Episode 49 | Why Ego is Your Enemy

with author and media strategist Ryan Holiday

David Hassell interview David Hassell interview


AWE Episode graphic Ryan Holiday

According to Ryan Holiday, there is an enemy within us.

This enemy has derailed the careers of promising young geniuses, decimated great fortunes, and run companies into the ground. It’s made adversity unbearable and turned struggle into shame.

It’s name? Ego.

Ryan Holiday is a media strategist, best selling author, and the former marketing director of American Apparel. He has been in the trenches building brands and designing media strategies, and today is one of the most highly regarded thinkers and marketers of his generation. But by his own admission, he hasn’t been immune to the dangers posed by Ego.

In his new book, Ego is the Enemy, Ryan lays out a strategy for defeating the enemy Ego, and he was gracious enough to share some of this insight – and some incredible stories – with the Awesome Office audience.

In this interview, Ryan shares how luck played a role in his success, and why the stories we tell ourselves about our successes (and failures) are so important; how the schism that formed between Ryan and his parents after he dropped out of college at the age of 19 played an important role in his career development; and why we must embrace uncomfortable moments in order to become the best version of ourselves.

This episode also marks the first time we’ve recorded with a live audience, as we set up the mics in front of 70+ Awesome Officers at SnackNation HQ.

Here’s a full length video from the event:

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Key Takeaways

  • Ryan explains why the things you’re most excited about are often the things that cause the most anxiety. 3:33 
  • Ryan tells us about his childhood in Northern California, and how everything from his parents’ professions to their decision to live in Sacramento affected his life’s journey. 6:18
  • Ryan describes the moment he realized that education and schooling aren’t necessarily synonymous. 8:02
  • Ryan talks about his decision to drop out of college at 19, and the fallout it caused with his parents. 9:49
  • Ryan relays how he became author Robert Greene’s research assistant, and how it almost fell it apart before it began. 11:38
  • Ryan dives into the premise of his new book, explaining what he means by the phrase “Ego is the Enemy.” 14:59
  • Ryan helps us distinguish the difference between confidence and ego, and why one serves us while the other hinders us. 18:35
  • Ryan shares a strategy for removing your ego when you receive constructive criticism. 20:38
  • Ryan tells us about the many times luck played a part in his success, and explains why the story we tell ourselves matters so much. 20:55
  • Ryan uses a story about Bo Jackson to illustrate why you need an “internal scorecard.” 27:26
  • Ryan and Sean talk about the pitfalls of comparing yourself to others, and why it’s ultimately a fool’s errand. 30:30
  • Ryan breaks down the misconception that you need to “find yourself” before you can identify work that’s meaningful to you. 31:40
  • Ryan shares a tactic for training people to derive satisfaction from the internal things you can control rather than the external things you can’t. 37:15
  • Ryan makes a case for life as “continuous training.” 42:40
  • Ryan explains why we need to embrace life’s uncomfortable moments and not always try to “fill them up with stuff.” 43:44
  • Ryan explains what we can do to minimize ego in the workplace. 46:18


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