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Insights From Ego Is The Enemy Pt. 1 - Aspiration (#20)

Here is Pt.1 of my insights from Ryan Holiday’s Ego Is The Enemy (8 min read).

Definition of Ego

  • The ego we see most commonly goes by a more casual definition: an unhealthy belief in our own importance. Arrogance. Self-centered ambition.
  • It’s that petulant child inside every person, the one that chooses getting his or her way over anything or anyone else. The need to be better than, more than recognized for, far past any reasonable utility.

Pitfalls of Ego

  • Ego is the enemy of what you want and 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.
  • We can’t work with other people if we’ve put up walls. We can’t improve the world if we don’t understand it or ourselves. We can’t take or receive feedback if we are incapable of or uninterested in hearing from outside sources. We can’t recognize opportunities - or create them - if instead of seeing what is in front of us, we live inside our own fantasy.
  • “If you start believing in your greatness, it is the death of your creativity” - Marina Abramovic

Three Stages of Life

  • Three stages of life - we’re aspiring to something, we have achieved success, or we have failed.
    • Aspiration leads to success (and adversity). Success creates its own adversity (and, hopefully, new ambitions). And adversity leads to aspiration and more success ⇒ which is an endless loop.
  • Ego is stolen. Confidence is earned.


  • Be slow in your deliberation, but be prompt to carry out your resolves.
  • Among men who rise to fame and leadership two types are recognizable - those who are born with a belief in themselves and those whom it is a slow growth dependent on actual achievement.
  • One might say that the ability to evaluate one’s ability is the most important skill of all. Without it, improvement is impossible. 
  • We will learn that though we think big, we must act and live small in order to accomplish what we seek. Because we will be action and education focused, and forgo validation and status, our ambition will not be grandiose but iterative - one foot in front of the other, learning and growing and putting in the time. 


  • “Those who know do not speak. Those who speak do not know” - Lao Tzu
  • “Never give reasons for what you think or do until you must.”
  • A man’s best treasure is a thrifty tongue. 
  • Talk depletes us. Shut the f***k up and get the work done.
  • Success requires a full 100% percent of our effort, and talk flitters part of that effort away before we can use it. 
  • They work quietly in the corner. They turn their inner turmoil into product - and eventually to stillness. They ignore the impulse to seek recognition before they act. They don’t talk much. Or mind the feeling that others, out there in public and enjoying the limelight, are somehow getting the better end of the deal. 

To Be Or To Do

  • To be somebody or to do something. In life there is often a roll call. That’s when you will have to make a decision. 
  • What is your purpose? What are you here to do? Because purpose helps you answer the question “To be or to do?” quite easily. 
  • If your purpose is something larger than you - to accomplish something, to prove something to yourself - then suddenly everything becomes both easier and more difficult. Easier in the sense that you know now what it is you need to do and what is important to you. The other “choices” wash away, as they aren’t really choices at all. They’re distractions. It’s about the doing, not the recognition. Easier in the sense that you don’t need to compromise. Harder because each opportunity - no matter how gratifying or rewarding - must be evaluated along strict guidelines: Does this help me do what I have set out to do? Does this allow me to do what I need to do? Am I being selfish or selfless?

Become A Student

  • Each fighter to become great, he said, needs to have someone better that they can learn from, someone lesser who they can teach, and someone equal that they can challenge themselves against. - Frank Shamrock, MMA fighter
  • To become great and to stay great, they must all know what came before, what is going on now, and what comes next.
  • A real student is also his own teacher and his own critic.
  • “It is impossible to learn that which one thinks one already knows”
  • The art of taking feedback is such a crucial skill in life, particularly harsh and critical feedback.

Don’t Be Passionate

  • Passion typically masks a weakness. It’s breathlessness and impetuousness and franticness are poor substitutes for discipline, for mastery, for strength and purpose and perseverance. You need to be able to spot this in others and in yourself, because while the origins of passion may be earnest and good, its effects are comical and then monstrous. 
  • What humans require in our ascent is purpose and realism. Purpose, you could say, is like passion with boundaries. Realism is detachment and perspective. 

Follow The Canvas Strategy

  • Greatness comes from humble beginnings, it comes from grunt work. 
  • What is the Canvas strategy?
    • Find people, thinkers, up-and-comers to introduce them to each other
    • Find what nobody else wants to do and do it
    • Find inefficiencies and waste and redundancies.
    • Produce more than everyone else and give your ideas away.

Restrain Yourself

  • “I have observed that those who have accomplished the greatest results are those who never grow excited or lose self-control, but are always calm, self-possessed, patient, and polite”. - Booker T. Washington
  • Our own path, whatever we aspire to, will in some ways be defined by the amount of nonsense we are willing to deal with. It will be tough to keep our self-control. 
  • When you want to do something - something big and important and meaningful - you will be subjected to treatment ranging from indifference to outright sabotage. 
  • Those who have subdued their ego understand that it doesn’t degrade you when others treat you poorly; it degrades them.
  • When someone doesn’t reckon you with the seriousness that you’d like, the impulse is to correct them.
  • It is a timeless fact that the up-and-coming must endure the abuses of the entrenched. 
  • But you’re not able to change the system until after you’ve made it. 

Get Out Of Your Own Head

  • “A person who thinks all the time has nothing to think about except thoughts, so he loses touch with reality and lives in a world of illusions.” - Alan Watts
  • Don’t live in the haze of the abstract, live with the tangible and real, even if - especially if - it’s uncomfortable. Be part of what’s going on around you. Feast on it, adjust for it. There’s no one to perform for. There is just work to be done and lessons to be learned, in all that is around us. 

Danger of Early Pride

  • “A proud man is always looking down on things and people; and of course, as long as you are looking down, you cannot see something that is above you.” - C.S. Lewis
  • Receive feedback, maintain hunger, and chart a proper course in life.
  • “If you can’t swallow your pride, you can’t lead.” - Genghis Khan
  • What we cultivate less is how to protect ourselves against the validation and gratification that will quickly come our way if we show promise. What we don’t protect ourselves against are people and things that make us feel good - or rather, too good. We must prepare for pride and kill it early - or it will kill what we aspire to. We must be on guard against the wild self-confidence and self-obsession. “The first product of self-knowledge is humility.” - Flannery O’Connor
  • Privately thinking you’re better than others is still pride.
  • Don’t boast. There’s nothing in it for you.

Work, Work, Work

  • “The best plan is only good intentions unless it degenerates into work.” - Peter Drucker
  • Our ego wants the ideas and the fact that we aspire to do something about them to be enough. Wants the hours we spend planning and attending conferences or chatting with impressed friends to count toward the tally that success seems to require.
  • “When you are not practicing, remember, someone somewhere is practicing, and when you meet him he will win.” - Bill Bradley
  • Make it so you don’t have to fake it - that’s the key.
  • Every time you sit down to work, remind yourself: I am delaying gratification by doing this. I am passing the marshmallow test. I am earning what my ambition burns for. I am making an investment in myself instead of in my ego. Give yourself a little credit for this choice, but not so much, because you’ve got to get back to the task at hand: practicing, working, improving. 
  • Work is pushing through the pain and crappy first drafts and prototypes. It is ignoring whatever plaudits others are getting, and more importantly, ignoring whatever plaudits you may be getting.
  • “I am going to be myself, the best version of that self. I am in this for the long game, no matter how brutal it might be.”

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