Episode Description:

What happens when you build a business, sell it for millions, and still feel like something's missing? In this episode of Mission Driven You, Will talks with Howard Pearl, CEO of CARS (Charitable Adult Rides & Services), about the winding path from private sector success to mission-driven leadership—and why our biggest life shifts often begin after the exit.

Howard shares how he moved from building and exiting high-growth companies to leading a nonprofit that helps fund over 11,000 charitable organizations. Along the way, he opens up about navigating grief, learning to listen more deeply, and reinventing himself multiple times without losing his center.

This is a story about reinvention, yes—but also about the difference between achievement and meaning, and why sometimes, the best thing we can do is trade ego for impact.

🧭 What You’ll Learn in This Episode:

• Why a successful exit often brings more grief than glory
• How Howard went from startup founder to CEO of a nonprofit vehicle donation platform
• What it takes to lead a purpose-driven organization at scale
• The power of asking better questions—and actually listening to the answers
• How ego and attachment to identity block meaningful transformation
• The importance of legacy—and the question Howard asks himself every day: “What kind of ancestor am I being?”
• How to move from a transactional life to a transformational one

“I didn’t need another company. I needed something that mattered.”

“A founder exiting a company is like a death—and no one warns you about the grief.”

“Listening isn’t about patience. It’s about humility.”

“You can’t outsource your legacy.”

“It’s not about what you drive. It’s about what drives you.”

🔗 Resources + Links:

• Howard Pearl – CEO, CARS (Charitable Adult Rides & Services)
• Website: careasy.org
• LinkedIn: Howard Pearl
• Host: Will Samson
• Substack: drwillsamson.substack.com
• LinkedIn: Will Samson

✨ Reflection Questions:

• Where in your life are you chasing success instead of meaning?
• What would reinvention look like if it started with legacy, not ego?
• Are you building something the world needs—or something your resume wants?

💡 Final Takeaway:

True reinvention doesn’t come from a pivot. It comes from letting go of who you think you’re supposed to be—and choosing to serve from who you are.

Mentioned in this episode:

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