Episode 48- Ryan Holiday on How to Turn Obstacles into Advantages

The New York Times calls him “a sought-after guru to NFL coaches, Olympians, hip-hop stars and Silicon Valley entrepreneurs.” Ryan Holiday is a marketing expert…

Episode 48- Ryan Holiday on How to Turn Obstacles into Advantages

The New York Times calls him “a sought-after guru to NFL coaches, Olympians, hip-hop stars and Silicon Valley entrepreneurs.” Ryan Holiday is a marketing expert…

The New York Times calls him “a sought-after guru to NFL coaches, Olympians, hip-hop stars and Silicon Valley entrepreneurs.” Ryan Holiday is a marketing expert who made a name for himself as the director of marketing for American Apparel and has gone on to work with clients like Google, Tony Robbins and Tim Ferriss. He’s the bestselling author of The Obstacle Is the Way and Ego Is the Enemy, and his books have sold more than 1.3 million copies. On this episode, Ryan shows us how to turn even the most insurmountable obstacles into advantages. We talk about what we can learn from the ancient philosophy of stoicism, the power of staying present, and why most of our failures are self-inflicted.

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Show Notes

How he decides what book projects to pursue (2:00)
The core principles of stoicism (3:18)
How Ryan first embraced the ancient philosophy of stoicism and how it applies to our world today (4:25)
Ryan Holiday’s following in the sports world and the hunger to gain a mental edge (6:02)
The relentless focus on improvement as a wall against ego (9:06)
Fearlessness stays present (11:57)
The discipline of managing your energy (13:00)
How to turn a setback into a pathway forward (14:30)
The discipline of perception: “it’s not things that upset us; it’s our judgment about things.” (19:28)
Why purpose is a more important driver than passion (22:33)
Purpose is passion at a directed level (24:18)
The things we control: our reactions, our thoughts, our emotions, the ability to change direction (26:25)
A defining moment in Ryan’s life (29:23)
A reminder he uses to stay present in the moment (33:10)

Resources / People Mentioned

The Obstacle Is The Way by Ryan Holiday
Ego Is The Enemy by Ryan Holiday
Trust Me I’m Lying: Confessions of a Media Manipulator by Ryan Holiday
Brass Check (marketing agency)
Tony Robbins, motivational speaker
Tim Ferriss, author
Tucker Max, author
Robert Greene, author
The 48 Laws of Power by Robert Greene
American Apparel
Alexander the Great
The book on stoicism that’s taking the NFL by storm (Sports Illustrated)
Bill Belichick, NFL coach
Nick Saban, college football coach
Mike Krzyzewski, college basketball coach
John Calipari, college basketball coach
Lane Kiffin, college football coach
Tiger Woods, golfer
Phil Jackson, former NBA coach
Marcus Aurelius, Roman emperor
Meditations by Marcus Aurelius
The Collected Autobiographies of Maya Angelou
Jon Gordon, author and speaker
Ryan Holiday Sells Stoicism as a Life Hack, Without Apology (New York Times)

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