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Insights From Ego Is The Enemy Pt. 2 - Success (#21)

This really is a 12/10 book IMO. Really well-researched, full of insights and historical examples that I really can't summarize in 7-8 minutes.

Here is Pt.2 of my insights from Ryan Holiday’s Ego Is The Enemy (7 min read)


  • Why is success so short-lasting? Ego shortens it. We stop learning, we stop listening, and we lose grasp on what matters.

  • As success arrives, like it does for a team that has just won a championship, ego begins to toy with our minds and weaken the will that made us win in the first place. 

  • Ego has the same roots as people with a major drinking and drugs problem - insecurity, fear, a dislike for brutal objectivity. 

  • Unbridled personal egotism blinds a man to the realities around him, more and more he comes to live in a world of his own imagination. 

  • “Man is pushed by drives, but he is pulled by values” - Viktor Frankl, author of Man’s Search For Meaning (

  • “Without the right values, success is brief".

  • We can’t keep learning if we think we already know everything.

  • We have to build an organization and a system around what we do - one that is about the work and not about us. 

Always Stay A Student

  • Genghis Khan was not born a genius - his was a “persistent cycle of pragmatic learning, experimental adaptation, and constant revision driven by his uniquely disciplined and focused will”.

  • He was the greatest conqueror the world ever knew because he was more open to learning than any other conqueror has ever been. 

  • Khan learned the importance of winning hearts and minds. 

  • As we first succeed, we will find ourselves in new situations, facing new problems. The freshly promoted soldier must learn the art of politics. The salesman, how to manage. The founder, how to delegate. 

  • “As our island of knowledge grows, so does the shore of our ignorance” - John Wheeler, American physicist

  • It takes a special kind of humility to grasp that you know less, even as you know and grasp more and more. 

  • Humility engenders learning because it beats back the arrogance that puts blinders on. It leaves you open for truths to reveal themselves. You don’t stand in your own way. 

  • How can you tell when someone is truly humble? I believe there’s one simple test: because they consistently observe and listen, the humble improve.

  • At every step and juncture in life, there is the opportunity to learn - and even if the lesson is purely remedial, we must not let ego block us from hearing it again. 

  • Too often, convinced of our own intelligence, we stay in a comfort zone that ensures that we never feel stupid (and are never challenged to learn or reconsider what we know). 

  • The second we let the ego tell us we have graduated, learning grinds to a halt. 

  • Pick up a book on a topic you know next to nothing about. Put yourself in rooms where you’re the least knowledgeable person.

  • An amateur is defensive. The professional finds learning (and even, occasionally, being shown up) to be enjoyable; they like being challenged and humbled, and engage in education as an ongoing and endless process.

  • Peter Drucker says that it’s not enough simply to want to learn. As people progress, they must also understand how they learn and then set up processes to facilitate this continual education. 

Don’t Tell Yourself A Story

  • "If the players take care of the details, “the score takes care of itself”. The winning would happen". - Bill Walsh, American football coach who won Three Super Bowls 

  • Your story should be : I hoped. I worked. I got some good breaks. 

  • Crafting stories out of past events is a very human impulse. It’s also dangerous and untrue. Writing our own narrative leads to arrogance. 

  • Narratives don’t change the past, but they do have the power to negatively impact our future. 

  • Once you win, everyone is gunning for you. During your moment at the top you can afford ego the least - because the stakes are so much higher, the margins for error are so much smaller. 

  • The founding of a company, making money in the market, or the formation of an idea is messy.

  • When we are aspiring we must resist the impulse to reverse engineer success from other people’s stories. 

  • Paul Graham warns start-ups against having bold, sweeping visions early on. 

  • “The way to do really big things seems to be to start with deceptively small things.”

  • Instead of pretending that we are living some great story, we must remain focused on the execution - and on executing with excellence. 

What’s Important To You

  • “To know what you like is the beginning of wisdom and of old age.” - Robert Louis Stevenson, British author during 1800s

  • We’re never happy with what we have, we want what others have too. We want to have more than everyone else. We start out knowing what is important to us, but once we’ve achieved it, we lose sight of our priorities. Ego sways us, and can ruin us. 

  • All of us waste precious life doing things we don’t like, to prove ourselves to people we don’t respect, and to get things we don’t want. 

  • Ego leads to envy and it rots the bones of people big and small. Ego undermines greatness by deluding its holder. 

  • The farther you travel down that path of accomplishment, whatever it may be, the more often you meet other successful people who make you feel insignificant. 

  • euthymia (a normal, tranquil mental state or mood) - is the sense of our own path and how to stay on it without getting distracted by all the others that intersect it. In other words, it’s not about beating the other guy. It’s not about having more than the others. It’s about being what you are, and being as good as possible at it, without succumbing to all the things that draw you away from it. It’s about going where you set out to go. About accomplishing the most that you’re capable of in what you choose. 

  • It’s time to sit down and think about what’s truly important to you and then take steps to forsake the rest. 

  • Maybe your priority actually is money, influence, or change. All of these are perfectly fine motivations but you do need to know. You need to know what you don’t want and what your choices preclude. Because strategies are often mutually exclusive. 

  • Life requires those trade-offs but ego can’t allow it. 

  • Find out why you’re after what you’re after. Ignore those who mess with your pace. 

Entitlement, Control, and Paranoia

  • Achieving success involved ignoring the doubts and reservations of the people around us. It meant rejecting rejection. It required taking certain risks. 

  • “He who indulges empty fears earns himself real fears.”

Managing Yourself

  • “It is not enough to have great qualities; we should also have the management of them.” - La Rochefoucauld, French author during the 1600s

  • The system and work habits that got us where we are won’t necessarily keep us there. When we’re aspiring or small time, we can be idiosyncratic, we can compensate for disorganization with hard work and a little luck. That’s not going to cut in the majors. In fact, it’ll sink you if you can’t grow up and organize. 

  • As you become successful in your own field, your responsibilities may begin to change. Days become less and less about doing and more and more about making decisions. Such is the nature of leadership. This transition requires evaluating and updating your identity. It requires a certain humility to put aside some of the more enjoyable or satisfying parts of your previous job. It means accepting that others might be more qualified or specialized in areas in which you considered yourself competent. 

  • Sometimes systems are better decentralized. Sometimes they are better in a strict hierarchy.

  • Maybe you can run your business remotely, or maybe it’s better for everyone to see each other face-to-face. 

Beware The Disease Of Me

  • For us it’s beginning to think we’re better, that we’re special, that our problems and experiences are so incredibly different from everyone else’s that no one could possibly understand.

  • Ego needs honors in order to be validated. Confidence, on the other hand, is able to wait and focus on the task at hand regardless of external recognition. 

  • “Play for the name of the front of the jersey, and they’ll remember the name on the back”. - Tony Adams, former soccer player and winner of 4 league titles

Meditate on the Immensity

  • “A monk is a man who separated from all and who is in harmony with all.” - Evagrius Ponticus, Christian monk

  • Ego tells us that meaning comes from activity, that being the center of attention is the only way to matter.

  • When we lack a connection to anything larger or bigger than us, it’s like a piece of our soul is gone.

Maintain Your Sobriety

  • The ego tells us we’re invincible, that we have unlimited force that will never dissipate. 

  • “You can’t solve...tasks with charisma” - Angela Merkel, Chancellor Of Germany

  • There’s an old line about how if you want to live happy, live hidden.

  • Most successful people are people you’ve never heard of. They want it that way. 

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