Ryan Holiday
Ryan Holiday, author of, ‘The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph’

We are stuck, stymied, frustrated. But it needn’t be this way. There is a formula for success that’s been followed by the icons of history—from John D. Rockefeller to Amelia Earhart to Ulysses S. Grant to Steve Jobs—a formula that let them turn obstacles into opportunities. Faced with impossible situations, they found the astounding triumphs we all seek. These men and women were not exceptionally brilliant, lucky, or gifted. Their success came from timeless philosophical principles laid down by a Roman emperor who struggled to articulate a method for excellence in any and all situations. In this episode we speak with Ryan Holiday, author of the bestselling book, The Obstacle Is the Way, as he reveals what these principles are, and how to turn our own adversity into advantage.

Ryan Holiday is a media strategist and prominent writer on strategy and business. After dropping out of college at nineteen to apprentice under Robert Greene, author of The 48 Laws of Power, he went on to advise many bestselling authors and multiplatinum musicians. He served as director of marketing at American Apparel for many years, where his campaigns have been used as case studies by Twitter, YouTube, and Google and written about in AdAge, the New York Times, and Fast Company.

His first book, Trust Me I’m Lying —which the Financial Times called an “astonishing, disturbing book”—was a debut bestseller and is taught in colleges around the world. He is the author of two other books and is now published in 16 languages. He currently lives in Austin, Texas with his rebellious puppy, Hanno and pet goats


“Wealth is created by scarcity. It’s the fact that there are not many people who have been successful at the thing you are trying to do that makes it worth doing.”

– Ryan Holliday

Quotes from Ryan:

[shadowbox]“If you do one thing you have to focus totally on it, and mastering that one thing is quite difficult. If you do two things, especially two different things is quite difficult. But doing three, or four, or five things that have some overlap may be even easier than the other options because there’s all this energy swirling about and you can mix it together.”

“Just because you’re good at something and you can make a lot of money at it doesn’t mean it’s the only thing you could do and it’s the only thing you are allowed to do. There are a lot of wealthy people who hate their lives.”

“A lot of the rules and assumptions about things are supposed to be were made up by people who are either less successful, less ambitious, or more willing to compromise than you are.”

“You don’t magically figure out what it is you want to do. It is a slow gradual thing. Epiphanies are much more rare than people assume.”[/shadowbox]

What we learn in this episode:

  • How to find what you want to be when you grow up?
  • Why are obstacles a good thing?
  • What is stoicism?


The Obstacle Is the Way


Twitter: @ryanholiday

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