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Book Notes: “Ego is the Enemy” by Ryan Holiday


Ego is the Enemy by Ryan Holiday (2016) is a book about the biggest obstacle to individual success: ourselves. More specifically, Holiday takes aim at the subject of ego which he defines as “an unhealthy belief in our own importance.” Under Holiday’s definition, ego encompasses negative traits such as arrogance, self-centeredness, vanity, and delusional thinking. The book explores the nature of ego and the ways we can learn to manage it in order to achieve the success and fulfillment we all desire.

Early in the book, Holiday describes the three phases that comprise the continuous experiential cycle of life: aspiring to something, achieving success, and experiencing failure. The book is structured around these three stages of life. In Part 1, Holiday describes how ego interferes with and sabotages our aspirations. An important lesson concerns the gap between perception and reality. Ego engages in the fantasy of what we want to believe. Holiday, however, admonishes the reader to see things for what they are and eschew these self-made fictions. Success comes through diligent work and continuous effort. It might be slow, iterative, and (at times) boring, but that’s the reality behind many meaningful accomplishments.

Part 2 considers the impact of success on our ego. “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.” The remedies are humility, sobriety, and a continuous focus on learning. Part 3 explores how ego responds to failure. Failure is seen as a natural consequence of living. How we respond to failure determines whether we improve and grow or wallow in misery and resentment. Once again, ego (or rather, lack thereof) is critical. Holiday asserts that we must focus on the things we can control (our purpose, our effort) and let go of the things we cannot (external rewards and validation).

I appreciate the message of Holiday’s book. Self-centered thinking is deeply-rooted in the human experience and seems to be amplified even more in the era of social-networking and the “attention economy.” Spending time to reflect on our values and looking beyond our ego is always a valuable exercise. Holiday presents a welcome, soft-spoken antidote to the more bombastic look-at-me-now books from some of his contemporaries.

Pros: Subject matter is more relevant than ever. Author cites engaging and eclectic stories from ancient history alongside more familiar modern anecdotes.

Cons: The message in certain chapters gets repetitive.

Verdict: 7/10

Notes & Highlights


  • “Wherever you are, whatever you’re doing, your worst enemy already lives inside you: your ego.”
  • Definition of ego used in the book: “An unhealthy belief in our own importance. Arrogance. Self-centered ambition…the need to be better than, more than, recognized for…the sense of superiority and certainty that exceeds the bounds of confidence and talent.”
  • “Without an accurate accounting of our own abilities compared to others, what we have is not confidence but delusion.”
  • “Ego tells us what we want to hear, when we want to hear it.”
  • Social media and the internet make it easier than ever to talk ourselves up and present the facade of success to our followers and contacts.
  • “We’re told to believe in our uniqueness above all else.”
  • Three stages we encounter throughout life (as a constant cycle):

    1. Aspiring to something.
    2. The achievement of success.
    3. The achievement of failure.
  • The book is structured around these three stages of being (aspiration, success, and failure).
  • “Your ego is not some power you’re forced to satiate at every turn. It can be managed. It can be directed.”

Part I: Aspire

  • “If your belief in yourself is not dependent on actual achievement, then what is it dependent on? The answer is nothing. Ego.”
  • Cultural values make us dependent on validation, entitlement and emotion. Self-esteem is a part of the problem.
  • “It’s easy to be emotionally invested and infatuated with your own work. Any and every narcissist can do that. What is rare is not raw talent, skill, or even confidence, but humility, diligence, and self-awareness.”
  • Focus on action and education. Eschew validation and status-seeking.
  • “Our ambition will not be grandiose but iterative—one foot in front of the other, learning and growing and putting in the time.”

Talk, Talk, Talk

  • “It’s a temptation that exists for everyone—for talk and hype to replace action.”
  • “It was easier to talk about writing, to do the exciting things related to art and creativity and literature, than to commit the act itself.”
  • Talking is easy. Action and doing are difficult. Most of us are guilty of substituting or confusing the former for the latter.
  • “While goal visualization is important, after a certain point our mind begins to confuse it with actual progress.”
  • “After spending so much time thinking, explaining, and talking about a task, we start to feel that we’ve gotten closer to achieving it.” [me: reminds me of our propensity for pointless business meetings]
  • “Success requires a full 100 percent of our effort, and talk flitters part of that effort away before we can use it.”

To Be or To Do?

  • Story of Col. John Boyd and his advice on the “fork in the road” to a protege (Boyd was famous for the "OODA loop"):

    • Choice one: “If you go that way you can be somebody. You will have to make compromises and you will have to our your back on your friends. But you will be a member of the club and you will get promoted and you will get good assignments.
    • Choice two: “You can do something for your country and for your Air Force and for yourself. If you decide you want to do something, you may not get promoted and you may not get the good assignments and you certainly will not be a favorite of your superiors. But you won’t have to compromise yourself…your work might make a difference.”
  • The choice in a nutshell: To be somebody or to do something.

  • “Often we fall in love with an image of what success looks like.”

  • “Impressing people is utterly different from being truly impressive.”

  • The ego can confuse what is important with what isn’t.

  • Boyd’s choice asks a fundamental question: “What is our purpose? What are you here to do?

    • Do you seek reputation and attention?
    • Do you seek comfort?
    • Do you seek to prove something to yourself?
    • Do you seek something larger than yourself?
  • “Do I want to be like everyone else or do I want to do something different?”

  • Ask yourself: Do I need this (whatever you are pursuing) or is it driven by ego?

Become a Student

  • When guitarist Kirk Hammett earned the job of lead guitarist for Metallica, one of his first acts was to get a guitar instructor so that he could improve his skills.
  • Teacher Joe Satriani (guitarist) on Hammett: “What separated Hammett from the others was his willingness to endure the type of instruction they [others] wouldn’t. He was a good student. Many of his friends and contemporaries would storm out complaining thinking I was too harsh a teacher.”
  • “The power of being a student is not just that it is an extended period of instruction, it also places the ego and ambition in someone else’s hands.”
  • “An education can’t be ‘hacked’; there are no shortcuts besides hacking it every single day.”
  • Frank Shamrock (MMA pioneer) and the “plus, minus and equal” system: “Each fighter, to become great…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.”
  • Continuous feedback is a critical part of the learning process. Learn about what you know and what you don’t know from every possible angle.
  • “We must all become our own teachers, tutors, and critics.”
  • Self-satisfaction is the antithetical to continuous learning: “The temptation is to think: I’ve made it. I’ve arrived.”
  • “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.”
  • “You cannot get better if you’re convinced you are the best.”
  • The ability to take and actively seek out honest feedback and harsh criticism is a rare but valuable skill.

Don’t Be Passionate

  • Choose reason over passion.
  • We often fail because of passion (defined by the author as unbridled enthusiasm and zeal).
  • John Wooden (basketball coach): Described as dispassionate. “Wooden wasn’t about rah-rah speeches or inspiration. He saw those extra emotions as a burden…his philosophy was about being in control and doing your job and never being ‘passion’s slave.’”
  • “Passion typically masks a weakness. Its breathlessness and impetuousness and franticness are poor substitutes for discipline, for mastery, for strength and purpose and perseverance.”
  • “Passion is seen in those who can tell you in great detail who they intend to become and what their success will be like…but they cannot show you their progress. Because there rarely is any.”
  • “What humans require in our ascent is purpose and realism.”

    • Purpose is a kind of passion with boundaries.
    • Realism gives perspective and detachment.
  • Passion is “about” (e.g. “my passion is about…”) and purpose is “to and for” (e.g. “my purpose is to…”).
  • Purposeful people “get started with small steps, complete them, and look for feedback on how the next set can be better. They lock in gains, and then get better…leveraging those gains to grow exponentially rather than arithmetically.”
  • Progress is a slow, iterative and not flashy.
  • “Passion is form over function. Purpose is function, function, function.”

Follow the Canvas Strategy

  • Common attitude in people of certain tasks or situations being viewed as “beneath them.”: “An unwillingness to take a step back in order to potentially take several steps forward.”

  • An all-or-nothing approach often leads to nothing.

  • Anteambulo: In Roman times, a person who clears the path for an important patron.

  • “Clear the path for the people above you and you will eventually create a path for yourself.”

  • Realities when starting a career or new endeavor:

    1. You are not as good or as important as you think you are.
    2. You have an attitude that needs to be readjusted.
    3. What you think you know or you learned is wrong.
  • “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.”

  • “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.”

  • The canvas strategy: Helping yourself by helping others. Some examples:

    • Coming up with ideas for your boss.
    • Making useful introductions to different people.
    • Finding what nobody else wants to do and doing it.
    • Identifying inefficiencies and subpar processes.
    • Producing more than everyone else and giving your ideas away.
  • Everyone else wants credit. You forego credit. You are playing the long-game.

  • “Let others take their credit on credit, while you defer and earn interest on the principal.”

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

Restrain Yourself

  • Branch Rickey (baseball manager) famously asked Jackie Robinson (first black player in baseball): “Do you have the guts? I’m looking for a ball player with the guts not to fight back.”
  • “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.”
  • “Getting angry, getting emotional, losing restraint is a recipe for failure.”
  • Expect and be ready to deal with a range of detrimental treatment from anywhere on the spectrum between indifference and sabotage.
  • “Those who have subdued their ego understand that it doesn’t degrade you when others treat you poorly; it degrades them.”

Get out of Your Own Head

  • Anne Lamont (writer): “Out of the right speaker in your inner ear will come the endless stream of self-aggrandizement, the recitation of one’s specialness, of how much more open and gifted and brilliant and knowing and misunderstood and humble one is. Out of the left…self-loathing, the lists of all the things one doesn’t do well…”
  • We all fall prey to the internal narration that can both overstate or understate what we are capable of.
  • “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 reality.”

The Danger of Early Pride

  • C.S. Lewis (writer): “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.”
  • “Pride is a distraction and a deluder.”
  • “Our ability to learn, to adapt, to be flexible, to build relationships, all of this is dulled by pride.”
  • Beginner’s conceit: The unfounded pride that we have early in life and early in our learning journey.
  • “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.
  • John D. Rockefeller (businessman): “What a pitiful thing it is when a man lets a little temporary success spoil him, warp his judgment, and he forgets what he is!”
  • Ask yourself: What am I missing that a humble person might see?

Work, Work, Work

  • Exchange between Degas (artist) and Mallarmé (poet):

    • Degas: “I can’t manage to say what I want, and yet I’m full of ideas.”
    • Mallarmé: “It’s not with ideas, my dear Degas, that one makes verse. It’s with words.”
  • Ideas are insufficient. Work is necessary to bring your ideas to life.

  • Henry Ford (businessman): “You can’t build a reputation on what you’re going to do.”

  • Nina Holton (artist): “That germ of an idea does not make a sculpture which stands up. It just sits there. So the next stage, of course, is the hard work.”

  • “Is it ten thousand hours or twenty thousand 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.”

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

    • Story of Bill Clinton’s note cards on which he would write names of people he met and who might help him in the future. Each night Clinton would work on this index (from a young age): updating the index, making phone calls and writing letters.
  • Learn to embrace work and the struggle and the act of practice. Learn to enjoy the process and the act itself (not the results).

  • “Do we love practice, the way great athletes do? Or do we chase short-term attention and validation—whether that’s indulging in the endless search for ideas or simply the distraction of talk and chatter?”

  • Bill Bradley (athlete and politician): “When you are not practicing, remember someone somewhere is practicing, and when you meet him he will win.”

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

For Everything That Comes Next, Ego Is the Enemy

  • Taste/Talent Gap: Idea where a creator has good taste at the outset but lacks the talent or skill to match that level of taste. Only over repeated practice, learning and failure does the talent (skill) eventually catch up to the taste.

Part 2: Success

  • “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 wants us to think: I’m special. I’m better. The rules don’t apply to me.”
  • “Success is intoxicating, yet to sustain it requires sobriety. 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”

  • “It takes a special kind of humility to grasp that you know less, even as you know and grasp more and more.”
  • Wynton Marsalis (musician): “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…”
  • “If you’re not still learning, you’re already dying.”
  • “Learn from everyone and everything. From the people you beat, and the people who beat you, from the people you dislike, even from your supposed enemies.”
  • Even basic or remedial ideas should not be blocked by ego. There is always value in hearing and relearning things again with an open mind.
  • “An amateur is defensive. The professional finds learning to be enjoyable; they like being challenged and humbled, and engage in education as an ongoing and endless process.”

Don’t Tell Yourself a Story

  • The example of football coach Bill Walsh and the San Francisco 49ers.

    • The story the media recounted: Bill Walsh was a genius who turned around a losing team in a mere 2 years time.
    • The reality: Bill Walsh (who almost quit one year in) “wasn’t focused on winning per se. Instead, he implemented what he called his ‘Standard of Performance.’ The is: What should be done. When. How…Walsh had only one timetable, and it was all about instilling these standards.
  • “The Standard of Performance was about instilling excellence…if the players take care of the details, the score takes care of itself.”
  • Walsh was humble enough to know that while he could manage his habits and standards, he could not know WHEN winning games or a championship would happen.
  • “Narrative is when you look back at an improbably or unlikely path to your success and say: I knew it all along. Instead of: I hoped. I worked.”
  • Creating retroactive narratives or stories can result in ego-driven fantasy and failure to see the truth: how hard, uncertain and challenging achieving success really was.
  • “Once you win, everyone is gunning fro you. It’s during your moment at the top that you can afford ego the least—because the stakes are so much higher, the margins for error are so much smaller.”
  • “Facts are better than stories and image.”
  • “Resist the impulse to reverse engineer success from other people’s stories.”
  • Paul Graham (investor): “The way to do really big things seems to be to start with deceptively small things.”

What’s Important to You?

  • “We start out knowing what is important to us, but once we’ve achieved it, we lose sight of our priorities.”
  • “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.”
  • Eurthymia (tranquility): Holiday describes this as understanding our path and staying on it without being distracted by other people and things.
  • “The more you have and do, the harder maintaining fidelity to your purpose will be, but the more critically you will need to.”

Entitlement, Control and Paranoia

  • An absolute sense of certainty is a huge liability.
  • Entitlement: “This is mine. I’ve earned it.” Entitlement fails to value OTHER people’s time, efforts and desires.
  • Control: “It all must be done my way…even inconsequential things.” Fighting battles for the sake of it. Being right for the sake of it.
  • Paranoia: “I can’t trust anyone. I’m in this totally by myself and for myself.” Causes you to think everyone else is an idiot or scheming behind your back.
  • Seneca (philosopher): “He who indulges in empty fears earns himself real fears.”

Managing Yourself

  • Urgent and important are not the same.
  • Discipline, organization and planning become increasingly critical in order to maintain success and achieve even higher goals.
  • Must be adaptable and open to change since your role and responsibilities will change throughout your career and your life.
  • You must constantly reevaluate and update your identity.
  • Delegation must be learned and embraced in order to progress.
  • “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.”

Beware the Disease of Me

  • “It’s beginning to think that 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.”
  • “We never earn the right to be greedy or to pursue our interests at the expense of everyone else.”
  • Magnanimous: A word not used often enough. To be gracious and forgiving and generous in thought and action (rather than petty or vindictive) especially when you hold power or rank over someone else.

Mediate on the Immensity

  • Sympatheia: The stoic concept of feeling connected to the world.
  • Going out into the wilderness is inspirational because it gives a kind of cosmic perspective and sense of your small place in the world.
  • Meditation is an opportunity to focus on the important and cut out the noise and distractions of the world.

Maintain Your Sobriety

  • People are impatient. They want fast success, the easy path, the shortcut or “hack.”
  • Sobriety: Defined by the author as command of oneself.
  • Shelby Foote (historian): “Power doesn’t so much corrupt; that’s too simple. It fragments, closes options, mesmerizes.”
  • Example of Angela Merkel: She is described as rational. She focuses on the situation and never makes it about herself. She doesn’t reflect on her image. She is concerned about results.
  • “Sobriety is the counterweight that must balance out success.”
  • “No more obsessing about your image; treating people beneath you or above you with contempt; needing first-class trappings and the star treatment; raging, fighting, preening, performing, lording over, condescending, and marveling at your own awesomeness or self-anointed importance.”
  • Many of the best examples (in people) remain hidden from us. The flashy, ego-driven people are who we see and hear about.

For What Often Comes Next, Ego Is the Enemy

  • Aristotle’s “golden mean” is a kind of middle ground between extremes.
  • “Courage, for instance, lies between cowardice on one end and recklessness on the other. Generosity, which we all admire, must stop short of either profligacy and parsimony in order to be of any use.”
  • “We can use the golden mean to navigate our ego and our desire to achieve.”
  • “Reversals and regressions are as much a part of the cycle of life as anything else.”

Part III: Failure

  • Failure and adversity affect everyone, rich and poor, and are unique to each individual.
  • “Almost without exception, this is what life does: it takes our plans and dashes them to pieces.”
  • Bill Wash (American football coach): “Almost always, your road to victory goes through a place called ‘failure.’”
  • “You can do most everything right and still find yourself in deep shit.”
  • Life isn’t fair but ego would have you believe otherwise. Ego loves arguing about whether things are fair or not.
  • Narcissistic injury: Psychological term for “when we take personally totally indifferent and objective events. We do that when our sense of self is fragile and dependent on life going our way all the time.”
  • “Whether what you’re going through is your fault or your problem doesn’t matter, because it’s yours to deal with right now.”
  • “Failure always arrives uninvited, but through our ego, far too many of us allow it to stick around.”
  • “The only way out is through.”

Alive Time or Dead Time?

  • Robert Greene (author) describes two types of time in our lives:

    • Dead time: When we are passive and waiting for something to happen.
    • Alive time: When we are active, learning and engaged in progressing.
  • “This moment is not your life. But it is a moment in your life. How will you use it?”

  • Learn to see the opportunity in these moments and turn “dead time” into something productive and positive (alive time).

The Effort Is Enough

  • Example of the Roman general Belisarius repeatedly saved Rome but was constantly treated as a threat and conspirator. “He was just doing his job…he knew he had done what was right. That was enough.”
  • “There will be times when we do everything right, perhaps even perfectly. Yet the results will somehow be negative: failure, disrespect, jealousy, or even a resounding yawn from the world.”
  • You cannot control whether or not your work will be appreciated or recognized.
  • You must learn to view the act of good work, in and of itself, as sufficient. Earn your joy and satisfaction from the process and the journey.
  • Avoid attachment to the outcomes or results of our work (if our work meets our purpose and standards).
  • Ego sets expectations that will result in disappointment: it wants recognition, compensation, praise and attention.
  • Story of Diogenes: “Alexander approached Diogenes, who was lying down, enjoying the summer air, and stood over him and asked what he, the most powerful man int he world, might be able to do for this notoriously poor man. Diogenes could have asked for anything. What he requested was epic: ‘Stop blocking my sun.’”
  • John Wooden (basketball coach): “Success is peace of mind, which is a direct result of self-satisfaction in knowing you made the effort to do your best to become the best that you are capable of becoming.”
  • Marcus Aurelius (Roman emperor): “Ambition means tying your well-being to what other people say or do…sanity means tying it to your own actions.”

Fight Club Moments

  • Katabasis: Concept of “going down” in Greek mythology. Characters are forced down in some way: retreat, depression, into the underworld. However, when they emerge from the trial, they gain new knowledge and wisdom.
  • William A. Sutton (priest): “We cannot be humble except by enduring humiliations.”
  • These ‘fight club moments’ (where we are made low) are opportunities for reflection and change and moments to confront the truth.
  • These moments have the following characteristics:

    1. They are prompted by an outside force or individual.
    2. They involve things we already knew about ourselves, but were unable to admit or acknowledge.
    3. They offer an opportunity for progress and improvement (depending on our response to the challenge).
  • “The world can show you the truth, but no one can force you to accept it.”

Draw the Line

  • “Only ego thinks embarrassment or failure are more than what they are. History is full of people who suffered abject humiliations yet recovered to have long and impressive careers.”
  • “When we lose, we have a choice: are we going to make this a lose-lose situation for ourselves and everyone involved? Or will it be a lose…and then win?”
  • Each phase in the aspiring-succeeding-failing cycle is TRANSITORY and should not be seen as reflective of who you are as a person.
  • “He who will do anything to avoid failure will almost certainly do something worthy of a failure.”

Maintain Your Own Scorecard

  • Great people “hold themselves to a standard that exceeds what society might consider to be objective success…they don’t much care what other people think; they care whether they meet their own standards.”
  • “Your potential, the absolute best you’re capable of—that’s the metric to measure yourself against.”
  • “Anyone can win. But not everyone is the best possible version of themselves.”
  • The ego likes to exploit the shortcut, the grey area, things that are not technically legal.

Always Love

  • The Streisand effect: Phenomenon in which attempts to hide or censor information on the internet results in increased notoriety and visibility.
  • “Attempting to destroy something out of hate or ego often ensures that it will be preserved and disseminated forever.”
  • Love is a better response to attacks and slights from others.
  • When love is too much to ask for, just consider “letting go” and moving on.
  • Frederick Douglas (abolitionist leader) when asked to move to the baggage car and a white supporter approached him to apologize for the offense: “They cannot degrade Frederick Douglass. The soul that is within me no man can degrade. I am not the one that is being degraded on account of this treatment, but those who are inflicting it upon me.”
  • Seek empathy and pity for your enemies rather than hate.
  • “This obsession with the past, with something that someone did or how things should have been…is ego embodied. Everyone else has moved on, but you can’t, because you can’t see anything but your own way.”
  • “Hate defers blame. It makes someone else responsible.”

For Everything That Comes Next, Ego Is the Enemy

  • Harold Geneen (businessman): “People learn from their failures. Seldom do they learning anything from success.”
  • Self-awareness is the way out from failure.


  • “Training is like sweeping the floor. Just because we’ve done it once, doesn’t mean the floor is clean forever. Every day the dust comes back. Every day we must sweep.”

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