In my opinion, Ryan Holiday is one of the best Stoic thinkers in our time. That is why I’m reading him again. After The Obstacle is the Way, this is the read I needed. Where that book is about meeting adversity and using it to your advantage, this one is about the quieter saboteur that rides along with us in the good times and the bad alike: ego.
Mr. Holiday structures the whole book around the arc our ambition usually travels, in three parts: Aspire, Success, and Failure. That framing is what makes it resonate with me, because ego doesn’t strike once and leave. It shows up wearing a different mask at each stage and, unless on constant guard, is very very difficult to see and root out of ourselves:
- Aspire — before we’ve done anything, ego whispers that we’re already special, and talk quietly starts to replace work.
- Success — the moment we have something to protect, ego creeps in as entitlement, control, or paranoia and shuts down the learning that got us to succeed.
- Failure — its loudest moment, where ego turns a setback into an identity instead of a lesson.
I’ll share a few memorable lines I marked from each section:
… the ability to evaluate one’s ability is the most important skill of all. Without it improvement is impossible… We will learn that though we think big, we must act and live small in order to accomplish what we seek.
Entitlement assumes: This is mine. I’ve earned it. At the same time, entitlement nickels and dimes other people because it can’t conceive of valuing another person’s time as highly as its own.
Think of Martin Luther King Jr., over and over again, preaching that hate was a burden and love was freedom. Love was transformational, hate was debilitating. In one of his most famous sermons, he took it further: “We begin to love our enemies and love those persons that hate us whether in collective life or individual life by looking at ourselves.” We must strip ourselves of the ego that protects and suffocates us, because, as he said, “Hate at any point is a cancer that gnaws away at the very vital center of your life and your existence. It is like eroding acid that eats away the best and the objective center of your life.”
It seems like we’re hard-wired for self-importance. It’s definitely the easiest story to tell ourselves and the hardest one to fix. Based on what Mr. Holiday explains, keeping ego in check isn’t self-deprecation, it’s actually clarity: being able to truly see yourself, the people around you, and your own faults accurately enough to actually act on them… and improve! As he keeps returning to, ego is the enemy of our true desires and of what we already have. Ego costs us the thing we’re chasing and blinds us to the thing we’re holding.
And perhaps the best part of the entire book, and the best part because it aligns with my world-view. After the chapters on how we build ourselves up, lie to ourselves, see ourselves as a success, and our inevitable downfall in failure, he leads us not to more will power, but to love. Love is the antidote. It’s always love. Love for others, love for improvement, love for humility. It’s making room for what really matters in our lives. Connection. Humility. Love.
Read it. Reflect on yourself. Love.