35: Ego is the Enemy with Ryan Holiday

“Is it 10,000 hours or 20,000 hours to mastery? The answer is, it doesn’t matter. There is no end zone.”

—Ryan Holiday, Ego is the Enemy

What happens when you reach previously unimaginable pinnacles of success . . . and still find yourself miserable? I’m stoked to bring you today’s Pivot Podcast with Ryan Holiday—marketing master, studier of Stoic philosophy, and author of several bestselling books. His first, Trust Me, I’m Lying—which the Financial Times called an “astonishing, disturbing book”—was a debut bestseller. His next books, Growth Hacker Marketing and The Obstacle is the Way were both published by Penguin/Portfolio, and his latest, Ego is the Enemy launches in two weeks! Fun fact: he has the last two book titles tattooed on each arm.


If you pre-order 1 copy of the book before June 14th, you’ll receive:

  • 1 exclusive BONUS chapter of Ego is the Enemy titled “Take Care of Yourself.”

  • 1 exclusive copy of “Ego is the Enemy Reading List”, which details all the books and sources that led Ryan to writing Ego is the Enemy.

  • Instant access to the Introduction & Prologue of Ego is the Enemy, before anyone else.

  • 1 free Ego is the Enemy temporary tattoo. (Like with Obstacle, Ryan got a matching tattoo for the maxim behind this book and his publisher made a replica for anyone that preorders)

Click here to pre-order 1 copy, then email your receipt to ryholiday@gmail.com with “Preorder #1” in the subject.


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. He currently lives in Austin, Texas and writes at RyanHoliday.netThought Catalog and for the New York Observer.


  • How he landed a gig as Director of Marketing for American Apparel at 21 years old—and how he knew it was time to leave

  • Why he turned down his first book deal offer from a traditional publisher at 23 years old

  • How he made himself superfluous at American Apparel . . . and therefore indispensable

  • How he connected with Robert Greene at such a young age

  • His philosophy on excellence before ego: “When you’re a talented person and you can do good work for people, you tend to find they pass you around like a good restaurant recommendation.”

  • What it was like watching a friend and mentor build, then destroy, a company worth billions of dollars

  • How some of his biggest financial and prestige successes led to feelings of dread and despair

  • Why Ego is the Enemy when it comes to temptation from “loud and shiny” opportunities

  • Examining the part of ourselves that has urges that are destructive and unhealthy

  • His original proposal for Ego is the Enemy got rejected three times

  • How those rejections made the book stronger: “The constraints are ultimately what created this book.”

  • “You have to deeply believe in what you’re doing, but you also have to be willing to abandon that opinion, go back to the drawing back and re-evaluate.”

  • The distinction between ego and confidence

  • Why he rejects the trope, “Fake it ’til you make it”

  • The Canvas Strategy: do grunt work, and expect no credit

  • “There are times we do everything right, even perfectly, and still experience failure.”

  • “You don’t get an award when you get to 10,000 hours.”

  • A day in the life of a book in Ryan Holiday’s house (how he takes notes, catalogs ideas)

  • The anti-library: “Collect knowledge to have at your fingertips for when you need it.”

  • The thing that most surprised him from the time he started writing to now


Listen below or on iTunesSoundCloudOvercast, or Google Play Music:


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