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Ryan Holiday On The Perils of Ego & Inherent Value of Humility

By July 24, 2016January 26th, 2024No Comments

“[E]go is the enemy of what you want and of what you have: Of mastering a craft. Of real creative insight. Of working well with others. Of building loyalty and support. Of longevity. Of repeating and retaining your success. It repulses advantages and opportunities. It’s a magnet for enemies and errors. It is Scylla and Charybdis.”

Ryan Holiday

Ask today’s guest and he’ll tell you our culture is currently mired in an unprecedented epidemic of ego — a societal blight of apocalyptic proportions precipitated by the advent of selfie-crazed social media, self-esteem parenting and spurious self-help gurus fomenting an illusory sense of entitlement.

The result is a woefully misplaced celebration of ubiquity over meaningfulness: Of endless distractions over devotion to work ethic. Of self-congratulatory passion over fidelity to process. Of unbridled hubris over humility. And of rampant self-seeking over service.

We often equate ego with confidence, self-assuredness and ultimately success. The domain of the great visionary. 

But what if this notion is utterly false? A personality trait that, at every turn, thoroughly undermines that which we seek?

And what if modesty, humility and self-honesty are not actual weaknesses but in fact our greatest asset?

This week Ryan Holiday graces the podcast to explain.

An autodidact of astute intellect that belies his 29 years, Ryan is many things — a voracious reader, prolific writer, shrewd observer of culture, media strategist and the author of four acclaimed bestselling books.

Dropping out of college at 19, Ryan began his multi-faceted career as an apprentice under Robert Greene, the acclaimed author of The 48 Laws of Power*. He went on to amplify the work of several New York Times bestselling authors before serving as the director of marketing for American Apparel – a job he held at the ripe age of 22.

When he’s not penning books or thought pieces for The Observer or Thought Catalog, Ryan oversees Brass Check— a consultancy firm he founded that advises New York Times bestselling authors like James Altucher, Arianna Huffington and even Tony Robbins, as well as corporate clients that include Google, Casey Neistat’s video sharing app Beme, Creative Live, Complex and Refinery 29.

About a year ago, Ryan and I went deep on his life and his heralded book, The Obstacle Is The Way*— a primer on the functional applicability of stoic philosophy for turning modern-day obstacles into opportunities and adversity to advantage. Now translated into 17 languages, it’s a read that achieved cult status among some of the world’s most successful CEOs, political leaders, world class athletes and NFL coaches. One of my most popular episodes, I highly suggest you check out RRP 168 if you missed it the first time around.

Today, Ryan drops in to talk about his new book, Ego Is The Enemy*. His best work to date, it’s a philosophical and historical exploration of the difficulties we unnecessarily create for ourselves throughout the various phases of life.

If The Obstacle Is the Way is a roadmap for facing and overcoming external challenge, Ego Is The Enemy is a natural extension of that map, plotting practical strategies to optimally navigate our biggest internal limiter.

This is a conversation about the menace of ego at every stage of life and career. How early in life, ego impedes learning and the cultivation of talent. How ego can blind us in success. How ego magnifies failure to hold us back. It’s a conversation about why we should be purposeful over passionate. And, to coin Ryan’s words, its about why we should be humble in our aspirations, gracious in our success and resilient in our failures.

Specific topics discussed include:

  • collaborative process of writing the book
  • the fall of American Apparel
  • reverence and ego
  • constructive criticism
  • defining ego in the context of book
  • being humble in our aspirations
  • being gracious in our success
  • being resilient in our failure
  • egoism and narcissism in social media
  • the cost of achieving greatness
  • satisfying the ego and seeds of destruction
  • discussing the root of an unhealthy ego
  • the concepts of passion & purpose
  • creating healthy boundaries
  • developing a healthy sense of confidence & humility
  • justifiable ego in the face of injustice
  • the decline of irresponsible journalism (i.e. Gawker)

Intellectually curious, poised and self-effacing to a fault, Ryan is a rare breath of fresh air in a culture of bloviators and white noise. Plus, he’s a really good runner. He kicked my butt on the trail right after we finished the podcast.

I sincerely hope you enjoy this conversation as much as I did.

Peace + Plants,


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Thanks to Jason Camiolo for production, interstitial music and audio engineering; Chris Swan for production assistance & show notes; Shawn Patterson for graphics; and Ana Leimma for the theme music and interstitial music. This week we feature a new demo track entitled Moonlight Sparks  by Ana Leimma. If you enjoyed it, subscribe to their channel on Soundcloud and leave a comment there letting them know how much you enjoyed it!

*Disclosure:Books and products denoted with an asterisk are hyperlinked to an affiliate program. We are a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for us to earn fees by linking to and affiliated sites.

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