Ryan Holiday is the bestselling author of “Trust Me, I’m Lying…” and “The Obstacle Is The Way: The Timeless Art Of Turning Trials Into Triumph.” He is the former Director of Marketing at American Apparel, an editor-at-large at the New York Observer, and a noted media strategist, columnist and entrepreneur. 

1. What is the most liberating thought you’ve ever had?

“It’s just life.” Nothing is so serious. We’re not building monuments for all time here. We’re just alive, trying to stay alive, and do what we can while we are.

2. What did it liberate you from?

A liberating thought and actual liberation are very different things, obviously. It first helped when I was dealing with the stress and terror of dropping out of college. I realized it was all going to be ok, whatever the outcome. It was not as serious as it felt. Since this, it helps me with anxiety and fear and high stakes.

3. What does it mean to live a good life?

Be a good person; do what you love. Those are the ingredients to ‘the good life.’

4. What illusion have you suffered from the most?

Let’s go back to the first question and then the question that comes after this one. That everything is so serious and important—it isn’t. Realizing this sucks at first. There’s a line from Ellison: “How does it feel to be free of illusion?” PAINFUL AND EMPTY,” he answers. I think that’s what we fear it’s going to be like. We build up these edifices and complexes to make us feel important, it feels very frightening to challenge them.

5. If you could go back and whisper in the ear of your 16-year-old self, what is the one thing you would tell them?

Chill the fuck out, man. It’s going to be ok.

6. What does love feel like? (Real love, not hormonal love or I-like-the-idea-of-you-so-I’m-on-a-high love).

Security. Being understood. A desire to protect that person and understand them in return.

7. What does your daily routine look like?


8. What’s your favorite thing to look at?

Water. Ocean. Lake. Reservoirs. Rivers. Preferably while running.

9. Describe your perfect weekend.

Few emails. Writing. A long swim or a very long run. Maybe a trip to Costco to get all the samples.

10. What do you worry about the most?

Too many things.

11. Why?

Because it’s the human condition. We want everything to go our way. We want things to be in control. And we sign up and commit to things that exacerbate this.

12. What makes you cry?

Making my wife hurt.

13. What do you doodle on the sides of your papers?

Scribbles. Squares within squares.

14. What is the most serendipitous thing that has ever happened to you?

Being in the same town as someone else at the same time on the other side of the world.

15. How did your biggest struggles become the pathways to your greatest success?

Struggles are relative, certainly. I was in a relationship for most of high school and the first year of college, which ended and pushed me to get serious about reading and writing. I dropped out of school which imploded my relationship with my parents and forced us to rebuild it over time. I worked myself into an unsustainable ball of stress and anguish, until I had to blow that apart and figure out something new. First world struggles, but they put me on the path I am on now.

16. What’s the first thing you do in the morning?


17. What do you wish you had more of in your life?


18. What do you find to be the most genuinely beautiful thing in the world?

Cute little kids following their parents, trying to behave and do what they know they’re supposed to do. Same with dogs, trying to adjust or change based on what they think they remember you told them one time or what it might take for you to release the ball or treat.

19. If you could be free of one thought or fear, what would it be?

You know that quote “Our deepest fear is not that we’re inadequate but that we’re powerful beyond measure?” Goddamn that quote is bullshit. I don’t think there is one fear or thought I’d want to get rid of, but I do really dislike that quote. I think it is exactly what 90% of the population does not need to hear and should not tell themselves. If there was one thought I could change, I’d like to get rid of this need for more, more, more. It’s exhausting and doesn’t do one any favors.

20. If you had the chance to tell every single person in the world just one thing, what would it be?

Think: If everyone did this, would I like it? Use that standard to benchmark your own behavior.