Ryan Holiday

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. . . .

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