Transcript

Episode 28: The Art of Living With Ryan Holiday

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Paul Kix:

Hey, it's Paul Kix, welcome to another episode of Now That's a Great Story. The podcast examines a single story from our most singular writers, as a way to reveal an artistic worldview and along the way, help you be just as creative. My guest today is one Ryan Holiday an entrepreneur, common man philosopher, and multiple New York Times bestseller, whose latest book Stillness is the Key, had just a profound impact on me. It helped me reevaluate a lot about my life and today we're going to discuss the chapter that left me, no joke, nearly weeping. So Ryan, thanks for coming on and for getting me into that emotional state.

Ryan Holiday:

Yeah. It's good to be here and I'm very curious to hear what chapter this could possibly be.

 

Paul Kix:

Before we get to that chapter, look you're a fascinating dude to me, right? Because I came across something you wrote maybe just 18 months ago. And since then I've read three of your books, dozens of your essays, at the heart of them all seem to be how we should live. What motivates you in life?

Ryan Holiday:

I guess that question, because I don't think I know the answer. I think when I look at what I read and what I write about, it's kind of trying to find what that is. I mean, to me that's the primary aim of philosophy, that's what religions are trying to get to the answer of, that's what I feel like we're all kind of groping around in the dark to find. And so, I guess I'm just interested in that, how should a person be? How should they live? What's the way to do this? And I mean, the interesting thing about life is you only get to do it one time. And so, it's kind of weird that we just figure it out by trial and error.

Paul Kix:

Yeah.

Ryan Holiday:

And so I guess when I fell in love with ancient philosophy, it was discovering that, oh, really smart people have been kicking this thing around for a long time.

Paul Kix:

Have you always been this fascinated?

 

Ryan Holiday:

I mean, generally I get, like do you mean always been fascinated or always been fascinated with this question?

 

Paul Kix:

I think probably both in the end.

 

Ryan Holiday:

I think I've always been someone who's a bit obsessive, who sort of goes down rabbit holes and gets really interested in things. I don't know exactly when that question sort of occurred to me, but I think it struck me that there's not a lot of instruction anymore related to these questions. Like as someone who loves history, I think what's interesting is, when you read the history that people used to read. So when you read someone like like Plutarch, who's sort of you know the historian for most of the generations before say like the mid 1800s, or the late 1800s. If you wanted to learn about ancient Greece and Rome, you didn't learn about it from a Harvard professor, from a documentary, obviously, you learned about it from, or even from a textbook because these things didn't exist. There was just a few classic texts that you might read, and Plutarch's one of them.

 

When you read someone like Plutarch, it's so obvious and retrospect, that a lot of what he's talking about is just sort of not correct, it's just sort of impossible, or exceedingly unlikely that things went the way that he's saying. But you realize, I don't think he was like a particularly naive person, I think it's that he saw his job as a historian to teach people lessons, not to teach them verifiable facts. I guess, long way of saying, I feel like I was searching for something that I wasn't getting from my parents, from school, from sort of popular culture. I was, wanted instruction on how to live, how to be, and it's something I think doesn't really exist anymore, and maybe that's what I try to attack on my writing.

 

Paul Kix:

Is there something in your personal life that led you to seek out this sort of ancient wisdom?

 

Ryan Holiday:

Not really. I mean, it was sort of a strange, I'd been interested in history and sort of been interested in reading but, I was at this conference in college, I was writing for the college newspaper, and I was at this conference, it was sponsored by Trojan condoms, of all things. It was for college journalists. And for whatever reason, Dr. Drew Pinsky was the speaker, and afterwards I just went up to him and I asked him, what was he reading? And did he have any recommendations? And he told me about Epictetus, it was sort of the first stoic philosopher that I had ever heard of. And so clearly, just the idea that an 18 year old would go up to someone that they'd seen on television, who mostly talked about sex and drugs and things, and my impulse was to ask them for a book recommendation, clearly there's something I was looking for? Why and what that was, I'm not exactly sure.

 

Paul Kix:

There's something I kind of want to know about just you and your path and expose the audience to this as well. You start out, walk through this, are you in American Apparel for a while, and then you're with Tucker Max because, if I can just be honest for a second, somebody who's writing the chapter in the book that we will discuss today, is not exactly at least, from my perspective, the same sort of guy who would work at American Apparel or, would work at Tucker Max and anybody who doesn't know his books, like one of them was called I hope They Serve Beer in Hell, right? So-

 

Ryan Holiday:

Yes.

 

Paul Kix:

How does that guy become this guy?

 

Ryan Holiday:

So it's actually weird. The reason I ended up sort of meeting and connecting with Tucker is that on his website Tucker had a list of books that had been influential in his life. And obviously, people's sort of perception of him is primarily through his books and his sort of relatively obscene brand and personality. But, Tucker went to Duke Law School, he graduated from University of Chicago, he's a extremely smart person. So, I don't remember how I came across his stuff, but I remember coming across that list of books, and reading all of them. And those were some of the first really smart books that I ever read.

 

Paul Kix:

What are some of those books and how old are you when you're reading them?

Ryan Holiday:

I'm in high school. So I remember that's how I heard about Robert Greene, so I read the 48 Laws of Power, I read The History of the Peloponnesian War, that's how I read my first couple books about evolutionary psychology. So they were not, these were sort of graduate level classics in some cases. These were like smart books, right?

 

Paul Kix:

Yeah.

 

Ryan Holiday:

And these are, I didn't know anyone that went to University of Chicago, or law school really at all probably. So, all of a sudden this is like an introduction to a world that I'm not familiar with. But Tucker and I connected, my sort of personal life could not have been more different than his. I think we connected primarily over that, and I ended up becoming sort of like a research assistant for him, and then I worked on the marketing for his books, and I helped him build out the company that he built. I worked on the movie that they built, or that they made around the books. So, my connection with Tucker was much more sort of intellectual than it somehow was based on the actual material of his stuff.

And it was, so through Tucker I met Robert Greene, because I had read the 48 Laws of Power, and then it happened that they knew each other. And through Robert Greene, who's on the board of directors at American Apparel, that's how I ended up working at American Apparel.

 

Paul Kix:

Before we go to Stillness is the Key. I think there's one other thing that the listeners should kind of understand about you. And that is that Stillness ... This is the final chapter in a trilogy of books that are each arguing something different. So, would you mind just briefly walking us through what you were hoping to do with each of these books and how Stillness is in some sense, the epitome of what you're trying to argue?

 

Ryan Holiday:

Yeah, so the first book in this series is a book called The Obstacles The Way which is built around a quote from Marcus Aurelius basically it says, what stands in the way is the way. And it's about this stoic exercise of taking difficulties, or obstacles, or adversity, and sort of finding good in them, finding opportunity inside them. Sort of how one goes through that process. So that book came out in 2014, and let's just say that people were not expecting big things from it. My first book had been this sort of controversial marketing book that had gotten a lot of attention, I'd written another marketing book. And-

 

Paul Kix:

Yeah, what was the, just real quick, what was the title of that first one, that first marketing book? I am lying to You?

 

Ryan Holiday:

Trust Me, I'm Lying.

 

Paul Kix:

Yeah. 

 

Ryan Holiday:

And so yeah. So when you go to your publisher and you're like, for my next book I want to write about an obscure school of ancient philosophy, they were not super excited. And look, I remember people, a close friend was sort of like, I heard about this after, but it sort of predicted that the book would be a colossal failure, that it sold like 5,000 copies, and so I didn't really know what to expect with it. But the book came out and it it sort of created this kind of resurgence, this renaissance about ancient philosophy, particularly stoicism, the books now in like 30 languages and it's sold really well and it made its way through professional sports, and politics, and the military, and business. But it was sort of the first book in this series.

 

And then the second book, which I actually started working on before, Obstacle had really blown up, Obstacle took kind of a while to get going, the title is, Ego is the Enemy. And a good portion of that is sort of built around the, or was influenced by the collapse of American Apparel, the collapse of my relationship with Tucker, with a handful of other people who had been very influential in my life, and sort of looking at how we often get in our own way, this sort of toxic force of ego, which I think affects everyone, but primarily ambitious people. And so that came out in 2016 right before anything to do with the election was sort of on the radar, so also ended up being a little bit, sort of perfectly timed.

 

 And then Stillness is the same style, same structure, same approach, but the argument is that sort of Stillness or the ability to slow down, or steady oneself as the world is kind of spinning around, that this ability to access that stillness or that insight, or that clarity is sort of the key to not just elite performance, but also personal happiness and contentment, and all the things that are important in life.

 

Paul Kix:

Yeah. So let's get to the part that nearly had me crying.

 

Ryan Holiday:

Okay.

 

Paul Kix:

Can you tell people what happened that day that Kurt Vonnegut and Joseph Heller went to that rich guy's house?

 

Ryan Holiday:

Yeah, well, it's probably something you can relate to as a writer. You get invited to these parties sometimes and you show up and you're kind of like, why am I here? I have no business being here. And you realize that one of the things that rich people do is they, one of the things that rich people do is they kind of collect writer intellectual types, and they invite them to parties and just sort of see what happens. But Joseph Heller and Kurt Vonnegut, Joseph Heller writes, Catch 22, Kurt Vonnegut writes Slaughterhouse Five. They're at this party of this billionaire, and it's, in some place, probably in the Hamptons or something like that, someplace outside New York City.

Vonnegut is kind of teasing Heller, he says, "How does it feel to know that that this guy made more money this week, than Catch 22 will make in its entire lifetime?" And Heller says, "I think I've got something with this guy doesn't have." And Vonnegut says, "What could that possibly be?" And he says, "I have enough. I have a sense of what enough is." Vonnegut's just bowled over by this, just the beauty of that one word, enough. And when I read that exchange for the first time, it's actually told in a poem in Vonnegut's book, Man Without a Country, I think I had the same reaction. It's like, wow, that's amazing. What would it be like to have enough? What would it be like to feel enough? And yeah, it was just so, it was a really important story to me that I wanted to tell in the book.

 

Paul Kix:

How did you know, how do we know that Heller felt that way? Or how he got to that point where he realized that, oh, I actually have enough right now.

 

Ryan Holiday:

Yeah, I mean, I guess we don't know.

 

Paul Kix:

We don't know for sure, yeah.

 

Ryan Holiday:

Yeah. I think I think it's a struggle within every person. I mean, I could imagine people who knew him would sense that it was a constant wrestling match, and I sort of feel that in my own life. But, to just even get there fleetingly, to even get there for a few minutes I think it's really powerful. And even if he's totally full of shit, I mean, just I think there's something in that quip there that, the idea of having enough is really powerful. And, one of my favorite stories in the ancient literature is this exchange between Diogenes the cynic and Alexander the Great. And there's a a bunch of exchanges between them and they're, who knows they're probably all made up, they all come to us from Plutarch. But the idea is that Alexander the Great's the most powerful human being the world has ever known.

 

He's conquered all of the world's and Diogenes is a guy who has nothing. He walks the street, he lives in rags, he has sort of forsaken all worldly and material pleasures, or material goods. And Alexander the Great walks up to Diogenes who's sort of laying there sunbathing and he says, "Diogenes, I'm Alexander the Great, I'm the most powerful man in the world, what can I do for you?" And Diogenes says, "You could you could move you're blocking the sun." And, the idea, the moral of that story is that, here Diogenes has gotten so powerful, and so independent and self sufficient that there's nothing the most powerful man in the world can do for him, or that he needs from the most powerful man in the world. And Alexander the Great as he leaves this exchange supposedly says, "If I were not Alexander the Great, I should be Diogenes."

 

And that's to me that idea of enough that, if you can get to that place of self sufficiency, or having met your basic needs, you have an incredible power because now people can't buy you, they can't bribe you, they can't make you feel insecure, they can't make you feel less than. And so what would it mean to produce work or to live a life from that place?

 

Paul Kix:

Yeah, and that is the, see so this, now we're starting to get to the thing that I found really powerful. And for me personally as I was reading this chapter, there's this line that you use, "You will never feel okay by way of external accomplishment, enough comes from within." And what you end up arguing is, there's this common refrain that money will never buy happiness. But what you're arguing here, and I would almost want to ask you this, if this is the argument of the book is that, you need to find a way to feel that even your accomplishments are, but money by another means, right?

 

Ryan Holiday:

Sure.

Paul Kix:

Everything that you're doing is for some sort of furtherance, whether it's money, or respect, or fame, or security, or whatever, and what this chapter really highlights through examples like this, like the ones you just cited is that, no you actually like, if you can just find a way to step back, you actually have everything you need in front of you right now.

 

Ryan Holiday:

Yeah that's one of the things that stoics talk about, [inaudible 00:17:23], very little is needed for the happy life. What I think is so interesting about this stoics, and I think this is an argument I'm trying to make in the chapter. It's not that stuff isn't nice, it's not that accomplishments aren't nice, and I think this is where maybe the Buddhist kind of get it wrong, or at least my reading of it strikes me the wrong way, is that Buddhism seems to be sort of a striking off of those things. It's sort of saying that, these things are inherently worthless, that you shouldn't need them, that they're meaningless, that all that matters is sort of the inside.

 

And I like the stoic model which is like, Seneca goes like, "There's sort of good and there's bad," and then he says there's, and then you should be indifferent to everything else, right? And then he says, "But there are some things that we might call preferred indifference." So he says, like it's better to be rich than poor, it's better to be tall than short. A wise person would be able to manage either of these, but doesn't need them either way. So look, when Stillness came out, it debuted at number one on New York Times, which is the first time that's happened for any of my books. It was fantastic and wonderful, but it didn't change anything for me. So it's like, if you said, Ryan, you can choose this book is going to not hit the New York Times list or it's going to debut at number one on the New York Times list, what do you choose?

 

Obviously, I'm going to choose hitting the list. But, what I was trying to do, where I've tried to work myself in my life, and in my career, is to get to a place where I don't need it one way or another. So it's a preferred indifferent, like it's great that it happened but if it hadn't happened, it wouldn't have changed my opinion of the project, it wouldn't have affected my mood in any way. In fact, I sort of actively, as I was going through the process, tried to prepare myself for the likelihood of it not happening, because it's so much outside of my control, and I've been stiffed by the list on several occasions in the past. And so, trying to work myself to a place where the happiness and the pride that I'm taking in the project are primarily rooted in what I have, and that there's no, sorry, what I've done, what I control, and that there's no external thing that somebody else controls that gets to decide whether I'm good or not.

 

Paul Kix:

Yeah, yeah. And at the risk of kind of turning this interview into a therapy session, honestly like, that's the thing that I struggle with the most, and it's not about money, right? Like, I'm a writer, I'm a journalist, I gave up the idea long ago that I'm going to be the richest guy in town. But it's the thing, the thing that I want and still struggle with is the acclaim, or at least the, even just not, sometimes when it's not even the acclaim, it's just the accomplishment itself, for that to live out there and to draw some sort of satisfaction from. And to a certain extent that's fine, but also, what this is kind of arguing is that, you should try to be industrious, but if you are going to be judged by your industriousness, that's actually not all that great. And I found that to be something profound and something that until I read this book, I hadn't fully considered. How long did it take you to come to this to this assessment?

 

Ryan Holiday:

Yeah a long time. I mean, look, I think it's complicated. because, and even that thing you said that even deciding I'm not going to be the richest guy in the world, that's a mistake I see a lot of writers and creative people, or people in all professions make, right? It's like, I'll be talking to writers and I'll be talking about how much money they want to make from project or whatever, and how big their deal is, and it's like, look if money was the most important thing to you, you picked the wrong profession. Like go sell drugs, or go work on Wall Street, or go be a consultant, like you picked a bad ... If money is the primary way that you're going to judge success, this is is the wrong profession. It's not that you can't make money, and it's not that you shouldn't make money, but you picked the wrong one.

 

And so, or I would argue you picked the right one, deep down money is not actually the most important thing to you, but because that's an easy metric to judge oneself by, you are defaulting to that, or you're trying to sort of straddle two mutually exclusive strategies at the same time. So, it's just going like, okay, money can't be how I judge my success, because it's just not the right metric for the industry that I'm in, right?

 

PAUL KIX:

Yeah.

 

Ryan Holiday:

It's just not what it is. But, you said the word industriousness, I think industriousness is a great measurement of success because you control how hard you work. What you don't control is how recognized that industriousness will be. You don't control the results of the industriousness. So I think the insight for me, and this comes from the stoics, but it's also in the Bhagavad Gita, it's in most of the ancient traditions. It's this idea that, you control the effort, but you don't control the results. The story that I find quite compelling is, and I think this is in The Egos is the Enemy, is the story of John Kennedy Toole who writes A Confederacy of Dunces. And it's immediately rejected by his agent, it's rejected by his publisher. He's so devastated by this rejection that he ends up, he kills himself.

 

And his mother finds the manuscript in a desk drawer and she takes it to Walker Percy who's a professor at Loyola Marymount in New Orleans, he sees it as a work of genius, he publishes it, and it wins the Pulitzer Prize. It's the same book, right? Like he's dead, he does not adjust the book in any way, and yet somehow, a book that was rejected is also the book that wins the Pulitzer Prize. And you just realize, oh, the recognition, the what other people say or think about it, is totally arbitrary, it's totally outside your control, and it's often very, very wrong. And so to decide that you're going to hand over, the thumbs up or thumbs down on something you're writing to these people, I mean, look even, like let's say, you worked your whole life to be a Nobel Prize winning scientist and then it turns out that the committee is like, got this horrible sexual harassment scandal, and it's corrupt.

 

And it's, you know, it's like ... And even to go back, it's like, wait, this is like a prize put on by the guy that invented dynamite. The idea that you're going to let an external group who is primarily composed of people who don't know what they're talking about, decide whether you've done the thing that you set out to do or not, to me is just a bad way to live. But it's also a dangerous way to live. Marcus really says it, "Insanity is tying your success to what other people say or do." And so I think that thinking sort of has wormed its way into what I'm talking about in that chapter, and how I try to run my career, which is primarily judge it based on what I control, which is, did I do the work? Did I get close or as close as I think it's possible for me to get to the idea I had in my head? Those sort of things. That's how you've got to judge yourself.

 

Paul Kix:

Yeah. And that's actually Aurelius's quote, and I think it's one of the more famous ones in meditations is something to the effect of, you can control your thoughts, and you can control your actions, and you can control nothing else, right?

 

Ryan Holiday:

Yes.

 

Paul Kix: 

And when I was finishing my book, there was a part of me that was just stressed the hell out because it's like, man, there was this movie option attached to it, and there was all this pressure like, okay, are they going to exercise the option? And what's going to be the critical response? And it was really like, I turned to Aurelius and I was just like, okay, I've done, to your point a minute ago Ryan, I have put in the work, I have written the best book I possibly can, and sort of fuck all what can happen from here on out, because this isn't my game anymore. So that's helped me. But I want to return to Enough because I don't know if I quite phrased it correctly, but it's the, for me and let me put myself back on the couch for a second.

 

Ryan Holiday:

Okay.

 

Paul Kix:

For me, the thing that really got me when I read this, I don't know, three or four months ago, because it's a fairly recent book. It was published when?

 

Ryan Holiday:

It came out October 1st.

 

Paul Kix:

Yeah, but I actually got an advanced copy so I probably read it a little bit over the summer, right?

 

Ryan Holiday:

Yeah, I think so.

 

Paul Kix:

Okay, so what got me was this sense that I have that, okay, accomplishment is one thing, industry, excuse me, industriousness is one thing, but the actual practice of industriousness and wanting to do more, and more, and more, I mean, I'm not just an editor, I'm also a journalist, I'm not just an author, now, I'm also a podcast, right? Like, it's the sort of accumulation of all of these things that end up, in some ways driving me on, but also in some ways driving me almost mad, right? Like-

 

Ryan Holiday:

No I can relate. I mean look, I've done, I'm 32 years old I've written nine books, and I'm in the middle of 10. So I have that same impulse to do, and it's there, right? There's no, rational reason that, I'm selling the next book right after I finished the other one, if there wasn't some sort of childhood issue, or some sense of, if I can just do X, then finally I'll feel good, or my parents will be proud of me or, I'll be accepted by that group or, I'll be part of the club, right? So I have that, and I relate to it and I'm criticizing myself in this chapter as much as anyone else. But, when I think about why the books ... So it's so it's like that insatiability, that's what gets me the deals. That's what gets me to rush out the proposal to sell it, to get myself on a deadline that I now have to meet.

 

But when I actually look at why the books have worked, or why I'm proud of them, or why they're good, it didn't come from that place. So, it came from a, like it didn't come from that place of craving or the needing to do, it came from the actual love of the process, or the experience, or the moment. And so to me those sort of parts of myself are kind of in a tension, and I guess what can happen is you kind of give yourself over to that sort of more motive driving part, the craving part, because you see that it's taking you somewhere. But the problem is, you tell yourself that this is going to get you somewhere good. It's like, hey, when I win a World Series, then I'll be good. When I hit number one then I'll be good. When I get a check for a $1 million, then I will feel like I've arrived. We tell ourselves that when we get that thing, then we'll be good.

 

And the truth is, and I think this is what Heller is talking about, you actually have enough right now. It doesn't mean you need to stop, or that you even should stop, it's just don't keep doing under this, why that on the other side of it is going to be the thing that you could actually have right now if you just looked for it.

 

Paul Kix:

So what is it that ... So, okay, so you've tried to separate this and I'm just curious now. For your own ambition, and, again, you're a fascinating dude to me because, you're not just writing books. You're an entrepreneur, so can you talk a little bit about that and what you do?

 

Ryan Holiday:

Yeah, I mean, this morning, I spent most of it writing a book that I sold for someone else, and then I had a meeting with my partners, we were talking about, we've built out this business called Daily Stoic that has these cool products that are about the philosophical ideals I write about. And then, Monday I'm leaving, I got to go travel overseas for a talk. So, yeah I'm busy, I'm doing stuff all the time. I guess where I'm trying to get, and where I think I've gotten closer to, is just actually sort of being present for all of it and enjoying all of it, and not needing any of it. So it's like am I going on this talk because I need the money because I want to buy something? Am I going on this talk because, if I can just get in front of that crowd I'll feel good? Or is it more like, hey, life is short, it's cool to go here, I'm in the middle of writing I can write anywhere.

 

Ryan Holiday:

To me what I'm interested in is, can you, and I guess this isn't really answering the question. But it's a question I try to, I think informs a chapter, and it's trying to inform my life. Which is, can you be great? Can you be world class at what you're doing and do it from a place of fullness, not from a place of craving? Like, here's an example. I was thinking about Kevin Durant leaving the Warriors to go to the Nicks, I'm sorry, to the Nets.

 

Paul Kix:

To the Nets, yeah.

 

Ryan Holiday:

If he's leaving because he wants a challenge it's like, hey, I want these championships, I want to not do the same thing over and over again. I want to continue getting better, I just want to live in New York City. I love the process of building a team from scratch, I love learning a new system, I want to play in a different division, blah, blah, blah, blah, blah. Those to me would all be great reasons to leave and to me, that'd be a place from fullness right? Like, I've had this great career, I want to continue having a great career, I'm going to do that. If, and I think some of his comments give this maybe lend itself more to the second interpretation. If it's because he's mad that Draymond Green was hassling him, and that he wasn't getting the respect that he deserved in Golden State. If he's leaving, because he feels like he has to win a championship by himself to prove that he is actually a legit contender.

 

If it's because he thinks it will be different in Brooklyn than it was in San Francisco to win, that's a bad reason, to me that's a place of craving. And so, I think that's what Heller is talking about. Heller, it's not like Heller stopped writing because he had enough, because he'd done Catch 22 he never wrote another thing, he wasn't Harper Lee. He did write, but it just seemed like he actually enjoyed his life, that it wasn't coming from this place of desperation and insecurity, and the need to you know pile up accomplishment on top of accomplishment to show that he was a worthwhile person.

 

Paul Kix:

And this this isn't actually, I'm going to break the rules of the show for a second because, what I would like you to talk about, I don't think is actually in the chapter enough, but it is within Stillness is the Key. Could you tell the story about Dave Mustaine?

 

Ryan Holiday:

Oh yeah that's in Ego is the Enemy.

 

Paul Kix:

Oh I'm sorry see now I'm confusing the books.

 

Ryan Holiday:

No, no, they're similar stories. And I actually have my friend Mark Manson, also told us like a different take on the same story in the Subtle Art of not Giving a Fuck. But Dave Mustaine is a fascinating person, if you're not into heavy metal, Dave Mustaine is the original lead guitarist in the band Metallica. And basically in a band that had a horrible sort of drug and alcohol problem, he was too much of an alcoholic and they fired him. And, he goes on and he creates a band called Megadeath. And Megadeath is also a great heavy metal band, probably top 10 best ever, sells millions of albums, tours the world, he's widely considered one of the greatest guitar players and musicians of his generation. But he had the bad luck of having been kicked out of the number one heavy metal band of all time. And actually, I don't think the number one, but they're definitely the biggest heavy metal band of all time.

 

Paul Kix:

They're the only band that anybody ever knows.

 

Ryan Holiday:

Yeah. And so, this just eats in him and if you've, everyone should watch the documentary, Some Kind of Monster, because I think it's one of the great musical documentaries of all time. But in the documentary, many years after getting kicked out of the band, they interview Dave Mustaine and he's still angry about it. So if he had, you watch it and if you didn't know who Dave Mustaine was, you would get the sense that he ended up living under a bridge somewhere. That he had sort of died, his career had died and he was broken and bloodied, and forever harmed by this thing. And in fact, he's gone on to have this incredible legacy, and this incredible career. But because all he could think about is what he lost, or what he'd been deprived of, or how he'd been screwed over, you could argue that he was still locked in this place of craving and insecurity, but also anger and bitterness, and rage about what had happened to him. And so-

 

Paul Kix: 

Because he is what? He's like, is he counting the number one albums that Metallica has, and with respect to what Megadeath does? Which was also a very successful heavy metal band, he was a millionaire many times over. But he wasn't the multi millionaire and the Grammy winner, and like the band, is that what's eating him?

 

Ryan Holiday:

Yeah, it's like they're touring in stadiums and he's playing in small arenas. They're making hundreds of millions of dollars and flying in private jets, and he's living the life of a

successful musician.

 

Paul Kix:                    

Yeah.

 

Ryan Holiday:

And it goes to that Theodore Roosevelt quote that, comparison is the thief of joy. And I think what happens, whatever success you, it's ironic that he's doing it, comparing himself to Metallica, but the irony is, if he was in Metallica, he would just be comparing himself to

other bands, and other genres of music.

 

Paul Kix:

Like the Beatles.

Ryan Holiday:

Yeah, that's what we do. We're incapable of, like we even do this to ourselves, right? For me, when I decided I wanted to be a writer, having success was a book. It was like, if I could publish a book someday, that would be amazing. Could you imagine being able to do that? And it's not even before it's gone to the printers, do you start thinking about where it's going to hit on the bestseller list. And then before you even frame your appearance on the bestseller list, you're like, how can I get a bigger deal for my next book? Or like, why isn't the publisher giving it enough marketing support? Or, why isn't my speaking fee as high as so and so, or whatever it is. The mind, I have a quote from Stefan Zweig, I think this is actually the epigraph for the Enough. But he says, "Never in history, do we have an instance of a conqueror being surfeited by conquests."

 

Nobody gets to the other side of the mountain and goes, I did it, I can go home. You look to the next mountain range. And that is undeniably good for the human species, evolutionarily this makes perfect sense. But at the individual level, as a person trying to be happy, this is a horrible way to live.

 

Paul Kix:

So this conversation mirrors the book in that, and this is what I love about your books and your essays. They aren't new agey, they aren't the constant sort of, I have to make put on appearance of being happy. And they're there trying to help you but they're not self help because so many of these chapters, and so many of your ideas are rooted themselves in anecdotes and stories. How do you even begin to research something like this? Because I'll be honest, I've been kind of blown away by the breadth and depth of other writers you're citing here. Because it's from ancient philosophy, to modern politics, to sports, I mean, like I said, like this conversation, you can go anywhere. So, do you have some sort of amazing card catalog at home, how do you do it?

 

Ryan Holiday:

I literally do have a card catalog, yes. See that's what I actually love doing. And so the funny thing is, when I read the 48 Laws of Power, what I did when I was reading it is that I was just taking notes. And then as I would read other books, I would be like, oh, man, this is a great example of, law number two, or law 37, or whatever. And when I met Robert Greene for the first time, and he was looking for a research assistant, it was like, seriously, this is what I was put on the planet to do. I was already doing this for free, never thinking I would meet you, solely for my own education. And so yeah, that's what I love. I love collecting stories, I love collecting anecdotes-

 

Paul Kix:

And just real quick, have you always been the sort of reader that is also keeping a separate notebook? Or when did that start?

 

Ryan Holiday:

I really don't know why I started doing that. I don't know why or when, but it just happened and yeah now I've been doing it for probably 15 plus years, maybe more. So yeah, I love collecting and I think this goes with that idea of wanting to know how to live. I'm just collecting this information, maybe I'll use it, maybe it'll go in a book, maybe it'll go in an article, maybe I'll give it to someone else. But that's what I really love doing.

 

Paul Kix:

Another sort of craft and process question. Because you've got your own business, businesses, and because you're writing, and because you're doing these essays on Medium and I don't know, Daily Stoic too, right. So, I'm just curious, can you walk us through a day in the life of writing, or a week, or how do you even begin to organize it?

 

Ryan Holiday:                Yeah, I think a lot about this because I do talk about routines in Stillness. So this morning, I woke up at 6:30, and I took my two kids for a walk, so my wife could catch up on sleep. So I went for a walk, and then I cooked breakfast, then I went upstairs and started writing. It sort of depends whether I'm going to write at home, or I'm going to go to the office or whatever but, I just, I sat down and I started writing. And so, I do a little bit of journaling in the morning, but for me the key is like, don't use your phone in the morning. Don't get sucked into email in the morning, don't agree to meetings or interviews, or phone calls in the morning, go right into the writing as early as possible, and try to knock it out early. So like I was done by by noon, not done for the day, but I was done with the writing that I really needed to do by noon.

 

Paul Kix:

Okay. And then what, this is just sort of, just to bring it full circle because I want to sort of impress on people how busy you are to a certain extent. Because you have another book called Perennial Seller and-

 

Ryan Holiday: 

Yeah.

 

Paul Kix:

Can you describe the business that you have started behind Perennial Seller?

 

Ryan Holiday:

Well so, Perennial Seller is, there's a term perennial seller in publishing and I decided to use it as the title of the book because, perennial sellers are explicitly excluded from the New York Times bestseller list. They deliberately don't show the books that are selling consistently over time, they show sort of whatever's hot and of the moment. But yeah, I do ghost writing and marketing, and sort of consulting for people who are trying to create businesses, or books, or creative projects that ... My criteria is like, is this meaningful? Is it interesting? Does it have a chance of enduring in some way or another? If not, life's too short to want to work on it. Like I got an email from someone I got to reply today, and it's obvious that they're writing a book because they want it to be a business card not because they give a shit about what they're saying or working on.

So, I just try to work on interesting projects that get me excited. And I guess what I'm mostly thinking about is like, somewhat selfishly is like, is this giving me reps for my own writing? So the project I'm ghostwriting at the moment is like, I think coming out of the other

side, I'll be a better writer for having worked on it, and that's mostly what I'm aiming at.

 

Paul Kix:

Do you, because a lot of writers email me about the podcast and they're like, "Hey, what advice can you give?" You have given a lot of great advice over the years, especially for people who want to be authors, or for those who are publishing. And again, this is sort of the focus of Perennial Seller, and I want to just briefly touch upon it. Because I think it's important for this audience. In the book, you specify pre and post publication, right? So,, pre publication, what is the big thing that you think authors should be trying to do?

 

Ryan Holiday:

I would actually be thinking about whether there's a real audience for the idea you're thinking about. So, most of the time what I see people do is they go off and just make something, and then afterwards they try to figure out, who it's for. I feel like most of the heavy lifting is done. like, I'll give you an example. Ego is the Enemy I sold as a book about humility, it could have been the same message but if I'd published that book as a book pro humility, versus a book that's anti ego, I think the results would have been exponentially different. And so, it was sort of having the humility and having the interest to really sort of sit there and stare at it from a bunch of different directions and come up with the idea that will allow it to resonate most with readers, and teach the most is really, really important.

 

I just see way too many people work way too long, on books that ... Like, I'll give an example. I edited a biography for someone, a friend I was giving notes on it and it was like, you haven't decided whether you like this person or not. And I'm not saying you have to like them or love them, but it has to be one of them, because why the fuck would I read a biography about a person that you're not sure about? Do you know what I mean? I think people, authors just see other authors they know be successful and go, "Oh, I can do that." And they don't really think about what goes into a successful book, or what elements is a successful book need to have? They just think like, oh, I'm talented, I can put words together, my book deserves to be a success. And it's much more complicated than that.

 

Paul Kix:

So, that you should almost be thinking well in advance of publication how eventually you will be marketing the book?

 

Ryan Holiday:

Yeah, just like, where does this fit into the market? Who's buying this? Do you know what I mean? Like a friend of mine wrote a book and it was, if I say too much I'll give away who it obviously was. But the point was, the book was like, the premise of the book was like, it's complicated. And it's like, if it's still complicated, you are not ready to publish this book. Do you know what I mean? And not just because it'll be hard to market, but who will want to read it? What am I paying you $15 for if you're just going to tell me that it's complicated. You're telling me you don't have the answers which means this isn't a book worth reading. Not that every book has to have all the answers but my point is, people don't really think about what their product is going to do for people.

 

In Perennial I talk about Max Martin, who's probably the most successful songwriter of all time. He subjects his music to the Pacific Coast Highway test, which is he plays it on the stereo was driving up the PCH and it's like, ah, he gets it, right? How does this sound in the car because that's where most people are going to be listening to the music, right? And like, authors don't do that, they just go like, smart people should read smart books. And so they end up publishing the 40th anti Trump book, and they can't figure out why it's not breaking through.

 

Paul Kix:

Yeah. And in post publication, because this is the thing that I was like, I've actually recommended Perennial to other authors. I just like hey, if you're about to go promote your book, you should read this. And I sadly had had read it about like a year after my own was published so I'm like damn it, most of the lessons here don't directly apply. But what are some of the lessons for post publication?

Ryan Holiday:

Well just first off that marketing is your job, right? If you don't want to do the work marketing and promoting it like what does it say? It says you don't believe in it and it says you think you deserve it because you're a genius. But just that writing the book is a marathon, and then right then marketing the book is a second marathon. The Obstacle is the Way really took off almost a year after it came out. And that was possible because I didn't quit on it and I kept writing about the ideas, I kept giving away copies, I kept sending emails to people-

 

Paul Kix:

That's big for you, you gave away a lot of copies of the books.

 

Ryan Holiday:

Yeah, of course.

 

Paul Kix:

Why is that?

 

Ryan Holiday:

Well, because what's a better advertisement for the books than the book itself?

 

Paul Kix:

Yeah. I mean I got my free copy from you because I said I liked your stuff. And now here we are-

 

Ryan Holiday:Of course.

 

Paul Kix:                     

... And here we are today. So it worked on me didn't it?

 

Ryan Holiday:Yeah look, I've probably given away 5,000 copies of the books, maybe more. Because yeah if they do the job, almost every book you've ever read, you read because you heard someone say it was good, not because you watched a CNN story about it. You know what I mean?

 

Paul Kix:

Or even read a New York Times review of it. Because I've seen at least my own ... I've seen my stuff spike because of, oh, look, I got reviewed by the Times, right?

 

Ryan Holiday:

Yeah for a very short period that can work but, if it's still selling six years later, why is it selling? It's because people are talking about it and bookstores are continuing to put it out in front of people, and Amazon is continuing to recommend it because it's doing the job.

 

Paul Kix:

How does this this talk of marketing and the work that needs to be done, and living in this very much tactile real world, how do you square that with the lesson of enough?

 

Ryan Holiday:

Yeah, right. There's a tension, right? Because if it really was enough, just publishing it would be-

 

Paul Kix:

Just publish it.

 

Ryan Holiday:

... Sufficient.

 

Paul Kix:

Yeah, there it is.

 

Ryan Holiday:

But I think, you wrote the book because ... If if it was purely about the creative expression, then you wouldn't even need to write it down, you could just express it in your head, right? There is something about a book that is both the process of writing it and having it be read. Now, I think as writers we have to be honest with ourselves and go, okay we have a lot more influence over the writing part than the other people reading it part. But I just see the marketing as a second creative, artistic challenge, and one that I want to work on and succeed at. But, what I'm not doing is sitting around going, why haven't you booked me on Good Morning America? Or, why am I not being reviewed in the Wall Street Journal? I think about it more as, what are articles that I can write? What are people I can meet? I try to focus more on the parts of the process I control, and then also giving myself enough runway that I'm not like, look, if it doesn't succeed in the first two weeks, the whole thing was a bust.

 

Paul Kix:

Yeah, yeah. So hence the essays that you write, are they a reflection then of you, in some sense, trying to continue to market the books that are already out there?

 

Ryan Holiday:

Yeah, it's both, it's both. I mean I think what I'm doing is, I'm building, the best way you you meet your readers is by giving them things to read. And so, Daily Stoic I started in 2016, I write an email for it every single day. I did the math a while ago, I think I've written like three full books for free. And so ... But the process of writing that every day has made me, has transformatively impacted my ability to write, I think my repertoire of stories and and the research I've done. But also now I have a, that email goes out to 200,000 people every morning. So when I have a new book coming out, a huge chunk of my marketing plan is just saying like, hey, this exists, and they sell.

 

Paul Kix:

Wow, wow.

Ryan Holiday:

And that's, I mean I'm sure the podcast is like that for you, right? It's like, you enjoy the process of the interviewing, you enjoy what you get out of the interviews, but you also now have an audience of X number of people who listen to every episode that you ... To me, the ideal place to be as a writer is to be at a place where no one gets to decide whether what you've written gets seen by an audience or not. I just really hate editors being like, "No, we don't want to run that." And so I think one of the reasons I've sort of built my platform, and I've tried to build my career in a way that it's like, if I have something to say, I say it, and the people who like what I say they hear it.

Paul Kix:

Well I mean, you were part of the reason why I started the email that I've started, the email newsletter-

Ryan Holiday:

Oh, that's awesome.

 

Paul Kix: 

... And it became from, I think it was Perennial Seller to answer your question, yeah. I mean, I wanted to launch the podcast because I wanted to try a podcast but, at the same time I was like, well, this can be at least implicit promotion of the existing book, and perhaps some sort of way to build a base for a future audience as well.

 

Ryan Holiday:

Well, no, I love it, and I loved the book also, I thought it was really good. So to go to what we were talking about earlier, you did it. Whether the book sold one copy or a million copies, you wrote a great book about a fascinating person with an interesting story and you did it.

 

Paul Kix:

Yeah. Well thank you, thank you.

 

Ryan Holiday:

Of course.

 

Paul Kix:

That's probably as good a point anyone, and I get the praise and I feel like-

 

Ryan Holiday:

Yeah.

 

Paul Kix: ... A good point to end the interview. The music for Now That's a Great Story comes from Jeff Willett. If you liked this podcast, please rate and review it wherever it is that you listen to podcasts. If you'd like to know more about the artists and writers who inspire me and my might inspire you too, head to paulkix.com/newsletter, and sign up for the newsletter. I'll be back next week. Until then, have a good one, everybody. Bye-bye.

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