in: Advice, Character, Podcast

• Last updated: September 28, 2021

Podcast #212: Ego Is the Enemy

In the quest to become the men we want to be, we’re often our own worst enemies, especially when it comes to our egos. Ego is what prevents us from being humble and teachable when we’re first starting out in an endeavor. It blinds us to our own weaknesses during success, and it can cause us to wallow in self-pity when we fail. My guest today on the podcast has recently published a book filled with insights from history on how ego can get in the way of our success and what we can do to mitigate its downsides.

His name is Ryan Holiday and his book is Ego Is the Enemy. Today on the show, we look at examples from history of eminent men whose hubris caused their downfall, and others who were able to successfully harness their ego to attain greatness. We also discuss steps that you can take to prevent ego from causing you to stumble.

Show Highlights

  • What is ego [02:00]
  • How ego is related to hubris and what the Ancient Greeks did to help them keep their hubris in check [04:00]
  • How our modern culture of self-esteem and self-promotion is actually hurting our individual and societal progress [05:00]
  • Why most people think outside forces are thwarting their progress when it’s actually their own ego [07:00]
  • The three phases in any endeavor where you need to check your ego [11:30]
  • Why people who’ve been successful are often the most susceptible to failure [15:00]
  • What General Sherman can teach you about staying humble when you’re first starting your career and once you’ve gained success [17:00]
  • How General Grant’s success as a Civil War commander caused him to bite off more than he could chew by running for president [21:30]
  • What John Boyd can teach us about not letting our ego get in the way when we begin an endeavor [26:30]
  • Why passion is overrated and you should focus on purpose [31:30]
  • Why success can lead to your downfall [36:30]
  • What you can learn from Genghis Khan about staying humble in victory [37:00]
  • Why routine, planning, and discipline become more important after you’ve gained success [38:30]
  • How not being able to delegate is a sign of ego [44:30]
  • How ego is your enemy when you fail [47:00]
  • Can ego be your friend? [52:00]

Resources/Studies/People Mentioned in Podcast

Ego is the enemy by Ryan Holiday, book cover.

Ego is the Enemy is filled with great insights and lessons from history on how to stay humble and hungry. No matter what line of work you find yourself in, you’ll find some useful, thought-provoking nuggets in this book.

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Read the Transcript

Brett McKay: Brett McKay here. Welcome to another edition of The Art of Manliness podcast. In the quest to become the men we want to be, we’re often our own worst enemies, especially when it comes to our egos. Egos is what prevents us from being humble and teachable when we’re first starting out in an endeavor. It blinds us to our own weaknesses during success, and it can cause us to wallow in self-pity when we fail. My guest today is Ryan Holiday. In his latest book, Ego Is the Enemy, he discusses how ego can thwart our personal progress in success as men.

Today on the show, we look at examples from history of great men whose hubris caused their downfall, and other men who were able to successfully harness their ego to attain greatness. Along the way, provide actual steps that you can do to prevent ego becoming your enemy. After the podcast is over, make sure you check out the show notes at, where you can find links for resources mentioned throughout the show. Without further ado, Ryan Holiday and Ego Is the Enemy.

Ryan Holiday, welcome back the show.

Ryan Holiday: Yeah, it’s good to be here. I think the last time we talked you were recording this from your closet, and I could see you on the thing.

Brett McKay: Yeah. Well, I’m still recording from my closet.

Ryan Holiday: All right. Okay, very cool.

Brett McKay: You just can’t see me. Still going old school here. You got a new book out, Ego Is the Enemy. Before we talk about the details of the book, let’s start off talking about what do you mean by ego exactly? Are we talking Freudian ego? What is it?

Ryan Holiday: Yeah, so definitely not Freudian ego, not even psychologist ego. I think I’m referring to it … Well, I know I’m referring to it. I’m referring to it in the colloquial sense, the “know it when you see it” ego, what Bill Walsh would say, “When self-confidence becomes arrogance.” I’m using it as an umbrella term to define all of the characteristics in which the normal confidence, normal self-assurance, normal goal-seeking behavior bleeds over into the toxic self-absorption and toxic selfishness and compulsion that leads to negative outcomes.

I’m referring to not, “Oh, is that guy literally an ego maniac,” but much more, “What are these traits that make us our own worst enemy, that put us at odds with the things that we say that we’re trying to achieve?”

Brett McKay: Okay. All right. I think what you’re talking about is a timeless idea. It seems like a lot of the major religions or philosophies have talked about how ego can get in the way of yourself.

Ryan Holiday: Yeah, certainly. I think at the root of every Greek tragedy, for instance, is hubris. Hubris would be a form of ego, even if that word didn’t necessarily exist. The idea of what happens when our sense of realism is replaced with delusions of grandeur, what do we do? What happens when we overestimate our own importance? It’s a thing that essentially every religion and every philosophy ever has warned against. It just happens that today, instead of warning against a lot of these things, we actually hold them up as positive attributes. This is what every motivational speaker is out there encouraging, is ego in one form or another, sadly.

Brett McKay: Yeah. It seems like our culture today promotes this unhealthy, exaggerated ego. You just talked about the motivational speakers, but a lot of the books about business and entrepreneurship, it’s all about being self-promoting, name it and take it, it’s yours, and all this other stuff.

Ryan Holiday: Yeah. Just think of what social media is. It’s not supposed to reflect your actual life. It’s supposed to reflect your idealized life. I think a lot of it is rooted in what you were just saying, this idea of faking it until you make it. That’s a seductive, egotistical idea that, in my experience, doesn’t normally work out well for people. Here, you’re supposed to dare greatly and have these grand visions of success and ambition and pursue your passion and your calling. We say a lot of these things, but they’re not tempered with any real purpose or any real understanding. In a lot of cases, we’re encouraging them without any hard work either. Right? It creates a scenario in which our grandiose impulses are encouraged and excited, and then the things that are supposed to temper and balance that out are left by the wayside.

Brett McKay: Got you. We’ll get into more of those things into detail. What inspired you to write this book, Ego Is the Enemy? Was it events in your own life, just observations from culture, or is it in some way a continuation of your work you started in The Obstacle Is the Way?

Ryan Holiday: It’s a little bit of both, I think. Obstacle Is the Way was about extra obstacles and how people can be rational and creative and strategic about dealing with those obstacles and using the stoic mindset in which to do so. I was thinking about what comes next after that. I was really thinking, “Okay. What makes doing that so hard for people, and what is the biggest obstacle that most people face?” In my own experience, in a lot of the people I get emails from, my client work, the powerful and important people I’ve worked for, what I kept sensing was that the enemy for most of us is ourselves.

DJ Khalid likes to talk about the “they” that are … “They don’t want you to have this.” In reality, the world is indifferent to you. What prevents people from achieving what they want to achieve is often times their own bad habits, their own bad impulses. It’s their own ego that’s getting in their way. Ego is what prevents looking at a situation rationally, not taking it personally. It’s what prevents persistence and perseverance because we feel like we shouldn’t have to do these things. It was sort of a co-lesson of these two different trains of thought that I had, that ego prevents the hard work of overcoming obstacles and, ironically, ego tends to be its own enormous obstacle. That’s where I was coming from in the book.

Originally, the book was going to be about humility, which I know you guys have written a lot about. You can tell me if you think I’m off base here, but I found that talking about humility, one, it’s a difficult thing to talk about because the first question is, “Are you humble?” It’s a difficult thing to talk about. Also, humility doesn’t tend to be very inspirational to people. Right? It’s difficult.

I found that almost all the stories of humility sound more or less the same. They’re not super action-oriented, and so when I was thinking about writing about humility, I was trying to think of, “What is a way to come at it that would captivate people’s attention and actually be of practical use?” I realized that, in many ways, ego is the opposite of humility. I decided to focus on ego as being this impediment to the humility that we want and that we need. That’s where the book came from.


Brett McKay: I see you inverted. Right? Instead focusing on humility, you focused on the opposite of it.

Ryan Holiday: Yeah. Yeah.

Brett McKay: By doing that, you were able to talk about humility.

Ryan Holiday: Yes, exactly. I think, one, talk about humility in a way that is actionable and interesting to people, but two, it’s a little bit of the message of the book itself, in that you sit down and you think you have one idea for a book. This is what you think you’re going to do. I had a contract to write a book about this topic, and then as I was going through the material, and most days I was doing my research and writing my notes and starting to sketch out this book, I realized that my vision or my plan was flawed and it wasn’t going to work as I originally planned it.

When people ask, “Why does humility matter? Why is ego bad?” in the most practical sense, any sort of creative pursuit or entrepreneurial adventure, you start out with a gut instinct or an idea, but if you’re not going to be open to feedback from the world, if you’re going to be so certain that you are instinctually right, you’re not going to be able to adapt and change when it turns out that things were more complicated than you thought, or that maybe you didn’t have the experience, or you hadn’t considered something yet. It’s only in actually doing the thing and then being open to learning from it that you’re able to grow and improve. This book wouldn’t have been possible had I been convinced that I was immediately unassailably correct with my original plan.

Brett McKay: Right. You had to overcome the ego to write your book about overcoming the ego.

Ryan Holiday: Yeah. You write a book proposal and the publisher says, “We don’t like it.” You can say, “Hey, screw you. I’m going to self-publish,” or, “Screw you. I’m going to sell to someone else,” or you can say, “Well, maybe I don’t agree with why you don’t like it, but something is clearly not right.” I need to go back to the drawing board and do another pass at this, and then another pass, and then actually making the book, or making any project, is … I think craft is inherently ego-killing because everyday you’re struggling against some problem or you’re falling short in the pursuit of perfection.

Brett McKay: Yeah. The way you organize the book is interesting. You break it up into three sections, and they correlate to three phases that you say people constantly find themselves in.

Ryan Holiday: Yeah. I mean, this might be getting a little too insider for people, but I believe that every book should have a three-part structure, and this came to me from Shawn Coyne, who’s Steven Pressfield’s editor, who’s done amazing books like The War of Art and Gates of Fire. Going back to Greek literature, in Aristotle, you’ve got your three-part structure. I was trying to think, “What is the three-part structure?” In my last book, it was perception, action, and will.

The three-part structure of Ego, I felt, was that when we’re starting out, ego is destructive because it prevents us from learning. It makes us think we’re better than we are. It makes us want to move too quickly, a number of destructive traits. Then, after we aspire, if we’ve conquered it and you go there, then we achieve success in some way. We’ve gotten a great job. We’ve signed our first deal. We’ve been chosen in the draft, whatever it is. We’re achieving some measure of success.

Now, ego manifests itself in another number of ways. Right? It’s feeling like you’ve suddenly arrived, that you’re better than everyone else, that it’s going to be amazing from here on out. Now, maybe you’ve got people working under you. The corruptive nature of power is warping onto your ego. Maybe you feel like you’ve learned everything that there is to learn. These are the effects of ego in the success phase of our life, and then, as we know, successful people either aspire to some new level of success, they’re essentially going back to the next step, or they fail in some way or they find out that success has a new set of difficulties.

All of a sudden, they’re attacked by a media outlet or the market shifts or a competitor comes after them. Now they’re dealing with adversity or difficulty or failure. Ego, here, manifests itself in a number of other ways that are also destructive. It’s taking this thing personally, believing that you’ve been screwed over and giving in to resentment or hatred, or maybe you found yourself in a state of difficulty because you screwed up. You did something wrong. Well, can you admit that you did something wrong and can you learn from this, or do you decide, “Hey. I’m doubling down on the problems that got me here”?

Whether you’re aspiring or you’re succeeding or you’re dealing with some form of adversity, ego is really the least helpful variable that you could introduce into any of those phases of your life. I feel like we’re in a constant fluid transition along that spectrum over the course of our entire lives.

Brett McKay: I imagine it’s possible to be in different phases at the same time in different facets of your life.

Ryan Holiday: Totally.

Brett McKay: Right. Aspiring with your career, but you succeeded in some other … I don’t know. You’ve run a marathon, or something like that, and you did well. You’re that-

Ryan Holiday: Yeah, absolutely. Or you’re successful on the one hand, and then you’ve started this other venture on the other. If you’re bringing your ego of success, like someone’s a rapper then they decide to become an actor, you could be egotistical in your musical profession, and maybe you’re getting away with it because you’re so successful even though it’s causing problems for you, but if you bring that ego to this new thing that you are starting and you’re convinced that that ego is transferable, you’re going to be rudely surprised when you’re not nearly as good at that thing as you maybe sensed that you are. You’re not going to be able to improve and take feedback and work well with others and hustle and build the relationships that you need to succeed in that other field.

That’s where ego is such a tricky thing, is that we’re never permanently in any of these phases. We’re also doing and trying new things. Maybe a project is partially successful and partially not successful, and our ego is what’s going to determine that balance, I think.

Brett McKay: Like you did in Obstacles Is the Way, you went to history to find examples of individuals who were good models of ego either getting in the way or them overcoming ego in these different phases of life. In the aspire phase, you talk about the Civil War, General Sherman, who is a controversial figure, but what can Sherman teach us about managing our ego in the aspire phase?

Ryan Holiday: Yeah. I mean, I do think it’s interesting that he’s a controversial figure. I don’t totally understand the controversy 150 years removed from the event, but what I think’s so fascinating about Sherman is that he was unlike our typical stereotype of a great general, maybe it’s a MacArthur or a McClellan or a Napoleon who believed themselves to be marked for greatness from the day that they were born. Sherman never really had any of that.

In fact, he was basically orphaned as a young boy. He grew up. He was adopted. He got into West Point, but he was not particularly distinguished there. He had a series of backwater postings. He was a figure during the Gold Rush in that he actually held the original gold nugget that was discovered that set off the Gold Rush, but he made no fortune in the Gold Rush.

Even in the early days of the Civil War, he was a mediocre general, but what people didn’t understand is that he was learning this entire time that he was … B.H. Liddell Hart, who wrote this amazing biography of Sherman, which I used in the book, is talking about, for the person who thinks that they’re destined for greatness, they never really accomplish enough, and they never really enjoy what they’re experiencing because they felt entitled to it. Whereas someone like Sherman, his slow, gradual rise was a much sweeter process in that it’s the accumulation of actual confidence and the accumulation of actual accomplishments.

I think what Sherman managed to do was focus on what he was trying to accomplish more than his personal vanity or goals. At the Battle of Vicksburg for instance, Sherman … No, sorry. Donelson, the Battle of Fort Donelson, Sherman technically outranked Grant, and similarly at Vicksburg, he could have been in a superior position, but he decided to subsume his personal ego and vanity to serving this greater mission. They built a team where they functioned quite well together.

In fact, Sherman’s role at Vicksburg was actually one of a feint, a distraction, and he did not participate in the main thrust of the battle, but he would tell Grant over and over again, “Hey. Look, I’m just here to do my part.” What they discovered together at Vicksburg … and I talk about this in Obstacles. What they discovered at Vicksburg was accidentally a strategy that Sherman would then use to win the Civil War, his March to the Sea, which in itself was an exercise in the restraint of ego. The reason the U.S. Civil War went longer than it needed to, and why so many people died, is that the generals were convinced that it would be decided in a series of head-to-head battles.

McClellan, who was much smart than Sherman, who had all the credentials, who was given a superior command, would spend weeks and months waiting and maneuvering for these large, decisive battles that he thought would decisively win the war, and they never happened. What Sherman realizes is that if he took the war to the enemy, if he took this march to the South, and he avoided these confrontations, and he instead focused on the objectives, the cities that he needed to take and bringing what he called “the hard hand of war” to the southern people, he would win, but that required a certain awareness and disdain for the vanity that had motivated these other generals.

The final thing I talk about in the book related to Sherman is, after the war, Sherman was one of the most influential people in all of America, and he’s essentially offered the presidency. He says, “You know what? No. I don’t like politics. I have all the rank I want.” The Shermanesque statement is his famous statement declining to run for presidency. “If nominated, I will not run. If elected, I will not serve.” He doesn’t run for presidency. Grant wins the presidency. It’s the worst thing that basically happens to him.

Sherman was this model, for me, of someone who’s very self-contained, very self-motivated, very realistic, not a pessimist, but realistic in his assessment of himself and his own abilities. I think that’s what made him such a powerful force ultimately, for the good of the United States and for his own personal happiness.

Brett McKay:      Right. Yeah. That contrast between Sherman and Grant was interesting. Grant went on to be the president, and he was an okay president.

Ryan Holiday: Yes.

Brett McKay: I think he had some problems. There was a lot of corruption.

Ryan Holiday: It didn’t go well for him.

Brett McKay: A lot of corruption within his presidency, et cetera.

Ryan Holiday: Yeah. He basically bit off more than he could chew. Grant, I love Grant. I raved about him in Obstacles, but Grant was a great general because he didn’t play politics. He focused on the task at hand, and that’s why he worked so well with Lincoln. For him to run for president was, I think, in a large part a complete misunderstanding of his own strengths and weaknesses, but whatever. Eisenhower ran for president and did pretty well, but he ran for president and he did terrible. It caught him by surprise how poorly it went because he wasn’t a great judge of character politically. This is where the corruption happened.

After his presidency, he starts a brokerage house with his son and an investor named Ferdinand Ward, who turned out to be basically a Bernie Madoff of his day. Financially, Grant is bankrupted and ruined. He ends up having literally to pawn his Civil War mementos, his sword, to pay off the debts that he incurred. I remember Sherman wrote a letter. I don’t remember if it was to Grant or someone else, but basically he was saying how sad it was that Grant was trying to … He said, “Grant aimed to rival the millionaires who would have given anything to have won one of his battles.” It’s his inability to know what’s important to you, what you actually value, and trying to compete with everyone else that often gets us into trouble.

Brett McKay: Right. This is the perfect example of individuals who, they succeeded in one area of life and they think, “Oh, well, I can succeed in this other area of life just because I was successful in this one other.” That’s not how it works. Not how it works.

Ryan Holiday: No. It’s definitely not how it works, and we think, “Hey. It was easy last time. It’ll be easy this time,” and we don’t really understand what went into our success the first time, often times because we take it for granted. We give ourselves a little bit of the halo effect. “Because I was dominant in this area, naturally I must be dominant in this other area,” and so you see so many people waste so much time and money.

Ultimately, Grant died at like 63, partly reeling from these failures and what might America have looked like, what might have his life had looked like if he had managed to resist that impulse. I think that’s very sad. It’s a cautionary … I’m not judging him. I’m saying it’s a cautionary tale for me that I try to live in my own life. It’s like when you accomplish something or you’ve built some level of success for yourself, all of a sudden these opportunities start coming your way, and you have to decide, “Hey. Which of these opportunities are in any way adjacent or similar to what I’m already good at?” Do you even have an understanding of what you’re good at? Ego can be this seductive force that really leads you astray.

Brett McKay: You also talk about John Boyd. We can’t leave this podcast without talking about John Boyd because he’s one of my favorite characters from history. He’s this really complex character.

Ryan Holiday: But super complex.

Brett McKay: You used him as an example of not letting ego get in the way during the aspire phase. What can we learn from the life of John Boyd about overcoming ego in that part of our life when we’re just starting out on some venture?


Ryan Holiday: Yeah. What I would say is, first off, if you don’t read my book, you should definitely read The Art of Manliness piece on the To Be or To Do speech, which obviously I was familiar with this speech before from Robert Coram’s amazing biography of Boyd, but that speech is what I based this story of Boyd on in one of the chapters. Basically, what Boyd was famous for doing, people don’t really know who he is, he was one of America’s greatest fighter pilots and then ultimately became a warrior inside the Pentagon for reform and efficiency and strategy change inside the U.S. Military.

He was much more influential, a groomer of men, than he was as an actual leader of troops on the battle field, but one of the things he would do is he had this speech. As a young accolade would come into his orbit, he would see them for all their potential. He would know that this trajectory that most young officers would go through, which is they would show promise and then they would start to become addicted to the status, to the trappings of politics and power of their office, or of their post, and how it would lead them astray and eventually make them do more harm than good.

He would give this speech where he would draw them in and he would say, “Look. You’re coming to a fork in the road. Are you going to be someone that does thing, or are you going to be someone who is something?” Basically he’s saying, “Are you going to choose between status or influence? Are you going to choose between credit or accomplishment?” That speech was what … I talk about that because we as young people have to make that same choice as we’re starting. Are we going to focus on purpose and mission, or are we going to focus on impressing people or financial rewards or any number of these superficial concerns that often lead many, many people astray?

I read that speech when I was 19 years old, and it was very influential to me and the idea of, “Man, credit is this seductive, egotistical thing that really prevents a lot of people from fulfilling their true and deepest potential.” I’ve held him up as a model in my life, of someone who said, “Look. I’d rather be the guy behind the scenes. I don’t really care what people think of me, but I’d rather have influence than, let’s say, power or I’d rather have accomplishment versus credit and recognition.”

Brett McKay: Right, and that’s what happened in his life. He wasn’t able to advance to general. He started a lieutenant colonel for his career.

Ryan Holiday: Yeah.


Brett McKay: Yeah. He was focused on reforming the Pentagon, and the Top Brass didn’t like that. In the end, the tactics and the strategy and the whole approach to warfare that he developed, that was used during the first Gulf War by the Marines. It’s what led us to basically end the war in a few days.

Ryan Holiday: Totally. Yeah. He did not lead troops in battle, but he influenced the entire scope and battle plan of all of the troops across the different branches of the Armed Forces. He really lived what he was talking about. There’s no aircraft carrier named after John Boyd, and he died, they were saying, in a somewhat dingy apartment, but he was uncorrupted and he was pure and true to what he believed in. He, I think, ultimately accomplished far more than he would have had he coveted these other things.

That’s something that I think every young person faces. You’ve got to say, “Look. To be or to do? Who am I going to be? What is important to me?” I think Sherman faced this, and I think a lot of great people. What path am I going to follow in life? Am I going to follow the one that maybe gets me paid really well right out of the gate, or am I going to put in the time and the hours to be self-sufficient and free and able to do the things that I actually think are important and that I need to be done?

Brett McKay: Another thing you talk about in the book, in the aspire phase, that trips the young people up is this idea of passion. We’ve had other guests on the show talk about how passion can trip people up. Instead of passion, I know we shouldn’t have passion and we can talk about why, but what should we have instead of passion?


Ryan Holiday: I’m using passion in the more pure sense of its definition, like when the Greeks would say, “The passions.” Right? The uncontrollable urges and energy that they saw as dangerous, I think. When I hear people go, “I’m following my passion,” I get the sense that they’re just being whipped around by something that they don’t quite control. I would contrast passion with purpose. Purpose is the John Boyd approach. It’s, “This is what is important. This is what I’m trying to do. This is the larger mission that I’m serving,” rather than, “I’ve just got to do this. I’m so passionate. I’m so excited. Let’s go. Let’s go. Let’s go.” I think purpose is deliberative and patient and controlled, and passion is zealous and unrestrained.

I think someone with purpose is able to sacrifice. They’re able to play a longer game. They’re able to put up with things that maybe they would rather not have to. Jackie Robinson was not passionate about baseball. Jackie Robinson integrated baseball as someone on a mission of immense purpose, and that’s what allowed him to not punch someone in the face who deserved to be punched in the face. Branch Rickey said, “You know, I want someone who has the guts not to fight back.” Someone with purpose has that. Someone with passion is, I think, a vessel that can barely contain itself.

Brett McKay: Right. I had Angela Duckworth on the podcast last week, and that’s what she … She’s like the Grit lady.

Ryan Holiday: Yeah.

Brett McKay: Yeah. She says, “Purpose is the thing you’ve got to have. That’s one of the factors that allows you to have grit, to see things to the long through, and you have this purpose that you’re dedicated to. Even when things get tough, you’re still going to stick to it.” Yeah. Passion is fleeting. Right? It’s emotionally based. One day you might feel great and super passionate, excited, but the next day, not so much.

Ryan Holiday: Yeah. I see this with a lot of authors. They’ll go, “Oh, I’m passionate. I want to do a book.” I’ll be like, “About what?” They’re like, “I don’t know.” It’s like, “Okay.” Someone who has purpose is saying, “This is what I believe, and this is what I want to communicate to the world. Maybe a book is the best way for me to do that,” or when they decide that a book is the best way to do it, then they’re all in. Passion is, “Hey. Someone said I should do this, and now that’s why I’m doing it, and let’s go right now.” You know what I mean?

Was it Christopher McCandless? He’s passionate about the wild. “I want to go into the wild. I’ve got to pursue this calling.” Then he goes there and he’s not remotely trained or knowledgeable enough to do it, and he dies a tragic, unnecessary death there. “Hey. We’ve got to make it to the summit of Everest, even though all the warnings are against it and everyone is saying it’s a bad idea.” Passion is able to override that and get passed it. That’s not admirable to me. Shackleton, “I’ve got to get back to my men. I’ve got to rescue my men,” that’s purpose. That is admirable to me.

Brett McKay: All right. You’ve been talking about the aspire phase. I can see how this part of the life cycle of any venture can trip up a lot of young people because we get these grandiose ideas. We get those motivational posters, put them on Instagram, talk about how we’re going to do great things, blah blah blah. It’s a lot more talk, a lot less action. Yeah. I guess the bottom line is, in the aspire phase, just more action, less talk.


Ryan Holiday: Yes. Yes. More action, less talk, and more openness and less certainty and self-absorption.

Brett McKay: Okay. Let’s move on to the success phase. You’ve aspired to it. You’ve set your goals. You’ve worked. You’ve achieved success. Now, I think it was Napoleon who said, “The most dangerous moment in any battle is at the moment of victory.” Why is that? How does success get in the way of success?

Ryan Holiday: Well, I think what Napoleon is saying is that it’s at that moment of victory that you think that you’ve earned the right to relax. That’s where you make your grievous mistakes. In many ways, the stakes are highest at that moment as well. You might have been disciplined when you were on the assent because you knew you needed to be, but now you’re successful, or you feel like you’ve earned some victory, now chaos and disorder may take over, or bad habits that were suppressed early on now come home to roost.

What I think success needs is not ego, not complacency, but a doubling down on the good habits that created that success in the first place. If it was your dedication to learning that took you to this place, one cannot say, “Well, now I know everything I need to know so it’s all good.” Genghis Khan says … I talk about Genghis Khan in the book. Really, what was so profound about him as a conqueror was that at every new country he took over, he saw essentially a superior culture that he needed to absorb into his empire and into his way of thinking. “What can I learn from this enemy that I just vanquished? What is the best that their society has to offer?” He was saying, “If you feel pride, you cannot lead.”

This idea that one must always remain a student, and one must always resist the impulse to feel like this success that they’ve achieved says something about them as a person, that it says that you’re better than you were before you had the success.

Brett McKay: I get the idea about always being a student, maintaining that white belt mentality.

Ryan Holiday:Yeah.

Brett McKay: I thought one of the chapters that you had was interesting. It was about, like you mentioned earlier, doubling down on the habits or actions you did to get you to success and continue that and actually developing a system for that.

Ryan Holiday: Yes.

Brett McKay: That’s hard for a lot of entrepreneurs, artists, writers. They think that’s stodgy and stifles creativity, but you argue that that’s actually what’s going to allow you to continue your success that you’ve gained.

Ryan Holiday: Sure. I’ll give you an example of this. It’s a somewhat current one. Donald Trump has run probably one of the most impressive presidential campaigns of the last century. I don’t admire him as a politician at all. I think he’s a horrendous person, but one cannot help but be blown away that the fact that this guy beat out 16 or 17 other candidates totally on his own with a staff of like 5 people. It’s astounding when you think about how little he spent, how little experience he had in this, and the billions of dollars of free media attention that he’s been able to do to cobble together this nomination. Right?

You could argue that previously he was in the aspirational phase, and now he’s achieved some measure of success in that he’s now the presumptive nominee as we’re talking. I don’t know when this comes out, if he’ll actually be the nominee. I don’t think so, but he’ll be the nominee. Right? He could be forgiven for thinking … let’s say, God forbid, he wins the presidency. If he thinks that the amateuresque tiny team that he managed to win the campaign with is going to function the same way, in terms of governing one of the most powerful countries in the world, he’s going to be sorely mistaken.

In fact, we saw the same thing happen with the Obama campaign. When they won in 2008, they felt like … I remember there was a lot of interesting articles. They built this technologically-based team. It was decentralized. It was fast-moving. It was filled with lots of young people, all this stuff, and then they just assumed it would naturally transfer over to the bureaucracy that is the executive branch of the United States. They were rudely surprised when they weren’t using the same computers, that there were legal constraints, and that you had to run things through certain processes. All of a sudden, the things that got you there aren’t the things that are going to allow you to be successful once you’re there.

I think that’s similar to a lot of us. We can be scrappy and fluid and loose on our way up, and I’ve certainly had to go through some of these growing pains myself, but then once you’ve arrived, now you’re the man. You know? You were railing against the man before, but now you’re the man and people are counting on you and expecting certain things from you. You’re expected to perform and operate at a certain level, that things you were able to get away with before are not possible now.

You could argue maybe that that’s what some … Ulysses S. Grant versus Dwight D. Eisenhower, who came in and really instituted a sense of order and purpose and discipline to the White House, but that requires a sense that, “Hey, maybe the way that I want to do things are not the way that things are going to have to be. I’m going to be okay accepting that. I’m going to put in the hard work to do what needs to be done.”

Brett McKay: Well, I’m curious, Ryan. You’re a writer, and you’re a successful one. How has your approach to your craft and your business changed since you’ve gained success? Obstacles Is the Way is a New York Times Best Seller. Right?

Ryan Holiday: Not New York Times, but it has sold very very well. In some ways, I don’t want to say it caught me off guard, but it certainly sold better than I expected. As I finished this book, I think one of the things you have to do in that position is … Now the expectations are higher. I’m not freed from those expectations. I have to deliver to an audience. I have to hit a certain mark. Ideally in a career, you’re always getting better than you were before. Now the expectations have changed and that’s something that’s managed, or has to be managed.

I think the big thing that happens when people are successful, whether you’re a writer or an entrepreneur or even an executive, is that more responsibilities and obligations are thrust upon you. Where I was able to write the last book without as many interruptions, now I’ve got interviews that I have to do or speaking gigs that I have to do or my business is taking off. I have more clients. Now, if I don’t have the discipline to institute a system or a schedule that I stick to or if I’m not able to prioritize and I treat everything that happens equally, that is a recipe for dropping some major balls, making errors, letting people down.

I mentioned Eisenhower. You guys have an amazing post on Eisenhower’s priority matrix, about urgency versus important. That is the situation that success puts you in, is you’ve got so many demands on your time that if you can’t properly prioritize and order them and deal with them accordingly, you’re going to find yourself consumed with some trivial matter that used to be part of your job, but you’re too egotistical to delegate. Those are just some of the ways that you find yourself in a position of abundance, certainly, but that doesn’t mean that there are not problems related to it.

Brett McKay: Right. I think that it’s just in the delegation. Right? There’s lot of books and articles about delegating. Yeah. I think the thing that keeps people from delegating is ego. They think, “I can do this better than the other guy I’m going to delegate this to.”

Ryan Holiday: Totally. Here’s why it’s egotistical. You’re right. I can do most of the things that I have to delegate. I mean there’s the stuff I don’t like, like booking travel or scheduling. I don’t like that, but a lot of the things that I now have to delegate, I like doing or I know that I’m really good at, but you have to be able to do the calculation that says, “Hey. I’m handing this off to this person, and it’s going to be done 10% not as well going forward, but the trade off for that is I have to do this other thing and I’m the only person in the world that can do that thing. I’m the only one that can write my books.” I guess theoretically there’s ghost writers, but given that this is my job, I’m the only one that can do that.

Kobe Bryant, he’s the only one that can get on the court and play as Kobe Bryant. As these endorsements and … Maybe he’s actually great at negotiating contracts, and it seems silly to give someone a 15% commission for negotiating your contracts for you, but if that’s distracting from the training that he has to do, or that’s occupying his mind so he’s not thinking about the next game with the same dedication that he did before, all of sudden his performance on the court is going to suffer. I’m not Kobe Bryant. I’m not saying that, but all of us deal with that problem in our own way, that we’re the only ones that can do some of the things, and if we’re not able to delegate, those things are going to suffer.

There’s a quote I have in the book from Eisenhower’s chief of staff. He’s saying, “The president does the most important things, and I do the next most important things.” If you can’t build the approximation of that into your own life once you’re successful, I don’t think success if going to last that long for you, or it’s going to be very miserable.

Brett McKay: Yeah. Let’s talk about failure.

Ryan Holiday: Yeah.

Brett McKay: Everyone’s going to fail at some point in their life. How is ego the enemy when we fail? The moment we fail, it’s when you think people wouldn’t have any ego. Right?

Ryan Holiday: Or you think that ego was helpful because it would help you, protect you, in that moment of vulnerability.

Brett McKay: Right.


Ryan Holiday: In fact, the vulnerability is good. By preventing you from having it, it’s preventing you from capitalizing on it. Let’s say you were egotistical in your success, and you alienated people, and you made some mistake or you overreached. Failure, in that way, is a moment of truth. Right? It’s exposing this thing that maybe you didn’t want to be true. The worst thing that could happen is for you to bury your head in the sand. The worst thing that could happen is that you hit what should be rock bottom, but you’re too hardheaded to accept that that’s what in fact has happened. That happens a lot.

Think about Steve Jobs. Steve Jobs was fired from Apple by John Sculley because he’d become unmanageable. He was unaccountable. He was basically unhinged. He could have taken that and said, “This guy screwed me over. He screwed me over. This is the worst thing that’s ever happened to me. I’m going to retire with my money and millions and live a life of luxury,” or whatever. Instead he said … and he was an egotistical person, but he started two other companies, and those companies were better than Apple. He learned from those mistakes, and one of those companies was Pixar. He learned from those mistakes. He went on a journey of self-improvement and introspection.

Ultimately, he came back to Apple and built it into the world’s most valuable company, but that’s not what most people do when they’re fired. Most people get fired and then they hold a grudge, and they believe that they’ve been screwed over or wronged, and they continue down that negative path. It becomes a downward spiral for them. What ego does when we fail is it refuses to learn the lessons inherent in that failure and set us up for greater failure.


Brett McKay: Right. I think you called this narcissistic injury.

Ryan Holiday: Yeah. Yeah. Narcissistic injury, it is a psychological term. It’s like when something happens and we take that as an injury to our identity and to our fragile sense of self. When gang members kill each other, it’s funny. It’s tragic, but it’s funny. The things they kill each other over are these things that a normal person would be like, “Wait, what do you care that he said that about you?” Because their narcissistic ego is so fragile, the idea that someone would bump up against them or that someone would disrespect them in quotes leads them to do this horrible thing that is … Obviously, going to jail is far worse than somebody tagging a wall in your neighborhood or whatever, but the narcissistic injury, it’s so fragile that it has to deal with this threat in an overblown, preposterous fashion.

I think so much of what happens to us when we’re consumed by ego is that we take the success that we’ve achieved and we say that it says something about us as a person, and then logically, when we fail or when we’re snubbed by someone or we’re disrespected by someone, we take that as a statement about our identity as well. Often, that makes us overreact in a such a damaging way that’s it far worse than whatever had happened already.

Brett McKay: Right. On the flip side, it doesn’t even have to be someone else doing something to you. It could just be like fate, just like luck, chance.

Ryan Holiday: Totally.

Brett McKay: Caused you to fail. You started your business at the wrong time. There’s a downturn in the economy, yet because of that narcissistic ego, you think, “Well, it’s something I did. I messed up,” even though anyone else in your position would have done the exact same thing.


Ryan Holiday: Sure. Ego makes it hard to ask for help. It makes it hard for you to reevaluate your decisions. It makes it impossible for you to see this thing objectively because you’re so tied up in it. It either makes what could have been a small problem into a full blown catastrophe, or it just delays the inevitable. It’s kicking the can down the road, and when you come back to it, it’s worse. There’s so many people, they narrowly dodge a crisis, but instead of learning from it, the next crisis is just 10X more explosive.

Brett McKay: Ryan, we’ve been talking about how ego can be the enemy, but is ego always a bad thing? Look, I’m a big student of history. Churchill was an admitted egoist, extremely. He was supremely to get to his goal. Even Teddy Roosevelt, you could say, was extremely egotistical. Yet ego is what drove these guys, what they were going. They feel like they had something to offer people. Right? There’s that narcissism. They felt that they were the guys who were there to save democracy, or Teddy Roosevelt in his case, clean up the muck and the corruption that was going on. I mean, how can you balance that? What is going on there? Would you call that ego, or is it something else, or can ego sometimes be beneficial in small doses?

Ryan Holiday: Yeah. That’s the fascinating question about this. Why are there so many incredibly successful, accomplished, even admirable people who did have big egos? A friend of mine, Daniel Brian, wrote a book about presidents. He starts, he’s like, “Look, to be told when you’re 10 or 11 years old that the president is the most powerful man in the world, and to think, ‘Oh, that should be me,’ requires a certain amount of ego and maybe even a bit of insanity.” There’s no question that an unending drive to not just be successful but to be the number one person on Earth, that’s going to require a certain amount of ego, I think.

When you look at people like Winston Churchill or … We’ll start with Churchill. Churchill was, on the one hand, incredibly talented, super smart, courageous, wise, honorable, all these amazing things. I think that’s why he was successful, not because of his ego. Now, a lot of musicians were drug addicts, but that wasn’t what fueled their music. In fact, that took away from it. When you look at Churchill’s life, he was right so often but he alienated many people, and he would hurt his own chances of success because he didn’t understand that the way that he dominated conversations, the way that he overstepped his bounds, the way that he impeded in other people’s thing. He was convinced that being right all the time was all that mattered. In fact, if he’d had a little bit more empathy and a little bit more understanding, he’d have been probably more successful.

His deep conviction that he was right about Nazi Germany whereas everyone else was wrong, that worked when he was right in that instance, but there was other times in his career where he felt he was equally right and had unending confidence, and egotism convinced that he was that, and he was wrong. It’s a double-edged sword. I think someone like T.R. is similar in the sense that, if you watch the Roosevelt documentary that Ken Burns just did, it’s the same thing. You see this guy who, at the end of this life, has so clearly been driven by this compulsion that he cannot be still, he cannot do anything, that it forced him to run for his disastrous third term. He turned on his protégé, who was one of his close friends. He did this adventure in South America that nearly killed him. He forced his kids to fight in World War I where they died. It wasn’t necessarily easy to be Theodore Roosevelt, and I think some of us would be aghast at the cost of that ego in his personal life as well.

Brett McKay: Yeah. It’s a double-edged sword.

Ryan Holiday: I think so. It forces you … In some ways, you have to be a little bit crazy to go this far, but it’s a gamble whether that craziness is ultimately going to take a hard toll on you as well. It’s like when we look at these really successful egotists, we also want to look back and think, “Okay. Is there a politician who was just as egotistical as Winston Churchill, who’s career ended disastrously because of that ego?” Almost certainly so.

Brett McKay: Adolf Hitler.

Ryan Holiday: Yeah, right. The survivorship bias gives us a warped picture of these things, I think.

Brett McKay: Right. Well, Ryan, this has been a great conversation. Now, where can people learn more about Ego Is the Enemy?

Ryan Holiday: The book is available everywhere, Amazon, Barnes & Noble. It’s coming out in a bunch of different languages, which I’m really excited about, and then you can go to my website,, and read my stuff there.

Brett McKay: Awesome. Well, Ryan Holiday, thank you so much for your time. It’s been a pleasure.

Ryan Holiday: Thanks, man. I appreciate it. It’s always good to talk to you.

Brett McKay: My guest today was Ryan Holiday. He’s the author of the book Ego Is the Enemy. You can find more information about his work and the book at, and it also is available at and bookstores everywhere. Also, make sure to check out the show notes for this podcast at

Well, that wraps up another edition of The Art of Manliness Podcast. For more manly tips and advice, make sure to check out The Art of Manliness website at, and if you enjoyed this show, I’d really appreciate it if you gave us a review on iTunes. Help us spread the word about the show. As always, I appreciate your continued support, and until next time, this is Brett McKay telling you to stay manly.

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