35: Ego is the Enemy with Ryan Holiday
8 Dec 2025 · 39 min
Ryan Holiday talks about his book Ego is the Enemy, his apprenticeship with Robert Greene, and why he turned down a book deal early in his career. He discusses stoic philosophy, his writing process, and how he uses commonplace cards to capture ideas from his reading.
Questions this episode answers
ryanholiday.net
Ego is the Enemy
Penguin Portfolio
21
19
Chapters
Hi, this is Charles Michael Davis. Toyotathon is on so stop by your local Toyota dealer for incredible year end deals on the cars, trucks and SUVs known for their legendary reliability like the stylish and efficient Camry, the Ready for anything RAV4 or check out a rough and rugged Tacoma or Tundra, all with great financing and lease options available to qualified customers. Visit buyatoyota.com to find out more. Toyota let's go places.
Hello everybody. Welcome to another episode of the Pivot Podcast. Lucky us. We have Ryan Holiday here today to talk about his new book, Ego is the Enemy. Ryan is a media strategist and prominent writer on strategy, business and stoicism. After dropping out of College at 19 to apprentice under Robert Greene, who wrote mastery and the 48 laws of power, Ryan went on to advise many bestselling authors and multi platinum musicians. He served as Director of Marketing at American Apparel for many years, starting at a very young age when he was just 21 years old. His first book, Trust Me, I'm Lying, was a debut bestseller and is taught in colleges around the world. And his subsequent books, Growth Hacker Marketing and the Obstacle is the Way were both published by Penguin Portfolio. We share the same publisher. Today we're talking about his latest book, Ego is the Enemy and Fun Fact. Ryan even has his last two book titles tattooed on his arms. Welcome to the show, Ryan.
Yeah, it's good to talk to you.
This podcast is about mostly about career and business pivots and how to be agile in our economy. I would love to know, because American Apparel is a big brand, big job. How did you know it was time to leave?
So I actually left American Apparel twice. It was a somewhat unusual situation. So in 2011 I was director of marketing and worked there I think five years at that point and I decided I wanted to write a book. I'd actually come to American Apparel through Robert Greene, who was on the board of directors. I'd worked with a lot of authors previously. I'd gotten an offer for a book deal a while before, but I passed on it and I had this idea that I wanted to write a book that was sort of an expose of the media system that showed what I'd learned working for a really provocative company and brand and what that showed about how the news was made. And so I thought about it for a long time and I called Dove, who was the founder and the CEO at the time, and I said, look.
I appreciate everything you've done for me, I love this company, but I have to leave. I have to write this book and.
It'S just time. He sort of said, well, what if you didn't leave? What if you.
Went to write your book and when you were not writing you responded to email and you helped us with stuff. Basically they said, we don't know who we're going to replace you with. Not that I was irreplaceable. They didn't have any candidates in mind. What if you stayed on in sort of in an editorial capacity? They call this an editor at large position or an academia. Be like professor emeritus. What if you just stayed on and the.
The department ran itself and you just helped when things were difficult? That's what I did for almost three additional years. So I wrote the book, the book came out, did really well. I got a book deal and I could have been a full time writer, but it was such an ideal situation that I got to have one foot in both camps, although I'd been ready to make a clean break. And then right about the time that my third book came out, American Apparel went into a sort of another.
State of chaos and disarray. Dove was fired by the company, by the board.
A hedge fund tried to take it over. And I was actually called back to the company that said, hey look, we need you for about six months during this transition time. Can you come on full time? And I was in a position to say yes. So I did that. Then at the end of that six months, I resigned and I walked away. And now I'm where I thought I would be in 2011.
I'm finally there in late 2014, 2015. So somewhat of an unusual way to do it, but I think I knew it was time because I knew what I wanted to do next. I didn't just leave for the sake of leaving.
What I find so interesting is that you turned down your first book deal offer when you were 23. That must have been a tough decision.
Tough probably doesn't describe.
Was terrifying because I think one of the things that happens with opportunities that you really want to take, when you say no to them, you're worried that you'll never get a better that you just passed on a once in a lifetime thing. But I talked to a mentor of mine at the time and what we sort of worked out was that.
I wasn't ready to write that book, although someone was willing to pay for.
Wasn'T the best was gonna get and that every day that I waited I would be better. And they ended up being right. The book that I ended up writing four years later was the obstacle is the way. And I don't think I would have been in a position to write that book at 23 years old. The same way that I was able to Write it at 26 or 27.
Takes a lot of discipline. It reminds me of John Steinbeck wrote a letter to his son that made the rounds around the Internet where he said, nothing good ever gets away. And it's like whether relationship or in your case, this dream of becoming an author that you are will to say, not right now, I'll be more ready for it later.
That's certainly a very reassuring thought. I wish I'd known that at the time. I think my thinking was.
I've got this great thing, I should take it as far as it's going to take me before I jump onto the next thing. And I think what people don't realize often is that if you can work yourself into a like. So I'd run my department in American Apparel in a way that eventually I became somewhat superfluous. Like I created an independent, really strong, successful department that didn't need a lot of day to day management. And I think some people are scared to set something up like that because they're afraid like someone will realize that they're not totally necessary and then they'll get fired or someone will find more work for them to do. What happened for me is that I was ultimately rewarded for that. Right. I made a product that department that really didn't need me day to day. And so they said, well, look, we don't need you day to day. You can go do this other thing. And so when you make yourself both, when you can make yourself very valuable to a company in terms of your advice and your contributions, but you're not so locked in on a specific task, that's where.
At least in my experience, you can find that companies are a lot more flexible.
Much more flexible than you think. But they're not flexible on your first day and they might not even be flexible on your first couple years. But you can work yourself into a position where you really get to dictate and set your own terms.
That's so true. I'm curious to know, how did you get connected with Robert Greene in the first place and have all of the expertise and obviously innate talent that you had brought to the table as well at such a young age? So how did you get connected with Robert and then parlay that into the American Apparel role?
Yeah, I mean, I don't think I had very much innate talent. I feel like I owe Most of what I know to my time with him. But what had happened is, is that I'd been writing for my college newspaper, and I set out to interview people that I liked and that I wanted to know. And I reached out to one author and I interviewed him, and we sort of became friends. And then I became his assistant, and I was working for him, and then he knew Robert and he introduced me to Robert, and then I started working with Robert. And then Robert. I did a really good job for Robert as his assistant in doing some marketing stuff for him. And then he introduced me to Dove, who was the. The owner of American Apparel. And so when you're a talented person and you can do good work for people, you tend to find that they sort of pass you around, like a good restaurant recommendation or something.
That's awesome. Yes. The highest compliment. Let's talk about ego as the enemy. There's so much that is in this book. I would describe it as a tough love treaties, essentially saying, you're not that special, at least not yet. You need to earn it and don't let your ego run away from you. What I found funny is that I'm such a rah rah cheerleader. I give so much encouragement, and you sort of take the opposite tack, which is like, sit back down, get yourself in check before you've really earned it. And I enjoyed that perspective that you take because it was so different from what we usually read.
Well, thank you. I mean, I'm not so much talking about you. I'm talking about, like, I'm talking about me and I'm talking about everyone. Right. So it's not that you're not special. It's that we're not as special as we tend to think that we are. Right. And so I think I end the intro saying something like, at the end of this book, I want you to think less of yourself. And I mean that literally. I want you and me and everyone to spend less time thinking about themselves and more time thinking about the work. And I think that's one of the things people think that ego, because they use it as a synonym for confidence. They think that ego is like this secret weapon that helps you succeed. In fact, ego is draining you. It's distracting you from every ounce of energy that you spend obsessing about yourself that you spend disembodied and floating up above yourself admiring how awesome you are. That's time and energy that's sucked away from the actual work or craft that you're supposed to be practicing. So as a Writer, the better you think your work, it's sort of like golf. The harder you're trying, the worse you're inevitably going to be at it. You got to sort of be natural and unthinking about it, and ego.
Is an impediment to that happening.
What got you fired up enough about this to write a whole book about it?
I would say it's two things. One was some of the. I'm sure you get this as an author. You get really well intentioned emails from people.
Who relate to you and your work and then they tell you about their problems. And it's so obvious as an outsider that they really don't have any problems, except that they continually get in their own way. I get these emails and it's like, I don't know what you're talking about, but I know that it must be the way that you're saying it. I can tell from the way you're saying it to me that this problem is probably one entirely of your own creation of how you interact and deal with people. So that was a big thing. I just get a lot of emails from young people and I just could tell how often they were getting in their own way and I wanted to help there. The other thing is, when you watch a friend and a mentor of yours build a company that was at one point worth, well.
Billions of dollars and destroy it, you start to ask yourself, man, what is happening?
How does one become this and how does one avoid becoming this? Because it's sort of your worst nightmare.
I really loved your personal story that you share in the introduction to the book. So in the prologue I just want to read one paragraph that really jumped out to me because it was so powerful. You say despite my successes, I found myself back in the city. I started in, stressed and overworked, having handed much of my hard earned freedom away because I couldn't say no to money and the thrill of a good crisis. I was wound so tight that the slightest disruption sent me into a sputtering, inconsolable rage. My work, which had always come easy, my became labored. My faith in myself and other people collapsed. My quality of life did too. And that that was all a result of success, not failure.
Yeah, I mean, I sort of alluded to this earlier, but you know, so I'd. I'd worked, I'd worked myself into this ideal position, right? Like I was an author, but I was also, you know, on salary at a big company. And I had this, you know, lots of people aspire to be full Time writers. And, you know, that's what I was in. And then they get this call and they say, will you come back and work in American Apparel and help us with this stuff? And I was like, oh, sure. I didn't even think, hey, is this what I want? Is this going to be closer to the life I want or further away from the life I want? Is this something I'm equipped to handle? And it turned out that it very much wasn't. I mean, I appreciate the opportunity because of what I ultimately learned from it, but.
I've just found that I dive unthinkingly into opportunity opportunities because they make sense financially. But what's harder for me is to stop and think, hey, is this what I actually want?
Is this going to lead towards me accomplishing any of my personal goals? Or am I getting distracted because someone is sort of dangling something loud and shiny in front of my face?
One thing that I've struggled with when it comes to this concept that ego is the enemy. I know you are really big into stoic philosophy. I've read a lot of about Buddhism, and there is this idea that ego is the enemy. Don't let it run away from you. And yet, at the same time, how do we not reject a part of ourself that if we say, oh, it's the enemy, are we now fighting within ourselves? How do you reconcile that?
I don't have a problem accepting that we have impulses and urges that are destructive and unhealthy. Right. So.
When one feels jealousy coming on or envy or a temper.
I find that those are parts of myself that I wish weren't there. And that obviously one does not simply fight them without thinking or questioning why they're there, what's causing them. But one doesn't also go, oh, this is me, and it's natural. And so it's totally okay.
I think.
You can entertain both these thoughts at the same time, which is okay. This feeling is coming from this place, and I need to address.
That source, and I need to resolve.
The impetus. But I also need to fight this symptom here, and I need to make sure that I'm not giving the symptom control over me and my life.
Did you have to grapple with that at all during the writing of the book?
Yeah, of course. I mean, you write a book and we're both at the same publisher. You write a book and you hand it in and you think it's the best you could possibly do, and then someone tells you that it's not, or they tell you, hey, I don't like this, or hey, what about this? In any creative venture where you're getting feedback, the ego is inherently part of the equation because you have to ask yourself, okay, am I, when you say, hey, I don't like chapter one, are they right? And if your ego gets up and you override them, are you doing the work a disservice? Or are they wrong? And you have to know, hey, this is just one person. And they don't understand what I'm saying. But I can't imperil the entire work to please this singular person. I have to know what I stand for and I have to know what's important. I think I went, I think in selling the book, I went through three radically different proposals before it ultimately sold and then.
A dozen or so different drafts and a year of editing to get it published. So it was a lot of. I think we went through 20 cover options. There was battle after battle with this book. Some of the times I was right, some of the times I was totally wrong. And ego is the variable that makes it confusing and murky to know which one of those two things it is.
It's funny that you bring that up because I had it marked to ask you about the proposal getting rejected a couple times. And here you are. That's a multi best selling author. You clearly know what you're doing. This isn't your first run out the gate. How did you know? Okay, it's worth me revising and showing it to them again. And then again and again versus it would have been so easy to say, they just don't get me, I'm taking it somewhere else.
Yeah. Or I could have said, nobody gets me, I'm just gonna self publish it. And I wouldn't have like the. I'm. I can say unequivocally that the idea that they were rejecting was not the idea that this book became right. So I think, you know, if they hadn't rejected it, if they hadn't forced me to go back to the drawing board and we hadn't had these discuss. It wouldn't have.
The constraints were what ultimately created this book, which I'm very proud of.
I can't tell you. Oh, I knew it for X, Y and Z reasons, but I think I just felt.
I trust the people at Penguin. We have a good working relationship. I was trying to make a mainstream work, not a work of personal therapy. And so part of, part of the, as frustrating as it can be, part of the role of the intermediaries at a Publisher is to help you approximate generally what your audience and what the market is going to need to see.
If the author is given carte blanche to do whatever they want when they happen to. A broken clock is right twice a day. When your instincts happen to be right, it's great. But what about all the times that your instincts are wrong? I guess I know that my instincts are wrong quite often.
I was utterly convinced that the first proposal was exactly what the book should be. And when it came back and they didn't like it.
And then I remade it, I was convinced that the second time was right.
And then when I actually sat down to write the book after it was sold, I realized that we were both wrong, that that wasn't what the book should be at all. And it became a very different thing, which I ultimately wrote. And so you have to have this flexibility. You have to have. There's this line, I think Malcolm Gladwell said it, about Stephen Drumner of Freakonomics. He was saying, strong opinions loosely held. So you have to deeply believe in what you're doing. But then when the evidence starts to line up that maybe you're not right here, you have to be willing to abandon that opinion and go back to the drawing board and figure out what the right thing is.
Can you share what one of your early iterations was?
Well, I mean, the whole. The initial. There's a chapter in the book on the narrative fallacy, which is like how we tend to believe that our life is a story and we try to make it this grand, exciting story. The whole book originally was just about that, which I realized in retrospect, there's not enough material there to make it a book that people need to read. So that's a big one. And then.
The book pivoted and it was about humility. And that's what it sort of sold at. It was a book about humility. And I think humility is fascinating ultimately, what this book is about. But coming at it from that, coming from a pro humility standpoint, I found made for a difficult writing process. It just wasn't. It's not there.
All the stories about humble people are exactly the same. It's like, oh, they didn't let it go to their head. It's not really interesting. So I realized I had to come at it from the opposite. What prevents humility and ego is what prevents humility. So it's. You think you have an idea, you have the germ of the idea, but it's really in the testing and the working with other People and then sitting down and trying to write the damn thing that you figure out what it actually needs to be to achieve what you're trying to achieve.
I had a very similar experience. My book is so much better than what I proposed to them, and I'm so grateful. Yeah, it's funny because for any creative work, I remember feeling this way when I first started blogging almost 10 years ago, which is, you have to have some amount of ego to raise your hand and say, I think I can write a book. I think somebody should listen to what I have to say other than my parents, and yet at the same time, then release that ego. So it's kind of weird because in order to even assume that you should be working on this big creative project requires building up that ego. And then you almost have to cut it down ASAP so that you're open and flexible.
I try to make the distinction then between ego and confidence. Confidence is, hey, I think, think I can write a book because I'm good at writing. I've done it for a short amount of time. People have responded well to what I've made.
I know myself and that I'm going to be able to figure out this difficult thing, and I'm not going to quit until I do it. That's confidence. Ego is, I'm going to write the world's greatest book and everyone is dying to hear what I have to say. And if you're getting in my way, you're just a suit who doesn't understand. You know what I mean? I think that's the critical difference. The quiet confidence to raise your hand. That's very essential to being able to create a book. The ego. It might look like that at the starting point. It might be mistaken for that quiet confidence. But I've seen so many authors because I deal with a lot of authors. I work with them, with my company. And it's like I've heard them say, we've got a million copy seller here and it sells 500 copies because they have no. They have no ability to objectively judge their own work or understand the place that it occupies in the world. And so that's the difference between ego and confidence and why I think ego is so destructive.
I'm really glad you brought that up. It's the perfect segue. There's one of my favorite parts that I want to read aloud so people can get a feel for. Your style of writing is actually about confidence. So thank you. You read my mind.
All right.
This is from the chapter called Work Work Work. Which reminds me of the Rihanna song My Friend and I.
I think this came out before.
Okay, you say back to that popular old trope, fake it till you make it. It's no surprise that such an idea has found increasing relevance in our noxiously bullshit nerf world when it's difficult to tell a real producer from an adept self promoter. Of course, some people will roll the dice and manage to play the confidence game. Make it so you don't have to fake it. That's the key. Can you imagine a doctor trying to get by with anything less? Or a quarterback or a bull rider? More to the point, would you want them to? So why would you try otherwise? I love that.
Thank you. You know, you hear that all the time. You just fake it till you make it. And I just don't. I just. I find that there is almost no situation where that advice applies, you know, or is. Is valid. I think you're. You're so much. What are you faking? And who. Who are you. Who are you fooling with this faking? Other than yourself, maybe? I think it's far better. It's like, no, don't fake it. Actually make it. Do the work. Until you have the skill.
You see this all the time. People will ask comedians or successful musicians. They'll be like, can you give me some marketing advice? And almost always, when you dig into what the person asking for the marketing advice really ought to focus on is improving the work itself. The work isn't good enough to just. Even if there was this magical marketing button that you could hit that would make your thing, like I say, it'll just put you on the front page of the New York Times or the front page of Yahoo or whatever. Even if that button existed, the work's not good enough. All faking really does is put you in a position to be exposed as not good enough.
In my career and as a writer, I've just tried to. I try to reject that advice as much as humanly possible. I think all that energy that you're spending faking would be better off. Spent making.
Very true. And also, I think most people have a bullshit detector that even if it's very subtle, they can sense that. And so if you're attracting people who get through that, you don't really probably want that kind of an audience anyway.
Yeah. Yeah. I was talking to someone recently, and he said something smart. He was saying the. With being a little bit full of shit is that people think you're entirely full of shit. And so I think that's people go, oh, what's the harm? I'm just sort of leading where I'm going to be in a few months anyway. And it's like, yeah, except for the people who see through that, who think you're a fraud. And I just don't see much upside there.
One antidote to that you share in the book is do grunt work and expect no credit. And that also ties in with the canvas strategy. Can you explain?
Yeah, look, I didn't start as the director of marketing at American Apparel. I just started as a guy who just worked there. Like, Dove hired me to be an advisor, and I worked directly for him. I didn't report to anyone in the company. I didn't have an ID badge. I didn't have an office. I just worked there.
I worked on enough projects and I helped enough people that I started to develop a reputation over time as someone who was just talented, who could just get things done. And one of the projects that I was ultimately assigned to was helping sort of organize and rebuild some of the marketing structure inside the company because it was spread out in these different departments. So I ultimately ended up combining the marketing efforts into a single department. And then someone said, you know, I started talking, who are you going to hire to be the director of marketing? I wasn't even seeking that position for me, and it was sort of an ongoing discussion. I ended up just filling in that role as sort of an interim way for a number of months. And then eventually people just started referring to me as that.
That's how I found myself as the marketing director of a publicly traded company, 21 years old.
If I'd gone in there expecting to get credit, if I'd gone in there expecting feeling entitled to this bit of status or that bit of status or I needed this certainty or that certainty, it never would have happened. I think you're far better focusing on doing the work. Focusing on doing work that makes you invaluable and essential to other people and understanding eventually you will get rewarded, if not at this company, at a future company, when one of those people leaves or another company sees your value and tries to steal you away.
It seems like that worked really well for you with other authors who are, I'm sure, your friends as well, guys like Tim Ferriss, where you didn't set up some giant fee structure at the beginning. You were probably just helping them out and giving advice.
No, that's exactly right. I think I worked on Tim's first two books for free, and then I was paid on the third book. But it doesn't really matter to me. You know what I mean? I wasn't starving on the first two because I had other projects. And I was able to learn enough on those first two projects that it put me in a position to get paid on the third and put me in a position to get paid by other artists and other authors, like you.
Said, get passed around then, like a good restaurant recommendation, which is awesome.
Exactly. And you find that if you do an amazing job for someone and you're not getting paid, they feel like they don't just recommend you because they're good. They understand that part of the arrangement is that they understand. It's like, look, if I'm not paying this person, I got to find someone who will. And so they. They are incentivized to help you advance your career as well.
And often they'll send five people, so maybe you pass the revenue from one, but now you got five new clients as a result. I'm sure you probably, having worked with Tim and Robert, have more demand than you could possibly handle just from doing a great job for both of them, among many others.
Yeah, absolutely. And they've been incredibly good to me, and they've paid me whatever minuscule fee my services were worth when I was just a kid and I didn't know anything, paying me back a hundredfold.
And now I try to do the same thing with the people that I work with. When someone comes to me and they help me, and then I think, okay, what resources do I have? What relationships do I have that I can put to use to help this person succeed?
And I think that's sort of. That's a cycle that's existed for thousands of years.
Yes.
Toward the end of the book, you talk about failure. And a really poignant part was you say, there are times we do everything right, even perfectly and still experience failure. And that kind of got to me because I think. I don't know. I mean, I would love to hear if that's happened to you, where you felt like you did everything perfectly and still experience this, but how painful. Where we've done everything we could and yet we're not entitled to anything on the other side.
Yeah. I mean, the stoics talk over and over again about how the effort that you put into a project is what you control, and what you don't control is the external outcome that's a result of that.
You have a book coming out. I'm working on this book. I can slave away on it. I can hustle the hell out of it. But ultimately, I don't control what happens on release day. Not only do I not control whether people like it or not and come out and buy it, but I don't control whether there's a natural disaster or a presidential election. I don't control what happens that might distract people or change plans. And so those are the kinds of failures that hurt the most because they feel the most unfair. We tend to think, hey, I held up my end of the bargain, how dare you? But that doesn't. That doesn't change the reality of your situation. It might be fair, but it's still your problem. Or, sorry, it might be unfair, but it's still your problem. I think what I've always tried to take from those events and what I try to remind myself in advance before those events possibly happen, is, hey.
What'S the part that's inside your control? And can you focus your. Your happiness exclusively on the result of that, not what happens when it leaves your control?
To me, that's the recipe. Otherwise, any creative profession is essentially a recipe for misery because the response to your work is not. You don't control what a critic writes about you in a newspaper. You don't control Amazon's algorithm. You don't control whether the person at Barnes and Noble takes your books from the back to the front. You don't control whether the studio puts up enough advertising for your opening weekend. You don't control any of that. If you're not happy with the process itself and the creative act itself, you're essentially just hoping that things go right in order for you to believe that you did a good job or not.
And like you say, that's pinning our happiness on some future state that may or may not occur that we don't even have control over, full control over. I laughed out loud in the book. You said, is it 10,000 hours or 20,000 hours to mastery? The answer is, it doesn't matter. There is no end zone. I just love that because people have unpacked the 10,000 hours thing over and over these last few years, and you're basically saying, forget about it, be a lifelong student. And I think that's one of the things that I love about you and your work, is that you have that mindset of being a perpetual student. You say books are your biggest expense. I just think that's great.
Well, I mean, look, you don't get an award when you get to 10,000 hours. Like, maybe. Maybe it turns out that it's for whatever you've chosen, that it's actually 30,000 or, you know, maybe it turns out that somebody beat you to 10,000 and now nobody cares. Right? It's, there's not these are, first off, these are general rules. But also, you know, for most of us who are not, you know, pursuing chess professionally, there's not some official recognition that you achieved a state of mastery. And even if you are a mastery, that doesn't mean you're going to be financially successful. That doesn't mean your work's immediately going to be received with open arms. I think because pursuing a creative profession is so difficult and uncertain, we lock in on certain forms of certainty and then we're crushed when this artificial creation of ours doesn't. Doesn't hold up.
Okay, as we start to wrap up from a fellow bookworm, I would love if you could share. For people who aren't familiar with your work and your methods, talk to us about A Day in the Life of a Book in Ryan Holiday's House. So when you're reading, I would love for you to share with listeners about Marginalia, your commonplace book note cards. I know that's a lot, but maybe just give us the highlights.
I mean, the Day in the Life of a Book in my house is a hard, it's a hard life for the book. It's good for me, but I sort of beat the crap out of books. I remember a couple years ago I bought this book. I didn't know on Amazon that it was old, and I got this first edition review copy of a book that was published in 1939. It still had the little note card in it that was like, dear the New York Times, please enjoy this book. And the first thing I did was read it and start taking notes in it and folding the pages. When I read, I fold pages that I like. I write in the margins, I highlight and underline things that I like. And then I usually put a book aside after I've finished, and by the time I finish, they're covered in food and dirt and water stains and stuff. But then I put the book aside and then I return to it and I transfer all that information to physical note cards, four by six note cards, which I store in boxes. So each one of my books, it is a box of note cards. Ego is probably, I don't know, two or three thousand note cards all in. And obstacle was about the same. And they started as just random note cards that I'd written down. And.
As I accumulated more note cards around the same theme, I realized, oh, there's something here. I'm Going to use this. And that became a book.
That's amazing. I know. We both also share the anti library strategy. I don't know if Nassim Talebi coined that term or what, but having Roberto.
Eco came up with it. But it's from. Yeah, he put it in the Black Swan, I believe.
Yeah. Which is having almost more books that are unread in the bookshelf or the library than read.
Yeah. Yeah. There's books that I started reading five years ago that I didn't really understand or I didn't think were good and I had to stop. That I returned to when I was researching this book. The idea is that you. You collect knowledge to have at your fingertips for when you need it. It's not when someone comes over to your house and they say, oh, have you read all these? They're sort of missing the point.
Yeah, exactly. So many people ask me that too, and I'm like, nope, it's more like a menu that when the time is right, the right book jumps off the shelf too.
Yeah, exactly. I'm collecting this knowledge, this access to this knowledge that I'm going to need for my job, basically.
Last question. What was the thing that surprised you most from the time you started writing? Ego is the enemy to now when it's launching?
That's a great question. Obviously, it became a totally different book than I set out to write, so that's a pretty huge one.
I did not intend to be in the book at all. I didn't want to be in the book. And that was the result of some of the discussions we were talking about earlier. The needing to.
Hearing feedback from editors and readers telling me, hey, I appreciate why you don't want to be in the book, but you can't make this point if you don't tell us where you're coming from at the beginning and stuff like that. It became a radically different book than I set out to write from start to finish. But day by day, it was really a gradual process. I think that's one of the things that people miss about writing. Sitting down every day and struggling with these decisions.
Yes. And the book emerges and becomes its own thing. Kind of shows you what to do.
Yeah. A book is hundreds of hours of writing and struggling and beating your head against the desk.
Well, I'm so glad you included your story. It really is incredibly powerful and you kept it brief, but I think it does add so much and it pulled me in immediately within a few pages. I've was just totally compelled. So I'm glad You did. Yeah. Ryan, thank you so much. This has been very illuminating, and I'm so impressed by all that you've built and done in your career. Where can people find you if they want to keep in touch and buy your new book?
Yeah. So obviously the book's on Amazon. It's called Ego is the enemy. My website's ryanholiday.net and I'm Ryan Holiday on Twitter.
Awesome. At some point, I think you should post pictures of your tattoos as well. Obstacles play and EHO's the enemy. So awesome. Thanks, Ryan. Thanks, everyone, for listening.
More from Jenny
215: Stay Relevant, Sense What's Next, and Solve Difficult Problems with Stephen Shapiro
12: Belly of the Pivot Beast: On Bouncing Back from Zero with Adam Chaloeicheep
218: We've Gone Over-Bored (Part 2) with Michael Karsouny (Listen at Your Own Risk!)