Close Up: Ryan Holiday
Welcome to IWT’s Close Up, where we sit down with today’s leading entrepreneurs, authors, movers, and shakers. We get up close and personal to see how they work, think, and live.
In today’s Close Up: Ryan Holiday.
What gets you really excited these days?
Writing. I feel like I am getting better at it every day and I wake up excited at the opportunity to do more of it.
Besides your business and your family, what’s the single biggest success in your life?
What else is there? I don’t mean that as a joke, though I kind of do. My work is a source of great pleasure and I take a lot of pride in my marriage and my personal relationships. That’s success to me.
I do have some personal goals — I’m a runner for instance, but I don’t make a huge distinction between goals like that and my business. Running has always helped me think, being in shape allows me to fulfill my obligations in business and my personal life. I don’t know, maybe I am missing the point but that’s success to me.
What conventional advice did you flagrantly ignore and still manage to succeed?
Traditional education would be one of them. I dropped out of college and still did fine, though I think that is becoming increasingly common. I think being successful early is both related but a separate bit of advice I ignored.
The whole “be quiet and wait your turn” is not necessarily something I’ve abided by. Dropping out did let me put in more hours early so that when I did develop my skills I was still younger than I otherwise would have been, but also I didn’t see why I had to wait before I could write my own books — even about complicated or deep topics.
I would rather work very deeply and intensely on something than drag it out slowly over time, which is something I think a lot of people do — because they think they have to be a certain age or at a certain point in their lives. You know, “Oh I can’t buy a house/get married/start a company/write a book, I am not there yet.” Well, get there.
What was the biggest disaster you’ve faced? How did you recover?
I hate this question. First off, because I don’t like to spend a lot of time dwelling on the past and I don’t like neat stories about failures or great successes but I think — and people ask it a lot — that it profoundly misses the true nature of adversity in our lives.
The big disasters are rare and inconsequential. What makes us who we are are the little events — the near-failures. You get an email about something that’s gone wrong on a random morning, how do you respond? The next morning, something else has gone wrong. How do you respond? You have a bad week of those mornings, how do you keep going on without getting discouraged? You didn’t get into the college you wanted, your girlfriend dumped you, the project was only half as successful as expected, you had a falling out with a friend, an employee makes a mistake.
These are not disasters, they are the common events of life. Every day we face a world that does not behave exactly how we would like it to. It’s not about recovery. It’s about taking them in stride. Making the most of them, moving on and forgetting all about it. That’s how I try to live my life. And what you find is that most of them recede from memory — even the so called big ones. You’re too busy in the present moment to care, you’re already focused on the next one.
What’s your favorite project that you’ve ever worked on?
Having had the privilege of being involved with Robert Greene’s books (The 50th Law and Mastery) is a source of great pride for me. That I would have ever gotten to work with my favorite living author, that he allowed me to contribute in even a small way? It’s crazy for me to think about.
It was such an exciting time because it was all new to me at the time, too. I knew nothing about how books were made, I knew so little about the world, too. Every day exposed me to something new. I made a million mistakes but even those were learning opportunities. It was just a great (though stressful) time in my life.
I wish sometimes I could go back to it. Things were simpler then. It was for me, I think, what other people loved about college. And who wants that cocoon to end?
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What do you wish you could teach your 20-year-old self?
I would tell myself to relax. I was so intensely focused at 20, but so anxious and high strung that it sucked a lot of the pleasure out of it. I was worried that it would all go away. I was worried that I would screw it up. I was worried about a lot of things I really had no control over.
I would imagine that these traits did help to some degree, but they contributed to a fair amount of misery as well. Most of the things I was worried about never came to pass. Most of what I was intense about in retrospect was meaningless. What mattered was that I did good work and my luck held.
What does a “Rich Life” mean to you?
Doing what I want, when I want to do it — within reason, obviously. People tend to conflate money with the rich life, but I think ultimately wealth is about what you can afford.
The most valuable thing is freedom. That can be had for less money than people think, provided you make the right choices. If I want to travel somewhere, being able to afford the ticket is one obstacle. But the bigger ones: Do I have the time? Do I have too many other obligations? Would I allow myself to go?
I’ve tried to shape my life in such a way that yes, I can go. If I want to write about something or I have something to say, do I have the ability to do that? Or do I have to watch my words or do I have to beg someone else to give me permission? Freedom in areas like that is richness to me.
What will be the next big thing in your industry?
I really don’t know. I think we are seeing exciting stuff with video. I don’t quite know how I want to get involved yet, but clearly, that’s where a lot of eyeballs and dollars are going.
If you could have lunch with anyone, living or dead, who would you pick and what would you ask them?
I’d like to have lunch on the River Queen with Abraham Lincoln, Ulysses S. Grant, David Porter and William T. Sherman in 1865 as the end of the Civil War approached.
I don’t think I would ask much — that seems a bit presumptuous given that I’ve already asked for the ability to time travel and be set at the center of America’s greatest conflict. This was a momentous meeting and four of my heroes were all in the same room at the same time. I would just love to be there.
RYAN HOLIDAY is a strategist and writer. He dropped out of college at nineteen to apprentice under Robert Greene, author of The 48 Laws of Power, and later served as the director of marketing for American Apparel. His company, Brass Check, has advised clients like Google, TASER, and Complex, as well as many prominent bestselling authors. Holiday has written numerous bestselling books, most recently The Daily Stoic and Ego is the Enemy. He lives on a small ranch outside Austin, Texas.