Ego Is The Enemy

Ego Is The Enemy – by Ryan Holiday

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Ego Is The Enemy – by Ryan Holiday

‘The fight to master our greatest opponent’

All of us, at every stage of life, are the victims of our own ego. Our ego leads us to strive too far, expect too much, assume that we’re deserving – all before we’ve even done the work. If we achieve success our ego makes us do things that lead us to failure, if we fail our ego crushes our attempts to get up and try again.

“It’s always nice to be made to feel special or empowered or inspired. But that’s not the aim of this book”. Instead, Holiday has tried to arrange the passages of the book so that you may end in the same place he did when he was writing it: you think LESS of yourself. He hopes you will be less invested in the story you tell yourself about your own specialness, and as a result, you will be liberated to ACCOMPLISH the world-changing work you’ve set out to achieve.

The aim of the book is simple: to help you suppress ego early before bad habits take hold, to replace the temptations of ego with humility and discipline, when we experience success, and cultivate strength when you go through failure. Hopefully the book will help us be humble in our aspirations, gracious in our success, and resilient in our failure.

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We also covered Ryan Holiday’s first book in this trilogy. Check out The Obstacle Is The Way.


Ego Is The Enemy – by Ryan Holiday

‘The fight to master our greatest opponent’


Ego Is The Enemy. “It’s always nice to be made to feel special or empowered or inspired. But that’s not the aim of this book”. Instead, Holiday has tried to arrange the passages of the book so that you may end in the same place he did when he was writing it: you think LESS of yourself

He hopes you will be less invested in the story you tell yourself about your own specialness, and as a result, you will be liberated to ACCOMPLISH the world-changing work you’ve set out to achieve.

Maybe you’re brimming with ambition. Maybe you’re young and you’re struggling. Maybe you’ve made that first million, signed your first deal, been selected to some elite group, or maybe you’ve already accomplished enough to last a life time. Maybe you’re stunned to find out how empty it as at the top. Maybe you’re changed with leading others through a crisis. Maybe you just got fired. Maybe you just hit rock bottom.

Whatever you are, whatever you’re doing, your worst enemy already lives inside you: your ego.

“Not Me”, you will probably think… “No one could ever call me an ego maniac”. Perhaps you’ve always thought of yourself as a pretty balanced person. But 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/entrepreneurs, what drives us to the top of those fields, makes us vulnerable to this darker side of the psyche


The ego we see most commonly goes by a more casual definition: an unhealthy belief in our own importance. Arrogance. Self-centred ambition. It’s that petulant child inside every person, the one that chooses getting his/her way over anything or anyone else

The need to be BETTER than, MORE than, RECOGNISED for… far part any reasonable utility: that’s ego. It’s the sense of superiority and certainty that exceeds the bounds of confidence and talent.

Just one thing keeps ego around: COMFORT. Pursuing great work is often terrifying (whether its in sports or arts or business or anything). Ego soothes that terrifying fear. 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’s a short term fix with long term consequences.


The book is broken up into the three places ego shows up and does its damage

  • Aspiration
  • Success
  • Failure

The aim of the structure is simple: to help you suppress ego early before bad habits take hold, to replace the temptations of ego with humility and discipline, when we experience success, and cultivate strength when you go through failure

Hopefully the book will help us be:

  • Humble in our aspirations
  • Gracious in our success
  • Resilient in our failure

Ego Is The Enemy.


PART 1 – Aspire

Ego Is The Enemy. Here, we are setting out to do somehting. We have a goal, a calling, a new beginning. Every great journey begins here – yet far too many of us never reach our intended destination. Ego more often than not is the culprit.

To whatever you aspire, Ego is your enemy.

“Among men who rise to fame/leadership/prominence, two types are recognisable: those who are born with a belief in themselves and those in whom it is a slow growth dependent on actual achievement.”

“To the men of the last type their own success is a constant surprise, and its fruits the more delicious, yet to be tested cautiously with a haunting sense of doubt whether it is not all a dream.”

And of the first type?

One must ask: if your belief in yourself is NOT dependent on your actual achievement, then what is it dependent on?

The answer, too often when we are just setting out, is NOTHING.

Ego. Ego Is The Enemy.

And this is why we so often see precipitous rises followed by calamitous falls.

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’.

What is rare is not raw talent, skill, or even confidence, but humility, diligence, and self awareness.

Talk, Talk, Talk

Lao Tzu: “Those who know do not speak. Those who speak do not know”


In 1934 campaign for the Governorship of California, author and activist Upton Sinclair took an unconventional route on his campaign. He published a book called “I, Governor of California and How I Ended Poverty”… writing in past tense about the brilliant policies he had enacted as governor… the office of which he had not yet won… It was an untraditional move, but he knew that as an accomplished writer he could dominate all of his other opponents and blow them out of the water when it came to the written word. It was well received but it immediately had an impact on Upton himself: in the vivid story telling and in his imagination, he had already achieved everything he wanted to achieve – so he already had the glory he craved and lost intensity to win the campaign battle itself.

The book was a best seller, the campaign was a failure. It’s a temptation that exists for everyone – for talk and hype to replace action.

Today we’re prompted more and more to talk and share: the status box on Facebook or LinkedIn, the empty tweet space sitting there on Twitter, the comments at the bottom of the article we just read (instead of taking real action on what we just learned). Everywhere, there are blank spaces begging to be filled with thoughts and stories. More often than not, we’re talking about what we’re GOING to do, with what things SHOULD or COULD be, or what we HOPE will happen next.

It’s easier to talk about things than to actually do them. Talking depletes us. TALKING and DOING fight for the same resources. Research shows that while goal visualisation is important, but after a certain point our mind begins to confuse it will actual progress. The same goes for verbalisation – talking aloud to ourselves or others while we work through difficult problems has been shown to significantly decrease insight and breakthroughs. After spending so much time thinking / explaining / talking about a task, we start to feel that we’ve gotten closer to achieving it. Or worse, when things get tough, we feel we can toss the whole project aside because we’ve given it our best try, although of course we haven’t.


The achievers are the ones working quietly in the corner. They ignore the impulse to seek recognition before they act. They don’t talk much. They’re too busy working to do anything else – and when they do talk, they’ve earned it. Let others slap each other on the back while you’re at the lab or in the gym or pounding the keyboard


Become a Student

EPICTETUS: “It’s impossible to learn that which one thinks one already knows”

You can’t learn if you think you already know it. 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. 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

The art of taking feedback is such a critical skill in life, particularly harsh and critical feedback. We not only need to take this harsh feedback, but actively solicit it, labour to seek out the negative precisely when our friends and family and BRAIN are telling us that we’re doing great. The ego avoids such feedback at all costs… but its vital for the next phase of growth and evolution.



The danger of early pride

‘A proud man is always looking down on things and people; and of course, as long as you are looking down, you cannot see something that is above you’ – CS Lewis

Pride blunts the very instrument we need to own in order to succeed: our mind. Our ability to learn, to adapt, to be flexible, to build relationships – all of this is dulled by pride. Most dangerously, this tends to happen either early in life or in the process – when we’re flushed with beginner’s conceit.

Pride takes a minor accomplishment and make it feel like a major one. It smiles on our cleverness and genius, as though what we’ve exhibited was merely a hint of what ought to come

Pride and Ego say:

  • I am an entrepreneur because I quit my job and struck out on my own
  • I am going to win because I’m currently in the lead
  • I am a writer because i published an article on medium
  • I am rich because I made some money
  • I am an investor because I bought a stock
  • I am special because i was chosen
  • I am important because I think I should be

We all engage in this gratifying label making, yet every culture has warning against it

  • don’t count your chickens before they hatch
  • don’t cook the sauce before catching the fish
  • the way to cook a rabbit is to first catch a rabbit
  • game slaughtered by words cannot be skinned
  • pride goeth before the fall

Let’s call it what it is: FRAUD. If you’re doing the work and putting in the time, you won’t need to cheat and you won’t need to overcompensate with words.





There is an old saying; “say little, do much”

Ultimately this isn’t about deferring pride because you haven’t got there yet

It isn’t “don’t boast because it hasn’t happened yet”. It’s just “don’t boast”. There’s never anything in it for you.

Work, Work, Work

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

Paul Valery explain i 1938 – “a poet’s function is not to experience a poetic state, that is merely a private affair. His function is to create it in others”

HENRY FORD: “You can’t build your reputation on what you’re GOING to do”

BEN HOROWITZ: “The hard thing isn’t setting the big, hairy, audacious goal… The hard thing isn’t dreaming big. The hard thing is waking up in the middle of he night in a cold sweat when the dream turns into a nightmare”

Sure, we all know that everything requires work… but do we REALLY understand that? do we have any idea just how much work it’s going to take?

It’s not ‘work until your big break’ or ”work until you get a name for yourself’ – it’s work, work work forever and ever

It’s all within reach and it only take work, but it’s going to take a lot of work. Rather than letting that daunt you, it should be encouraging to know that it’s possible.

Bill Bradley, basketballer – “When you are not practicing, remember, someone somewhere is practicing, and when you meet him on the court he will win”

The Bible: “Blessed are those servants whom the master finds awake when he comes”

Every time you sit down to work, remind yourself:

  • I am delaying gratification
  • I am passing the marshmallow test
  • I am earning what my ambition burns for.
  • I am making an investment in myself instead of in my ego

Give yourself a little credit for making this choice, but not too much, because you’ve got to get back to the task at hand: surprising the ego, practicing, improving, WORKING.

Ego Is The Enemy.



Ego Is The Enemy. Here we are at the top of the mountain we worked hard to climb – or at least the summit is in sight. Now we face new temptations and problems.

We breathe thinner air in an unforgiving environment. Why is success so ephemeral? Ego shortens it.

Whether a collapse is dramatic or a slow erosion, it’s always possible and often unnecessary. We stop lerning, we stop listening, and we lose our grasp on what matters.

We become victims of ourselves and the competition. Sobriety, open-mindedness, organisation, and purpose – these are the great stabilisers. They balance out the ego and pride that comes with achievement and recognition.

To whatever success you have achieved, Ego is the enemy…

Always stay a student

In part 1 = Become a Student. Now in part 2 = always stay a student

As we first succeed, we will find ourselves in new situations, facing new problems

  • The freshly promote solider must learn the art of politics
  • The salesman, how to manage
  • The founder, how to delegate
  • The writer, how to edit others
  • The comedian, how to act
  • The chef, how to run the restaurant front-of-house

“As our island of knowledge grows, so does the shore line of our ignorance”. In other words, each victory advances you towards a new situation to which you haven’t yet encountered before. It takes a special kind of humility to grasp that you know less, even as you know and grasp more and more. No matter what you’ve done up to this point, you better still be a student. If you’re not still learning, you’re already dying.

It’s not enough to be a student in the beginning – it is a position that one has to assume for life


Don’t tell yourself a story

Ego needs honours 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.

In 1979, Bill Walsh took over as coach of the 49ers. He took them from the worst team in in the league to a Superbowl in less than three years. It would’ve been tempting to tell himself as he lifted the trophy above his head that this, the quickest turnaround in NFL history, was his plan all along. It would be tempting, years or decades later when crafting his memoirs, to form that narrative as well. It’s a sexy story – his takeover, his turnaround, and his transformation and success – that it all happened the way he wanted it to because he was just that good and talented. But he utterly refused. Whenever he was asked what his schedule/timeline for winner a superbowl was, he never had an answer because planning for a Superbowl when you’re the worst team in the league would be delusional. The year before he arrived they had 2 wins 14 losses. the first year under his tutelage they also had 14 losses. Half way through his second year it wasn;t looking much better and he almost quit, but just over a year later, they won the Superbowl and he was label an all-time genius. The only timetable he ever set was not how long until they won a championship, but instead merely what they needed to do and how they needed to do it, instilling ultra-high standards of sportmanship and professionalism.

Crafting stories out of past events is a very human impulse. We like to think that things happen for a reason and that it’s all part of a grander plan. But this is very dangerous and almost always untrue. It can then lead to arrogance – it turns our life into a story even while we’re still trying to live it. We desperately want to believe that anyone who has built a great empire SET OUT to build it. We want to believe this is how it works, because we want to start going about planning our own empire. Indulging in the big dreaming and planning your vision is pleasurable.

Then, when it happens, we want to be able to take full credit for everything good that happened, then we can fully own the riches and respect that will come our way. Instead, it is rather the case that the ‘narrative’ is formed when looking back, not when looking forward. The path isn’t set out perfectly from the start. Instead, it is only when looking back that we can see the highlights and cobble together the main points into some kind of made-up but coherent flow

Narrative is when you look back at an improbable or unlikely path to your success and say: I knew it all along”. Instead of – I hoped OR I works OR I got some good breaks OR EVEN I thought this COULD happen but I wasn’t totally sure. You never really knew it all along, and if you think you did, that was merely just good faith, hope and a serious dose of Ego. But we don’t like to remember all of the times we doubted ourselves.

Whatever we do, instead of pretending we’re living some great story, we must remain focused on the execution. We must execute 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.


What’s important to you?

We spoke about Ulysses S Grant and William Sherman at the start in Part 1. They were the dual leaders and orchestrators of the Union’s victory in the Civil War.

Afterwards, Sherman turned down all of the approaches people made to him and instead retired happily in New York and lived out his days in happiness and contentment, having mastered his ego.

On the other hand, Grant was always looking for more. He hadn;t any prior interest in politics, but decided to run for President and won in a landslide. After his Presidency came to an end, he invested almost every penny he had into a financial brokerage house with the controversial Ferdinand Ward, who was the Bernie Madoff of his day, and the Ponzi Scheme publicly bankrupted Grant.

Not content with the ultimate level of success he had achieved, he was always striving for more – looking to be president, looking to become a mega millionaire… Sherman told Grant: he had aimed to rival the millionaires, but they would’ve given everything they had to win just one of Grant’s many battles”


For what often comes next, ego is the enemy…

Here you are at the pinnacle. What have you found?

Just how tough and tricky it is to manage. You thought it would get easier when you arrived; instead, it is even harder. You found that you must manage yourself in order to maintain success.

Endless ambition is easy; anyone can put their foot down harder on the gas. But we must avoid what Jim Collins calls the “undisciplined pursuit of more”, as well as the complacency that comes with praise and plaudits.

Endless ambition is easy. 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.

NAPOLEON: “Men of great ambition have sought happiness… and have found fame”

What he’s saying is that, although their initial intention was to get better for the sake of their own happiness, soon Ego too over and shifted their goals

Behind every goal is the drive to be happy and fulfilled, but when egotism takes hold we lose track of our goal and end up somewhere we never intended.




Here we are experiencing the trials endemic to any journey.

Perhaps we’ve failed, perhaps our goal turned out to be harder to achieve than anticipated. No one is permanently successful, and not everyone finds success on the first attempt.

We all deal with setbacks along the way. Ego not only leaves us unprepared for these circumstances, it often contributed to their occurence in the first place.

The way through, the way to rise again, requires a reorientation and increased self-awareness. We don’t need pity – our own or anyone else’s – we need purpose, poise and patience.

To whatever failure and challenges you wil face, Ego is the Enemy.


  • JK Rowling finds herself seven years after college with a failed marriage, no job, single parent, kids she can barely feed, and approaching homelessness.
  • A young Lyndon Johnson is beaten up by a farm boy over a girl, shattering his picture of himself and the big dog in town

There are many ways to hit rock bottom – almost everyone does it in their own way at some point.


Alive Time or Dead Time?

Maclolm X was a criminal He wasn’t Malcolm X at the time.

He was called Detroit Red at the time, and he did a little bit of everything – ran numbers, sold drugs, armed robbery, worked as a pimp, ran a burglary gang

Finally he was arrested for trying to sell an expensive watch that he’d stolen, while carrying a gun

At age 21, he was sentenced to 10 year prison

He faced what Robert Greene calls “Alive Time or Dead Time”

GREENE – there are two types of time in our lives: dead time (when people are passive and waiting) and alive time (when people are learnign and acting and ultilising every second)

Every moment of failure, every moment or situation that we did not deliberately choose or control, presents this choice: alive time / dead time

Malcolm X chose Alive Time. He began to learn. He taught himself to read by getting a pencil and a dictionary and copying out the words and definitions by hand, from cover to cover. “From when I went in until I left prison, if i wasn’t reading in the library I was reading in my bunk”. He read history, sociology, religion, classics, philosophy. When people ask what school he went to, he says “books”

  • Francis Scott Key wrote a poem that later became the US national anthem while hewas trapped on a ship during a prisoner exchange in the War of 1812
  • Viktor Frankl defined his theories of psychology while he was suffering during ordeals in three different concentration camps
  • Ian Flemming was on bed rest and forbidden to write another Bond novel as doctor’s said it would be too much for his body to handle and was ‘t allowed to use a typewriter – so instead he wrote chitty chitty bang bang by hand
  • Walt Disney was hospitalised after stepping on a rusty nail, and it was here that he decided to pursue cartooning

It may feel good to become angry, sad, down, depressed, deprived or heartbroken during times of failure. But a far more productive approach is to not be so shortsighted and instead look to the future.

We all have this choice.

At all time, we are faced with the same decision: Alive Time or Dead Time.

Even more pressing is in times of failure – do we wallow in our own sorrow, depressed about what we’ve just lost? Or do we scrap this dead time and instead choose the alive time of learning from our mistakes and planning our next steps forward?


The effort is enough

MARCUS AURELLIUS: “Ambition means tying your well-being to what other people say or do… Sanity means tying it to your own actions”

If you can seperate the effort from the result, then only focus on the effort portion, you’re doing it right. Putting in the effort, doing the work, creating and delivery – this is what’s importnat. You can;t entirely control how it will be received, so you can’t waste time worrying about other people and instead focus solely on what YOU can do about it

Ego Is The Enemy.


Maintain your own score card

On April 16, 2000, the New England Patriots drafted an extra Quarter Back fromt he University of Michigan.

They’d scouted him thoroughly and had an eye on him for some time, but weren;t overly keen on him. Seeing that he was still available, they took him in the 6th round with the 199th overall pick

His name was Tom Brady.

Now, having played in 9 Sueprbowls and won 6 of them (the most in history), you could look at it and say that was a pretty goood pick… But the Patriots, using their own internal scorecard rather than an external measure of success, were deeply deeply disappointed in themselves. They let him slip through to the 6th round?? they picked 5 other guys ahead of him?? they allowed 198 other opportunities for another team to draft him. Even more so than the initial pick, he was overlooked for a game in his first year and it wasn’t until their starting QB injured himself that they were forced to give him an opportunity.

So, even though the pick paid off, the Patriots honed in on the intelligence failures that could have prevented the pick from happening in the first place. It wasn’t nit-picking, it was about setting a higher internal standard and constantly looking for ways to adhere to it

For us, the scoreboard can’t be the only scoreboard. Ego Is The Enemy.

Warren Buffet makes the distinction between his external scorecard (ROI and stock price of Berkshire Hathaway ) versus his own internal scorecard (his own measures for evaluating his investment decisions)

Your POTENTIAL – the absolute best you’re capabe of – that’s what you should be measuring yourself againt, not the performance of those around you

People can get lucky and win. People can be assholes and win. Anyone can win. But not everyone is the best version of themselves.

Ego Is The Enemy.

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