Ego Is The Enemy by Ryan Holiday

Ego Is the Enemy


Date read: October 2017

How strongly would I recommend? 7/10

Lasting Thoughts

There are three stages of any endeavour in life: aspiration, success, failure. At each stage, there are aspects of ego to be aware of. The most important thing is to check in with yourself regularly and maintain your focus on the process and on the work. Missteps are inevitable, but it is what we learn from those missteps that is important. Keep learning, keep striving, keep working. Stop to appreciate and reflect on your progress but don’t let it distract you from the path still ahead. The cycle of aspiring toward success and failure never ends. There is no one summit to reach. For every mountain you climb or fail to climb, there are countless more to begin anew on. 

How The Book Changed Me

It reminded me to focus on the process and not the outcome. It showed me that everyone starts from the same place when they are beginning, but it is the few that successfully deal with the plights of their egos along the way that ultimately sustain and create the most meaningful change. Success comes from learning to contend with failure, not from being perfect at something right away. 

Most Memorable Quote

“As our island of knowledge grows, so does the shore of our ignorance”.

John Wheeler

My Notes

For reference:
The bold highlights are my own emphasis
The blue highlights are passages I found noteworthy or interesting


There is no one moment that changes a person. There are many.

Ego: an unhealthy belief in our own importance. Self-centered ambition. The need to be better than, more than, recognized for far past any reasonable utility.

We can’t improve the world if we don’t understand it ourselves.

We can’t recognize opportunities – or create them – if instead of seeing what is in front of us, we live inside out own fantasy.

“If you start believing in your greatness, is is the death of your creativity.” – Marina Abramovic

At any given time in life, people find themselves at one of three stages. We’re aspiring to do something – trying to make a dent in the universe. We have achieved success – perhaps a little, perhaps a lot. Or we have failed – recently or continually.

Part 1 – Aspiration

One might say that the ability to evaluate one’s own ability is the most important skill of all. Without it, improvement is impossible.

Detachment is a sort of natural ego antidote. 

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 – on foot in front of the other, learning and growing and putting in the time.

Talking is always easy.

Talking and fighting fight for the same resources.

After spending so much time thinking, explaining, and talking about a task, we start to feel that we’ve gotten close to achieving it.

“Mere gossip anticipates real talk, and to express what is still in thought weakens action by forestalling it” – Soren Kierkegaard 

“A man’s best treasure is a thrifty tongue.” – Hesiod 

[We] often fall in love with an image of what success looks like. 

Appearances are deceiving. Having authority is not the same as being an authority. Having the right and being right are not the same either. Impressing people is utterly different from being truly impressive.

Duty, Honor, Country -VS- Pride, Power, Greed

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 what matters is you – your reputation, your inclusion, your personal ease in life – your path is clear: Tell people what they want to hear. …

To be or to do – life is a constant roll call.

A philosopher must know deeply, and also how little they know, as Socrates did. A writer must be versed in the canon – and read and be challenged by her contemporaries too.
— Why? To become great and to stay great, they must all know what came before, what is going on now, and what comes next. 

A true student is like a sponge. Absorbing what goes on around him, filtering it, latching on to what he can hold. A student is self-critical and self-motivated, always trying to improve his understanding so that he can move on to the next topic, the next challenge. A real student is also his own teacher and his own critic. There is no room for ego there.

You can’t learn if you think you already know. You will not find the answers if you’re too conceited and self-assured to ask the questions. You cannot get better if you’re convinced you are the best.

To become what we ultimately hope to become often takes long periods of obscurity, of sitting and wrestling with some topic of paradox.

“When student is ready, the teacher appears.” – old Chinese proverb

Remember, “zealot” is just a nice way to say “crazy person.”

A flash of inspiration: I want to do the best and biggest ____ ever. Be the youngest ____. The only one to ___. The “firstest with the mostest.” 

  • The reality: We hear what we want to hear. We do what we feel like doing, and despite being incredibly busy and working very hard, we accomplish very little. Or worse, find ourselves in a mess we never anticipated. 

Passion is seen in those who can tell you in great detail who they intend to become and what their success will be like – they might even be able to tell you specifically when they intend to achieve it or describe to you legitimate and sincere worries they have about the burdens of such accomplishments. They can tell you all the things they’re going to do, or have even begun, but they cannot show you their progress. Because there rarely is any.

If the definition of insanity is trying the same thing over and over and expecting different results, then passion is a form of mental retardation – deliberately blunting our most critical cognitive functions. 

What humans require in our ascent is purpose and realism. Purpose, you could say, is like passion with boundaries. Realism is detachment and perspective.

Passion is about. (I am so passionate about ___.) Purpose is to and for. (I must do ___. I was put here to accomplish ___. I am willing to endure ___ for the sake of this.) Actually, purpose deemphasizes the I. Purpose is about pursuing something outside yourself as opposed to pleasuring yourself.

More than purpose, we also need realism. Where do we start? What do we do first? what do we do right now? How are we sure that what we’re doing is moving us forward? What are we benchmarking ourselves against?

Passion is form over function. Purpose is function, function, function.

Find canvases for other people to pain on. Be an Anteambulo. Clear the path for the people above you and you will eventually create a path for yourself.

Greatness comes from humble beginnings; it comes from grunt work. It means you’re the least important person in the room – until you change that with results.

There is an old saying, “Say little, do much.” What we really ought to do is update and apply a version of that to our early approach. Be Lesser, Do More. Imagine if, for every person you met, you thought of some way to help them, something you could do for them? And you looked at it in a way that entirely benefited them and not you? The cumulative effect this would have over time would be profound: You’d learn a great deal by solving diverse problems. You’d have countless new relationships. You’d have an enormous bank of favors to call upon down the road. 

  • That what the canvas strategy is about – helping yourself by helping others. 

The person who clears the path ultimately controls its direction, just as the canvas shapes the painting.

Our path, whatever we aspire to, will in some ways be defined by the amount of nonsense we are willing to deal with.

Up ahead there will be: Slights. Dismissals. Little fuck you’s. One-sided compromises. You’ll get yelled at. You’ll have to work behind the scenes to salvage what should have been easy. All this will make you angry. This will make you want to fight back. This will make you want to say: I am better than this. I deserve more. 

  • Instead, you must do nothing. Take it. Eat it until you’re sick. Endure it. Quietly brush it off and work harder. Play the game. Ignore the noise; for the love of God, do not let it distract you. Restraint is a difficult skill but a crucial one. You will often be tempted, you will probably even be overcome. No one is perfect with it, but try we must.

It is natural for any young, ambitious person (or simply someone whose ambition is young) to get excited and swept up by their thoughts and feelings. Especially in a world that tells us to keep and promote a “personal brand.” We’re required to tell stories in order to sell our work and our talents, and after enough time, forget where the line is that separates our fictions from our reality.

The more creative we are, the easier it is to lose the thread that guides us.

Our imagination – in many senses an asset – is dangerous when it runs wild. 

Living clearly and presently takes courage. 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.

Pride and ego say: I am an entrepreneur because I struck out on my own. I am going to win because I’m currently in the lead. I am a writer because I published something. I am rich because I made some money. I am special because I was chosen. I am important because I think I should be. 
— Let’s call this attitude what it is: fraud. If you’re doing the work and putting in the time, you won’t need to cheat, you won’t need to overcompensate.

“Even the tallest mountains have animals that, when they stand on it, are higher than the mountain” – Genghis Khan 

We must prepare for pride and kill it early – or it will kill what we aspire to.

“The first product of self-knowledge is humility.” – Flannery O’Connor 

  • This is how we fight ego, by really knowing ourselves.

The question to ask, when you feel pride, then, is this: What am I missing right now that a more humble person might see? What am I avoiding, or running from, with my bluster, franticness, and embellishments? 
— It is far better to ask and answer these questions now, with the stakes still low, than it will be later.

“The best plan is only good intentions unless it degenerates into work– Peter Drucker

The distinction between a professional and a dilettante occurs right there – when you accept that having an idea is not enough; that you must work until you are able to recreate your experience effectively in words on the page.

“You can’t build a reputation on what you’re going to do.” – Henry Ford 

“The hard thing isn’t setting a big, hairy, audacious goal. The hard thing is laying people off when you miss the big goal … The hard thing isn’t dreaming big. The hard thing is waking up in the middle of the night in a cold sweat when the dream turns into a nightmare.” – Ben Horowitz 

Is it 10000 hours or 20000 hours to mastery? The answer is that it doesn’t matter. There is no end zone. To think of a number is to live in a conditional future.

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. It wants to be paid well for its time and it wants to do the fun stuff — the stuff that gets attention, credit, or glory.

Where we decide to put our energy decides what we’ll ultimately accomplish.

Bill Clinton began a collection of note cards with names & phone numbers of friends and acquaintances who might be of service when he eventually entered politics. His collection grew to 10000 cards.

Fac, si facis. (Do it if you’re going to do it.)

You can lie to yourself, saying that you put in the time, or pretend that you’re working, but eventually someone will show you up. You’ll be tested. And quite possibly, found out.

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 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 finding yourself alone at the track when the weather kept everyone else indoors. 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. Because there is work to be done. Work doesn’t want to be good. It is made so, despite the headwind.

You know a workman by the chips they leave. It’s true. To judge your progress properly, just take a look at the floor.

Part 2 – Success

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. The writer, how to edit others. The comedian, how to act. The chef turned restaurateur, how to run the other side of the house.

“As our island of knowledge grows, so does the shore of our ignorance” – John Wheeler 

With accomplishment comes a growing pressure to pretend that we know more than we do. To pretend we already know everything.

No matter what you’ve done up to this point, you better still be a student. If you’re not still learning, you’re already dying.

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).

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.

As people progress, they must also understand how they learn and then set up processes to facilitate this continual education. Otherwise, we are dooming ourselves to a sort of self-imposed ignorance.

Crafting stories out of past events is a very human impulse. 
— It’s also dangerous and untrue. Writing our own narrative leads to arrogance. It turns our life into a story—and turns us into caricatures—while we still have to live it.

When we are aspiring we must resist the impulse to reverse engineer success from other people’s stories. When we achieve our own, we must resist the desire to pretend that everything unfolded exactly as we’d planned. There was no grand narrative. You should remember – you were there when it happened.

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

A great destiny, Seneca reminds us, is great slavery.

Only you know the race you’re running. That is, unless your ego decides the only way you have value is if you’re better than, have more than, everyone everywhere. 
— More urgently, each one of us has a unique potential and purpose; that means that we’re the only ones who can evaluate and set the terms of our lives. 
— Far too often, we look at other people and make their approval the standard we feel compelled to meet, and as a result, squander our very potential and purpose. 

According to Seneca, the Greek word Euthymia is one we should think of often: it is the sense of our own path and how to stay on it without getting distracted by all the others that intersect it.

Maybe your priority actually is money. Or maybe it’s family. Maybe it’s influence and change. Maybe it’s building an organization that lasts or serves a purpose. All of these things are perfectly fine motivations. But you need to know. 

  • You need to know what you don’t want and what your choices preclude. Because strategies are often mutually exclusive. One cannot be an opera singer and a teen pop idol at the same time. Life requires those trade-offs, but ego can’t allow it.

So why do you do what you do? That the question you need to answer. Stare at it until you can. Only then will you understand what matters and what doesn’t. 
— The more you have and do, the harder maintaining fidelity to your purpose will be, but the more critically you will need it.

Find out why you’re after what you’re after. Ignore those who mess with your pace. Let them covet what you have, not the other way around. Because that is independence.

A smart man or woman must regularly remind themselves of the limits of their power and reach.

“He who indulges empty fears earns himself real fears.” – Seneca 

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.

Responsibility requires a readjustment and then increased clarity and purpose. First, setting the top-level goals and priorities of the organization and your life. Then enforcing and observing them. To produce results and only results.

Creativity is a matter of receptiveness and recognition. This cannot happen if you’re convinced the world revolves around you.

It’s hard to be self-absorbed and convinced of your own greatness inside the solitude and quiet of a sensory deprivation tank. It’s hard to be anything but humble walking alone along a beach late at night with an endless black ocean crashing loudly against the ground next to you.

“Fear is a bad advisor.” – Angela Merkel 

“Fight to be the person philosophy tried to make you.” – Marcus Aurelius 

Most successful people are people you’ve never heard of. They want it that way. It keeps them sober. It helps them do their jobs.

Part 3 – Failure

We don’t need pity – our own or anyone else’s – we need purpose, poise, and patience.

“We are at a wonderful ball where the champagne sparkles in every glass and soft laughter falls upon the summer air. We know at some moment the black horseman will come shattering through the terrace doors wreaking vengeance and scattering the survivors. Those who leave early as saved, but the ball is so splendid no one wants to leave while there is still time. So everybody keeps asking – what time is it? But none of the clocks have hands.” – George Goodman

  • He was speaking of economic crisis, although he may as well have been talking about where all of us find ourselves, not just once in our lifetimes, but often. Things are going well. Perhaps we’re aspiring to some big goal. Perhaps we’re finally enjoying the fruits of our labors. At any point, fate can intervene.

“Almost always, your road to victory gores through a place called ‘failure’.” – Bill Walsh 

  • In order to taste success again, we’ve got to understand what led to this moment (or these years) of difficulty, what went wrong and why. We must deal with the situation in order to move past it. We’ll need to accept it and to push through it.

“[the great failing is] to see yourself as more than you are and to value yourself less than your true worth.” – Goethe 

According to Robert Greene, there are two types of time in our lives: dead time, when people are passive and waiting, and alive time, when people are learning and acting and utilizing every second.
— Every moment of failure, every moment or situation that we did not deliberately choose or control, presents this choice: Alive time. Dead time.

“Cast down your bucket where you are.” – Booker T. Washington 

  • Make use of what’s around you. Don’t let stubbornness make a bad situation worse.

You will be unappreciated. You will be sabotaged. You will experience surprising failures. Your expectations will not be met. You will lose. You will fail. 
— How do you carry on then? How do you take pride in yourself and your work? Change the definition of success.

[Good story of perseverance] John Kennedy Toole’s failure to publish his book before it became famous after his death when his mother spent years trying to get it published.

“The world breaks everyone and afterward many are strong at the broken places. But those that will not break it kills.” – Ernest Hemingway 

The world can show you the truth, but no one can force you to accept it.

In the end, the only way you can appreciate your progress is to stand on the edge of the hole you dug for yourself, look down inside it, and smile fondly at the bloody claw prints that marked your journey up the walls.

“He who fears death will never do anything worthy of a living man” – Seneca 

  • He who will do anything to avoid failure will almost certainly do something worthy of a failure.

The only real failure is abandoning your principles. Killing what you love because you can’t bear to part from it is selfish and stupid. If your reputation can’t absorb a few blows, it wasn’t worth anything in the first place.

A person who judges himself based on his own standards doesn’t crave the spotlight the same way as someone who lets applause dictate success.

“People learn from their failures. Seldom do they learn anything from success.” – Harold Geneen 

“See much, study much, suffer much, that is the path to wisdom.” – old Celtic saying

There is a quote from Bismarck that says, in effect, any fool can learn from experience. The trick is to learn from other people’s experience.

Every day for the rest of your life you will find yourself at one of three phases: aspiration, success, failure. You will battle the ego in each of them. You will make mistakes in each of them. You must sweep the floor every minute of every day. And then sweep again.

New Words:
Scylla and Charybdis 
Admonish – warn (someone) of something to be avoided.
Circumspect – wary and unwilling to take risks.
Ignominy – public shame or disgrace.
Iterative – denoting a grammatical rule that can be applied repeatedly.
Gubernatorial  – relating to a state governor or the office of state governor.
Ossifying – cease developing; be stagnant or rigid.
Genteel – polite, refined, or respectable, often in an affected or ostentatious way.
Dilettante – a person who cultivates an area of interest, such as the arts, without real commitment or knowledge.
Impetuousness – sudden or rash action or emotion; impulsive. 
Surreptitiously – in a way that attempts to avoid notice or attention; secretively.
Fracas – a noisy disturbance or quarrel.
Ennui – a feeling of listlessness and dissatisfaction arising from a lack of occupation or excitement.
Onanistic – pulling out during intercourse so that ejaculation occurs outside the vagina
Ostentatious – characterized by vulgar or pretentious display; designed to impress or attract notice.
Avidity – extreme eagerness or enthusiasm.
Assiduously – with great care and perseverance.
Ensconced – establish or settle (someone) in a comfortable, safe, or secret place.
Harangue – lecture (someone) at length in an aggressive and critical manner. Lengthy speech. 
Magnanimous – very generous or forgiving, especially toward a rival or someone less powerful than oneself.
Palatial – resembling a palace in being spacious and splendid.
Artifice – clever or cunning devices or expedients, especially as used to trick or deceive others.
Profligacy – reckless extravagance or wastefulness in the use of resources.
Parsimony – extreme unwillingness to spend money or use resources
Self-immolation – the offering of oneself as a sacrifice, especially by burning; such suicidal action in the name of a cause or strongly held belief.
Capriciousness – a person or thing that is impulsive or unpredictable. ie. bride leaving alter.
Recalcitrant – having an obstinately uncooperative attitude toward authority or discipline.
Plaudits – praise

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