Holiday has written several books in which he uses the ancient philosophy of Stoicism to guide modern life, including the concepts of staying humble and humility. They include Ego is the Enemy, which would be a good place to start, even if it is to simply read the bibliography that features many books on this topic.
Holiday has found that books on this topic fall into a few distinct categories: Advice, Cautionary Tales and Inspiration.
The next [second] are what might be called cautionary tales—biographies that chart the fall of egomaniacs or stories from history about the costs of letting things go to your head.
The struggle against ego is existential and ubiquitous across religions, countries and generations. Frankly, it would be difficult to seek out any sage person who did not warn against ego.
If you can’t swallow your pride, you can’t lead
– Genghis Khan
Ego sucks us down like the law of gravity
– Cyril Connolly
Your ego can become an obstacle to your work. If you start believing in your greatness, it is the death of your creativity
– Marina Abramovic
So rebel against ego. Much depends on whether you win the war. Maybe Holiday’s books can help.
***
Cautionary Tales:
What Makes Sammy Runby Budd Schulberg — Sammy is the all-American heel. He’s your Ari Gold without the slightest bit of human decency. He rises through the ranks of Hollywood without ever writing a word. He is shadows and illusions, and the ultimate power-player. Sadly, as Schulberg mentions in his introduction, the message has been perverted.
Our society tends to see Sammy as a hero instead of a villain—or at least someone to pity. What Makes Sammy Run? is a novel that reminds us that even with egotists “win,” they lose.
Ask the Dust, Dreams From Bunker Hill:
The Young Napoleon: George McClellan:
The Young Napoleon: George McClellan by Stephen W. Sears — In Union General George McClellan, you have a delusional egotist who fought poorly for a good cause. It’s interesting because McClellan was such a smart and talented man yet he nearly lost the war on several occasions (and also lost chances to win the war).
The title of the book comes from the nickname his friends gave him due to his outsized ego, and the book really stands as an important, cautionary tale. Related, I also recommend Tides of War by Steven Pressfield (Alcibiades’ monstrous ego—fictionalized here—is a similar cautionary tale).
But ultimately, you know where the cliché must take us. Robert Moses was an asshole. He may have had more brain, more drive, more strategy than other men, but he did not have more compassion. And ultimately power turned him into something monstrous. If you like this, read Caro’s four-part series on Lyndon Johnson which is a similar meditation on ego and power.
What I Learned Losing a Million Dollars:
What I Learned Losing a Million Dollars by Jim Paul and Brendan Moynihan — There are lots of books on aspiring to something. Very little are from actual people who aspired, achieved, and lost it. With each and every successful move that he made, Jim Paul, who made it to Governor of the Chicago Mercantile Exchange, was convinced that he was special, different, and exempt from the rules.
Once the markets turned against his trades, he lost it all — his fortune, job, and reputation. That’s what makes this book a critical part in understanding how letting arrogance and pride get to your head is the beginning of your unravelling. Learn from stories like this instead of by your own trial and error. Think about that next time you believe you have it all figured out.
Atlas Shrugged:
Atlas Shrugged by Ayn Rand — Why Atlas Shrugged? Because the entire premise of the book, “You guys don’t appreciate me so I’m taking my ball and going home,” is an exercise in ego and petulance.
There is something deeply appealing to an egotistical teenager about leaving the world behind to selfishly pursue your craft. The question is: Would you want everyone else to do that? Of course not. At the end of the day, Plato’s allegory of the cave is a far better way to live your life than Galt’s Gulch ever will be.
The Great Beanie Baby Bubble: Mass Delusion and the Dark Side of Cute:
This book is a study of ego and entitlement but also fascinating from a variety of perspectives: psychology, economics, popular culture, leadership, creativity. It intersects all of them as the story of a financial bubble, a cultural fad, a poorly run company and an eccentric creative. It is one of the best narrative business books out there.
Grand Delusions: The Cosmic Career of John DeLorean:
Grand Delusions: The Cosmic Career of John DeLorean by Hillel Levin — Just like Ty Warner, John DeLorean, the brilliant engineer and car designer followed a similar trajectory. He was brilliant creatively, but no amount of brilliance could compensate for the destructiveness of his ego.
It was ego and his inability to work well with others that drove him out of General Motors. His ego mired his new company in chaos and dysfunction. Ultimately, instead of being able to reflect on these failures and resolve them, he hatched a plan to save his company from insolvency with a $60 million dollar cocaine deal instead of, you know, anything but that.
Billion Dollar Lessons: What You Can Learn from the Most Inexcusable Business Failures of the Last 25 Years:
There you have it! Some cautionary tales from persons who have let their ego get in their way, recommended by Ryan Holiday, to help you avoid letting your ego get the best of you.
Check out the other instalments in this series by clicking the links below
PS> If you have some egotistical friends, and we all do in the literal sense, then please Share this pots with them through the Social buttons around this post.
where I am sharing Ryan Holiday’s reading list of 35 books about humility.
What Makes Sammy Run by Budd Schulberg — Sammy is the all-American heel. He’s your Ari Gold without the slightest bit of human decency. He rises through the ranks of Hollywood without ever writing a word. He is shadows and illusions, and the ultimate power-player. Sadly, as Schulberg mentions in his introduction, the message has been perverted.
