Are you an egotist? Here’s why the answer is probably yes.

Ryan Holiday is an entrepreneur, marketing strategist, and author of Trust Me, I’m Lying and The Obstacle Is the Way. His latest book, Ego Is the Enemy, may be his most interesting yet. Using various historical figures as case studies, Holiday illustrates the perils of egotism and explains how un-self-awareness is our greatest impediment.

I spoke with Holiday recently about his new book, his love of Stoic philosophy, and why he thinks ego is everyone’s enemy. Our conversation, edited for length and clarity, follows.

Sean Illing

You write that you hope people think less of themselves after reading this book. What do you mean?

Ryan Holiday

I confess that was a weird line to put in the introduction of a book. I'm sure my publisher was less than thrilled about it. Most books are designed to sell, and making people feel good about themselves is reliable way to do that. So this is an understandable bias in writing, and I'm certainly subject to it myself.

But my thinking here was simple: It's not so much that I want people to think less of themselves, it's that I want them to think rationally and objectively about their skills, not optimistically. Questioning ourselves is what drives us to improve and get better. In addition to that, the less time you spend thinking about yourself, the more time you spend thinking about others and the work you're doing and the standards you set for yourself. This is how you stretch and grow and throw off selfish, egotistical things.

Sean Illing

“Ego” is a term without a fixed definition. How do you understand “ego” in this book?

Ryan Holiday

What I think is interesting about "ego" is that we have a clear psychological definition, and I know that I'm not referring to that one. I'm referring to the colloquial definition of ego. I'm thinking of ego in the Trumpian sense, not the Freudian sense. I'm talking about arrogance over competence, complete certainty, self-absorption, etc. Bill Walsh, the former NFL coach who I discuss in the book, defines ego as the line at which confidence becomes arrogance. I'm talking about a belief in one's self that is at odds with reality.

Sean Illing

By egotist, then, you mean someone whose confidence scales with their ignorance?

Ryan Holiday

Yeah, I think that's exactly right. Obviously, successful people tend to have large egos, but, while part of that may be based on what's real, their sense of self still manages to outpace the impressiveness of their accomplishments. So when Kanye West admires his abilities as a rapper, you might call that confidence. But when he says "Edison, Jobs, West," he's being an idiot.

Sean Illing

Most people think of Freud when they think about the ego, but I wonder if you think Plato’s charioteer allegory is a better model of the psyche?

In Plato’s metaphor, the soul is a chariot guided by two horses. The charioteer is the logical part of the soul, but it’s continuously pulled in opposite directions by the horses, one of which represents our enlightened higher impulses and the other represents our irrational passions — greed, envy, self-love. How does ego, as you define it, fit into this image?

Ryan Holiday

I'm vaguely familiar with Plato's metaphor. Freud has a similar vision in which man is on the back of horse and the ego is trying to control the horse. In a weird way, the ego, as we define it culturally, tends to be the opposite of that. Ego is the horse, the wild urges within us, and we're trying to rein them in.

In that way, ego can be helpful to some people insofar as it drives them to do things. The problem is, they're not able to look at those things rationally, they're not able to understand themselves rationally. So when they get where they want to be, they inevitably imperil what they've achieved.

Sean Illing

Do you think egotism is an unavoidable byproduct of living in a status-driven society in which who you are is defined largely by what you have?

Ryan Holiday

I don't think it's unavoidable, but I do think it's related. The story of ego pervades all of human history. You can't pick up a play from Sophocles or Seneca or the poetry of Palmer or survey Buddhist thought without confronting warnings against egotism. The vocabulary may be different, but they're all referring to the same thing. Ego is a timeless theme throughout history, going all the way back to Gilgamesh. The warnings are there. It's clearly part of our shared history.

However, I would argue that today, instead of getting those warnings, we get the opposite of that. I can't think of single TED talk where the central message is: "Tone it down a bit." Instead, it's something like, "If you put your arms in a Superman pose, you can do anything, and you'll be more confident."

In the book, I talk about an imaginary audience as something that psychology has been aware of for a long time. One of the things that social media taps into is precisely this dysfunction, because it gives us an audience that feels real, however contrived. We're all performing for this crowd that doesn't really exist and it makes us see our own lives as a kind of performance.

Taghrid Chaabant

Sean Illing

You describe ego as a kind of inner narrator, that affirming internal voice that ensures we’re the heroic protagonist of the story that is our life.

Ryan Holiday

Well, I'm playing with definitions that fit. The "narrative fallacy" is our tendency to arrange facts in a coherent, chronological narrative when in reality what happens to us is mostly random and unrelated. The ego part of it is not the need to make sense of events; it's the desire to turn our lives into a movie or a novel. We all imagine we're living this heroic life in which we're the stars and everyone else is a supporting character.

I often say that Google is a company that has fallen prey to this. Google has this mantra that we're trying to change the world and invest in products that will change the world, but the reality is that Google started out as a PhD thesis. YouTube started as a dating site. The truth is that most large successes have humble beginnings. But we tell ourselves these stories about how we got where we got and these stories are often self-serving and dishonest. We're blind to the random luck that propelled us along the way.

Sean Illing

There’s a great Epictetus quote in the book to the effect that you can’t learn what you think you already know. And of course there’s the Socratic model of wisdom, according to which intelligence is knowledge of ignorance. Is ego the primary obstacle to self-awareness?

Ryan Holiday

I think ego is an incredible impediment not only to knowledge but also to potential and creativity and insight. It's particularly insidious to learning, though. If you think that you know everything that you can know, in a sense you're right. Because you're not going to learn anything else. If you see yourself as an eternal student who knows only a fraction of what there is to know, you will continue to grow and learn and progress.

How we think about the world and ourselves determines how we act and respond to it. Carol Dweck, a professor of psychology at Stanford University, calls this the "growth mindset." I think this is a much healthier and, ironically, a much more productive way of living and thinking. The alternative is basking in the glory of all that you know and all that you've done.

Sean Illing

How do you distinguish confidence or a healthy self-assurance from egotism?

Ryan Holiday

That's the million-dollar question. Simply questioning is a huge step and one that most people avoid. I've suffered from low confidence, and I suspect everyone is not confident enough in some ways and probably too confident in other ways. So it's very difficult to know where the line is.

One of the analogies I've happened upon while thinking about this book is running. I know that I can run a certain amount of miles in an hour because I've done that before, and I can also reasonably extrapolate when I want to run a marathon that this is physically possible for me because I've never quit on a run before, I've put in the miles and felt there was room left to go. I didn't assume I could do it because other people have done it. It's based on an understanding of your actual capacities and experiences and on the traits that are required to do the job or task.

Sean Illing

I like that you used historical figures as case studies to illustrate your arguments about the ego. What was the process there?

Ryan Holiday

I've been at this for a long time. I started as [The 48 Laws of Power author] Robert Greene's research assistant, and that's how he illustrates the arguments in his books. So I learned and absorbed this as a research assistant years ago. And as I was putting this book together, certain people struck me as useful models. For instance, I always admired George Marshall, who served as secretary of state and defense under President Truman, and knew that he was widely thought to be cut from a different cloth than, say, MacArthur or Eisenhower. So as I'm writing a book that lines up with that topic, I read everything I can about that person and try to discern what traits overlap with other successful people. Eventually, you find commonalities and deduce principles or primary lessons that comprise the book.

Sean Illing

Who do you think best exemplifies the virtuousness of egoless living?

Ryan Holiday

I don't know if egoless living is possible. One of the things I learned writing these stories is that there's rarely a single individual that embodies these traits in every single way. We're all flawed.

I wrote a book about Stoicism called The Obstacle is the Way. The majority of the examples I used were not people who studied or were explicit practitioners of Stoicism. But they were illustrating the principles of Stoicism, knowingly or unknowingly. I think it's the same with the characters in this book. People are complicated. There's good and bad in all of this. There's ego and egolessness in all of us. Here I wanted to find the stories where someone illustrated the highest ideal that we can embody and hold that up as example.

Sean Illing

Knowing and doing are different things. How do we translate our awareness of our egoistic impulses into meaningful action?

Ryan Holiday

Stoic philosophy is different from most philosophies in that it's not a set of precepts or systemic explanations of the universe. It's a practice. When you look at someone like Marcus Aurelius writing his "Meditations," he's not writing them … one time. He repeats himself throughout the book because he clearly knew what he should do and yet was unable to do it in his life. So it's a process.

My premise is here is not, "Read this book and you won't have an ego." Instead, it's: “Here are a set of exercises that remind us when ego has us in its sway.” I end the book with this image of sweeping the floor, which is a martial arts analogy I borrowed from [martial artist and academic philosopher] Daniele Bolelli. The idea is that enlightenment is like sweeping the floor — if you do it once, the dust comes back the next day. You have to continually sweep to keep the floor clean. Similarly, beating back the ego is a constant practice, like meditation.

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