What is our ego? For many of you, the thought of ego may conjure visions of a character like Megamind with a huge head and huge brain. I want you to think of the character whose head is huge not because they have a huge brain, but because they can’t get over themselves. They think they’re a gift to the world and everyone should feel blessed to exist inside their pull of gravity.

In his book Ego is the Enemy, Ryan Holiday works to address this type of ego — the ego we’re all susceptible to, that can ruin our highest accomplishments because we think we’re all that.

It’s always nice to be made to feel special or empowered or inspired. But that’s not the aim of this book. Instead, I have tried to arrange these pages so that you might end in the same place I did when I finished writing it: that is, you will think less of yourself. I hope you will be less invested in the story you tell 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 book is broken up into three clearly marked parts which, unlike many authors, Holiday calls out for us before we dive into them.

And therefore, the three parts that this book is organized into: Aspire. Success. Failure.

The aim of that 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 to cultivate strength and fortitude so that when fate turns against you, you’re not wrecked by failure.

The ego that Holiday is talking about is most commonly referred to, and seen manifest as, arrogance. That feeling that we’re entitled to all the good things even if we haven’t put in the work to get them. This is not the quiet ego that’s confident and sober. That quiet, confident ego is the one that Holiday is working to help us transform into.

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.


Almost universally, the kind of performance we give on social media is positive. It’s more “Let me tell you how well things are going. Look how great I am.” It’s rarely the truth: “I’m scared. I’m struggling. I don’t know.”

Take a look at Instagram or Facebook or Twitter, or at the people around you at the coffee shop. The glimpse you get here is often referred to as the ‘highlight reel’ of life. While I may show you a picture of my smiling kids at the top of a mountain which impresses you, I don’t show you all the times they complained on the way up and yelled at me.

This is not just something that happens on my social feeds — everyone we know is showing us a carefully cultivated glimpse of their life. Even if they share the “hard” times, there are hundreds more hard times they never show us. For most of us, though, the struggles far outweigh the successes.

And yet we feature the success, which in turn causes others around us to Aspire to that success while focusing on the dregs of their real life and comparing it to your highlight reel.

Even if you recognize this highlight reel phenomenon, how often do you let yourself be taught? Are you regularly working to be that professional that everyone looks up to?

The power of being a student is not just that it is an extended period of instruction, it also places the ego and ambition in someone else’s hands. There is a sort of ego ceiling imposed – one knows that he is not better than the “master” he apprentices under. Not even close. You defer to them, you subsume yourself. You cannot fake or bullshit them. An education can’t be “hacked “; there are no shortcuts besides hacking it every single day. If you don’t, they drop you.

Do you pretend to know everything and shy away from admitting what you don’t know? While I build web software — and in theory that’s code — it would be foolhardy of me to have anything but a very cursory opinion on building applications for desktop or mobile environments.

The pretends of knowledge is our most dangerous vice, because it prevents us from getting any better.

While I say that and it seems obvious, how often as we try to launch ourselves to some level of success do we forgo the three scary words “I don’t know” and make something up?

How often do we look at what our clients or bosses want us to do and lament how short-sighted they are in the face of our awesomeness? This prevailing sentiment is how we get sites like Clients from Hell, which assumes that all the fault is on the client while the creative or developer sits unassailable in superiority knowing that the client is stupid.

It’s a common attitude that transcends generations and societies. The angry, unappreciated genius is forced to do stuff she doesn’t like, for people she doesn’t respect, as she makes her way in the world. How dare they force me to groves like this! The injustice! The waste!

As we Aspire to be successful Holiday helps bring us down to earth. Down to a level of humble acceptance where we are. A level that’s willing to learn from mistakes, and admit those mistakes.

By being that quiet person that’s always learning, we avoid flash-in-the-pan success and instead create a body of work that speaks for itself. Something we can look back on years later and be proud of as we move toward success.


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.

With a bit of success under our belts it’s easy for us to believe we suddenly have it all figured out. We take that calm professional we need to be to succeed and turn them into an arrogant person who knows everything and stops learning.

We think all our ideas are the best, and in doing so, we miss the ideas that are going to disrupt our industry. We turn from that person who humbly shipped good work for clients or bosses into someone that everyone should be happy to have the privilege of working with.

Success is not the time to turn into that person — it’s time to double down on shipping good work to people humbly as we continue to learn.

The same goes for us, whatever we do. 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.

In the midst of success we also get so many opportunities thrown at us. New big clients and projects come our way and by doing them we show people how successful we are.

All of us regularly say yes unthinkingly, or out of vague attraction, or out of greed or vanity. Because we can’t say no — because we might miss out on something if we did. We think “yes” will let us accomplish more, when in reality it prevents exactly what we seek. All of us waste precious life doing things we don’t like, to prove ourselves to people we don’t respect, and to get things we don’t want.

Dave Ramsey says something similar about our spending habits.

We spend money we don’t have for things we don’t want to impress people we don’t even like. – Dave Ramsey

This need to be seen as successful and go big or go home means that many of us end up building businesses we would never work for. The irony is, we work long hours and weekends, when we started the work so we could be a great parent and hang out with our kids.

It’s time to sit down and think about what’s truly important to you and then take steps to forsake the rest. Without this, success will not be pleasurable, or nearly as complete as it could be. Or worse, it won’t last.

As we get some success, Holiday reminds us we need to stick with that calm person that did good work humbly and learned. We need to remember that most people will never hear of us, and that’s okay. Success is not some dollar amount, and his next section on Failure shows us what it success really is.

Most successful people are people you’ve never heard of. They want it that way.

It keeps them sober. It helps them do their jobs


The only real failure is abandoning your principles. Killing what you love because you can’t bear to part from it is selfish and stupid. If your reputation can’t absorb a few blows, it wasn’t worth anything in the first place.

Failure happens to everyone. Maybe it’s not on some grand scale of a multi-million-dollar business collapse like Enron, but it happens. We are the good parent who yells at their kid and tells them you don’t even want to see them anymore.

We are the business owner that misses deadlines, over and over and knows that it’s wrong.

The thing is, in the midst of success it’s easy to shortchange the things that really make us awesome. It’s easy to stop being true to our ‘authentic self’ and strive to grab back at the success we just had a fleeting glimpse of.

People make mistakes all the time. They start companies they think they can manage. They have grand and bold visions that were a little too grandiose. This is all perfectly fine; it’s what being an entrepreneur or a creative or even a business executive is all about.

We take risks. We mess up.

The problem is that when we get our identity tied up in our work, we worry that any kind of failure will then say something bad about us as a person. It’s a fear of taking responsibility, of admitting that we might have messed up. It’s the sunk cost fallacy. And so we throw good money and good life after bad and end up making everything so much worse.

As we had a hand on success and made that inevitable mistake that people make it’s so easy to lose our entire sense of self in the pursuit of sticking with that success. As our business crashes down around us, we feel like total failures because we’ve tied up our personal worth in that venture.

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In the movie Fight Club there is a scene where the men in the club are being told that ‘they are not their job’ and we should all take that to heart.

Your worth is not in how much you can charge a client for your services or how much you earn in a year or how many projects you launch. Your worth must be found somewhere else and being the best person you can be is a good place to start.

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

And with that quote near the end of the book, Holiday leaves us with something to think about. Are we striving every day to be the best possible version of ourselves? If the answer to that is ‘no,’ then it’s time for an ego check. If the answer is ‘yes,’ then good job — keep on quietly keeping on.


Just like The Obstacle is the Way (which I reviewed) Holiday writes a great book that gets us to think more about what it means to be true to ourselves. Unlike many books in this genre, it does not encourage us to be ‘authentic’ while entirely ignoring those around us and trampling them.

Holiday encourages us to be awesome to others and forget what we deserve as we help those around us get to where they want to be.

Get Ego is the Enemy on Amazon

photo credit: enigmabadger cc

2 responses to “Is your ego getting in the way of the life you want?”

  1. John Locke Avatar

    Ryan Holiday is one of my favorite writers, and finds a great intersection between philosophy and business.

    I love how he says many successful people are folks you’ve never heard of. This is so true. Things aren’t always what they seem, as there are so many people in the world intent on showing us their meticulously constructed highlight reel.

    99% of the people we strive to be like have no bearing on what our personal outcomes are. Oftentimes, we try to “get on their radar” or impress people with our accomplishments, all the while ignoring the other type of legacy we leave…what people think of our true face.

    It’s good to embrace failure and defeat, and not fear it. Most things we fear we can recover from, especially in business. Not that we’re trying to fail. We just shouldn’t feel like success is the one thing that defines our worth.

    Thanks for your detailed review. More people should check out Ryan Holiday’s work. It’s worth reading and pondering deeply.

    1. Curtis McHale Avatar
      Curtis McHale

      I certainly find it a hard balance to make sure I don’t always just show how ‘awesome’ my life is. In part I need to do that as I work on marketing my coaching services, but that’s not all I should do.

      As I’ve read more of what Holiday has written around the web I’ve been impressed as well. I highly suggest that people look around to see what he’s writing and take the time to read it.