Ryan Holiday

Ryan Holiday on Achieving Greatness Through the Lens of Stoicism

What does it mean to pursue true greatness? Is it defined by the amount of trophies, awards, or wealth you’ve accumulated? Or is it something less physical and perhaps only found deep under the surface of our character? On this episode of Conversations with Tom, bestselling-author Ryan Holiday joins Tom Bilyeu to discuss stoicism, character, and the philosophy of action and how it can be applied to your life today to create a drive towards your goals. They discuss how the stoics would interpret today’s political culture and identity politics, the power of moderation as a virtue, why character is crucial to play the infinite game of life, what true heroes look like, and equality in America.

Purchase Ryan’s book, ’Lives of the Stoics’: https://www.amazon.com/Lives-Stoics-Living-Marcus-Aurelius/dp/052554187X/ref=sr_1_1?dchild=1&keywords=lives+of+the+stoics&qid=1601318520&sr=8-1


Stoicism | Ryan and Tom discuss how the ‘stoics’ would interpret today’s culture wars. [0:46]

Be Involved | Ryan discusses how stoicism is a philosophy of action, not thought. [7:02]

Politics | Ryan discusses today’s identity politics and it’s consequences on one’s self. [12:00] 

Equilibrium | Ryan discusses virtues and their balance needed in today’s political culture. [17:55]

Preferred Indifference | Ryan reveals why you should seek independence in thought. [23:41]

Goals | Ryan discusses leadership, shared goals and how ego can be detrimental. [28:26]

Character | Ryan reveals why character is what you need for the infinite game of life. [34:54]

Elasticity | Ryan discusses the idea of ‘greatness’ and its elasticity. [41:48]

Greatness | Ryan shares the incredible story of James Stockdale. [49:18]

McCain | Ryan reveals why John McCain is in the same camp of greatness. [58:43]

Heroes | Ryan reveals why we don’t celebrate true greatness in today’s culture. [01:02:41]

Women’s Strength | Ryan discusses the power, courage, and impact of female heroes. [1:09:25]

Encouragement | Tom shares the encouraging impact his wife has had on his life. [1:15:09] 

Sink or Swim | Ryan discusses the consequences of today’s changing world. [1:18:44] 

No Shoving Principal | Ryan discusses the power of competition and the drive to win. [1:22:16]

Disadvantages | Ryan discusses the history of the unfair playing field in America. [1:29:00]

Context | Ryan reveals the approach and historical context of Booker T. Washington. [1:38:38]

Approaches | Tom discusses the different approaches to solving the same problem. [1:43:37]

Impact on Others | Ryan discusses the ultimate purpose of stoicism. [1:46:46]

Change | Tom and Ryan discuss the power to cause change. [1:49:00]


“To me, moderation is a key virtue of life.” [22:06]

“The podium and a prison is the same place.” [45:11]

“If they can force you to do it, you don’t know how to die.” [54:11]


Website: www.ryanholiday.net

Twitter: twitter.com/RyanHoliday

Instagram: instagram.com/ryanholiday

Facebook: facebook.com/ryanholiday


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