One of the sweetest joys of midlife is realizing that the wisdom you’ve gathered along the way isn’t meant to be stored—it’s meant to be shared. Over the years, I’ve had the privilege of mentoring people who would go on to leave their mark on the world in wildly different ways: Gavin Newsom in politics (30 years and counting in that relationship), Brian Chesky in hospitality innovation, Liz Lambert in boutique design, Marian Goodell in the Burning Man community, and Michael Franti in social impact and entrepreneurship. Each relationship has been unique, but all share a common thread: the pride that comes not from teaching, but from witnessing someone else’s evolution.
Mentoring reminds me that generosity of experience is one of life’s best returns. There’s a quiet satisfaction that comes when you see a seed you once helped plant grow into something extraordinary. Yet the moments that touch me most aren’t the ones tied to fame or success—they’re the surprise encounters years later when someone tells me, “You probably don’t remember, but something you said changed how I saw myself.” Those are the invisible mentorships—the ones you didn’t even realize you were offering. They reveal that mentorship isn’t a formal title; it’s a way of showing up with presence and curiosity.
I learned that lesson from one of my earliest mentors, Herb Kelleher, the legendary founder of Southwest Airlines. Herb and I were pen pals long before email made that quaint. Once a year (once his assistant gave me the green light), I’d write him letters about leadership and culture, and he’d respond with his trademark humor, kindness, and clarity. He never “taught” me in a traditional sense (and I never even met him in person), yet every note from him carried a masterclass in humanity—how to lead with heart, laugh at yourself, and treat people as your purpose, not your problem.
Herb showed me that mentorship is less about hierarchy and more about spirit. It’s about listening deeply, offering perspective without agenda, and modeling how to live with integrity. Whether I’m sitting across from a young entrepreneur or just chatting on a beach in Baja, I try to channel that spirit—because you never know who’s listening, or what small spark might ignite something lasting.
In the end, the pride of being a mentor isn’t about legacy—it’s about connection. It’s knowing that, through your example, someone else saw a wider horizon.
Laura, Gavin, Ethan, Eli, and me in Houston this past weekend
-Chip