When we first crossed paths in the mid-1990s, he was 28 and I was 35—both of us ambitious, caffeinated, and convinced we were running late for our destinies. His sister asked me to become his mentor since we were both hospitality entrepreneurs. He founded PlumpJack at 25; I launched Joie de Vivre at 26. He would come to my office near San Francisco’s Union Square on Friday afternoons for our mentorship sessions and I led a series of retreats for his leadership team.
That context framed our recent Midlife Chrysalis conversation—not as pundit and politician, but as fellow travelers reflecting on discovery, missteps, and meaning. Gavin’s forthcoming memoir, Young Man in a Hurry: A Memoir of Discovery, isn’t just about political ascent; it’s about the costs and consequences of velocity.
One of the most pivotal moments in our podcast interview was when we discussed what he did just weeks after he was elected San Francisco’s mayor at 36, by a razor-thin margin over Green Party candidate Matt Gonzalez. Within a month, Gavin made the surprise decision—known only to a tight inner circle team including me—to order the county clerk to issue marriage licenses to same-sex couples. It stunned nearly everyone, instantly reframed his political identity, and helped catalyze a national movement. But, it also hurt his short-term prospects as a politician outside of San Francisco. It was a reminder that sometimes the most consequential leadership acts aren’t poll-tested—they’re conscience-tested. As Gavin talks about this on the podcast, he sheds a few tears (recommend you watch this episode on YouTube).
Midlife, however, brought a quieter crucible. Gavin describes his eight years as Lieutenant Governor—his mid-to-late 40s—as a low point on the U-curve of Happiness: less spotlight, more reflection. It was his midlife chrysalis. During that period he hosted a show on Al Gore’s Current TV (where he once interviewed me), wrote Citizenville, and later a children’s book inspired by his dyslexia. It was a season of humility, patience, and recalibration—something many leaders, especially men, encounter but rarely name. It sounds like Gavin could have used the Modern Elder Academy at that time, but we weren’t open yet.
We also explored what leadership needs now. In a political era defined by reaction—Bush to Obama to Trump to Biden back to Trump—Gavin speaks about blending tenacity with grace: tough minds, tender hearts. He surprised me by acknowledging not just what he opposes in Trump, but what Trump has understood about power and grievance. Maybe it’s time to replace furious with curious.
What gives me hope is Gavin’s curiosity. Through his podcast—where he interviews people he deeply disagrees with—he’s resurrecting the lost art of civil disagreement: listen generously, get curious, and find at least one point of shared humanity.
We ended where midlife often leads: fatherhood, faith, and urgency. As a father of four, Gavin is still discovering who he is becoming and what will survive him. Yes, he’s in a hurry—but there’s also what I’d call a holy urgency: a sense of calling. But, I reminded him (and myself) about the Gandhi line, “There is more to life than increasing its speed.” The wisdom, especially at midlife, is knowing when to slow down—and when a moment demands that we move, decisively, toward repair. Gavin feels a sense of urgency about the wisdom of Isaiah in being a “repairer of the breach” at a pivotal time in the U.S.
I’ve been saying to Gavin for a few months that America needs to get reacquainted with the Serenity Prayer (I even wrote about this in a past post). We need to hear a Presidential candidate talk about why, during complicated and contested times, summoning wisdom is essential. I love that Gavin mentioned this in his recent The Atlantic “frontrunner” profile and I bet we’ll be hearing more from him on this as the Serenity Prayer knows no political party. Hope you enjoy this podcast episode, no matter your political stripes.
-Chip