Ryan Holiday
Rating: 7.5/10
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Reading Ease: Reading Time:6 hours

If Ego is the Enemy, then we're in for an endless war. At any point in our life, we are between the three cycles of Aspire, Success, & Failure. This book was born out of the need for a guide in facing the many obstacles that await through the pendulum of life's journey between these states. The thesis is that your ego is not an overachieving power that you're forced to satisfy at ever impulse. It can be managed and directed.

I felt the title of the book personifies and causes an anchoring effect, towards making one think they can "defeat" Ego. Ryan does try to emphasize the management of ego, and being cautious of extremes by re-adjusting one's attitude and finding a golden mean. I see Ego as something one can overdose on; it is a natural byproduct of growth and ambition, so it's not inherently bad. Similar to Medicine, in that it can heal us, but also kill us. Too much Ego can shorten success.

The tone of the book seems to lack compassion and leans too much on declarations that make it seem preachy, in an aggressive way. The latter seems to be a common pattern in Ryan's writing. Someone who is frustrated and whose anger tends to leak into his writing voice. I was surprised that there were fewer references to Stoicism in this book compared to his others.

Still, you can get some gems from the book. Ego is The Enemy provides us with the tools to keep our Ego in check and think less of ourselves. The stabilizers that balance out the ego and pride that comes with achievement and recognition are Sobriety, Open-mindedness, Organization, and Purpose. We should be Humble in our aspirations, Gracious in our success, and Resilient in our failures. Then we can suppress ego early, replace the temptations of ego with humility and discipline, and have more control over our fate.

Notetable Quotes

“Ego is the enemy of what you want and of 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. It is Scylla and Charybdis.” Ryan Holiday
“One might say that the ability to evaluate one’s own ability is the most important skill of all. Without it, improvement is impossible. And certainly ego makes it difficult every step of the way. It is certainly more pleasurable to focus on our talents and strengths, but where does that get us? Arrogance and self-absorption inhibit growth. So does fantasy and “vision.” Ryan Holiday
“If ego is the voice that tells us we’re better than we really are, we can say ego inhibits true success by preventing a direct and honest connection to the world around us. ”Ryan Holiday
“The first principle is that you must not fool yourself—and you are the easiest person to fool. ” — Richard Feynman
“Passion is form over function. Purpose is function, function, function.” Ryan Holiday

Motivations to Read

The term ego is very complex, with varying interpretations. This book does not use Ego in the Freudian sense of consciousness and identity but defines the term under the context of an unhealthy belief in our own importance. Arrogance. Self-centered ambition. I have been thinking about Ego in similar terms as well and have also pointed it out as an area of importance to keep in check. I enjoy most of Ryan's writing and was very excited to see he would be writing about this topic.

3 Reasons to Read

  • Learn how to manage and overcome Ego
  • A wide range of stories, from literature, philosophy, sports, media, and history revealing how ego has shaped many and broken much more
  • At every stage in life Ego has the potential to hold us back and stop our growth, learn about it's nature and cycle

Ego Is the Enemy
Summary & Notes

Ryan Holiday wrote this books because he wished it has existed at different turning points in his life. At the end of the book, he hopes you will think less of yourself.

The thesis is that your ego is not some overarching power you’re forced to satisfy at ever impulse. It can be managed and directed.

“For people with ambitions, talents, drives and potential to fulfill, ego comes with the territory. Precisely what makes us so promising as thinkers, doers, creatives, and entrepreneurs, what drives us to the top of those fields, makes us vulnerable to this darker side of the psyche.”

Ego

The term ego is very complex, with varying interpretations. This book is not referring to ego in the Freudian sense but goes with the definition that aligns with: An unhealthy belief in our own importance. Arrogance. Self-centered ambition.

Ego disconnects us from reality and taking ownership and personal responsibility for our actions.

Ego is more emboldened now than ever, as the growth of social media and other technologies gives us a bigger stage to over express ourselves.

The Book is separated into three parts:

  1. Aspire (Humble in our aspirations)
  2. Success (Gracious in our success)
  3. Failure (Resilient in our failures)

The goal of this structure is to help:

  • Suppress ego early before bad habits take hold
  • To replace the temptations of ego with humility and discipline when we experience success
  • To Cultivate strength and fortitude so that when fate turns against you, your not wrecked by failure.

Part 1. ASPIRE

“One might say that the ability to evaluate one’s own ability is the most important skill of all. Without it, improvement is impossible. And certainly, ego makes it difficult ever step of the way.”

Silence is not a sign of weakness.

Everyone can chatter on.

“So what is scare and rare? Silence. The ability to deliberately keep yourself out of the conversation and subsist without its validation. Silence is the respite of the confident and the strong.”

Military office William Sherman had a good rule he tried to observe in relation to this, “Never give reasons for you what think or do until you must. Maybe, after a while, a better reason will pop into your head.”

Our mind can confuse visualization with progress after a certain point. The same can go for verbalization, giving us a false sense of progress without doing the work.

“Appearances are deceiving. Having authority is not the same as being an authority. Having the right and being right and not the same either. Being promoted doesn’t necessarily mean you’re doing good work and it doesn’t mean you are worthy of promotion. Impressing people is utterly different from being truly impressive.

“The mixed martial arts pioneer and multi-title champion Frank Shamrock has a system he trains fighters in that he calls plus, minus, and equal. 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.”

“Professional athletes have teams of coaches, and even powerful politicians have advisers and mentors. [..] To become great and stay great, they must all know what came before, what is going on now, and what comes next. They must internalize the fundamentals of their domain and what surrounds them, without ossifying or becoming stuck in time.”

Passion

Excess passion can cause our own demise. It makes us lose patience and focus towards the process and the systems necessary to get the work down regardless of how we feel. We end up seeking sources of inspiration to get us back to our passion “highs” when we feel down. We also lose sight of reality by societies bias towards telling stories of passionate successful people, as opposed to the many passionate failures. Passion can mask weaknesses and leds us to speak about our passion rather than the reason or purpose behind what we are doing.

Instead, we should be more purpose oriented, Ryan argues. Purpose deemphasizes the I. It’s about pursuing something outside yourself as opposed to pleasuring yourself.

“It’d be far better if you were intimidated by what lies ahead — humbled by its magnitude and determined to see it through regardless. Leave passion for the amateurs. Make it about what you feel you must do and say, not what you care about and wish to be.”

Canvas Strategy Helping yourself by helping others. Making a concentrated effort to trade your short-term gratification for a longer-term payoff.

“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.”

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

In talking about Jackie Robinson’s discrimination, there was a good point about changing a system:

"But you’re not able to change the system until after you’ve made it. In the meantime, you’ll have to find some way to make it suit your purposes — even if those purposes are just extra time to develop properly, to learn from others on their dime, to build your base and establish yourself.

As Robinson succeded, after he had proved himself as the Rookie of the Year and as an MVP, and as his spot on the Dogers was certain, he began to more clearly assert himself and his boundaries as a player and as a man. Having carved out his space, he felt that he could argue with umpires, he could throw his shoulder if he needed to make a player back off or to send a message."

“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

“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.”

“Pride takes a minor accomplishment and makes it feel like a major one.”

"Pride and ego say:

  • I am an entrepreneur because I struck out on my own.
  • I am going to win because I am 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."

He calls it out as fraud.

“It’s worth saying: just because you are quiet doesn’t mean that you are without pride. Privately thinking you’re better than others is still pride.”

Love this:

“Is it ten thousand hours or twenty thousand hours to mastery? The answer is that it doesn’t matter. There is no end zone.”

Latin Expression: Materian superabat opus (The workmanship was better than the material

“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.”

Sobriety, open-mindedness, organization, and purpose are the stabilizers that balance out the ego and pride that comes with achievement and recognition.

Part 2. SUCCESS

“Sometimes ego is suppressed on the ascent. Sometimes an idea is so powerful or timing is so perfect (or one is born into wealth or power) that it can temporarily support or even compensate for a massive ego.”

“Every man I meet is my master in some point, and in that I learn of him.” — Ralph Waldo Emerson

The Mongol Empire

“While the Mongols themselves seemed dedicated almost solely to the art of war, they put good use every craftsman, merchant, scholar, entertainer, cook and skilled worker they came in contact with. The Mongol Empire was remarkable for it’s religious freedoms, and most of all, for its’s love of ideas and convergence of cultures. It brought lemons to China for the first time, and Chinese noodles to the West. It spread Persian carpets, German mining technology, French metalworking, and Islam. The cannon, which revolutionize warfare, was said to be the resulting fusion of Chinese gunpowder, Muslim flamethrowers, and European metalwork. It was Mongol openness to learning and new ideas that brought them together.”

“The great manager, and business thinker 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 setup a processes to facilitate this continual education. Otherwise, we are dooming ourselves to a sort of self-imposed ignorance.”

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

“Instead of pretending that we are living some great story, we must remain focused on the execution — and on executing with excellence. We must shun the false crown and continue working on what got us here.”

Euthymia: Greek word meaning the sense of our own path and how to stay on it without getting distracted by all the others that intersect it.

Success and the resulting power can lead to dangerous delusions like: entitlement, control and paranoia.

Learn how to manage yourself. Set top level goals, act, readjust and observe your outcomes.

Sympatheia: — A stoic terminology for a connectedness with the cosmos.

We are drawn to ask ourselves questions like Who am I? What am I doing? What is my role in this world?

Ego pulls us away from these questions it tells us that, “meaning comes from activity, that being the center of attention is the only way to matter.”

The detachment from something bigger than ourselves makes success feel empty.

“Go and put yourself in touch with the infinite, and end your conscious separation from the world. Reconcile yourself a bit better with the realities of life. Realize how much came before you and how only wisps of it remain.”

Maintain Your Sobriety

Don’t get drunk off your ego.

“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.”

Ambition

It is not wrong to have great ambition.

We must be vigilant and cautious of extremes.

“Endless ambition is easy; anyone can put their foot down hard on the gas. Complacency is easy too; it’s just a matter of taking that foot off the gas. We must avoid what the business strategist Jim Collins terms the ‘undisciplined pursuit of more.’ [..] To borrow from Aristotle again, what’s difficult is to apply the right amount of pressure, at the right time, in the right way, for the right period of time, in the right car, going in the right direction.”

Managing one’s self and your ambition

  • Protect Your Sobriety
  • Give up greed & paranoia
  • Stay Humble
  • Retain your sense of purpose
  • Connect to the larger world around you

It’s important to note that even if we manage ourselves well, prosperity holds no guarantees.

Part 3. FAILURE

“It is because mankind are disposed to sympathize more entirely with our joy than with our sorrow, that we make parade of our riches, and conceal our poverty. Nothing is so mortifying as to be obliged to expose our distress to view of the public, and to feel, that though our situation is open to the eyes of all mankind, no mortal conceives for us the half of what we suffer.” — Adam Smith

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

“To paraphrase Epicurus, the narcissistically inclined live in an ‘unwalled city.’ A fragile sense of self is constantly under threat.”

“As Plutarch finely express, ‘The future bears down upon each one of us with all the hazards of the unknown.’ The only way out is through.”

Alive Time or Dead Time?

“According to 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 utilizing every second.”

I enjoyed the lessons from Malcolm X’s story, which detailed how he decided to choose Alive time and better his life, even while incarcerated for almost a decade.

Having never gone to school and when an unknowing reporter asked him , “What’s your alma mater?” His one word answer was, “Books.” Prison was his college. He transcended confinement through the pages he absorbed.

“It’s far better when doing going work is sufficient. In other words, the less attached we are to outcomes the better. When fulfilling our own standards is what fills us with pride and self-respect. When the effort — not the results, good or bad — is enough.”

This reminds me of Scott Adam’s Systems over goals.

“A goal is a specific objective that you either achieve or don’t sometime in the future. A system is something you do on a regular basis that increases your odds of happiness in the long run. If you do something every day, its a system. [..] Goal-oriented people exist in a state of continuous presuccess failure at best, and permanent failure at worst if things never work out. Systems people succeed every time they apply their systems, in the sense that they did what they intended to do. The goals people are fighting the feeling of discouragement at each turn. The systems people are feeling good every time they apply their system. That’s a big difference in terms of maintaining your personal energy in the right direction.”

— Scott Adams

Duris dura fraguntur. Hard things are broken by hard things.

“It can ruin your life only if it ruins your character.” — Marcus Aurelius

When we get lost in our work, work our way back to aspiration by following first principles and best practices.

“And why should we feel anger at the world? As if the world would notice!” — Euripides

“At various points in our lives, we seem to have different capacities for forgiveness and understanding.”

“Aspiration leads to success (and adversity). Success creates its won adversity (and, hopefully, new ambitions). And adversity leads to aspiration and more success. it’s an endless loop.”

Self-awareness is the key to moving throw difficulties and improving oneself.

“Perfecting the personal regularly leads to success as a professional, but rarely the other way around.”

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