Ryan Holiday | Ego Is the Enemy (Episode 519)

Ryan Holiday (@ryanholiday), author of Ego Is the Enemy, talks about how learning to put our higher goals above a desire for recognition leads us to true accomplishment.

The Cheat Sheet:

  • What is the ego?
  • When does the ego go from being a fundamental part of our existence to an all-destroying enemy?
  • What are the downfalls of ego (and how can we avoid them)?
  • Learn how aspiration, success, and failure are influenced by ego.
  • Understand the delicate relationship between ego and envy.
  • And so much more…


Ego — while admittedly a distortion of reality that makes us the central heroes in our own stories — is a fundamental part of everyone’s existence. But what happens when we let our desire to be perceived as great get in the way of truly achieving greatness? How do we keep that distortion of reality in check?

Ryan Holiday, author of Ego Is the Enemy, joins us for episode 519 of The Art of Charm to discuss the downfalls commonly caused by an unchecked ego and how we can avoid them.

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The world is a certain way regardless of what we wish were true. But our egos allow us to navigate this world with a sense of purpose — where we figure as the central figures in our own stories. Because an ego is informed mainly by the perspective of its beholder, it’s not quite accurate. It’s a distortion of reality. As such, we need to make sure we keep this distortion in check and not let it control and consume us when we start to achieve some level of success — whether hard-earned or lucky.

We’re all susceptible to an overinflated sense of self when we let our egos get the better of us, but some of us take it to levels that alienate us from the rest of society. And society notices.

“I’m not saying you’re Nixon and I’m not saying you’re Kanye West in terms of the severity of your toxic ego,” says Ryan Holiday, author of Ego Is the Enemy, but it’s there in all of us and it’s essentially adding nothing positive to our lives.”

An ego gone amok is like building a beautiful mansion on a sand dune. You can stand back and admire this monument to your greatness you created with your own two magnificent hands, but it only takes a few external forces (e.g., wind, rain, time, bad press, gossip, etc.) to make it collapse upon itself.

The more successful we are, the greater the danger of ego manifesting in negative ways — such as paranoia and greed. “Oftentimes, it’s precisely those feelings that undermine or destroy what we built,” says Ryan. “Someone can steal something from you or there could be an economic collapse; now all of a sudden, you’re not aspiring or succeeding. You’re going through some sort of difficult circumstance. Or maybe you’ve failed and you’re looking at the wreckage of your life. Here, ego blames other people for your circumstance instead of learning from it. Or ego doubles down on whatever toxic decisions or bad choices you made that caused these problems.

“Or — and I think this is the hardest part — ego, which was so validated by your success, now abandons you and says, ‘Hey, you are worthless. You are a nobody. You are a loser because you failed. And everyone hates you and you’ll never recover!’ This is where resentment and hatred and bitterness come in.”

Envy and Ego

One of the ways ego gets ugly is when it goes head-to-head with the envy we feel toward the success of others. Our ego may make us feel entitled to the rewards of such success because the path to that success is invisible.

“I made a choice to pursue this thing instead of that thing,” says Ryan. “Where on Earth do I get off thinking that I should have been able to pursue my path — which makes me happy and I chose and wanted — but then I should also get the rewards of someone else’s path? If you decide to pursue classical music, you can’t sit alone at your hotel room and wonder why there’s not mobs of young fans waiting outside to take a selfie with you. If you wanted that, you shouldn’t have chosen classical music — you should have chosen pop music!

“Life is about choices and trade off, and you made a choice and a trade off. What did you expect?”

Listen to this episode of The Art of Charm to learn more about Ryan’s first-hand experiences with ego as the enemy when his friend and mentor Dov Charney was ejected as CEO of American Apparel (and how being involved in the fallout made him reevaluate his own path), how Ryan avoided letting early success get to his head, what we can dissect from the envy we feel toward others’ success, what we can learn from the failures of Ulysses S. Grant (one of Ryan’s heroes), how we don’t have to wait to achieve mastery in something in order to pursue it, and lots more.


If you enjoyed this session with Ryan Holiday, let him know by clicking on the link below and sending him a quick shout out on Twitter:

Click here to thank Ryan Holiday on Twitter!

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Jordan Harbinger - author of 930 posts on The Art of Charm

Jordan Harbinger has spent several years abroad in Europe and the developing world, including South America, Eastern Europe, and the Middle East, and speaks several languages. He has also worked for various governments and NGOs overseas, traveled through war zones, and been kidnapped -- twice. He’ll tell you the only reason he’s still alive and kicking is because of his ability to talk his way into (and out of) just about any type of situation. Here at The Art of Charm, Jordan shares that experience, and the system borne as a result, with students and clients.

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