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Still riding the wave of his last book, The Obstacle is the Way, Ryan Holiday takes on an even bigger obstacle — the human ego. Ego is the enemy is full of timeless truths that are sometimes deceptively obvious but exceedingly difficult to practice.

Authors and creators often say that they write or create to scratch their own itch. Meaning, they create the things they want to exist in the world. With Ryan Holiday’s outlier success as an author and media strategist over the last decade, he is perfectly suited to write and need this book.

He dropped out of college at 19 and ended up working for acclaimed author Robert Green who has written several best sellers including The 48 Laws of Power. Ryan wrote four books in the past four years while also serving as the director of marketing for American Apparel. His last book, The Obstacle is the Way, spent time on many best seller list and recently went viral in the professional sports community.

So why did he decide to write about ego?

In interviews he said The Obstacle is the Way is about external obstacles while Ego is the Enemy is meant to address the biggest internal obstacle.

Ego is a tricky topic for a non-psychological book and Ryan is definitely not trying to take on Freud. By Ego, he means the “Unhealthy belief in your own importance”. He is talking about the common use of the word ego as in “he is an egomaniac” or “she is a huge ego”.

Ego has many faces and is clarified best through examples rather than definitions. Throughout the book Ryan provides many examples of ego in himself and others. At times it felt like a stretch to say that so many things are ego. But continuing with the characteristic pragmatism of stoic philosophy, it makes sense to express these ideas through examples and stories.

One of the trickiest things about ego is that it’s hidden in plain sight. He says “Most of us aren’t “egomaniacs,” but ego is there at the root of almost every conceivable problem and obstacle”“From why we don’t have what we want to why having what we want doesn’t seem to make us feel any better.”

Hardest Lessons

Like many lessons from religion, history, and philosophy the ideas tend to be easy to digest, borderline obvious, and obviously appealing but very difficult to follow because they are often contrary to human nature. There are many hard lessons in the book but these three lessons are particularly difficult for me.

To Be or To Do

To be or to do—life is a constant roll call.

Maybe we’ve been asking each generation the wrong question this whole time. Instead of asking, “What do you want to be when you grow up?” maybe we should have been asking “What are you willing to do when you grow up”? Because as Ryan says ,“Doing great work is a struggle. It’s draining, it’s demoralizing, it’s frightening”.

This is a hard lesson for me because I love ideas. I love thinking about big ideas and dreaming about things that I’d like to do. But dreaming is the easy part. Doing is the hard part, and consistently doing is even harder.

Most people want to be rich or be famous or be successful but if they asked themselves: Do I want to get up at 5 am everyday? Do I want to take on huge responsibilities? Do I want to give up my time? The answer is at best “I guess if that’s what it takes”. In order to do, you have to want to do as much as you want to be. And the best way I’ve found for doing this is to figure out what’s important to you and focus on that.

Figure out what’s important to you

First things first, if you haven’t decided what’s important to you then you need to stop everything and make the decision. If you don’t know what’s important to you, how can you make any other decision?

I get it. It’s a really hard question. It is the hard question.

Sometimes thoughts like “I want to be happy” come to mind. And I think “Am I just being a hedonist” or “Will searching for happiness just lead selfishness?

This is one of those questions where you just have to be a Jedi and search your feelings. Start paying attention to how things make you feel. What turns you up and what turns you off. What you love about life and what you hate about it. Think about the big decisions you made in the past and what you did instead of who you want to be.

If you haven’t had the epiphone of what’s important to you then you need to make a decision anyway. It can change, and it will change, it will always change. It may be helpful to have a higher level purpose. One of the most important things for me to do is to grow everyday because some form of daily growth is 100% in my control and I think it is a catalyst for every other thing I want to do. Because daily personal growth is a higher level goal, what I do from week to week can change while still doing what is most important.

Restrain Yourself

Ryan says it best in these two quotes:

It doesn’t matter how talented you are, how great your connections are, how much money you have. When you want to do something—something big and important and meaningful—you will be subjected to treatment ranging from indifference to outright sabotage. Count on it.
Those who have subdued their ego understand that it doesn’t degrade you when others treat you poorly; it degrades them.

To me this is the classic ego problem. We’ve all seen people in the public eye blow up spectacularly. Angrily lashing out and seemingly defending themselves in a spectacular over reaction. But even if you’re not in the public eye, when your best friend says something you find critical, or your partner points out your weakness’ or your colleague throws a backhanded comment your way for the tenth meeting in a row. With millions of years of instincts to overcome, self restraint is really hard in the moment.

As Ryan points out later in the book, Love is the perfect antidote for anger and fear. And can be exactly what you need to restrain yourself. Martin Luther King Jr may be the best example of restraint to ever live. There is an incredible story about MLK Jr in Birmingham in Malcolm Gladwell’s David and Goliath. MLK Jr is giving one of his first speeches at the 16th Street Baptist Church and a massive 200lb Nazi walks on stage and attacks him. As everyone else in the church descends on the attacker, King covers the assailant with his body to protect the attacker and whispers in his ear: “You’re not going to win the battle. We’re going to win, and I love you” (source)

After hearing that incredible story I realized, I never have an excuse. Even if someone physically attacks me I still have a choice. And I can choose to react or I can choose restraint.

So what can we do about our often hidden but omnipresent ego?

Ryan gives the antidote as “What humans require in our ascent is purpose and realism. Purpose, you could say, is like passion with boundaries. Realism is detachment and perspective.” Your ego wants life to be easy. It wants to be rewarded without doing in the hard work. But that is the opposite of what you need to want in order to get what you want.

The booked is packed with many more hard lessons and insights. I really enjoyed the masterful blend of diagnosis and prescription that is the hallmark of great stoic writing.

Where can I find more about Ryan Holiday?

The best place to find him is through is website:

I’m not sure how he finds the time, but in addition to writing books every year, he reads five or ten books a month and sends out a newsletter with his thoughts. I really enjoy getting his email every month, if you’re interested you can sign up here:

If you haven’t read any of his books yet I recommend starting with The Obstacle is the way followed by Ego is the Enemy