Ryan Holiday on Turning Obstacles to Advantages

Ryan Holiday is a media strategist and the author of The Obstacle Is the Way and other books. Recently I had the opportunity to talk with him about his work and his advice for turning adversity to advantage. —Kirk Barbera

Kirk Barbera: When you dropped out of college at nineteen to work for best-selling author Robert Greene, what was your vision for your future at that time?

Ryan Holiday: That’s interesting; I don’t know that I had a “vision.” Sometimes I think this idea of having a grand vision can be misleading. For me, I remember not knowing whether I was going to drop out. I thought about it, did the math, and said, “Okay, if I were about to graduate from college and I had a job offer from Robert Greene, would I be pleased with that?” And the answer was yes. So why would I stay in school to potentially get this same opportunity that I’ve been offered right now? That’s why I made the leap.

I think I knew very deep down, but also somewhat vaguely, that I wanted to be a writer, and that the way to become a writer was to learn from a great writer. I knew that one day I could be a writer, but the plan for me then was to be in proximity of great people whom I could learn from.

It wasn’t like I had a plan to write a particular book at that time. I knew that I wasn’t ready to even think about such plans seriously. I had a lot to learn, and the best way to learn was to attach myself to someone who had the same sort of career, credibility, and respect that I eventually wanted for myself.

Barbera: As a successful media strategist and author, and having written The Obstacle Is the Way, what obstacles along the way shaped your career into what it is today?

Holiday: I get that question a lot, and it’s interesting. Maybe you don’t mean this, but when you refer to “obstacles along the way,” it seems like the implication is, first, that I faced massive adversity in the past, and, second, that adversity came to a stop at some point. Neither implication is true.

Obviously, dropping out of college was stressful and a type of obstacle. Then I was young and working in a high-stakes job; there was a lot of stress and difficulty around that. Some of my projects went poorly. Sometimes I faced controversy and public embarrassment. None of these problems stands out as what made me who I am.

Obstacles and adversity are part of our day-to-day reality. We wake up and deal with a world that in many ways we don’t control. I’m in the middle of a business deal right now that’s been a total bear to wrap up. In another project, I’ve had to be very patient with some incompetent people who make me want to strangle them. And all these things are happening right during tax season, and I’m also in the middle of a move. How I respond to this series of events is just as critical as what I might have faced at nineteen.

Adversity is something we face on a constant, continuous basis. It’s the process of struggling with it and overcoming it on a daily basis, rather than overcoming it once and then being done with it, that really makes us who we are.

Barbera: You’ve read widely in philosophy and history, and you recommend to people that they do the same. People are busy; why should a nonacademic businessperson read history and philosophy?

Holiday: I’ll mention a couple of reasons. First, often people are not actually as busy as they think they are. The average person engages in many trivial activities or a lot of busywork that they use as an excuse to not avail themselves of the vast stores of knowledge that humans have acquired over the past five thousand years. Starting with Gilgamesh, we have the oral and written tradition of articulating the human experience and attempting to detail our difficulties, our triumphs, our experiences. Over these five thousand years, human beings have been struggling with problems, many of which are more significant, difficult, and life threatening than whatever you or I woke up to deal with today. So why would we not make ourselves familiar with that information and those lessons?

There is a quote: “Any fool can learn from experience. It’s better to learn from the experience of others.” That’s what reading is, particularly with philosophy and history. Philosophy at its finest is designed to help us with the difficulties of life and help us with what they call the good life. And in history we find entrepreneurs; we find soldiers; we find executives; we find lovers, fathers, spouses; we find children; we find every imaginable person in every imaginable situation, and we can learn from their experience. I think you’re an idiot to not learn from it.

Barbera: To take an example, in reading about Napoleon Bonaparte, I learned not only about his military career, but also about his love letters to Josephine. Learning about the dimensions of a historical figure can help you understand yourself as well.

Holiday: Yes. And Napoleon traveled with this enormous library—even on the campaign trail. Look at Alexander the Great, one of the greatest conquerors to ever live. The first thing he does when he engages in a campaign is send for Aristotle so he can have a tutor to teach him about the world and teach him about philosophy. So the idea that you’re too good or too busy for such study, when some of the smartest and most successful people in the world attribute their success largely to their reading, seems to be a ridiculous claim.

Barbera: Many hard-working, intelligent people dislike their career paths and don’t know what to do about it. In a way, the problem is that the “good is the enemy of the great.” Do you have advice for people who may be in this situation, to help them get out of this rut?

Holiday: I think many people don’t seriously ask themselves what they want their life to look like. Early in my life, I didn’t necessarily know I wanted to be a writer, or a writer of a particular kind of book. But I knew and admired certain writers, and I wanted a similar life for myself. I knew I wanted to learn from those writers.

A lot of people have jobs where they’re surrounded by miserable, unfulfilled people, and then they wonder why they are unfulfilled and miserable themselves. It’s like someone saying, “I’m stuck in traffic.” No; you are traffic. You need to surround yourself with people who push you to be better and who challenge and inspire you with their example. And if you can’t physically be around those people, you need to surround yourself with their works, books, and teachings. I’ve been lucky enough to meet people who open doors for me, but I first had to put myself in a position to meet and interact with those people.

Another huge damper of success is the inability to see yourself objectively in the world, and to make adjustments and changes, because you’re so vividly living in your own fantasies or delusions.

Barbera: In The Obstacle Is the Way, you talk about mentors who intentionally put an obstacle in someone’s way. Did anyone you’ve worked with ever give you a project that you were incapable of taking on at the time but that ultimately helped you in your career?

Holiday: Of course. You get stronger by lifting weights that are too heavy, right? You don’t get stronger just lifting the same weight more times. There has to be that sort of struggle. I’ve experienced a mentor dumping more work on me than I thought I could handle, and I had to make my way through it. You can give yourself such challenges, too. You bite off more than you can chew, then you figure out how to chew it and get it down. The idea is not that a mentor should torture a protégé with overwhelming goals; it’s that whatever you think you’re capable of, that’s probably somewhat less than what you are actually capable of.

Barbera: In Sophocles’ Antigone, the character Haemon is questioned about his wisdom because of his youth. Haemon replies, “If I’m right my age shouldn’t matter.” You’re twenty-seven. What advice do you have to other young people who are belittled because of their age?

Holiday: Age can matter in terms of experience. I remember one of the things my parents told me when they were teaching me to drive. I was at a stop sign, and I went to go, and someone else went to go. My parents asked me what I was doing, and I said, “Well, I had the right of way.” My parents replied, “Look, it doesn’t matter that you had the right of way if you die in a car accident.”

Generally, of course, it shouldn’t matter what your age is. It should matter that you’ve been thoughtful and you’ve done your work. But often that’s just not how it goes. People are territorial. They’re afraid of change. They’re jealous. This goes to the value of a mentor and the need to attach yourself to someone who does understand and appreciate you and who will promote your work. The mentor system is not just about learning from someone; it’s also about having a mentor vet your work. When I was working for a talent agency, clients weren’t paying to get advice from a twenty-year-old; they wanted to know that the advice had been filtered through someone who knows what they are talking about. There’s probably some truth in the advice that minorities often give each other, “because of who you are you have to be twice as good.” So it’s not just about being right; it’s about being so right that in order to overcome the discrimination and the resistance that you are feeling, you’d better be overwhelmingly right.

Barbera: What do you have cooking for the future?

Holiday: I try not to talk about projects while they’re underway. I feel like that has an adverse effect. I don’t want to tell you what my idea is and then somehow get your validation for something that I haven’t taken all the way to fruition or culmination yet. I’ll take the credit when it’s done, but first I want to know that it meets my personal standards. That’s what motivates me every day to get up and work on it: I need to finish it and ship it. That’s the driving force. And I find that people can get very much seduced by talking about their work rather than doing it.

I’ll say this much: I’m working on a new book that in some ways will be a follow-up to Obstacle. It’s about ego and the adverse effects of self-absorption that I think is endemic to my generation and our current cultural landscape.

Barbera: Your point about the “need to finish it and ship it” reminds me of those people who are always “with book”—as in writing a book—but who never actually finish it. What are your thoughts about people who talk about their goals but never, in effect, “finish it and ship it?”

Holiday: There’s a hilarious book filled with tweets of people talking about the novels they are supposedly working on. That’s a very sad reality. These people thought it was more important to tweet about their unfinished novel than to write it.

In terms of technology, it has never been easier to start a business, to be an entrepreneur, to be a writer, to be a musician. It is certainly much more difficult to be successful at any of those things. So I think you have to adjust and talk about what you are doing less, to compensate for the fact that you’re going to need a lot more energy and skill to be successful at the thing you are talking about.

Barbera: I could talk with you all day, but I’ll end with that and say thank you very much. Hopefully we can chat sometime in the future. I’ll look out for your next book and anything else you’ve got coming.

Holiday: Thank you.

About Kirk Barbera

Kirk Barbera is a purpose coach and podcaster living in Southern California. Kirk works with professionals and small businesses by helping them formulate and coordinate their activities around a central purpose. His podcast is GL^2 Great Living Great Literature.

View all articles by Kirk Barbera →