When not advising bestselling authors like Timothy Ferris or Tony Robbins, Ryan Holiday works as a media strategist, marketer, entrepreneur and editor-at-large for the New York Observer. His most recent book, Ego Is the Enemy, shows how those who have attained lasting success have learned to keep their ego in check and embrace humility.
Holiday sat down with me to discuss what he learned after dropping out of college at 19, how to avoid some of the major pitfalls of ego and what he really thinks of social media.
1) You are a bestselling author, marketer, entrepreneur and media strategist, currently a columnist and editor-at-large for the New York Observer. You recently turned 29. How did you launch yourself so fast?
I was fortunate to get an early start, when I was around 19, instead of starting much later like most people. Back then, I wrote an article for the college newspaper about an author that I admired.
Because of it, we connected over email and I ended up working with him over the summer. And this was really the catalyst.
That summer opportunity led to an introduction to Robert Greene, best known for his 48 Laws of Power, who I ended up being a research assistant for.
About a year later, Robert was serving on the board of directors of American Apparel and introduced me to the CEO, who I collaborated with on some projects.
And that just started opening a lot of doors and opportunities—from becoming the Director of Marketing at American Apparel to writing my first book.
But there are a few things that have helped along the way. I’ve talked about this idea of being good at more than one thing. At one point I was a research assistant, a strategist and a marketer, and doing all those at the same time. What I’ve found is that ideas and frameworks from one field transfer over and help you get better in other areas exponentially faster.
Books have also been incredibly important as a source of learning and wisdom—I tend to read at least 5 or 6 books a month and send my favorites to my newsletter, which now has nearly 70,000 fellow book lovers who are subscribed to it.
I mentioned Robert, who has taught me a lot about the craft of writing and how to research, but there have been other mentors who have groomed me and helped me along the way. Their support has been paramount.
And of course, antithetical to a lot of the advice you hear, I’ve found that my wife has been one of the most important sources of strength and support in my life throughout these last 10 years.
2) How do you juggle your schedule and keep all the balls in the air? What do you do if you feel overwhelmed?
In terms of scheduling I have an assistant, and she is great at organizing my calendar and making sure the trains run on time. That has been key in terms of freeing up my time.
What I’ve found very helpful is that if I block my morning for the most important and critical tasks of the day, which for me would be writing an article or a chapter for a book, the rest of the day becomes much easier to handle because you know you have accomplished the most valuable stuff already. It is close to what Paul Graham has talked about in his maker vs. manager essay.
In regards to managing stress, there have been a few decisions in my life and habits that I’ve adopted that have been pillars I’ve relied on. After having lived in both New York City and Los Angeles, I decided that I wouldn’t live in a big city.
We now live on a small ranch outside Austin, surrounded by goats and donkeys—something I’d never imagined.
Compared to New York, there are fewer parties, fewer work obligations, fewer incidents where I feel pressured to impress other people, and that has removed a lot of the stress in my life. I also do strenuous exercise every day—usually swimming or running.
And lastly, I get 8 hours of sleep per night, period. I think it’s time to call bullshit on the whole “sleep when you’re dead” myth, because it’s ultimately destructive with minimal benefits.
I think as long as you have these foundational habits in place where you have a dedicated place to unwind and you work to create the conditions necessary to live the life you want to live, you are by definition removing a lot of the stress in your life.
3) You dropped out of college at 19. Have you ever regretted that? In retrospect, do you think college is important or overrated? If someone does go to college, what do you think they should be trying to get out of it?
It worked out pretty well (which honestly surprised me), so there is little to regret there. I don’t want to say it wasn’t terrifying. But it’s difficult to give a clean answer about the relative importance of college because the reality is very messy.
Maybe you are going to an unknown for-profit school that is trying to scam you into lifelong debt or you are learning a craft at a place that guarantees a lot of opportunities and opened doors after graduation. Like a lot of things, the answer is that it depends. What are the real opportunity costs? As in, do you have clear options in front of you that are better than college? Because I only dropped out after I had projects I was working on that I would have killed to get after graduation. It’s not strategic to abandon point A if there is no point B. And college is usually the best default.
I would suggest to anyone who is currently in college to really think about the opportunities that are available to them by virtue of being a student. The world is much kinder to students. The second you leave you’re now competition. As I mentioned earlier, part of what helped me get that first opportunity was the fact that I was a student.
4) You recently released a new book, Ego Is the Enemy, which advises putting your ego aside as it can actually hold you back. This seems to fly in the face of much of the advice out there today, which is often about believing in yourself and your own greatness. Isn’t ego an intrinsic part of self-confidence, and also key to driving us forward?
Yeah, exactly. This is what led me to write the book. It’s true that we do see successful people with inflated egos, but we often immediately commit two fallacies.
First, we see a causal relationship that may or may not be there. Was it their ego that drove their success or was it their inherent talent, hustle, dedication to the craft and hard work? And could they have been more successful if it wasn’t for their ego?
The second fallacy is that we do not see all the quiet and successful people who have no need to perform in front of an audience of people.
And don’t forget, what is also hidden from view are all the people who have flamed out because of their own ego-driven sabotage.
There is also a clear distinction between real confidence and ego. As I say in the book, ego is stolen but confidence is earned.
Confidence is based on objective assessment of your capabilities and is earned through hard work. Ego, on the other hand, just deludes us that we are the greatest thing in the world.
5) What are the major pitfalls of ego? How do you control it?
Entitlement. Self-absorption. Overconfidence. Complacency. Pride. Greed. Paranoia. I think one of the worst manifestations of ego is when it tells us that we know more than we do.
This is why there are two chapters in the book that I dedicate to this idea about remaining a perpetual student. There’s a quote from Epictetus in the book that I love: “It is impossible to learn that which one thinks one already knows.”
But this is exactly what ego does. It tells us that we are already the best, that we have it all figured out. This is the moment when you essentially kill your learning progress in its tracks.
I think the answer to that lies in self-awareness and humility. In the course of writing the book, I’ve found a handful of tactics that help. Anything that humbles you is key—think of picking up a book on a subject you know next to nothing about, or just trying a new hobby. Find yourself in a room where you are the least knowledgeable person.
Another one is spending time in nature and remembering how small you are in relation to the universe. Strenuous exercise is also good. All these have been useful.
6) What leaders do you look up to, and why? Why characteristics do you hope to emulate?
William Tecumseh Sherman. He came from nothing and accomplished great things without ever feeling he was entitled to the honors he had received. He forged a personality that was ambitious but patient, innovative without being brash, and brave without being dangerous.
To me, that’s what real leadership looks like. I find it sad that this model of the quiet, unglamorous realist is often forgotten in the history books or, worse, vilified. I highly recommend both his memoirs and the biography by B. H. Liddell Hart.
7) What advice would you give to a young up-and-comer who is trying to make a name for him or herself? What is the best way to set yourself up for success?
I would probably paraphrase the bit of advice that I was told when I was first starting out: Find canvases for other people to paint on. And what I mean by that is that when we are young and just starting out, chances are that we don’t know what we’re talking about.
There’s one fabulous way to work that out of our system: giving an extra push to people who are already good and then learning from them as they get to work.
I call this “The Canvas Strategy.” It is a different mindset than just making other people look good, an approach that tends to imply a lot of ass kissing. Instead it’s finding the direction someone already intended to head and help them get there, freeing them up to focus on their strengths.
It’s a simple but counterintuitive approach: advance by advancing others. And this is why mastering the ego is critical, because the strategy by definition requires one to forget about getting credit and recognition, at least in the short term.
8) What major pitfalls do you see for the next generation? What concerns do you have when you look into the future?
One thing that has really been exacerbated over the last few years is that our culture—and social media in particular—has made us all into unpaid performance artists. Ironically, all these tools that are supposed to help us share our realities are instead forcing us to create these artificial stories about ourselves that we know are not true.
The net effect is both separating us from our own actual experiences and separating us from the other people. Increasingly, the real world is left on the cutting-room floor. What is left is artifice and even deceit. And the results are perpetual envy and inferiority.
I am sure you’ve seen it: people who you know are going through financial difficulties, but who are apparently living it up on Instagram. Even in our own life, would we ever post when things aren’t going well? So I would probably say that’s one thing that concerns me.