Episode 130: Ryan Holiday – What Is Your Greatest Enemy? Your Ego

If you enjoyed the first conversation Ryan Holiday and I had, then you will absolutely love this one.  We went much deeper on a number of really interesting topics including: Destiny (does it choose us?), Ego, Stoicism, Risk, Metallica, Focus, Silence, and Gawker Media… I loved it.

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 most recent book, “Ego Is The Enemy” draws on a vast array of stories and examples, from literature to philosophy to his­tory. We meet fascinating figures such as George Marshall, Jackie Robinson, Katharine Graham, Bill Belichick, and Eleanor Roosevelt, who all reached the highest levels of power and success by con­quering their own egos. Their strategies and tactics can be ours as well.

Episode 130: Ryan Holiday – What Is Your Greatest Enemy? Your Ego

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“Ryan Holiday is one of his generation’s finest thinkers, and this book is his best yet.” – Steven Pressfield, author of New York Times bestseller “The War of Art”

The Learning Leader Show

In This Episode, You Will Learn:

  • The importance of always being a student – “One cannot learn that which they think they already know.”
  • The remarkable story of Kirk Hammett, lead guitar player for Metallica – His actions upon being hired will blow you away (and inspire you)
  • Ryan’s process for receiving feedback and coaching
  • Why it’s not wise to try and impress others
  • Being motivated to prove people right
  • The importance of your spouse
  • The power of silence and how it relates to Robert Greene’s work in The 48 Laws of Power
  • The phrase confident and secure leaders are willing to say that others are not
  • Don’t follow your passion, follow your effort – Nobody quits what they’re good at
  • What is destiny?  Is it predetermined?
  • Meeting your heroes in person
  • Why Ryan feels that Gawker is one of the worst media companies of all time and the piece he wrote about Peter Thiel
  • Great giveaways for his book

“Be an anteambulo – Clear the path for others to be successful.”

“One cannot learn that which they think they already know.”

Continue Learning:

You may also like these episodes:

Episode 107: Simon Sinek – Leadership: It Starts With Why

Episode 127: Adam Grant – How Originals Impact The World

Episode 117: Tim Urban – Using Procrastination To Perform A TED Talk

Episode 114: Cal Newport – Deep Work Is Your Super Power

Did you enjoy the podcast?

This was a jam packed episode full of great content.  Ryan Holiday is a leader who leads an very interesting life. Who do you know that needs to hear this?  Send them to The Learning Leader Show!

Episode edited by the great J Scott Donnell

From The Prologue of “Ego Is The Enemy”

“While the history books are filled with tales of obsessive visionary geniuses who remade the world in their image with sheer, almost irrational force, I’ve found that history is also made by individuals who fought their egos at every turn, who eschewed the spotlight, and who put their higher goals above their desire for recognition.”

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