversity and obstacles. And he's got this new book called The Obstacle is the Way. The timeless art of turning trials into triumph. And I've experienced so many obstacles and challenges, specifically in sports, when I think of injuries in my life, that it always seems like a big bummer and a big downer whenever I get injured and I

have to sit out for a few months or I think my career is over or I think the season is over, which has happened to me both. My season's been over because of injury. My career's been over because of injury. Lots of things have happened because of obstacles, but it always seems like those obstacles become my way. And I'm excited to dive into why obstacles are so important for our life and for our purpose and our mission. And how Ryan has really kind of cracked the code with all this in his research, in his writing. I think you guys are going to love this episode. So stay tuned for that. And without further ado, let's bring on the man, Ryan Holiday.

And welcome back, everyone, to the School of Greatness. I am extremely excited about today's guest. His name is Mr. Ryan Holiday. What is up, Ryan? Hey. Hey, man. How are you? I am exceptional today.

Good. It's because I get to hang out with you for an hour, and it's because I got to read your book, which is fascinating, probably because it's something that I'm already in tune with and already believe in. So to get it reinforced, you know, we were talking about this a little bit before, but to get this reinforced, that what I'm doing is working for me through your book and through the research that you've done, like the extensive, you know, pages of research that you have in the back. It's a, it's, it's a privilege to be able to go through something as amazing as this. So thanks for writing it. Thank you, man. That, that means a lot. I mean, that's why, uh, I think that's why people sit down and write books is for exactly that reaction.

So I appreciate it. Yeah. And the book is called the obstacle is the way the timeless art of turning adversity into advantage just to advantage not into and you know this this speaks to my heart big time because as there was a couple of uh there was a section in here i forget the page, but there was a section where you're talking about adversity. And actually, the moments where we have our biggest, quote unquote, failures or setbacks is actually the opportunity to turn it into our biggest advantage. And for me, I would say this has been true in my entire life. this has been true in my entire life. Every huge failure or setback or emotional breakdown or injury, physical injury, it's turned into like the greatest advantage of my life and set me in a path

of, you know, success and fulfillment and impact. So I am a huge believer in this philosophy as if you will. And I'm excited to dive in. So first off, you wrote a book before. Were you a New York Times bestseller with Trust Me? It was a national bestseller. So I had the Wall Street Journal list and a couple others. Nice. And you wrote this amazing book called Trust Me, I'm Lying, Confessions of a Media Manipulator. Is that right? Right. It's like a marketing expose about how the media works. Yeah. And this is a brilliant book. And you've written another book called, I think

it's called Growth Hacking. Yeah. And it's all about basically building your company without having to spend a lot of money and the marketing strategies and the mastermind that you've got, that you've been working for years with American Apparel and all these other influencers. that you've got that you've been working for years with American Apparel and all these other these other influencers uh I'll talk about that in the intro but I want to talk about uh why did you want to go into this type of book which has been different than your last couple books sure I mean first off I don't think anyone wants to do the same thing over and over again and I think it's when we challenge ourselves to do the things that maybe we're afraid of or we think that are a little bit beyond our reach that we end up sort of creating the stuff that we're most proud of. So for me, you know, stoicism,

which is which is the sort of philosophy that's at the root of this book. It's something that I've read for a long time. And I've studied I was introduced to stoicism. And when I was 19 years old by Dr. Drew, of all people, I read that. Yeah, I met him at this conference and he was like, look, you got to read this book. And so I read it and it totally, totally changed how I saw the world. And in the book that I read, there was this exercise about how, you know, he says, Marcus Aurelius, who wrote the book, he says, the impediment to action advances action, what stands in the way becomes the way. And this is, of course, something that went totally over my head at 19 years old. But as I got older, I started to understand what it meant. Because like you, I saw that every time I thought that something negative was happening, or something was holding me back or preventing me from doing what I wanted to do, when I really looked at and thought about it was actually presenting this sort of new opportunity or this new path. And so I wanted to write a book

that was both a reminder to myself about how that works, and it's sort of a series of like thoughts that I could use myself when I face stuff like that. And then also just communicate and maybe pass on what I've learned from these other people. There's a lot less of me in this book and a lot more of other people's stories, specifically the historical greats and how they've used this formula in their own lives. Yeah, I love it. And for the non-philosophers, including myself, before I had to look it up, what is stoicism, the definition of that? Yeah, so stoicism is a philosophy that was popular with the Greek and Roman elites that is very much a practical philosophy. So I know when people hear philosophy, they think like a college lecturer who's droning on and on about these complicated metaphysics and,

and ethics and stuff. Stoicism is a very simple philosophy that's about, that's basically rooted on one fact, which is we don't control the world around us. We only control how we behave and how we respond to that. And that we may as well respond with sort of strength, discipline, virtue, and rationality. And I wanted to, those skills, although philosophical and I think very wise, are also the same skills that are very advantageous if you're a lawyer, if you're a business person, if you're an entrepreneur, if you're a leader, you know, the two most prominent Stoics were Marcus, or the three most prominent Stoics were Marcus Aurelius, who's the emperor of Rome, the most powerful man in the world. Epictetus, who was a lecturer, who had formerly been a slave. And then Seneca, who was one of the most

powerful and influential political advisors and businessmen in Rome, all at different times. So it's like, this is really a philosophy that's designed for doers, not for academics. I like that. When I think of philosophy, I think of people that just think all day. Totally. And that don't take action. They just judge the actions of others. Right. And so for me, I like this way of thinking a lot better. And it's, you know, I've been doing a lot of emotional intelligence studies and research, and it seems like almost identical to what emotional intelligence is.

And I'm looking at the, I guess, the definition of it right now, which is the ability to identify, assess, and control the emotions of oneself, of others, and of groups. But really being able to manage your emotions under extreme obstacles, stress, adversity, and things like that so that you can propel yourself to achieving what you want to achieve. Yeah. The Stoics sort of saw emotions in some way as an enemy. Not that emotions are bad, emotions in some way as an enemy not not that emotions are bad but emotions they sort of pitted emotions versus rationality and how often uh harmful emotions might make us do irrational things so um they're basically looking at how do you make sure that you don't make situations worse in the way that you react to them, which I think is probably the definition

of an emotionally intelligent person is that they know how to make things better rather than worse. Yeah. And you've got three parts to your book. The first part is perception. And I think that goes perfectly into perception. I could have a horrible accident, quote unquote accident happened to me or lose a close family member or lose my job or something could go wrong, again, a car crash. And it's all about my perception on how I emotionally react or don't react and perception of everything that is happening around me in the world that's happened in the past, that's happening now, whatever it may be, but it starts with perception and, uh, you know, which is going to determine, I guess, our emotions and our outlook and our next actions. Wouldn't you say?

Yeah, totally. I think what the, what the Stoics point out is like, how, when you look at our emotions or our reactions objectively how how much the severity of them can sort of crumble away so it's like you know something happens to you and you feel like it's the worst thing ever there are a lot of people who would kill to have that happen to them right right and that's how you sort of it's it's like when you realize that you realize that your emotions are subjective and then if're subjective, then you have the ability to control them. And what the Stoics look at is, okay, you know, the bad things are going to happen, good things are going to happen. How can you make sure that your emotions don't get carried away in

either case? So it's like, if you're really happy, awesome. But you also don't want to delude yourself into thinking things are always going to be this way. So when bad things happen, you're not caught by surprise, right? And then on the other side, when bad things are happening, you want to remember and be able to remind yourself that things aren't always going to be this way. So you don't get depressed and, you know, want to kill yourself. Like the point is, can you prevent yourself from gravitating towards these extremes? And we all know people who are not in control of their emotions, and we see how they sort of whipsaw back and forth and how miserable that makes them. Yeah, and you give a great example.

I think of Tom Brady as a great sports figure who is pretty even keel throughout an entire football game, all the ups and downs. And you give a great example of Arthur Ashe in the book, um, you know, when he was playing tennis during the fifties and sixties during segregation and how he was able to manage his emotions, people were just in awe. Right. And, you know, talk about that. Yeah. I mean, and then you look at someone like John McEnroe, whose emotions are all over the place, the problems that that caught, like, it can have some advantages. But, you know, I think you're better off being able to sort of the samurai swordsman, he's saying there's the difference between perception and impressions. And, like, you want to stick with these first impressions. So it's like, hey, you know, they just intercepted the ball would be, like, the first impression. The second impression, which is something that someone like Tom Brady doesn't do, is like, the game is over because this happened. Like, you want to prevent yourself from these

extrapolations and adding on the implications. If you can live in that present moment, it's like, okay, they intercepted the ball because, you know, something happened. Now, I have to do X, Y, and Z in response. That's how you see these people pull off these sudden last minute wins was because you gave up in your head and they never did. They were sort of existing in that present moment where they had a job to do and a thing they had to accomplish. Whereas the rest of us, you know, something goes wrong and all of a sudden we're, we've extrapolated out to the point where like we're going to be homeless and we're going to die in the streets of starvation.

Um, when we would have been better off just taking the situation as it was and working with where it leaves us. I like that. Yeah. And you talk about, you say the difference between the right and the wrong perspective is everything. Yeah, totally.

I mean like the, the, our perspective changes what the event means to us. So if we tell ourselves that it's the worst thing ever, it's the worst thing ever. And if we don't, well, it's not.

And you know, I, like I liked, um, one of my examples in the book is Laura Ingalls Wilder, who wrote Little House on the Prairie. She sort of lived through all this terrible stuff. Right. But she had this weird spirit where she kind of saw it all as an adventure. fun and then it becoming fun because she thinks that it is, I think is really, is really important. And I'm not saying that you should, you have to go live on the Kansas prairies or something, but the point is what she went through is much worse than probably what you and I are going to go through. You know, the most of us, so many of our problems are these sort of first world problems, but because they're the only problems we know, we obsess about them and we make them

so much bigger than they actually are. And we don't remind ourselves, it feels weird to think this way, but we don't remind ourselves how much worse it really could be. Right. Like our car is breaking down every month. Oh my God. Or something. It's like people don't even have cars. Yes. Right. or what if you died in a car accident wouldn't that be worse right exactly yeah all great things and you talk about uh you give a you talk about steve jobs in the book as well and you and you say that he's he's famous for the reality distortion field now what is what does that actually mean yeah so he was sort of notorious for uh like people would say like oh you know this deadline is impossible or oh this

can't be done um like if you look at the iphone like the iphone is so much better than everything that came before it almost feels like um like magic right and that was because he ignored all the people who would say things like oh it's not possible like there's a famous story where this engineer um he wanted some mouse for one of the early Macintoshes and the engineers like, look, this mouse is impossible. We can't do it. And, you know, the guy's manager shows up the next day, that employee is gone. And the first words out of his replacements mouth were like, oh, I can do it. And it's sort of surrounding yourself with those people and inculcating that attitude and saying like, look, it's going to be okay. We're going to try this. We're going to take, we're going to push the boundaries of what we think isn't possible.

We're not going to be delusional, but we don't have to be realistic. Like everyone tells us to be realistic. And I'm sure there are so, I mean, when I hear your story, Lewis, there's so much stuff that you've done in your life that other people would say is unrealistic or impossible or crazy, but because you didn't think that they were, you were able to do them. Right. Yeah. I definitely believe in that attitude. So I like- I mean, like for me, it's like people are like, oh, you're 26 years old.

Can you write this book? And you have to be like, you know, no offense. It's like, screw those people. Right. Don't listen to them. Do what you think you can do and then, you know, play it out from there. Yeah. I mean, pretty much, I don't know if anyone would think that, you know, you'd be the head

of marketing for American Apparel. I think at 21 is when you started, right? Yeah. Look, things are a lot easier than people think and they're also a lot harder, but you don't average those out and then decide what is or isn't possible. It's like you take risks, you bet on yourself, and you don't worry about these risks because it doesn't give you anything and it's what makes you conservative and it ensures that you won't do certain things. Right, right. So, okay. So we have an obstacle coming our way.

Right. There's some challenge that's about to happen or has happened. And once you start attacking this obstacle, what kind of mindset should one consider? Sure. So I think I sort of break it down in three steps in the book. The first is like controlling how you perceive and see that obstacle, right? So, you know, you're not exaggerating how big it is. You're not freaking out. You're controlling your emotions. You're looking for the weaknesses or the opportunities within it, you know? So first step is just your perspective towards it. And then the second part is you have to take action, right? And I think there's a couple problems that

people face when they do obstacles that they don't deal with properly. And the first is they try to overthink it, right? So they look for this sort of like, I've got to have this miracle, I got to find the perfect thing for me. But really, you got off your ass, and you just started working and you made something from scratch, but you didn't totally know where you were going, right? Like no clue, you just worked. And you you channeled your energy towards something, and you didn't give up. And then you were able once you sort of got some momentum, then you were able to figure out where you wanted to direct this thing. So like when I see people my own age, it's like, oh, I graduated from college and then the market was terrible.

So I moved back in with my parents and now I'm waiting for a fortune 500 company to give me the, my dream job. Magically call me up and offer me a six figure job. Right. It's, it's not going to happen. And so I tell the story of Amelia Earhart, like people, people know Amelia Earhart for what she did, but they don't understand that the sort of the first offer her first flight over the Atlantic was this insanely dangerous, ridiculous offer where she had to be chaperoned by two men.

She wasn't paid. She got like none of the attention. She, she basically had to eat their shit, um, to, to, to, to be able to have the opportunities that she did later. So I think that first step is just like getting up and starting moving. Um, and then it's like a, you know, I think persistence is really important for, and obviously I talk a lot about the process, um, which is, which is a concept from Nick Saban, the football coach at University of Alabama, which I'm sure you know a little bit about. It's not about focusing on the championship. It's about focusing on the tiny pieces that get you to a championship. So the process is about finishing.

It's about finishing reps. It's about finishing runs. It's finishing plays. It's finishing downs. It's finishing quarters. It's about finishing uh runs it's finishing plays it's finishing downs it's finishing quarters it's it's about steps and like i trained in i do some still but i trained in brazilian jiu-jitsu and like the idea then is like if someone has pinned you to the mat it's not this one big movement that throws them off of you it's a process where you're sort of chipping away. You know, first you get your knee in, then you create some space, and then you're pushing away. And then, like, it's a process. And so I urge people to remember and sort of figure out this process

mindset. And then I think lastly, the sort of the final, if I'm summarizing the final actions are, lastly, the sort of the final, if I'm summarizing the final actions are, it's not always about strength against strength, you know, so sometimes, like, with you, if you wanted to, you've got this huge platform, maybe one day you want to have a TV show, the point is not before you have the platform to start planning this TV show, it's to build yourself up one by one until you've built an audience that other people want access to. So it's like, how can you do an end run around whatever gatekeepers or barriers have been erected to prevent you

from going where you want to go? Right. I like it. Yeah, and I talk a lot about trusting the process. You know, we don't, a lot of people don't trust the systems and what people have achieved before. It's very simple sometimes, and sometimes we overcomplicate it,

like the path to achieving X or Y or whatever it may be. People have done it before, and it doesn't mean you have to try to do something new, although you can. But really trusting something new, although you can. But really trusting the process, like you said, you're not just going to throw someone off your back or off of you who's on top of you. It takes you step by step and trust the process that even if they got you in a chokehold and you feel like you're going to die, if you trust the process, you're going to be able to breathe soon. Right. I think maybe a good way to describe the process is that a process is simple, but it's not easy and it doesn't necessarily go quickly either. And so I

think that's why people don't trust the process or they avoid the process because they want something like they'll try something that's harder, but won't take as long. And then they're disappointed when all that effort goes for nothing. And I think what, you know, you talk about this on this show, because it's about greatness is like, there's a path to greatness, that people that you know, what you're, whatever you specifically are trying to do might be a little bit different. But more or less, the path is pretty well carved. It's like, you got to put a certain number of hours in, you got to have a mentor, you got to, you know, you got to do this, you got to do that. Um, that's there and there's no shortcuts around that. So stop trying to find them. You got

to do that stuff and trust that it's going to be okay or you're never going to get there. Exactly. So how can we change our relationship with failure? Well, the metaphor that I like is how sort of startups have started to think about failure, right? So in the old days, this is like 10 years ago, but the model was like, look, you raise a bunch of money, then you invent this product, you perfect it, and then you put it out there and you make it a success, right? Like that's the launching of a business. Well, startups that they've launched with less and less money have gotten smaller and smaller and tried more. Like they use what in the lean startup community. There's a great book about this by Eric Ries called The Lean Startup.

community. There's a great book about this by Eric Ries called The Lean Startup. But basically, you try to launch your idea as a minimum viable product. So they say, what's the smallest version of this idea that you can put out there to get customer feedback from, right? So you don't launch this final completed thing, you put out little pieces. So it's like, if you have an idea for a book, don't go spend two years of your life writing a book and then hope people like it. Start publishing on a blog and get feedback and develop your voice and figure out what your readers are interested in. Right. So this idea of, of failing on purpose in a small way to get feedback is really, is really revolutionary and it's really beneficial. And so I urge people to stop trying to perfect things like in private or in the laboratory,

but to be more public with what they're doing to get it out there and then take that feedback and improve what you're doing as a result. So it's like failure can be a feature. It doesn't have to be this thing that you're afraid of. And that's what I want people to understand. And I think that's really, really important. Yeah. And I think a lot of people, I just did a video post about feedback, actually, the importance of feedback on my blog. And I think a lot of people are scared of feedback because they're so critical of themselves or they don't want people to not like what they're doing. They want to be liked. They want to be accepted. And I think the perception of this, which you talk about in your book is brilliant, is it's important to have the feedback and to hone in on the perception of this.

If everyone's attacking you or saying this is bad, look at it as it's not working or it's not effective for what the results you're wanting. Not, Oh, I'm a horrible person or I suck at this because that's going to bring you down. I tell this story in the book, but Winston Churchill knew that like, look, the British were going to have to face the Nazis directly at some point. Right. And he knew that at first it might not go well. And he didn't want it to go well in mainland Europe, right? Because that blow would be so catastrophic and so bad for morale that they would never recover. So the reason the Allies challenged the Germans in World War II in North Africa was that they wanted to sort of fail far away from home, right, in a smaller

contained way. And so like a lot of people are familiar with the sort of the brilliant German general Erwin Rommel. Well, the reason he ran roughshod over the British troops early on is that they were, they saw this as a learning experience. And it's like, it's one, it's obviously a very costly learning experience when you're like it's one it's obviously a very costly learning experience when you're doing it with human lives and and i think that that shows that that's a testament to william churchill's like sort of strength and fortitude that he he was able to do that he was able to see like look we're gonna have to lose somewhere and it's gonna be bloody and awful but it will make us stronger and we'll get better as we go as a result of it.

So when the Allies landed in Italy, they were better than when they landed in North Africa. And when they landed in France, they were better than when they landed in Italy. And so, like, whereas the Nazis were getting weaker as the war went on, the Allied troops were getting stronger because they'd sort of, they'd taken this iterative approach and they'd failed in a small way and learned those lessons in a small way rather than continue to delay that painful lesson and risk everything as a result. Yeah. You also talk about being an A to Z thinker. Yeah.

What is that? about being an A to Z thinker. What is that? Well, I think this sort of goes to the process again. We think the beginning and the end, and we sort of gloss over how hard it is in the middle, right? And we forget about all that stuff that we have to do there and that it takes, there's letters in between, right? And so, I mean, it's more of a quip in the book, but my point is, you know, we think A to Z, and then we just assume that B to Y is going to take care of itself. And it's not, that's us. The process is what helps us go from B to C and D. And you've got to trust that. And you've got to be willing to put in the time, resources, Trust that and you've got to be willing to put in the time, resources, and effort to get there. It's not just about, oh, I have an amazing idea. I talk about this with my employees and with companies I deal with.

Good ideas are not scarce. There are millions of good ideas out there. What's rare is the people who take those good ideas and execute on them in a flawless way. That's where you differentiate yourself from everywhere else. And that's the school of greatness right there is the people who take a good idea and then learn from it and improve it and iterate and fail and get better and fail and get better over and over and over again until they've achieved greatness. Because we're not geniuses.

It's very unlikely that the idea that just occurred to you two seconds ago is going to change the world. It might have a germ inside of it that has the potential to do that, but it's going to take a lot more than just a flash of inspiration. Yeah. One of my mentors early on in business, Chris Hawker, said that there's no such thing as a million-dollar idea, only million-dollar executions. That's a great way to put it. And yeah, everyone's got a million-dollar idea, I guess, but unless you execute it,

nothing's going to happen. And part two of your book is all about action and getting moving and using the obstacles against themselves. And you also talk about, you say, do your job and do it right. And when I think of that, I think of the book, The Four Agreements. I forget the author's name, but he says, always give your best is one of the four agreements. Right. And what is your definition of that? Or what do you mean by do your job and do it right? I think one of the quotes I like from the book is Andrew Carnegie.

He's talking about how often when we start a business, young people are introduced to the broom for the first time. And what he means is like you have to sweep the floors. That's the only thing you're qualified for. And they're making you sweep the floors. And he's saying the problem with a lot of successful people or people who are born into success is they never have to do that. So they don't learn how it works. And they're sort of embarrassed or ashamed by it, or they refuse to they refuse to humble themselves in that way. So in that chapter, I'm sort of I'm talking like President Andrew Johnson was a tailor before he became a politician. Andrew Garfield was a janitor.

That's how he paid his way through college. You know, Booker T. Washington was sort of one of the most amazing success stories in American history. His college admissions was like, there's this great story. It's not in the book. I read it after. But he walked like 80 miles or something because he heard there was this college that was accepting black kids. And he goes into the

admissions office and he's just sitting there and he's like, look, I'll wait all day for an interview. Just please let me into your school. And they're like, well, the president's not going to be here for like eight hours. You just got to sit and wait. And he's like, okay. And while he was sitting and waiting, he cleaned the waiting room. Like he swept it, he dusted, he moved everything around, he cleaned the waiting room. And when the president came in, he saw what had happened. He's like, you're in. And so I think what happens is we have these ideas about what we are entitled to or what we deserve. And that prevents us from hustling and taking advantage of opportunities that might seem a little beneath us, but are actually quite excellent. And so I think your job in every situation is to work hard,

to be honest, and to do your best, right? And that's your job. So you can never be prevented from doing your job. It might not be exactly where you want to do it. It might not pay you exactly as you want. But you can always try as hard as you can. And this sort of ties into the last third of the book, which I assume we'll talk about, which is no one can ever prevent you from trying as hard as you can, right? The economy can tank and wreck everything that you've built, but it can't prevent you from having tried as hard. You can have a bad boss who treats you shitty, but you can still try as hard as you can. Like you can, your effort is something that you independently control a hundred percent. And that means that it's an opportunity that that means

that you can never be impeded there and i think people get so focused on the areas that they can be impeded that they forget that they always control the amount of effort that they put towards a task yeah i think this is a you know a great example for you know for business like you talked about and getting a, you know, going to school, you gave that mention there, but I think it's like, it makes so much sense with sports. You know, every little kid dreams of being in the, in the professional leagues, being in the NFL or major league baseball, but there's no way that he, even if he wants to be there right then he's not entitled to it. He's got to go through the process. He's got to start with t-ball and then move up and every coach starts off being like an assistant you know unpaid totally film boy uh you know that's just

like taking film a practice all day and then works and works his way up i love these lawsuits where like interns have been suing like magazines and movie producers for like not paying them as interns and it's like look i get it's like cheryl shan cheryl sandberg got in trouble recently because like she's a billionaire and she put out a free job posting for an intern and it's like i don't i don't want to be flip about it but sometimes when you're young and you don't know anything your time is worthless all you have is effort right that's what like and and when you're young and you don't know anything, your time is worthless. All you have is effort, right? That's what like, and when you're working for someone really successful who can teach you, you, I would almost like I, if I was in a different place, I would pay Sheryl Sandberg

to let me work for her. Right, exactly. And I think people are so, they're so consumed by notions of fairness or equity or money or whatever that these opportunities, they pass on them deliberately when it could change their lives. Yeah. I mean, it's interesting. My brother, he's one of the top jazz violinists in the world. He used to teach at Berkeley School of Music and toured with paul for 10 years and is the guy in jazz violin and uh he has students that you know pay him for for coaching to be like mentored by him and pay him like 10 grand a year to do a certain amount of lessons and just

and supposed to going to school they just work with the best and it's basically become you know an intern for him right and uh they learn how to become a better jazz violinist because of it. So I, I, I agree with that philosophy of like, if you want to get the position that you want, go find the best person or the person that inspires you and say, Hey, I will work for you for free or I will pay you to like, you know, give me your time, you know, cause that's really, their time is really invaluable. And unless you're going to me your time, you know, cause that's really, their time is really invaluable. And unless you're going to bring so much to the table, why would they give you the time of day? So, right. Well, I like one of the other things I have in the book that I think is

stuck with me since I read it, someone gave me this book in high school, which is Viktor Frankl's book, the man's search for meaning. And he was the, which you would love, by the way, you should totally read this book. Um, he, he was the, which you would love, by the way, you should totally read this book. He was the survivor of three different concentration camps. He lost his whole family. It was terrible, right? And he became a psychologist afterwards and he sort of studied like the meaning of life. That was what he looked at. And he found that people sort of asked that question in a very presumptuous way.

They're like, what's the meaning of life? As though like life owes you an answer. And he's saying like, no, actually life is asking you that question and you have to find the meaning in what you do and how you behave. And you answer it, you answer the question, what is the meaning of life with action and with how you create and generate meaning through your relationships and through the people that you love and through the things that you do with your time. And that flip, I think is really important, you know, like too many kids and I see them too. And I was like this myself, but it's like, you know, what can you do for me rather than like, like what, what is Sheryl Sandberg going to pay me when really it's like, it should be a hundred percent the other direction.

Like, what can I learn from this person? What can I give them that will make them want to teach me? Exactly. Yeah. What can I give, uh, you know, focusing outward as opposed to inward, which is something you talk about as well in the book. You know, focusing outward as opposed to inward, which is something you talk about as well in the book. And, yeah, it's all about, in my opinion, it's all about giving and being of service and creating that meaning for yourself.

Totally. You talk about will. What is will? Yes. So I use the, you know, I think we know willpower, which I think we think of as sort of a strength. But the Stoics have a slightly different definition of will. Will was this idea of, like, look, we don't control the world around us. And how do we assent to these things that happen to us? So a lot of what I talk about in the last third of the book is not about so much what you can do, but how you respond to the

things that happen to you. So, you know, I talk about persistence a lot. I talk about this philosophy known as amor fati, which is sort of like loving everything that happens to you. So instead of just like, oh, I can tolerate that a bad thing happened, or I could tolerate that I fail. It's like, how can you see intensely that something amazing has actually just happened? So I tell the story of Thomas Edison and his laboratory burning down. And he actually runs this scene with excitement. He's enjoying seeing it burn down because it's this, one, it's a beautiful sight. And then two, it was like, he knew that now he would have to

rebuild and it would force him to be creative and try new things and um it would infuse him with a kind of energy again so i look at these people who've had terrible things happen to them and they responded with like a thoughtfulness and an acceptance and they also kind of, other people who had really bad things happen to them, and the first thing they thought of was other people. Like, what can I do for other people? So like one of the famous examples is in the prison camps of Vietnam, the handful of Navy and Air Force pilots who were shot down. It was this idea of like, okay, this is like one of

the worst things that's ever happened. But I have these men who depend on me. And I can't let them down by being weak, by giving in by giving away information, I've got to like, I've got to be strong for these other people. And so to me, will is this really strong, super attractive idea. And so to me, will is this really strong, super attractive idea. It's not about sheer strength. It's about endurance and fortitude and the ability to be flexible in front of unchanging things. I like that. Flexibility is definitely key because things are always changing.

Yeah. And if you're set in your ways and your way of thinking that it's supposed to be a certain way in any moment, you know, something can go in flames, you know, literally or, you know, not literally. But so being flexible and being able to adjust is a huge, huge component of success. And, you know, that's the obstacle when something big happens. So it looks like some situations you can't change and you've got to accept that. Like, I think strength and perception, those are all very important in terms of changing obstacles, but some obstacles are, are insurmountable, right? Like, you know, you get cancer or, uh, you lose your arm or, you know, really bad things can happen. And we, we have to accept that that does happen in life. And then it's, how can you use this thing as an

opportunity to inspire other people to be strong? Um, you know, recently, um, like my house got broken into and, uh, and a lot of my really prized possessions were stolen. And it was like, I could get, I could despair. I could be really upset. I could be pissed off, or I could remind myself that maybe it's not a good idea to have such, such a strong attachment to a bunch of material things that could disappear at any moment. Um, and, and I think will and willpower sort of pivoted around those ideas makes you extra strong. And it requires us doing some uncomfortable things. It's like, you know, I talk about, you know, sort of thinking negatively and thinking about like what really is the worst case scenario.

So you're prepared for it. Like, you know, when you launch a product or I'm putting this book out in May and it might not sell any copies. I don't think that's what's going to happen. And I'm working my ass off to make sure that it does sell. But like, you know, God forbid something happens and it doesn't sell. I can't let that come to me as a shock. And I can't let that say anything to me about me as a person. And I have to be prepared for that. One, so I can prevent it, but two, because I can never guarantee that it won't. And yeah, go ahead. I was just going to say, you know, a lot of people are attached to results. They're attached to the way they want it to look the way that they think it's supposed to

look. And like you said, you're going to launch this book. And if you were like, you know what, this has to be a number one New York Times bestseller. Otherwise, I'm going to feel X. And if you are attached to the way of results, then you're just screwed. You're going to be screwed. You're going to feel a lot of emotional stress. You're going to hesitate moving forward. You're going to be screwed. You're going to feel a lot of emotional stress. You're going to feel, you're, you're going to hesitate moving forward. You're probably not going to take as big of risks and you're going to, you know, not be as confident. All these things are going to hold you back. So I think that's a brilliant concept is not being, you know, attached to, I think you said it better than I've ever heard it said before, which is, yeah,

people are too obsessed with, with, or too attached to results. And, and you probably learned this in sports, which is what matters is how you played and whether you left everything out on the field. You don't, at the end of the day, you don't control the scoreboard. You don't control the reps, what happened at the last second, right? And you, you're gonna, there's going to be games where you did everything you could and you still lost and you have to accept that. And to go back to what we were talking about, about doing your job, what you want to be able to walk off the field or, you know, the boardroom or, you know, your computer every day is knowing that you did your job. Like you did everything that you could and you were, you were aiming towards the desired result, but whether or not you achieve it, does it impugn the purity of what you did

with your effort and with your attempts? Right, right, I like that. And I think you give examples about entrepreneurs and how they're flexible and they're not attached to results, at least the successful ones aren't. Right. Because they're launching things all the time, they're shifting, they're trying new things and they, their intention is to create a specific results. But if they're

attached to that, they're probably going to be a fail, you know, fail longterm. Just like you control your efforts, you control your intention. Like you set out to do this, you set yourself up and then sometimes the world intervenes. And then in that moment, you have the ability to decide whether you switch to something else, whether you use it as an opportunity to do something new, whether you use it as an opportunity to help other people. when you've put everything you had into something and then the world says, nope, I'm sorry, it's not going to happen for you, that's where you're being almost most severely tested and how you respond in that moment

says a lot about you as a person. Yeah. I want to shift a little bit out of the book. And I want to know what your personal vision is. My personal vision of what? What's your vision for yourself and the world? You know, it's really weird being, you know, I've been able to accomplish a lot in, you know, a relatively short amount of time. And I always wanted to be a writer. I sort of set myself on being like a best selling author. And I wanted to be able to reach people and have an audience. And I, I accomplished that

earlier than I set out to do. Right. And so for me that, that the vision is sort of, it's like, how do I, I get to, I I'm D I'm living like exactly what I dreamed that I would get to do. And now I, now I have to think about, you know, how can I get better at it? How can I help other people? How can I, how can I continue to challenge myself so I don't get complacent? And how do I present, like, you know, when you achieve success, temptations come along with success about, you know, starting to associate, you know, with money or with certain kinds of people or coasting on past success. So my personal vision is, is when I think about it, I think about discipline and I think about, you know, paying it forward to a certain degree. Those are, those are the two things that I think a lot about. And, and of course, um, getting the best

out of myself. So I'm not growing complacent and, you know, I never want to be in a position where I'm phoning it in. Okay. Now, why do you think that way? Why do I think that way? Why do you think that way about your vision? Like, why do you want to live that way? Um, I, I think, you know, I think, um, I think that's your, that's your obligation as a person with talent, right? And I think when you have skills, you owe it to the world to continue to pursue those skills and to be good at them and to display them and to teach them as best you can. I like that. Now, in my opinion, it's always someone with extreme talents and has

a lot of success early on. I've always seemed to find this thing in everyone who's had extreme talent and success early on, that there's been a huge obstacle, setback, emotional burden, that there's been a huge obstacle setback, emotional burden challenge that they face early on. Is that true with you as well? It's weird. I've like, I've been asked that question a fair amount and I know I'm going to get a bunch more with the book.

I'm kind of not trying to talk about my personal obstacles because like I, because like everyone's obstacles are relative. Right. And it's like, it's like the last thing i would want to do is talk about like some breakup i went through when i was like a kid and compare it to like somebody else who was born into like complete and abject poverty right sure um so everyone has everyone has their own you know emotional battles though and it's uh you know

whatever emotional battles we face it doesn't matter which one is bigger than someone else's. It's what drives us. Totally. And it's what those challenges and those obstacles are what make us who we are. And so for me, you know, like I dropped out of college when I was 19. self-taught, sort of been in the crucible of stress and high stakes and pressure for as long as I can really remember at this point, my entire adult life. So for me, my obstacles, I think it's less about like, oh, this big thing happened. And it's more of a sort of a daily test with myself and against like the other people around me to, to continue to show up every day, to do a

good job and to turn, to turn the stress and the pressure into something that makes me better rather than something that, you know, wears me down or feels like a burden. Right. Do you, have you ever always considered yourself an underdog? Um, I mean, I don't, I don't, I don't, I don't think about myself as like an underdog, but I do. I always, I think, I think there's always something that I'm trying to prove. I don't necessarily know who I'm trying to prove it to, but I, even if it's just myself, but I feel like I'm going out there and like, for instance, I'm like for exercise, I run. And when you you run you're challenging yourself

right that's the only it's how much further can i go how much faster can i go i don't want to go today but i'm going to go anyway so for me it's that sort of i think i'm always challenging myself and that's who i'm competing against like my own standards for myself rather than like i'm an underdog against these other people what do you think is more important having a wise mind or a big heart well i would say that without without either you're sort of you're sort of lost but um Without either, you're sort of lost. But what do I want?

I'd rather have more people out there with big hearts than wise minds. But weirdly, I would say that I think in some ways it's easier to have a wise mind than a big heart. Wow. Why do you say that? Because a wise, it's like, is it, a wise mind is about the sort of the journey and the things that you subject yourself to. And I think a big heart is about empathy and being able to put yourself in other people's shoes and think about other people. And maybe that's just more difficult for me personally, but I think one is a journey that only you go on and the other is something that you do with other people.

Wow. I love that interpretation of that. Do you ask everyone these questions? I don't think I've ever asked anyone that question. Interesting. It's a good question. It's a good question. I bet it reveals a lot about people. Why do you have a challenge? So, so do you, you say you struggle with that? Is that what you're saying? Yeah, I think so. I think, I think having a big heart is, uh, I think it's easy to be selfish and, and, you know, focus on yourself. Right. and focus on yourself. Right.

Huh. Interesting. Okay. Now here's a question that I asked Simon Sinek recently on an episode. And he wanted to come back and do a whole episode on this. So I'm interested in your interpretation of this being younger. How old are you now? I'm 26.

26. And I think he's like almost his late 30s or something like that. Yeah, I know Simon. He's great. Yeah. So I asked him, you know, I feel like you've got a big vision for the world, right? Like for your place in the world, you want to achieve big things, you want to have a big impact, you want to reach a large number of people and inspire them through your message, through your words your words, through your content. And, uh, do you think, and you also have a girlfriend who's fiance. That's right. Congratulations by the way. And she's lovely. And you guys have a goat, which is two goats, which is amazing.

I see your pictures on Instagram and stuff or her pictures anyways. And, um, mom, I'm curious since you guys have been together for like six years now, I think. Do you believe that you can have a huge impact on the world and also have a balance with a relationship, be married, and have children, and have an impact on them with as much intensity? Can you have both, basically? Can you have extreme success and can you can you have like extreme success and a balanced normal personal life yeah you know i think of like oprah i think of people who aren't married like oprah and some other people that are changing the world based on a lot of people's minds and um but don't think they can have kids and be married because of

sure well i mean i've dealt with a lot of really really successful people like people who have been way more successful than i intend to be or probably ever will be and what i see when i look at them and i compare myself to them is there's like something missing like they have an extra either drive or peace or perhaps a darkness or a need that has to be fulfilled that I don't, that I don't have as much. Right. And like, I love being home with, with, um, Samantha. I, I, I take a lot of great pleasure and value out of that relationship. And it means more to me than certain kinds of success. Like, so I, I feel like, like my work is what I'm meant to do. And it means more to me than certain kinds of success. Like, so I feel like like my work is what I'm meant to do. And it is it's very valuable and I feel obligated to it.

But I also don't feel like I think there are probably things that I could do or steps that I could take that would double or triple my income. Sure. that would double or triple my income that are not important to me because that money doesn't mean anything to me and the cost that it would have would be too much for me. So in a weird way, I feel like having been in this relationship for a long time, it's made me successful.

Has it held me back in some ways that other people were not held back? Yes. But I would say gladly and that it helped me because I don't – a lot of the really successful people that I know have a sort of a darkness or a demon that I bet they wish they could be free of. Wow. Interesting. Their own obstacle. Sure. Like, you know, there,

it's one thing to feel like you have something to prove and it's another thing to feel like you're never getting any closer to proving it. And that's like, that's a terrible curse. That's being like paralyzed to, you know, that, that way of thinking. Yeah. It's like, like, look, do you want to be Napoleon? Which, where you, you accomplish everything of thinking yeah it's like like look do you want to be napoleon which where you you accomplish everything and then lose it all um because you want more and more and more like that doesn't that's not appealing to me i would much rather stay at home and have a have a happy life and in obscurity right i like it man, any final thoughts on, uh, the obstacles, the way before?

Uh, no, no. I mean, I tried to leave it all out in the book. I'm really, really happy and proud of it. I think it's for me, it's weird to say this about something you did, but it's like one of those, if anyone has ever worked on something and then you sort of look at the final product, you're like, wow, where did that come from? For me, this is that. So I'm really happy with it. I really feel indebted to all the people who contributed to it and the people whose stories make up the book. I hope people enjoy it and if they ever have questions, they can reach out to me and I'm happy to help or answer anything. to me and I'm happy to help or answer anything. Yeah. And this is a book, you know, after going through this book and, uh, you know, I'm holding it in my hands right now. I'm like, I would be really proud if I could write a book this. Oh, thank you. So, uh, definitely congratulations. And I encourage everyone to go check it out and buy it on Amazon. Uh, where can we find you online? Where can we find the book? Where can we connect with you and, you know, so Ryan holiday.net is, is my site.

Um, I'm on Twitter at Ryan holiday and then I give out monthly book recommendations on my site. There's like a little thing that comes up and I like all the, all the books that made up this book I've, I've been recommending over the last six years to something like 15,000 people. I send out these, these, um, all, all the favorite books that I read every month. Um, I recommend them there and I, I hope to, to recommend some to, to the people that listen to this.

Yeah. I encourage you guys to go sign up for that. It's a, it's an awesome little, little email delivery there. So Ryan, final question. Yes. What's your definition of greatness? Ryan, final question. Yes. What's your definition of greatness? My definition of greatness. Greatness is maybe what we were talking about where it's when you've given everything that you have to a single idea or concept and you've built it. I like that line. There's a line from – what is his name?

There's a line from, what is his name? The playwright who wrote Streetcar, Ben Desire, he says, it's etching your name in a cake of ice on a hot day. I think that's greatness. I love it. Ryan Holiday, thanks so much for coming on, my man. I appreciate you. and thanks so much for listening to this episode with Ryan again make sure to check out his book The Obstacle is the Way the Timeless Art of Turning Trials into Triumph you can check him out at ryanholiday.net and his book is on Amazon and all over the place.

So check that out. Give Ryan some love and some support. Pick up a copy or two. Give one away to a friend and I know you're going to love it. It was a great read for me and I know you'll love it as well. And make sure to check out the show notes over at schoolofgreatness.com or lewishouse.com. And if you guys like this episode, go ahead and subscribe. Please subscribe over on iTunes and leave a review.

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