Publisher: Portfolio

Publication Date: June 14, 2016

ISBN-13 : 978-1591847816

Buy: Ego is the Enemy at  Amazon

Rating: ⭐⭐⭐

Introduction

Ambition comes with a built-in fight.

It’s the razor’s edge between confidence and arrogance, between steady self-assurance and outright delusion. And let’s be honest—our culture makes it worse. We’re told to “think big,” act like we’re special, and put on the mask of success before we’ve earned it. We are taught to build ourselves up, but rarely are we taught how to keep ourselves grounded.

That’s where Ryan Holiday’s Ego Is the Enemy hits hard. The core argument is simple: ego—an unhealthy belief in our own importance, arrogance, and self-centered ambition (18) —isn’t some outside obstacle. It’s the enemy inside. It sabotages us at every step, no matter how much talent or drive we have.

Holiday’s point is blunt: the real battle isn’t with rivals or external setbacks. It’s with ourselves. Ego is the root of so many failures, the invisible hand pulling us off course.

The book breaks it down into three battlegrounds where ego shows up again and again: Aspiration, Success, and Failure. Three phases, same enemy.

1. During Aspiration: When you’re just starting out, ego shows up as big talk with no action. It pushes you to chase titles instead of doing the work, to lean on passion instead of purpose. The fix? Humility. Stay a student, focus on the craft, and anchor yourself in a clear, realistic purpose.
2. During Success: When success finally comes, ego shifts gears. Now it feeds entitlement, paranoia, and the hunger to control everything. It spins self-serving stories that kill growth. The antidote is discipline—stay sober, keep learning, trust systems instead of narratives, and tie your work to something larger than yourself.
3. During Failure: And when you fail? Ego makes the fall catastrophic. It fuels blame, dodges accountability, and tempts you into self-destruction to protect your pride. The only way through is resilience. Use “dead time” as “alive time” to learn. Measure yourself by effort, not applause. Choose love and action instead of hate and bitterness.

The fight with ego never ends. It’s not a milestone you pass once—it’s daily work. Staying humble, clear-eyed, and grounded in reality is the only way forward.

The Book in 3 Sentences

• Ryan Holiday’s “Ego Is the Enemy” argues that ego, defined as an unhealthy belief in one’s own importance, is the primary obstacle to achieving and maintaining true success at every stage of life—aspiration, success, and failure. 
• Holiday suggests that ego distorts reality, prevents honest self-assessment, and hinders crucial qualities like creativity, learning, and working well with others. 
• To counteract this, Holiday advocates for cultivating humility, self-awareness, purpose, and diligent effort, emphasizing that true confidence is earned through continuous learning and focusing on the work itself rather than external validation or self-aggrandizing narratives.

5 Key Takeaways

1. Ego is an ever-present, destructive force that the book defines as an “unhealthy belief in our own importance”  leading to “arrogance” and “self-centered ambition”. (18 )It distorts reality, prevents genuine self-assessment, hinders creativity, and is identified as the root of nearly every problem and obstacle encountered in the three stages of life: aspiration, success, and failure.
2. Cultivate Humility and a Perpetual Student Mindset: True confidence is earned, while ego is artificial. To counteract ego, one must embrace humility, actively seek feedback, and constantly learn from everyone, recognizing that the “pretense of knowledge is our most dangerous vice” (49) and that, per Epictetus  “it is impossible to learn that which one thinks one already knows”. (51) 
3. Focus on “Doing” Rather Than “Being” or Seeking External Validation: A central theme is the choice between “to be somebody” (chasing titles, promotions, and recognition) and “to do something” (pursuing purpose and making a difference). The book advocates for silent, diligent work and an “action and education focused” (34) approach, as constant talking and seeking early validation can deplete energy and hinder true progress.
4. Practice Restraint, Self-Awareness, and Realism, especially in Success: Success can breed dangerous delusions like entitlement, control, and paranoia, causing individuals to overestimate their power and distort reality. Holiday uses examples like Howard Hughes to illustrate how ego can lead to self-destruction and waste talent, advocating for “sobriety” and clear-headedness to prevent these pitfalls.
5. Embrace Adversity as “Alive Time” and Define Success Internally: Failure and setbacks are inevitable, but ego can turn them into devastating blows. Instead, these moments should be viewed as “alive time”—opportunities for learning, acting, and growth. True success, according to Holiday, is not about external rewards or recognition, but about making the effort to do your best and fulfilling your own high standards and principles.

Top Quotes

• Wherever you are, whatever you’re doing, your worst enemy already lives inside you: your ego.  (18)
• …ego [is] …an unhealthy belief in our own importance. Arrogance. Self-centered ambition.. (18)
• It’s when the notion of ourselves and the world grows so inflated that it begins to distort the reality that surrounds us. When, as the football coach Bill Walsh explained, “self-confidence becomes arrogance, assertiveness becomes obstinacy, and self-assurance becomes reckless abandon.” This is the ego, as the writer Cyril Connolly warned, that “sucks us down like the law of gravity.” (19)
• 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.” (19)
• 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.” [John Boyd] (42)
• The pretense of knowledge is our most dangerous vice, because it prevents us from getting any better. Studious self-assessment is the antidote.” (49)
• It is impossible to learn that which one thinks one already knows,” Epictetus says. 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.  (51)
• With success, particularly power, come some of the greatest and most dangerous delusions: entitlement, control, and paranoia.” (115)
• 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.” [John Wooden] (162)

The Nature of the Enemy: Defining Ego

The core premise is that the worst enemy to our goals lives within us. As physicist Richard Feynman stated, “The first principle is that you must not fool yourself—and you are the easiest person to fool.” (18) This internal enemy is the ego.

Ego, as defined in “Ego is the Enemy”, is not simply confidence or self-esteem. It is something more specific and corrosive: “an unhealthy belief in our own importance. Arrogance. Self-centered ambition.” (18) It is an inflated notion of oneself that distorts reality.

It is the internal voice that tells us we’re better than we really are, creating a distortion between our perception and reality. This distortion is where the danger lies. 

As legendary football coach Bill Walsh explained, ego is what happens when virtues curdle into flaws. “self-confidence becomes arrogance, assertiveness becomes obstinacy, and self-assurance becomes reckless abandon.”  (19)

The Dangers of an Inflated Ego

An unchecked ego is the root of almost every conceivable problem, preventing us from achieving what we want and sabotaging what we already have. Ego is the enemy of nearly everything required for long-term achievement: 

• Mastering a craft: “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.” (20)  If we think we’re already great, we stop learning.
• Working well with others: “How are we supposed to reach, motivate, or lead other people if we can’t relate to their needs—because we’ve lost touch with our own?” (20)
• Creative insight: As the performance artist Marina Abramović states, “If you start believing in your greatness, it is the death of your creativity.” (20)
• Lasting success: Ego is a “magnet for enemies and errors.” (19)It repels opportunities and allies, making any success we achieve fragile and short-lived.

It is the enemy because it disconnects us from the real world we must operate in.

Ego persists because it offers comfort. It soothes the fear and insecurity inherent in pursuing great work:

Just one thing keeps ego around—comfort. Pursuing great work—whether it is in sports or art or business—is often terrifying. Ego soothes that fear. It’s a salve to that insecurity. Replacing the rational and aware parts of our psyche with bluster and self-absorption, ego tells us what we want to hear, when we want to hear it. But it is a short-term fix with a long-term consequence.  (20)

Ego vs. True Confidence: An Essential Distinction

It is important not to confuse ego with confidence. One is a dangerous liability, while the other is an essential asset. The difference lies in their foundation.

Ego is that puffed-up voice in your head whispering you’re the smartest, sharpest, most important person in the room. It’s arrogance dressed up as ambition. It twists reality, blocks honest self-awareness, and leaves you clinging to an inflated version of yourself. That’s not strength; it’s delusion.

Confidence feels different. It’s earned, not performed. Strip away the ego, and what’s left is a grounded kind of certainty, the kind that comes from putting in the work and knowing you can deliver. Ego needs applause. Confidence just gets on with it.

One is fake swagger. The other is solid ground.

A Cautionary Tale: Howard Hughes

The life of Howard Hughes serves as a powerful warning against the destructive force of unchecked ego. Hughes was a gifted visionary, a mechanical genius, and a brave pioneer of aviation. He had the ability to predict sweeping changes that would transform entire industries.

Yet his story is one of spectacular failure. Hughes was an egomaniac who “evaporated hundreds of millions of dollars” (94) and ran multiple companies into the ground. 

Usually, a bad businessman fails and ceases to be in business, but thanks to the steady chain of profits from his father’s company (which he found too boring to interfere with) Hughes was able to stay afloat, providing a clear, decades-long study of the damage an unchecked ego can wreak.

His immense ego fueled a lifetime of paranoia and waste, proving that talent is no match for an inner enemy. He ultimately died a “miserable, pathetic end” (94) in a secluded “asylum of his own making. He felt little joy. He enjoyed almost nothing of what he had. Most importantly, he wasted. He wasted so much talent, so much bravery, and so much energy”  (96)

The Three Delusions:

• Entitlement: Assumes “This is mine. I’ve earned it,” overstating one’s abilities and creating ridiculous expectations.
• Control: Insists “It all must be done my way,” leading to paralyzing perfectionism and pointless battles.
• Paranoia: Believes “I can’t trust anyone,” creating the very persecution it seeks to avoid and trapping its owner in a prison of delusion.

 

Purpose Over Passion

Modern culture tells us to follow our passion, but passion can actually hold us back. It’s often a weak substitute for discipline, skill, inner strength, clear goals, and the ability to keep going when things get tough. (56)

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 (57)

Passion and purpose are different things. When you’re passionate, you focus on something you love: “I’m passionate about music” or “I’m passionate about helping people.” But purpose goes deeper. Purpose is a rational, directed, and externally-focused mission. It’s about what you need to do and why: “I must teach children so they can have better lives” or “I was meant to build things that solve real problems.”

Purpose is calm and thoughtful. It takes your focus off yourself and puts it on the work that needs doing. Instead of asking “What do I love?”,  purpose asks “What needs to be done?” and “Who will benefit?”

This shift away from yourself is what makes purpose powerful. You’re not trying to feel good or chase an emotion. You’re pursuing something bigger than your own feelings.

But purpose alone isn’t enough. You also need to see reality clearly: What exactly should you do today? How will you know if you’re making progress? What might go wrong? Real achievement requires clear thinking, careful planning, and steady determination to do the work. 

The best guide isn’t what excites you: it’s a clear, selfless mission focused on reality and getting things done, not on your own story or feelings.

 

Purpose in Action: William Tecumseh Sherman

General William Tecumseh Sherman is a prime example of a man guided by purpose. During the Civil War, his “strong sense of purpose” (32) directly informed his military doctrine.

His entire strategy rested on deliberately avoiding frontal assaults or shows of strength in the form of pitched battles, and ignoring criticism designed to bait a reaction. He stuck to his plan because he was focused on the larger objective, not on his personal glory. 

After the war, despite being one of the most famous men in America, he sought no public office and had no taste for politics. Sherman just wanted to do his work and be done. His life was proof that when you put purpose above ego, you don’t need the spotlight to leave a mark.

The Defining Choice: “To Be or To Do?”

“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. You will be true to your friends and to yourself. And your work might make a difference. 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.” (42)

The most critical decision an aspiring person faces is the choice between appearance and action. This concept is exemplified by military strategist John Boyd, who framed it as a “fork in the road.” (42) In life, he explained, you must decide which path you will take:

• To Be Somebody: This is the path of ego. It involves chasing promotions, titles, and reputation. It requires you to “make compromises and you will have to turn your back on your friends” to become a member of the club.
• To Do Something: This is the path of purpose. It involves focusing on accomplishing important work that might make a difference, even if it means you don’t get promoted or recognized. On this path, “you won’t have to compromise yourself,” and “your work might make a difference.”

This choice—”To be or to do?”—is a constant roll call in life (45).  Purpose helps you answer it easily. If the purpose is self-aggrandizement, the path is to “be somebody.” If the purpose is larger than oneself, the path is to “do something,” which makes many other “choices” mere distractions.

At a Glance: Ego vs. Purpose

Concept	Core Idea	Guiding Principle
Ego	An unhealthy belief in one’s own importance.	“I must be seen as great.”
Purpose	A rational, externally-focused mission.	“I was put here to do this for…”

Key Lessons:

I. In Aspiration (When Setting Out to Achieve Something)

Starting out is dangerous.

This is the moment when you’re chasing something new, setting goals, building momentum. It’s exciting, but it’s also when ego slips in easiest, and does the most damage.

If you don’t fight ego here, you build on sand. Ego warps reality, convinces you you’re further along than you are, and blinds you to what actually needs work. Keep it in check, and you give yourself a shot at real growth and lasting success.

Key Strategies for Fighting Ego Early On:

Cultivate Virtues

• Embrace Modesty, Justice, and Self-control

These are essential virtues, particularly when young, for restraining character.

• Aim to think less of yourself: Strive to be “less invested in the story you tell about your own specialness”. (17)
• Be willing to re-evaluate your talents downward: Recognize that “updating your appraisal of your abilities in a downward direction is one of the most difficult things to do in life—but it is almost always a component of mastery”. (49)

• Approach Work with Deliberation and Focus

• • • Be Slow in Deliberation, Prompt in Action: Think carefully, but act decisively once a resolve is made.
    • Constantly Train Your Intellect: Prioritize developing a sound mind.
    • Act and Live Small: Even when thinking big, focus on iterative actions and education, rather than grandiosity, to achieve your goals.
    • Evaluate Opportunities Strictly: Before taking on any opportunity, ask yourself: 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?

• Choose Purpose Over Recognition

• • • Choose to “Do Something” over “Be Somebody”: Prioritize accomplishing meaningful work for a larger purpose (country, organization, yourself) over seeking personal recognition, promotions, or being a “member of the club”.
    • Focus on purpose, not just passion: Shift from “I am so passionate about…” to “I must do… I was put here to accomplish…” . Purpose is about “pursuing something outside yourself as opposed to pleasuring yourself” . (57)
    • Work quietly and avoid excessive talk:  Don’t chase public recognition. Work quietly by yourself and turn your problems and struggles into something useful. Staying quiet makes you stronger because you don’t need other people’s approval to keep going. Talking about what you’re doing can drain your energy and trick you into thinking you’ve already accomplished something when you haven’t. Save your energy for the actual work, not for telling people about it.

• Commit to the Process

• • Work, Work, Work:  Having good ideas isn’t enough. Success comes from doing the work consistently, not from being brilliant. Your ego wants ideas to be enough because it prefers the exciting, attention-getting parts over the hard, boring work that nobody sees. But real progress happens when you focus on actually doing things, not on getting noticed or praised. Don’t look for quick rewards or recognition. Instead, invest your time and effort in getting better at what you do. Learn to enjoy the daily practice and gradual improvement, even when it’s tedious. You can’t win without working hard
  • Delay gratification: Remind yourself, “I am delaying gratification by doing this… (84)I am making an investment in myself instead of in my ego”.  (84)

Master Self-Awareness and Learning

• Evaluate Your Own Abilities Accurately

• • • Practice seeing yourself with detachment to cultivate humility and self-awareness. 
    • Getting some distance from yourself helps you stay humble and see things clearly. It’s a natural way to keep your ego in check.
    • Regularly take an honest look at what you actually know versus what you think you know. This stops you from pretending to be smarter than you really are.

• Embrace Lifelong Learning and Stay a Student

• Core Mindset:

• • • Accept that you have much to learn. Epictetus’s maxim is central: “It is impossible to learn that which one thinks one already knows.” (51) 
    • Regardless of your current achievements, always seek more instruction. The moment we believe we have graduated, learning stops. Sustained success depends on the humility to continue learning, even at the peak of one’s power.
    • “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.” (51)
    • The Kirk Hammett Example: 
      • Days after being hired by his dream band, Metallica (already one of the biggest bands in the world), guitarist Kirk Hammett sought out lessons from guitar virtuoso and teacher, Joe Satriani. 
      • For two years, he subjected himself to rigorous, objective feedback and fundamental drills, recognizing that despite his success, he was not as good as he wanted to be. 
      • Despite having his dream job, Hammett had the humility to recognize he still had more to learn. 
      • He remained a student when his ego could have easily told him he was a rock star. 

• Active Learning Strategies:

• Actively solicit critical feedback: 

• Ego avoids feedback, believing it already knows everything and is “spectacular, perfect, genius” (51)”.  Actively seek out feedback.

• • • • MMA pioneer Frank Shamrock’s “plus, minus, and equal” system encourages continuous feedback from all angles to gain a realistic understanding of what one knows and doesn’t know. 
      • Have someone better to learn from, someone lesser to teach, and someone equal to challenge yourself against, to gain continuous feedback on what you know and don’t know. 

• Put yourself in uncomfortable learning situations:

• • • • Deliberately place yourself in rooms where you are the least knowledgeable person and where your assumptions are challenged.
      • Pick up a book on a topic you know next to nothing about. Put yourself in rooms where you’re the least knowledgeable person. That uncomfortable feeling, that defensiveness that you feel when your most deeply held assumptions are challenged—what about subjecting yourself to it deliberately? Change your mind. Change your surroundings. (102)

• Professional Approach:

• • • Be self-critical and motivated to improve: A true student “is self-critical and self-motivated, always trying to improve his understanding” (50)
      • As the jazz great Wynton Marsalis explains: “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… because they consistently observe and listen, the humble improve. They don’t assume, ‘I know the way.’” (101)

• Face the Struggle Head-On: 

• • • When faced with a challenge, choose to confront the difficulty directly. When faced with criticism or a new idea, is our first instinct to defend what we know, or to explore what we don’t? 
    • The answer reveals whether we are operating as a professional or an amateur, regardless of our title. 
    • 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. (102)

Manage Emotions and Expectations

• Don’t Be Passionate

Be purposeful and realistic. Passion can mask weakness and blunt critical cognitive functions. Instead, cultivate purpose (passion with boundaries, focused on something outside yourself) and realism (clarity, deliberation, and methodical determination, including planning for contingencies and seeking feedback).

• Restrain Yourself: 

Practice self-control, patience, and politeness, even when facing unfair treatment or abuse. Play the long game., and understand that others’ poor treatment degrades them, not you. 

• Maintain composure: Per Booker T. Washington, Strive to be “calm, self-possessed, patient, and polite” (65) to achieve great results.
• Avoid explosive anger and emotional reactions: “Getting angry, getting emotional, losing restraint is a recipe for failure” (67)
• Be willing to tolerate unfairness for a larger goal: 
  • Like Jackie Robinson, “put aside both his ego and in some respects his basic sense of fairness and rights as a human being”  (67) for a “larger plan”. (67)
• Understand that others’ poor treatment reflects on them: 
  • “Those who have subdued their ego understand that it doesn’t degrade you when others treat you poorly; it degrades them”.  (68)

• Get Out of Your Own Head: 

Do not lose touch with reality by constantly overthinking yourself.  Focus on the tangible and real, and be present in your surroundings. There is work to be done and lessons to be learned from what is around you, not from an imaginary audience. 

• “Don’t live in the haze of the abstract, live with the tangible and real, even if—especially if—it’s uncomfortable”. (74)

• Kill Pride Early: 

Guard against early self-confidence and self-obsession, as pride dulls your ability to learn, adapt, and build relationships. 

When you feel pride, ask yourself: “What am I missing right now that a more humble person might see?” (79) and “What am I avoiding, or running from, with my bluster, franticness, and embellishments?” (79)

“…just because you are quiet doesn’t mean that you are without pride. Privately thinking you’re better than others is still pride. It’s still dangerous.“ (79)

Follow the “Canvas” Strategy and Serve Others:  

When you’re starting out, your ego tells you that you’re an unappreciated genius who shouldn’t have to do grunt work and deserves credit for every idea.

Instead, use the Canvas Strategy: “Find canvases for other people to paint on.”(60) Find ways for other people to succeed, which creates a path for yourself.

The Canvas Strategy is rooted in the ancient Roman role of the anteambulo—the person who “clears the path” for their powerful patron.

How to do this:

• Make others look good by “providing the support so that others can be good”(60)
• “Clear the path for the people above you and you will eventually create a path for yourself” (60)
• Attach yourself to successful people and organizations to learn while moving forward with them
• Embrace “grunt work”.  Actively seek out and master tasks that others consider themselves “too good for” (62)
• Seek opportunities to promote others’ work. “Find ways to “promote their creativity, find outlets and people for collaboration, and eliminate distractions that hinder their progress and focus”. (64)
• Give away your ideas and let others take credit.

Why it works: 

• When you make others look good, provide support, find efficiencies, and give ideas away, you build a reputation for being essential. You learn a great deal and create a bank of goodwill that serves you later.

Examples:

• Benjamin Franklin wrote wildly popular pseudonymous letters and allowed his brother, the newspaper’s owner, to take credit,  while Franklin honed his craft and learned to shape public opinion
• Bill Belichick began his NFL career by volunteering to do the grunt work no one else wanted (analyzing film) and gave all credit to senior coaches, quietly mastering the game and making himself essential.

Aspiration sets the tone for everything that follows.

The whole point of this stage is simple: be humble when you’re aiming high, be gracious when you actually get there, and be resilient when you fall flat. If ego runs unchecked early on, it rots the foundation. That’s how talent turns sour and ambition eats itself alive.

Humility at the start is what makes real learning possible. It builds character, skill, and the discipline you’ll need when success shows up, or when failure knocks you down.

II. In Success (When You Have Achieved Something)

Success is hazardous.

It feels good, it dazzles, and it fades fast if you let ego take the wheel. Nothing kills achievement quicker than believing your own hype, shutting off the learning, and sliding into bad habits.

Howard Hughes is the caution sign blinking in neon. Brilliant, visionary, loaded with talent; and wrecked by his ego. He wasted talent, turned success into chaos, went on a “deranged crime spree” of mismanagement, and died isolated, simply because he was “so publicly and visibly unable to bear his birthright properly”.(97)

The real challenge of success isn’t getting there; it’s staying grounded once you arrive. Ego whispers that you’ve arrived, that you’re untouchable. Humility says: keep working, keep learning, keep your head clear. If you want your wins to last, you’ve got to be gracious in success and ruthless about stripping ego out of it.

 

Key Strategies for Fighting Ego During Success:

Maintain Balance and Perspective

• Stay Sober

Success can be like a drug that makes you lose your head. When you succeed, you need  “sobriety, open-mindedness, organization, and purpose” (91) in order to keep your ego in check. Stay clearheaded and humble. Don’t become obsessed with your image or start treating people badly. Success “clouds the mind precisely when it needs to be clear”

• Always Stay a Student

The more you learn, the more you learn you don’t know. Maintain a lifelong learning mindset, absorbing best practices, and being open to new ideas from all sources.

• Genghis Khan’s Model: The great conqueror was a “perpetual student.”(99) 
  • The Mongols systematically absorbed the best technologies, tactics, and people from every culture they encountered. 
  • This “persistent cycle of pragmatic learning, experimental adaptation, and constant revision” (91) was the key to their dominance.
  • “Khan’s first powerful victories came from the reorganization of his military units, splitting his soldiers into groups of ten. This he stole from neighboring Turkic tribes, and unknowingly converted the Mongols to the decimal system” (99)
  • “In his campaigns against the Jurched, Khan learned the importance of winning hearts and minds. By working with the scholars and royal family of the lands he conquered, Khan was able to hold on to and manage these territories in ways that most empires could not. Afterward, in every country or city he held, Khan would call for the smartest astrologers, scribes, doctors, thinkers, and advisers—anyone who could aid his troops and their efforts. His troops traveled with interrogators and translators for precisely this purpose.”  (100)
• Seek Discomfort: To combat ego, one must actively “pick up a book on a topic you know next to nothing about”, “put yourself in rooms where you’re the least knowledgeable person,” and embrace the uncomfortable feeling of having assumptions challenged.(102) Professionals “find learning… to be enjoyable” and engage in education as an “ongoing and endless process”. (102)

• Don’t Tell Yourself a Story: 

Resist the “human impulse” (105) to “craft stories out of past events,” (105), ie., to create heroic stories about your past success. Resist the urge to say “I knew it all along” or behave as if your success was due to some special genius.

Making up grand narratives about your success makes you arrogant and stops you from seeing what really happened. Instead of building myths about yourself, keep focusing on doing excellent work using the same principles that got you there in the first place.

Bill Walsh’s “Standard of Performance”

• When Walsh turned the 49ers from the worst NFL team into Super Bowl champions, he didn’t do it with a big vision. He focused on small details and perfect execution—his “Standard of Performance.” He knew that if you handle the details well, “the score takes care of itself.”The winning would happen.” (105)
• Walsh ignored the media calling him a “Genius” because he knew it wasn’t true. When his team started believing they were special, they played badly. They only won again when they went back to focusing on performance, not their story.
• These narratives about your success “don’t change the past, but they do have the power to negatively impact our future” (106) by making you think you’re more powerful than you actually are and work less hard.
• 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. Because that’s the only thing that will keep us here. (109)

Define Your Priorities

• Know What’s Important to You. 

Success brings lots of tempting opportunities and distractions. You need to know what actually matters to you. 

Ulysses S. Grant is a perfect cautionary tale. Even though he was a brilliant military leader, he “couldn’t decide what was important—what actually mattered—to him.” So he ran for president (a job he was bad at) and later got tricked by a financial Ponzi scheme. 

Just because you can do something doesn’t mean you should.

Practice Euthymia

• Understand your unique path and purpose, and resist distractions.
• The Greek word euthymia (meaning “tranquillity”) refers to the “sense of our own path and how to stay on it without getting distracted by all the others that intersect it”. (112)
• “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. That’s it. No more and no less.” (112)
• Be content with what you are and what you do best, without succumbing to external pressures or the desire to “have more than everyone else”.(111) 

• Learn To Say No And Accept Trade-offs: 

• • Be capable of saying “no” to opportunities that don’t align with your core values.  
  • “think about what’s truly important to you and then take steps to forsake the rest,”. (113)
  • “Ego rejects trade-offs. Why compromise? Ego wants it all.” (113)

• Keep Your Identity Small: 

• • Investor Paul Graham advises startups to avoid grand visions and instead “keep your identity small.” (108) The focus should be on the work and its principles, not a glorious headline.
  • “There is a real danger in believing it when people use the word “genius”—and it’s even more dangerous when we let hubris tell ourselves we are one.”  (108)
  • “These labels put you at odds not just with reality, but with the real strategy that made you successful in the first place. From that place, we might think that success in the future is just the natural next part of the story—when really it’s rooted in work, creativity, persistence, and luck. (108)

Guard Against Corrupting Influences

• Manage Entitlement, Control, and Paranoia:

Success, especially power, can breed dangerous delusions: entitlement, control, and paranoia.  Be aware of these dangerous delusions and get your perceptions under control. 

• Entitlement makes one overestimate their power, feel they’ve “earned it,” and devalue others’ time. 
• Control leads to “paralyzing perfectionism” and “pointless battles” (118) simply to exert one’s will. 
• Paranoia, driven by a fragile ego and the desire to “prove the doubters wrong,” (116) creates suspicion, a belief that one is “surrounded by fools,” and leads to self-inflicted persecution. 
  • Paranoia thinks, I can’t trust anyone. I’m in this totally by myself and for myself. It says, I’m surrounded by fools. It says, focusing on my work, my obligations, myself is not enough. I also have to be orchestrating various machinations behind the scenes—to get them before they get me; to get them back for the slights I perceive (118)
• These delusions harm not only the individual but also their loved ones and those they lead. It is crucial to “get yourself—and your perceptions—under control” (117)

• Beware the “Disease of Me”: 

Don’t let success make you prioritize personal importance or external honors over the collective good or what is right. 

• NBA Championships basketball coach Pat Riley describes a trajectory for successful teams: an “Innocent Climb” followed by the “Disease of Me”. In this stage, after a team begins to win, and media attention swells,  “players calculate their own importance. Chests swell. Frustrations emerge. Egos appear”. (125)
• General George Marshall is an antithesis to this disease, actively discouraging efforts to promote him and willingly deferring a monumental opportunity (commanding D-Day) to Eisenhower because it was the right decision for the war effort.  (127)
• Marshall demonstrated that “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”. (127)
• “This is one of the most dangerous ironies of success—it can make us someone we never wanted to be in the first place. The Disease of Me can corrupt the most innocent climb.” (127)

• Connect with Something Bigger Than Yourself:

Find ways to connect with something much larger than you are – like the universe, nature, or long-standing traditions. This helps shrink your ego, opens your mind to new ideas, and helps you think about your place in the world.

• Sympatheia: This means feeling connected to the universe, having “a sense of belonging to something larger.” (130) When you think deeply about how huge the universe is, like explorer John Muir did, you realize that “human things are an infinitesimal point in the immensity.” (130) This makes your ego smaller and gives you a better perspective on life.
• Your ego does the opposite – it “blocks us from the beauty and history in the world” (131) because it makes you think “the world revolves around you.” (132)

Adapt to New Responsibilities

• Manage Yourself (and Delegate): 

As you become more successful, you need to change how you see your role. Focus on the most important big-picture goals and trust other people to handle the things they’re good at.

• This change requires having the “humility to put aside some of the more enjoyable or satisfying parts of your previous job.” (123) It means trusting people who know more than you do in certain areas, and focusing on the “big picture” instead of getting caught up in “little things.”
• President Dwight D. Eisenhower was great at this – he knew the difference between things that were “urgent and important” (120) and trusted the people who worked for him to do their jobs.

Holding on to success takes constant watchfulness.

Ego sneaks in quietly, telling you you’ve earned the right to relax, to stop listening, to believe the story you want to hear. That’s when things start to slip.

The antidote is unglamorous: stay sober, keep learning, cut the self-congratulation, and keep your purpose front and center. Don’t let entitlement creep in. Lead with humility. Check your self-importance when working with others. And when in doubt, zoom out, connect your work to something bigger than yourself.

It’s a grind, but that’s the point. Success isn’t a finish line; it’s another round in the daily battle against ego. Humility and self-awareness are the only tools that keep you steady when new challenges show up.

III. In Failure (When Facing Adversity)

Failure happens.

Ego is what makes it permanent. It keeps you from learning, pushes blame onto others, and drags you into self-sabotage.

Handled right, failure is just another step; humbling, painful, but useful. It forces resilience. It shifts your focus back to what you can control. It teaches you, if you let it. But ego won’t let it. Ego takes every setback as a personal insult. It whispers, “See? You were never good enough,” or, “This isn’t fair—someone else messed this up.” That voice keeps you stuck, replaying the past instead of moving forward.

The real danger isn’t the failure itself—it’s ego turning it into a permanent wound. Every injury gets doubled when you pile on self-injury: bitterness, blame, hate. You lose perspective, and the setback becomes your identity. If you don’t learn, if you don’t face yourself honestly, ego cements the loss and makes it permanent.

Key Strategies for Overcoming Adversity with Humility:

Process and Learn from Setbacks

• Understand What Went Wrong: 

To overcome failure, it’s crucial 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. ” (151)

Stay Strong Mentally

• Avoid Narcissistic Injury: Don’t take indifferent or objective events personally. A fragile sense of self, dependent on life always going your way, leads to self-injury. Whether a setback is your fault or not, it’s your responsibility to deal with it.
  • “Ego loves this notion, the idea that something is “fair” or not. Psychologists call it narcissistic injury 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”  (151)
• Practice Stoic Resilience: Strong, humble individuals endure troubles with fewer complaints and less self-pity, as their identity isn’t threatened by external events. 
  • “A fragile sense of self is constantly under threat “ (152)

Turn Bad Times into Good

• Turn “Dead Time” into “Alive Time”:  

Every moment of involuntary idleness, stagnation, waiting, or unfavorable circumstance presents a choice:

• Dead Time: When you’re just waiting and doing nothing useful.
• Alive Time: When you’re learning, working, and making progress.

• Author Robert Greene’s Framework

• • 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 and utilizing every second  (155)
  • Every moment of failure, every moment or situation that we did not deliberately choose or control, presents this choice: Alive time. Dead time.  (155)
• Use setbacks as chances to learn, grow, and fix things you’ve been putting off. Work with what you have, where you are. Turn bad situations into fuel for your success.
• We cannot control when we encounter setbacks, but we absolutely control how we use that time. This is the ultimate reclamation of agency from circumstances. 
• Ego tells us to complain, to feel sorry for ourselves, to blame others. An anti-egoic approach asks: What can I do with this time? How can I use this setback as an opportunity to do what I’ve long needed or wanted to do? 
• By choosing alive time, we turn the worst parts of our lives into periods of profound growth.

The Malcolm X Example: 

• While in prison, Malcolm X chose to use his time well. He taught himself to read by copying the dictionary by hand, read constantly, and completely changed who he was. He said he had “never been so truly free in his life” (156) because learning freed his mind even when his body was locked up.

Other Examples

• Francis Scott Key wrote the US national anthem while trapped on a ship during a prisoner exchange in the War of 1812, Viktor Frankl refined his psychology in three Nazi concentration camps, and Walt Disney decided to become a cartoonist while laid up after stepping on a rusty nail. (156-157)

Redefine Success: Focus on Effort, Not Outcomes

• The Problem with External Validation

Everyone wants rewards, recognition, and praise. But you can’t control these things. When you base your self-worth on what others give you, you feel crushed when ignored and inflated when praised.

“Ambition,” Marcus Aurelius reminded himself, “means tying your well-being to what other people say or do . . . Sanity means tying it to your own actions.” (162)

• Let the Effort Be Enough:   

Your ego wants praise and rewards from others. Real strength comes from judging yourself by your own actions and standards.

Do the right thing and meet your own high standards. Don’t chase external rewards or approval. Take pride in your effort, not the results.

When your effort is enough, you’re protected from other people’s opinions. Praise won’t make you cocky, and criticism or indifference won’t crush your spirit. You judge yourself by what you do, not what others say. This makes you strong, focused, and free to do good work.

• The “effort—not the results, good or bad—is enough.” (161)

Examples That Show the Way

• • John Wooden’s Definition of Success: “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.” (162)
  • The Story of Belisarius: The great Roman general saved Western civilization multiple times, only to be rewarded with suspicion, humiliation, and poverty by the paranoid emperor, Justinian, he served. Yet Belisarius never complained. For him, doing his job well and fulfilling his duty was enough.

• The Tragic Cost of External Dependence

• • The case of John Kennedy Toole tragically illustrates the danger of relying on external validation. He committed suicide after his brilliant novel “A Confederacy of Dunces” was rejected. 
  • The book, unchanged, was found by his mother, and won a Pulitzer Prize after his death.
  • “Do your work. Do it well. Then “let go and let God.” That’s all there needs to be. Recognition and rewards—those are just extra. Rejection, that’s on them, not on us.” (163)

Embrace “Fight Club Moments”: 

• A “Fight Club moment” refers to a rock-bottom experience that forces you to confront harsh truths about yourself and your life—named after the psychological breakdown and revelation the narrator experiences in the movie Fight Club.
• It’s when everything falls apart so completely that you can no longer maintain your illusions or keep lying to yourself. These moments are characterized by:
  • Brutal honesty: You’re forced to see reality without the comfortable lies
  • Ego destruction: Your self-image gets shattered
  • Truth confrontation: You have to “make eye contact with a thing called Truth” (165) 
  • Opportunity: From the ruin comes an opportunity for profound progress
• The Greeks called this katabasis—”a going down”—where mythological heroes had to descend into the underworld before emerging with new wisdom.
  • Katabasis: “In Greek mythology, characters often experience katabasis—or “a going down.” They’re forced to retreat, they experience a depression, or in some cases literally descend into the underworld. When they emerge, it’s with heightened knowledge and understanding.” (164)
• While these rock-bottom moments are painful and often come from external forces beyond your control, they can be powerful catalysts for genuine change. They strip away pretense and force you to rebuild from a foundation of truth rather than self-deception.
• The key is recognizing that being “thoroughly demolished” (165) can actually be the beginning of authentic growth—if you’re willing to face what the breakdown is trying to show you.
• As Hemingway wrote, “The world breaks every one and afterward many are strong at the broken places. But those that will not break it kills.” (166)

Two Essential Responses to Crisis

1. Draw the Line:

When a situation becomes irredeemable, have the courage to make a full stop rather than digging deeper. Prioritize maintaining your dignity and character—live to fight another day. “The only real failure is abandoning your principles.” (173) If success is slipping, return to the aspirational phase and focus on “first principles and best practices.” (173)

2. Maintain Your Own Scorecard: 

Hold yourself to a higher standard than society’s definition of success. Measure yourself against your own potential and the best version of yourself, not external applause or conventional metrics of winning.

• “Your potential, the absolute best you’re capable of—that’s the metric to measure yourself against.” (176)
• This internal standard minimizes ego-driven behaviors, ensures ethical conduct, maintains long-term perspective, and allows you to prioritize team success over personal glory. Great people hold themselves to internal standards that surpass societal definitions of success, becoming “the best possible version of themselves.” (176)

Always Love, Not Hate: 

• In failure, it is easy to hate, to blame, and to seek revenge. This is a destructive and counterproductive path fueled by ego. Do not allow anger, hate, or an obsession with past wrongs to consume you. Choose love instead, which is “egoless, open, positive, vulnerable, peaceful, and productive.” (183)

The Futility of Hate

• Hate is ultimately self-defeating because it:
  • Defers blame and makes others responsible for your situation
  • Becomes an all-consuming distraction that drains vital energy
  • Prevents meaningful accomplishment and forward progress
  • Acts as a debilitating cancer that destroys the hater more than the target

Historical Lessons

• The Hearst Precedent 
  • William Randolph Hearst’s all-consuming campaign to destroy Orson Welles’s Citizen Kane backfired spectacularly. His hatred only cemented the film’s legacy while destroying his own reputation. 
  • Attempting to destroy something out of hate often ensures its preservation and immortalizes your own pettiness.
• The Streisand Effect is when trying to hide or suppress something actually makes it more famous and widely known.
• It’s named after Barbra Streisand, who sued a photographer in 2003 to remove aerial photos of her Malibu home from a website. Before the lawsuit, hardly anyone had seen the photos. But the legal action created a media frenzy, and suddenly millions of people saw her house and knew exactly where she lived.
  • The core principle: The harder you try to bury something, the more attention you draw to it. Your attempt to silence or destroy something becomes the very thing that amplifies it.

The Wisdom of Douglass and King 

Two giants of American history understood this principle:

• Frederick Douglass, when confronted with racism, declared: “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” (181)
• Martin Luther King Jr. taught that hate is a debilitating cancer, while love is transformational and freeing.
• Both men chose dignity and love over the easy path of hatred, transforming not only themselves but society itself.

Commit to Continuous Self-Improvement

• Learn from Mistakes: Failure teaches you about yourself and helps you avoid ego’s traps.
  • The Reverend William A. Sutton observed some 120 years ago that “we cannot be humble except by enduring humiliations. (165)
• Sweep the Floor Every Day: Fighting ego isn’t a one-time fix; it’s daily maintenance. Like dust, ego always comes back and needs to be swept away again.

Failure isn’t the end of the line. It’s part of the loop—aspiration, success, adversity, repeat. Ego “makes all the steps hard, but failure is the one it will make permanent” (184) if one fails to learn from mistakes and understand oneself better. 

That’s why the work never stops. The battle is daily, minute by minute. You sweep the floor, and then you sweep it again.

Failure, though, carries its own gift. Success rarely teaches much. Failure does—if you let it. Humility, self-awareness, resilience: that’s what turns a stumble into progress.

Conclusion: The Daily Battle

Life runs in loops—aspiration, success, failure, then back again. At every turn, ego waits to trip you up.

Managing ego isn’t something you “solve.” It’s daily work. As philosopher Daniele Bolelli puts it, sweeping once doesn’t mean the floor stays clean. “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.” (186) Ego is the same way; it piles back up unless you clear it out again and again.

This daily battle runs through all three phases:

•  Aspiration: when you’re chasing something new.
•  Success: when you’ve made it and risk losing your grip.
•  Failure: when setbacks tempt you to wallow or blame.

Ignore the battle and ego eats you alive. It turns temporary failures into permanent ones and erodes you over time. The only way through is to keep practicing humility in aspiration, grace in success, and resilience in failure. The ideas are simple. The discipline to live them isn’t.

And the goal? It isn’t just to “do great things.” It’s to become better people—happier, more balanced, more content, more humble, more selfless. Or if you’re lucky, all of the above. That’s what comes from the fight: peace, growth, and a steadier self.

Ego never sleeps. Which is why you “must sweep the floor every minute of every day. And then sweep again.” (190) 

The book leaves us with one question worth asking daily: in your own loop of aspiration, success, and failure, who’s really in charge—you, or your ego?

 

Recommended Reading:

The Obstacle is the Way by Ryan Holiday

Appendix

Here are the people presented as case studies

• Bill Walsh – Football coach and general manager of the 49ers, who implemented a “Standard of Performance” to achieve excellence and rejected the label of “genius”.
• Howard Hughes – An egomaniac whose brilliance was overshadowed by his destructive ego, leading to wasteful business practices and a miserable end.
• John DeLorean – Ran his car company into the ground due to ego and mismanagement, and attempted to save it through illegal means.
• Alexander the Great – Featured in an anecdote with Diogenes, highlighting his position of power relative to Diogenes’ lack of material desire.
• Isocrates and Demonicus – Isocrates wrote a letter to Demonicus offering advice on virtues such as modesty, justice, and self-control for young men.
• William Tecumseh Sherman – A U.S. military officer who achieved great success through a slow, gradual ascent, humility, diligence, and a strong sense of purpose, avoiding public office and flattery.
• John Boyd – An influential military strategist who exemplified choosing “to do something” for his country and Air Force over “being somebody” and seeking personal advancement or recognition.
• Kirk Hammett – Metallica’s guitarist who, despite joining a major band, sought out an instructor (Joe Satriani) to continuously improve, demonstrating the value of remaining a student.
• Frank Shamrock – A mixed martial arts pioneer who developed the “plus, minus, and equal” system for continuous self-assessment and emphasized the importance of always staying a student.
• Eleanor Roosevelt – Presented as a leader driven by purpose and reason rather than passion, which is often a mask for weakness.
• Lewis Alcindor Jr. (Kareem Abdul-Jabbar) – A basketball player who learned from coach John Wooden to be dispassionate, focus on control, and do his job, rather than being “passion’s slave”.
• John Wooden – A famous coach who emphasized dispassionate control and doing one’s job, and defined success as the peace of mind derived from making the effort to do one’s best.
• Martial – A Roman epigrammist who, despite his unique position providing insights into Roman culture, was bitter about serving patrons and desired personal glory, hindering his ability to see the value in his situation.
• Benjamin Franklin – Utilized the “canvas strategy” by publishing pseudonymous letters and allowing his brother to take credit, using the opportunity to learn and refine his skills without seeking immediate recognition.
• Bill Belichick – Rose in the NFL by excelling at unpopular “grunt work” like analyzing film and offering private, self-effacing feedback, demonstrating the “canvas strategy” and humble dedication.
• Jackie Robinson – Demonstrated extraordinary restraint and self-control in the face of intense racial abuse and provocation, prioritizing the larger goal of integrating baseball over his personal anger and ego.
• George McClellan – A Civil War general who failed due to his inflated self-perception, losing touch with reality and missing crucial opportunities for victory.
• George C. Marshall – A World War II general who consistently avoided seeking personal glory or advancement, famously turning down command of D-Day to serve in Washington, embodying selflessness and quiet accomplishment.
• John D. Rockefeller – As a young man, he practiced nightly self-admonition to guard against pride and prevent early success from corrupting his judgment.
• Bill Clinton – As a young man aspiring to politics, he meticulously built a network of contacts through consistent, unglamorous work, demonstrating the importance of continuous effort.
• Harold Geneen – A CEO who built ITT into a massive conglomerate and famously stated that egotism, not alcoholism, is the worst disease for business executives, as it blinds them to reality.
• Genghis Khan – A military conqueror renowned for his “persistent cycle of pragmatic learning, experimental adaptation, and constant revision,” demonstrating the importance of being a perpetual student who absorbs new ideas and technologies from others.
• Ulysses S. Grant – After his Civil War success, he pursued politics and financial ventures for which he was not suited, leading to a corrupt presidency, bankruptcy, and a tragic end, highlighting the danger of not knowing “what’s important to you” and wanting “what others have too”.
• Angela Merkel – The German Chancellor, known for her sobriety, modesty, and clearheadedness, consistently maintaining equilibrium and focusing on principles rather than personal image or power.
• Katharine Graham – Assumed leadership of The Washington Post Company at 46 with no prior experience and navigated immense challenges, including her husband’s suicide, the Pentagon Papers, and Watergate, demonstrating resilience and the ability to endure adversity without ego.
• Malcolm X – Transformed “dead time” in prison into “alive time” by intensely educating himself, reading the dictionary cover to cover, and exploring religion, turning confinement into fuel for his greatness.
• Belisarius – A Roman general who achieved brilliant military victories but was repeatedly betrayed, humiliated, and stripped of his wealth by his paranoid emperor. He never complained, embodying the idea that “the effort is enough” and internal satisfaction with doing what is right supersedes external rewards or recognition.
• Steve Jobs – Was fired from Apple due to his unmanageable ego but learned from his mistakes, started new successful companies (NeXT and Pixar), and returned to Apple, demonstrating personal growth through failure.
• Tom Brady – A quarterback drafted late who continuously honed his skills, holding himself to a higher standard than society’s objective measures of success, illustrating the importance of maintaining one’s “own scorecard”.
• Orson Welles – The director of Citizen Kane, whose film was suppressed and almost destroyed by William Randolph Hearst, but eventually found its place in cinematic history, showing that true greatness cannot be permanently stifled by ego or hate.
• William Randolph Hearst – A media magnate whose ego and perceived offense led him to a self-defeating campaign to destroy Citizen Kane, ironically solidifying its place in history and his legacy as a reviled figure.
• Richard Nixon – Even after his re-election post-Watergate, his continued fighting, persecution of reporters, and lashing out at critics due to ego ultimately caused more damage to himself than anyone else.
• Frederick Douglass – Refused to be degraded by racist treatment, asserting that the act of degradation falls on those inflicting it, not the one enduring it.
• Martin Luther King Jr. – Preached that hate is a “cancer” that “gnaws away at the very vital center of your life,” advocating for love as a transformative and liberating force.