Ryan Holiday hit the real world hard and fast. At 19, he decided to drop out of college because he was offered an opportunity any ambitious would-be writer would pounce on: a job as a research assistant to Robert Greene, author of The 48 Laws of Power. This would lead him to working with and advising several bestselling authors and multiplatinum musicians.

He kept the ball rolling from there and became the marketing director of American Apparel, where he put into place a very successful campaign that produced both big profits and heavy criticism. But he grew disgusted with the state of online media and released a book that put his name on the map, Trust Me, I’m Lying. The book detailed how easy it was to manipulate online media because of its lack of source verification and its traffic-driven outrage-porn business model.

After reading that book, I discovered and devoured all of his writings. I studied and applied a lot of his stoic principles about business, life, and writing into my own thought process and actions. He is one of the most unique, practical, and highly respected contemporary thinkers.

In his new book, Ego Is The Enemy, he seeks to advise the reader through the lives of notable and not-so-notable historical and current figures about what havoc an untamed ego can have on a person’s life and how one goes about controlling it.

Raul Felix: Ryan, in this book, you analyze how the ego can have destructive effects on people. You even mentioned seeing one of your mentors transform from someone you aspired to be like to never wanting to be like that person. Egos don’t only exist in people of high achievement or celebrity; it is also quite common in the general population. What common examples do you see today of people with high egos yet little substance to back it up?

Ryan Holiday: Yes, exactly. It is precisely because we see this type of behavior in a lot of prominent public figures that we try to reverse-engineer their success and manufacture the right pose. There are plenty of “wantrepreneurs” out there acting like mini-Steve Jobs and plenty of musicians who think that behaving like Kanye West is acceptable. We falsely assume that ego—manifested in their entitlement, arrogance, braggadocio, and swagger—is what drove success. In fact, it was the talent that compensated for the ridiculous, destructive ego. We don’t think about the survivorship bias that hides from view all the people who’ve failed and flamed out because of their own ego-driven sabotage. What is also hidden is the huge subset of successful people who are not clamoring for the limelight.

We also live in a culture that actively promotes constant self-promotion and grandiosity—all of it magnified by a thousand by social media. It is also hard not to think you’re the greatest if that is the message you’ve been hearing constantly from your parents since you were born. Combine these factors, and you see why we have a downright epidemic of ego.

Part of why I initially wanted to write this book is because I would get a lot of emails from really overconfident and brash young people who would send me all these ridiculous emails. And then at large, you see it for instance with people who are not willing to take entry-level positions—But I went to college! But it was the Ivy League! —or people who are not willing to listen or take any sort of feedback because they think they’ve already figured it all out. You see it with people bragging and boasting about what they’re going to do—their ego craving for validation and applause before the fact.

Raul Felix: A line that really stuck out to me was, “If you start believing in your own greatness it is the death of your creativity.” I’m sure any artist who has produced a piece or two of topnotch work has fallen into that trap—even gloating to themselves or others about their creative genius. I’ve done it a few times when I wrote some really good stuff. How does one avoid falling prey to that part of the ego while keeping the fortitude to drive on?

Ryan Holiday: I love that line, too; it’s actually from Marina Abramović, the performance artist. There is another quote from UFC champion Frank Shamrock that I try to think of on a regular basis: “False ideas about yourself destroy you.”

The second you start gloating and letting success get to your head—that you’ve figured it all out—that’s precisely when you make some critical mistake or miscalculation. In that moment of self-satisfaction, learning grinds to a halt. What I love about writing, actually, is that those feelings are constantly elusive. You can’t get a big head with a craft which requires decades and decades of work before you even begin to approach mastery. There is no “graduation.” If you think like a craftsman, become an eternal student, and adopt a beginner’s mindset, ego is suppressed and you can go on working and working.

The problem is when you start to listen to other people. My last book has started to sell very well, so I could let that puff me up. I’ve gotten some very kind and generous reviews. It would be a mistake to listen to those things too closely. For the next book, you have to continue to approach it with humility and self-awareness. Essentially you have to start from zero.

And in the book I talk about how ego separates us from reality—we start living in our heads. This sort of intoxication with positive feedback and success makes us forget that there are people in our field who are infinitely more successful than we are. Someone recently mentioned that one of the best things about attending TED is how humbling it is to be in a room with all these people. It doesn’t take away what you’ve accomplished, but it puts things into perspective—it grounds you back to reality.

Raul Felix: You also mention the incubation process, that period where you must trudge through a long period of obscurity as you wrestle with a topic or a paradox. What would the incubation process look like for the normal person, who can’t really drop everything and live in a cabin cut away from society as they hone their skills?

Ryan Holiday: I’ve mentioned the incubation process, which is what the strategist John Boyd called his ‘draw-down’ period. It is the time after we’ve had what we think is a brilliant idea and then take the time to process it and think it through before we embark on it.

I do not think it requires you to drop everything and go live in a cabin away from society—I certainly didn’t do that (although living on a ranch helps!). It’s simply the moment after you’ve had the idea, after you’ve put the first round of thinking into the project and then have to step back and say: “OK, what do I really have here?” “Do I actually have something?” “What is this really going to be?”

Otherwise, we have ego telling us that we have the best idea ever and blinds us to all the components that we need to work on. Ego Is the Enemy ended up being different from the initial book proposals precisely because there was time between conception and execution.

And wrestling with a topic or a paradox requires you to invest a serious amount of time in a state of what the author Cal Newport calls “deep work”—that place of intense concentration and cognitive focus where real progress is made. Two examples for me are walking and running, during which I wrestle with ideas. I also have an article on this site on how to accomplish more deep work in our lives where I give some other examples that can be helpful.

Raul Felix: You made an a sharp distinction of how the ego affected two Civil War generals: Ulysses S. Grant and William Tecumseh Sherman. Grant sought the high office of the presidency and chased after big money, causing him to have one of the most corrupt administrations in our nation’s history and going publicly bankrupt, while Sherman chose to be content and lead a private life afterwards. How can a person distinguish if what they’re chasing after is genuine or if it’s their ego yearning for more?

Ryan Holiday: It’s funny because I really admire both of them. This country we live in would not be possible without the personal heroism and bravery of both of them—probably Grant most of all. At the same time, I find the end of his life to be very sad. I wish he could have enjoyed the success he had.

In my view, the main reason doing that is so hard is because we try to have it. We want what we want and what other people have, too. We want to do our own thing but not be left out, either. We want a quiet life but also want to be the center of attention.

It’s our ego telling us to always say yes to more things, more projects, events, meetings. It will also always say yes to more money if given the opportunity. (Ego doesn’t care whether that’s the right decision for us.) Ego rejects trade-offs. It wants it all. It’s incredible how hard it is for us to say no to anything—again, especially money.

The solution? Really ask yourself: Why do I do what I do? What is important to me? What is the one goal or thing I want more than any other? That’s the question you need to answer. Stare at it until you can. It’s not easy by any stretch, and I am telling you that from my personal experience. I’ve had to do so in my own life and it’s why I have an entire chapter dedicated to that idea. Understand what’s important to you and know your priorities.

The goal is to make decisions with clarity and purpose—not ego. Only after spending time alone and asking ourselves these tough questions can we know which way we are swaying.

Raul Felix: Hitting rock bottom, whatever that may be for a person, is one of those humbling experiences that can make or break you depending on how your ego responds to it. I’ve been through a couple of hard times in my life where I needed to fight for every bit of progress while I got back on my feet. Along the way I learned some lessons. Yet I remember being warned that my actions would lead to that. What do you feel it is about our nature that makes it so we don’t always learn from others but have to fuck up big time in order to drive consequences of our actions through our skull?

Ryan Holiday: Nobody gets very far or lives very long without getting their ass kicked a few times. It’s not pleasant at the time when in retrospect we tend to appreciate those experiences—because we learned so much from them. The problem is that those lessons tend to fade over time, because we start to feel like we’ve moved past them—that we’ve got it. When I got Ego Is the Enemy tattooed on my forearm it is exactly this part of human nature that I wanted to warn myself against on a daily basis. It is this part of us that says that we know better, that makes us unwilling to listen to others, to remember to be objective and clear-headed and honest. I have made those mistakes myself, and having a daily reminder is one way to prevent it from happening again.

And it will always be the case that the hardest lessons are learned from direct experience. Plutarch says that we don’t “so much gain the knowledge of things by the words, as words by the experience [we have] of things.” That shouldn’t be an excuse to not study and learn to prevent those from occurring. Reading books—especially biographies—becomes helpful here. Whatever situation you are currently facing, others have gone through that and written about it.

There’s a quote from Bismarck that says, in effect, any fool can learn from experience. The trick is to learn from other people’s experience. It is why the book is full of cautionary tales—so that we see what ego-driven choices and decisions others made in history and how that led to their downfall. Still, though, I understand that we’re often going to need to experience some of that directly. I wish it wasn’t true, but it is.

~Raul Felix

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Read: Keep Moving, Young Man
Read: An Army Ranger Interviews A Navy SEAL On Resilience

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