In this Weekly Ramble, I’m breaking down one of the most powerful books I’ve revisited in years, Ego Is the Enemy by Ryan Holiday, and unpacking the lessons it taught me about leadership, humility, failure, and purpose.
I’ve lived this book. From corporate highs to entrepreneurial struggles, I’ve learned that ego isn’t confidence – it’s the voice that tells you you’ve arrived when you still need to grow. In this solo episode, I share real stories from my sales career, business building, and even parenting that helped me internalize this book’s message.
Whether you’re riding the wave of success or picking yourself up from failure, this episode is a reminder that ego will block your growth, isolate your relationships, and limit your potential, unless you learn to check it.
Key Talking Points of the Episode
00:00 Introduction
01:10 JJ’s Joke of the Week
02:09 A wild emcee story from a Farm Bureau trip 06:21 Why I’m bringing back book recaps & the return to reading
08:26 Book of the month: Ego Is the Enemy by Ryan Holiday 10:00 The three phases of life & where ego shows up in each 11:20 Ego vs. Confidence
12:23 How ego destroys your ability to become a student
13:23 The Belichick approach to silencing ego 15:30 Failure is your greatest teacher if ego doesn’t block it 17:31 Learning to detach your identity from outcomes
20:55 Be humble in your goals, gracious in your success, resilient in failure
23:54 What being “hard to kill” really means
25:06 Ego makes you talk a lot
27:35 Purpose over passion and why titles don’t mean anything 29:45 Favorite quote: “Ego is the enemy of what you want and what you have”
Quotables
“Ego makes us talk more than we act. Confidence makes us move in silence.”
“Your ego is not your identity. You are not your wins and you are not your losses.”
“Success feels good, but it’s where ego does the most damage if you’re not careful.”
Links
608B Capital
Ego is the Enemy
