Ego Is The Enemy by Ryan Holiday – a vaccine against failure in leadership – leadership book review

I. Overview

‘Ego Is The Enemy’ is a valuable book for leaders. There is a lot to learn for someone who is at the beginning of his leadership journey, and this book can help with setting up a good mindset and shaping a healthy way of thinking about this position before being influenced by other unfair events or people with their own agenda. But also, during every leader’s career, there will be times when things are not going so well and times when everything seems to be working perfectly. Both of this cases are turning points during which great leaders think and act in the best way possible in order to keep the motivation and raise the happiness of their teams and companies.

There is just one small possible negative aspect that came into my mind while reviewing this book: the impact on the readers which are just beginning their personal development study. Because the advice in this book can be misunderstood by inexperienced people, I personally recommend everyone empowering books to read books (eg. from Napoleon Hill or Tony Robbins) before reading this one. Being aware of your ego does not mean you should stop seeking to continually progress in life. Going after what makes you fulfilled and brings the most joy for you, those around you and the causes you really believe in is the most important thing in life.

In any moment in life we are in one of three states: we are either aspiring to achieve something, enjoying our success or trying to get over a failure. The key is to replace the temptation of the ego with modesty and discipline when you are successful, and increase you resilience and moral power when things are not going your way. The advice of the book can be summarized to:

  • be modest with our aspirations;
  • be tempered with our success;
  • be resilient when faced with failure;

Many people mix up the qualities that lead to success with the byproducts of success. If some successful person has a big ego, that is most surely not why they achieved something and most likely that person is a victim of success.

The book is structured in very small chapters, each one presenting an idea related to the main theme, which makes it easy to read. We will summarize the most important ideas from “Ego is The Enemy” with an emphasize on leadership advice.

A valuable book for those in leadership positions! It made me a better judge

Frederig Block – USA Judge and author of ‘Disrobed’

In the beginning of the book, the author presents his life experiences that led him to write this ‘Ego is the Enemy’ : he was a very promising student, worked for a big company and got a leadership position, created his own company, got invited to speak at events and earned a lot of money in the process. At 25 he published his first book which rapidly became a bestseller, gained fame and notoriety and a studio bought the rights to make a TV show after his life. But there were also other things that happened: the company he created went bankrupt twice, he was betrayed by people he admired, other companies he worked with were loosing money, and he became a workaholic person obsessed with winning. After all this experiences he got back up, but now he was even more aligned with the stoic philosophy which he presents in his books in a fresh and modern way. He even has tattoos on both arms with the titles of his most well-known books to date: ‘Obstacle is the way ‘ and ‘Ego is the enemy ‘.

II. The importance of modesty in leadership

General William Sherman was one of the most important military leaders of the American Civil War. Having a very calculated and cautious mindset, he lead the union forces to victory putting fame and recognition aside in favor of the most important objectives that needed to be accomplished in order to secure the success of the military campaign. There is a fragment from one of his biographies that summarizes his qualities and what patient and mindful leaders can learn from his actions:

“There are two groups of people who achieve success and fame. The people from the first group have an innate confidence in their abilities from the day they were born. The people from the second group gain more and more confidence as they see the amazing things they can accomplish with faith and discipline. It is the people from the second group that will be more pleasantly surprised and will gain more benefits from their achievements, but they have to be careful not to develop a big ego and continue to put in the work to get the best results. With time, they have to put aside the insincere sub-evaluation in favor of the modesty of moderation, as it is explained by the stoic Greek philosophers.

Even though we may have high ambitions, we must remain modest in order to achieve what we aspire, step by step. We must be focused more on education and action and less on gaining validation and status, because having the first two will automatically bring other rewards.

There will be times when some people will want to promote themselves in an aggressive manner in order to undermine you status as a leader. But with their aggressiveness, intensity, and endless self promotion, our adversaries do not realize that they are doing more harm than good to their progress and mental health. You are unstoppable as a leader as long as you are determined to continually improve your skills and you always have in mind the best for the people you work with. In the long run, doing what you know it is right will make you feel a lot more fulfilled than blindly chasing the approval of others.

If someone would have asked Sherman how he felt at the middle of his career, maybe he wasn’t going to brag. He hasn’t won big battles yet and he wasn’t very rich or popular either. Moments like this can make some people doubt the way they choose to go about leadership. But even if in the short run madness can pass as boldness, delusions as confidence and ignorance as courage, no one has said, reflecting to his life: “That monstrous ego that I had was really worth it”. What is truly ambitious for a leader to do in those moments is to confront life with a quiet confidence, despite the distractions. It’s a solitary work to say : “I am not giving up. I will not renounce my ideals, I will become the best version of myself. I am in this thing for the long haul, no matter how brutal the game may become. It is important to do, not to be.”

For Sherman, his choice was what prepared him for the moment in which the country and history needed him most. In this quiet and peaceful environment he forged a personality that was ambitious but patient, innovative without being impertinent and courageous without being dangerous. He was a true leader.

Is there something that would work better in your team if you put aside your ego? Can you help the people around you to come up with better ideas? Ask yourself this question: What would I see if I am a bit more modest?

III. The advantages of a silent leader

In our day and age it is often said that everyone needs to aspire to be a good salesman because you need this skill in every walk of life. The majority of people seem to know how to promote and sell themselves, but there is also a trait that is really hard to find these days: silence – the ability to willingly keep yourself out of discussions and be able to live without the validation of others. Many believe that being silent shows weakness, but in reality silence is power, especially at the beginning of a journey. It is the respite of the brave and strong.

Never explain yourself for what you think and do until you are obliged to. That is because, with time, you may come up with a better explanation.

General William Sherman

Great leaders do not burden their mind with petty things. They do not seek recognition before they act. They are not bothered about the fact that others seem to spend more time in public and gain more spotlight, they know that is not a guarantee of success. They are busy creating strategies, thinking about ways to solve problems or improve work that is being done. They are more action oriented and when they speak they do it with conviction because that is an ‘earned right’.

“Those who have accomplished the greatest results are those who never grow excited or lose self-control, but are always calm, self-possessed, patient, and polite.”

Booker T Washington (american educator, author, orator, and adviser to multiple presidents of the United States )

Great leaders do not panic in stressful situations – they see the threats and calmly think about ways to approach the situation. They transform their inner agitation into concentrated fuel that can lift up the morale of the team. All great achievers are busy working and investing their time and energy wisely while others lose time speaking just to calm down their spirits.

Showing pride to other people is often times of little use. The quiet ones, which are always looking for more information, more inclined to listen and understand than to expose their success are the ones who benefit most from social interactions.

IV. Remain a long time learner

Some people tend to put learning aside after they have achieved some kind of success. But the true masters are long time learners. Leaders should be continually improving their skills in order to assure the growth of their colleagues and company.

Reflect on improving yourself as a leader: what books can you read to enhance your people skills? What courses can you take in order to understand more about the issues your team encounters? Do you know a more experienced leader that can give you an advice?

The power a student receives during training is not just about the long period of perfecting, but also about the fact that the ego and ambition are being put into someone else’s hands. You know that the master is better than you and you admire him. There is no way you can cheat or lie to him, you have to practice every day or the master will stop teaching.

Even though Kirk Hammett was already a very good guitarist an member of the Metalica band, he knew he can improve his skills and searched the advice of the master Satriani, who introduced him to a rigorous training regiment. As a result, Kirk became one of the best heavy metal guitarists in the world, transforming trash metal from an underground movement to a global musical genre. Not only that, but Satriani also perfected his own technique thus making both the student and the teacher able to fill out stadiums and redefine the musical landscape.

Frank Shamrock, a pioneer of the MMA and multiple martial arts champion, has a system to train his fighters that he calls: plus – minus – equal; He believes that in order to become truly great, a fighter needs someone better than him so that he can learn something, someone equal who can provoke him, raise his ambition and fight with, and someone with a lesser skill so that he can learn to be tutor. The scope is simple: in this way you can have a better perspective, you can find out what you know and do not know from different angles, and you can eliminate the ego that can make you arrogant, self-doubting or being lazy;

When faced with failure, one of the best things a leader can do is to reflect on the past decisions and continue to invest time in learning more about the topics that can help him move forward. While being in jail for 7 years, Malcolm X used that time to read the entire library of the prison and come back a completely different man who could lead a powerful movement.

V. Protect your leadership from the ego traps

1. The pride trap

If you cannot eat your pride, you cannot lead

Genghis Khan 

As a feeling, by definition, being proud is not something inherently bad. It is a good feeling you get after you have achieved something great in the past. However, dwelling in this feeling has a lot of negative aspects since it can make people forget about developing and creating great things in the future. Our mind, our ability to learn, to adapt, to be flexible, to create relationships can be weekend by pride. What happened in the past should not dramatically change our perception about what is real. It is good to feel proud of a good job well done. Celebrate and be grateful for the experience and opportunities you had, but never forget that humility helped you get where you are and it will also help you in the future.

“What a pathetic thing it is when a man lets a short momentary success to ruin his judgement so that he forgets who he is”.

John D. Rockefeller – one of the richest people in history

In a moment of frustration, Rockefeller shouted at a clerk who did not want to give him a loan: “One day I will be the richest man in the world” Let’s consider Rockefeller the only one who said that and also managed to do it. But for each man like that there are dozens who said the same thing and did not achieve nearly as much, partly because pride worked against them and made other people hate them. This is the reason why each night Rockefeller asked himself questions like: “Are you going to get mad?”, “Will you let these money make you arrogant?”, “Keep your eyes open, do not loose your temper”.

As long as you are proud you cannot know God. A proud man is always looking down on thing and people. And, of course, as long as you are looking down, you cannot see something that is above you.

C.S. Lewis (one of the intellectual giants of the twentieth century and arguably one of the most influential writers of his day)

We need to protect ourselves from the ones who discourage us, but just as important is to be aware of the over-encouragements that come too early.

Even though he was very gifted person, a great mechanic and pilot and a brilliant visionary, Howard Huges did not end really well. His love for the spotlight affected his work that he began in different departments like aviation, military, Hollywood, industrial tools and others. Many believe that he wasted a lot of energy and talent on unimportant things that did not brought him happiness in the long term.

Don Draper was the leader of the creative department in many companies he worked for, but his brilliance was many times defeated by his big ego who made him always push his own ideas and practices even though they failed to produce desired results. That coupled with his lack of discipline and bad addictions caused him to loose almost everything he had.

If we extend this concept, we can ask this question looking at the big picture: why do empires always fall down and why this always seem to happen from the inside?

2. The “Vision” trap

Bill Walsh (The Coach) won against all odds. He took charge of a football team which was among the worst (with a record of only 2 games won out of 14 in the last season) and managed to won the super cup. That was not because he knew this was going to happen anyway, but because he made a lot of small adjustments ( what needed to be done and when: every training session and workout has to be respected, each player had specific tasks and goals for every training, players are not allowed to sit on the ground, the trainers must be serious and have their shirts tucked into pants).

When asked about it, Bill always responded that this wasn’t due only to his vision, but mostly on the focus he placed on the process. Sometimes people tend to over-indulge in the power of vision because this will permit them to continue planning without putting in the required work. When work is due, it must be done, otherwise all that you are doing is procrastinating; After that season, the team lost her place because the players bought the idea of the vision supplied by the mass-media. They thought they were special so they lost the focus and hunger for victory they one had.

Instruction and virtue are needed in order to support the results of luck


Katharine Graham became the leader of the Washington Post Company at 46 years old, after her husband died. With no initial experience, she overcame tremendous obstacles, took bold action and made the company more powerful than ever. Like Walsh, Graham did this by having a personal system of measuring progress while the outside world was too distracted by the supposedly signs of weakness.

After you succeed, do not invent stories. It is important to have a vision, but many times it is better to keep it to yourself, especially in the beginning. Amazon, Youtube, Google were not founded based on a vision to replace shops and television or completely revolutionize the world: they were either diploma projects or platforms to share funny videos.

3. The comparison trap

It is great if you are competitive and trying to always achieve the best results that you can. Competition stands behind the greatest improvements the world ever had. However, on the individual level, it is very important to know who you are competing against and why. Because we have different skills, comparing with other leaders is not always a healthy choice for you.

The gravest disease that can affect the work of the CEOs is not alcoholism but egotism. This is the same for middle and top management alike: personal egotism blinds the leader who begins to live in an imaginary world. Because he sincerely believes he can do no harm, he becomes a threat for the ones working for him.

Harold Geneen (the CEO who invested the concept of multinational company)

According to Seneca, the Greek word euthymia is one we should think about often: it is the feeling of our own way and how we follow it without being distracted by the ones we cross our paths with. In other words, is not about defeating the others, or having more then them. It is about being what you are and becoming the best version of yourself, going for what you really want and achieve as much as you can in the direction you choose, without giving up when confronted with all the obstacles you will face.

4. The creativity trap

As a leader it is a good thing to develop a creativity-friendly environment, but never in the detriment of good management and discipline.

John DeLorean was convinced that, at General Motors, the culture of order and discipline keeps the brilliant creators in place. So he founded his own company where he deliberately did everything different and despised the conventional wisdom and business practices. The result was not the free and creative sanctuary DeLorean naively dreamed to create, but an authoritarian political organization, dysfunctional and corrupt, who collapsed under its own weight, lost about 250 million dollars and was accused of illegal actions.

DeLorean could not manage himself and thus he could not manage others either. We usually think that we want to do things differently when we finally get control of a company, but it is wise to look at the things that worked before. Of course, there is no “right” system, sometimes having a strict hierarchy is better than working with a decentralized system and sometimes is the opposite, but a great leader always imposes good management, discipline and order before thinking of other improvements.

5. The technician trap

As you become more successful in your field of work, your responsibilities may begin to change. The days will become less and less about doing and more and more about taking decisions. This is the nature of leadership.

This transition requires a reevaluation and an update of your identity. A certain modesty is required in order to put aside the most enjoyable and fulfilling parts of your old post. It means you must accept that others could be more qualified or specialized in the domains where you considered yourself competent in the past and and they are investing their time in those things more efficiently than you.

Yes, it would be nice to continue to be involved in every minor thing and it could make you feel important if you are the person solicited to save the situation. Little things are always captivating and flattering while the overview image may seem unclear. But if you’re not thinking about the overview, then who is?

A great example of a leader who stood by those principles is General Marshall. He could have gotten a lot of praises if he was the one to command the D-Day assault, and president Roosevelt wanted him to. But he knew that general Eisenhower could do a better job with this and he was needed in Washington, so he let let him have the command. Also, there was another general who mistreated Marshal in the past, somewhere during the middle of his career, sending him on remote missions. Years later when he was the commander-in-chief of the army, Marshall choose not to revenge himself for that behavior because the general in question was doing a good job for his country.

VI. Leadership Trending

Each period of time requires its type of leaders. For example, Churchill seems to be exactly the leader that Great Britain and the free world needed during World War II. What we need today – in our rapidly changing times when there is a lot of information needed to be selected and so much competition – is a peaceful, quiet leader that has the ability to analyse things and make great decisions. A well-balanced leader with a clear mind that is modest and doesn’t aim to be the center of attention can make a great impact in our interconnected world.

There is a saying: “In order to live a happy life, you have to live a hidden life‘, which may be true but it can keep us away from good examples in leadership like the one provided by Angela Merkel – a firm, clear and patient leader who can make compromises without affecting the core principals a politician should abide to.

While climbing the ranks, Marcus Aurelius served the roman people in different capacities from his teenage years until his death. He always struggled against “imperialization” – the stain of absolute power that destroyed his predecessors. To do this he wrote that “he has to fight to become the person philosophy is trying to create”.

The Gold Average

According to Aristotle, virtue and excellence are points of the same spectre. Courage can be found midway between cowardice at one end and recklessness at the other. We all admire generosity but we must stop it before it becomes waste or parsimony in order to be of any use. We have to avoid “wanting recklessly much or being content because of the praise we get”.

There are two world leaders that could have achieved a lot more things if only they would have applied the principles mentioned above. Alexander the Great died at 32, far from home, probably killed by his own men who finally said “Enough!”. Napoleon said: “People with great ambition searched for happiness…and they found fame”. Maybe what he was tying to say is that behind every objective we see the opportunity to be happy and fulfilled, but when egoism takes control, we loose the focus we had on the objective and we arrive somewhere we never intended. That is why, just a few years after Napoleon lost his power, the map of Europe looked almost the same as it was before his ascension to power 20 years in the past. All those deaths, effort, greed and glory – for what?

VII. Do not let failure keep you down as a leader

When you lead you people, they do not only look up to you, they also tend to absorb a part of your energy and mood. It is your job to make sure the dynamics in the team are healthy and the attitude is right in order to complete the tasks at hand. During a leader’s journey there will be multiple setbacks – there is no question about that. The question is: how do you respond to them in such a way that will not let you or your people down.

In life there will be moments when we would do everything right, maybe even perfect, but the results will somehow still be negative: failure, lack of respect, envy or indifference. It could be someone getting promoted to the leadership position that you deserved, or you getting that salary raise later than expected, or other external factors that can affect your business or carrier. Depending on the thing that motivates us, the answer we give back can be crushing: if ego is the master, we would not accept anything else than the full appreciation of others and we would not see why we put in all that effort and energy knowing that the result is not guaranteed.

This is a dangerous attitude because, when someone works at a project – be that a book, a business, a new concept – at some point that thing goes out of his hands and into the world. It is judged and influenced by other people and it stops being controlled by only one person. Often times we have little control over the rewards for our work and effort – but this does not mean we should give up or work. We can think of all the activists that couldn’t promote their cause further, or all the leaders who were assassinated before they could finish their work and all those inventors whose ideas stagnate because they are head of their time. According to the principal values of society, they were not rewarded for their work. But shouldn’t they have done it anyway?

We should not base our vision of success on the ambition to be recognized by others as a success

So what’s to do if you are not appreciated enough for your work. What do you do as a leader if you are ahead of your time? How do you manage the difficult moments that will come, if your bosses or clients do not understand you? The answer is: Redefine success as a leader. Success is the peace of mind given by the self-satisfaction resulted from knowing that you put in the effort to do everything you you could to become the best version of yourself. Rewards and acknowledgments are a bonus, and we should not base our vision of success on the ambition to be recognized by others as a success, because that is not always in our sphere of influence. And always remember: if your reputation can’t handle a few hits, then it wasn’t strong to begin with. A lot of leaders seemed to have lost their place and influence only to come back even stronger, exactly like Steve Jobs did.

One particular leader who continued to do his work even though he was not correctly rewarded was the byzantine general Belisarius. He was responsible for reconquering most of the former roman land taken by the barbarians, but many of his successes were not acknowledged as they should because of the fear emperor Justinian had that Belisarius wants to overthrow him. The general continued to do his job for the remainder of his life because in the end he was fighting for his people, beliefs, honor and faith.

VIII. Conclusion

‘Ego Is The Enemy’ is truly an important book for every leader because it teaches the values of humility and modesty bringing to life a type of healthy mentality that seems to be forgotten in the past. I did not rate this book higher because of some issues I had with its structure and because at some points the message can be misinterpreted into a discouraging lecture. If I had to summarize the lessons of the book in just three sentences, they will be:

  1. “Do not aspire or crave just because of your ego”;
  2. “Have success without the ego”;
  3. “Overcome failures with strength, not with your ego”.

Related resources can be found on the website created by the author:

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