Ego Is the Enemy — Ryan Holiday

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Ryan Holiday's bio as featured on this book reads as follows:

"RYAN HOLIDAY is a bestselling author and media strategist. He dropped out of college at nineteen to apprentice under Robert Greene, author of The 48 Laws of Power, and later served as the director of marketing for American Apparel. His company, Brass Check, has advised clients like Google, TASER, and Complex, as well as many prominent bestselling authors. Holiday has written several other books, including The Obstacle Is the Way, which has been translated into twenty-eight languages and has a cult following among NFL coaches, world-class athletes, TV personalities, political leaders, and others around the world. He lives on a small ranch outside Austin, Texas. Visit"

Holiday isn't one of today's most rich, famous, or most powerful men, so one might question his qualifications to write a book on taming ego. Yet, as we find out in his book, it is not only the rich, famous, and powerful who are vulnerable to the depredations of ego - we all are. And who is most at risk? Those who've achieved recent, early success.

Holiday charts 3 phases in the human endeavor, which I've summarized as:

  1. aspire: work, work, work. "You can't build a reputation on what you're going to do" - Henry Ford

  2. success: don't let it get to your head.

  3. failure: don't take it personally. Doing the work is enough.

Holiday stresses the iterative nature of this cycle. Be action and education focused, he -- informed predominantly by Stoic philosophy -- tells us, and forgo validation and status. Eschew a grandiose ambition and always keep one foot in front of the other. Never stop growing.  Work hard, succeed, be brought painfully low - duris dura franguntur: hard things are broken by hard(er) things - but then recover and work again. Just as in Superforecasting, we are told that evaluation and re-adjustment after failure are the keys to success: TryFailAnalyzeAdjustTry, with the two A's being the most important and prohibited by ego.

`Ego is the Enemy` reads like a modern Aesop's Fables: it's full of short, self-contained historical examples that prove the book's title and the author's point: ego, an inevitable product of success, is the enemy and a monster of your own creation that'll preclude continued success unless controlled.

We're therefore advised to be detached from our outcomes, and to fulfill our own standards. For:

 "It is a sore thing to have labored along and scaled arduous hilltops, and when all is done, find humanity indifferent to your achievement." - Robert Louis Setevenson

All in all, Ego is the Enemy is made more relevant in a world such as ours where we've been told that self-esteem is one of the most important things you can impart to a child. For the symptoms of success are not the same as success itself. Indeed, self-esteem and ego are nearly indistinguishable but the latter will prevent you from hearing the potential feedback that you so very need to succeed.


Narcissistic injury: taking totally indifferent and objective events personally, i.e. ego telling you "this isn't fair"

Some quotes directly from the book

"As Irving Berlin put it, 'Talent is only the starting point.' The question is: will you be able to the make the most of it? Or will you be your own worst enemy? Will you snuff out the flame that is just getting going?"

"Some part of us wants to believe that those who have great empires set out to build one. Why? So that we can indulge in the pleasurable planning of our own. So we can take full credit for the good that happens and the riches and respect that come our way. Narrative is when you look back at an improbable or unlikely path to your success and say: I knew it all along. Instead of: I hoped. I worked.

Some of the examples I enjoyed:

  • George McClellan, chosen to command the Union forces in the Civil war because he ticked all the boxes of a great general. Except he was quite possibly the worst because he was constantly thinking about himself... "The idea that his task was relatively straightforward, that he just needed to get started, was almost too easy and to obvious to someone who had thought so much about it all." He was caught up in his imaginary audience, convinced that his every move was being watched the rest of the world, caught in his own ego.

  • Genghis Khan, the greatest conqueror the world ever knew because he was more open to learning than any other conqueror has ever been... "as our island of knowledge grows, so does the shore of our ignorance" - John Wheeler, a physicist who helped develop the hydrogen bomb. Success necessitates an even opener mind as you encounter necessarily more difficult and complex situations.

  • Malcolm X, whose time in prison was his educational experience. He not only read the dictionary from start to finish, but copied it down from cover to cover. He chose 'Alive time' over 'Dead time.'

  • Katherine Graham, who took over the Washington Post after her husband's suicide and ran it successfully despite the odds (constant internal insurrection, lack of experience), to be not only the first female CEO to run a Fortune 500 company, but perhaps one of the best ever. "To love what you do and feel that it matters how could anything be more fun??" - Katherine Graham