Getting fired once is humbling. Getting fired four times forces you to confront something deeper — not just what you're doing wrong, but who you're being as a leader.
After my fourth CMO role ended abruptly, I spent nine months with a coach unpacking two decades of patterns. Here are the five lessons that emerged — lessons I now share with every CEO and founder I coach.
1. Your Greatest Strength Is Also Your Greatest Weakness
The intensity that made me successful at Google — the drive, the relentless pace — was the same energy that burned bridges at startups. I learned that leadership isn't about doing more. It's about knowing when to step back.
2. Vulnerability Is Not Weakness
For years, I confused vulnerability with weakness. It took getting fired, divorced, and starting over to realize that the most powerful thing a leader can do is say "I don't know" or "I need help."
3. Culture Eats Strategy for Breakfast
Every company I struggled at had the same pattern: brilliant strategy, broken culture. The teams that thrived were the ones where people felt safe to speak up, take risks, and fail forward.
4. Purpose Is Not Optional
When I finally connected my work to a deeper purpose — helping others find careers of meaning — everything changed. Not just my effectiveness, but my happiness.
5. The Best Leaders Are Coaches, Not Commanders
The shift from "I have all the answers" to "let me help you find yours" was the most transformative change in my career. It's why I became a coach.
Speaker, executive coach and author of Step Back and LEAP.
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