Ego is the Enemy - Ryan Holiday


Ego is the Enemy is the second book in “The Way” series by Ryan Holliday. I had read the first book, “Obstacle is the Way,” and enjoyed my first exposure to the stoic principles of which the author is a big proponent.

This book uses some of those same principles and real-life examples to help us understand how our Ego can cause problems during the three stages of success.

Here are some of the topics in each section that I found inspirations and take-away worthy -

  • Aspiration Towards Success
    • Don’t be passionate (have a purpose instead)
  • During Success
    • Always Stay a Student
    • Maintain your Sobriety
  • During Failure
    • Draw the Line
    • Maintain your Own Scorecard
    • Always Love

Don’t be Passionate

This is a confusing message. However, Ryan Holliday argues that having a purpose is better than being passionate.

Passion is form over function. Purpose is function, function, function.

Purpose gets you to further to your destination, and it is what drives mastery.

Passion typically masks a weakness. Its breathlessness and impetuousness and franticness are poor substitutes for discipline, for mastery, for strength and purpose and perseverance. You need to be able to spot this in others and in yourself, because while the origins of passion may be earnest and good, its effects are comical and then monstrous.

What humans require in our ascent is purpose and realism. Purpose, you could say, is like passion with boundaries. Realism is detachment and perspective.

Always Stay A Student

The title of this section is self-explanatory. However, the message here is that often ego can get in the way of admitting you have gaps in your knowledge and that it is time to learn.

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.

Maintain Your Sobriety

The author points out that Ego can drive short-term success but cannot sustain the long tail of success. And people that rely on it are often driven to failure or burnout.

The author describes how Angela Merkel was a quiet ego-less leader and how she differed from the European leaders of old that relied on ego and charisma. Europe had evolved and required a leader like Merkel.

We almost excuse ego because we think it’s part and parcel of the personality required to “make it big.” Maybe a bit of that overpoweringness is what got you where you are. But let’s ask: Is it really sustainable for the next several decades? Can you really outwork and outrun everyone forever?

Draw the Line

The message here is that you don’t need to prove your greatness. Realize when you have lost and move on.

There is an example of DeLorean, who doubled down even while his company failed and met serious trouble.

“If you cannot reasonably hope for a favorable extrication, do not plunge deeper. Have the courage to make a full stop.” - Hamilton

If your reputation can’t absorb a few blows, it wasn’t worth anything in the first place.

Only ego thinks embarrassment or failure are more than what they are.

Maintain Your Own Scorecard

Failure is not always evident and can be overshadowed when Success is overwhelming.

The example in this chapter was of the NE Patriots. Even though they had a winning quarterback in Tom Brady, they recognized early on that their draft/scouting process needed improvement because they had picked him in the 3rd round.

We should have our own scorecard of what it means to be successful. This helps override Ego, revealing failures masked by objective success.

This is characteristic of how great people think. It’s not that they find failure in every success. They just hold themselves to a standard that exceeds what society might consider to be objective success. Because of that, they don’t much care what other people think; they care whether they meet their own standards. And these standards are much, much higher than everyone else’s.

Always Love

When failure happens, it is essential to continue to love. Or conversely, this isn’t the time to hate. One’s ego may drive a person to hate or to feel bitter. Negative feelings hold you back.

There are several notable examples in this section -

Orson Welles vs. Hearst on the release of the movie - Citizen Kane

Hearst’s ego caused him to view the movie Citizen Kane as a direct attack on him and caused him to use all his power to prevent the movie from getting released, thereby only promoting the movie even more.

Orson Welles was never bitter about the movie getting initially panned and being a financial failure and went on to make other movies.

Dave Mustaine

Dave Mustaine was the guitarist kicked out of Metallica. He then formed the band Megadeth, which was equally successful. However, in interviews many decades later, he admitted that he remained bitter for a long time despite Megadeth achieving worldwide fame and success.

Frederick Douglas

And lastly, when Frederick Douglas was forced to move to the back of a bus, his reply to a white supporter’s apology was as follows.

“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.”