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I Turn 65 Today. I’m Not Retiring


October 31, 2025
Today I turn 65 — the age when society gently suggests I should take up golf, buy more beige clothing, and start referring to my past in the past tense. Instead, tonight at my Halloween birthday party, I’m retiring The Phoenix Hotel — not myself. After nearly four decades of watching that funky San Francisco landmark rise, burn, and rise again (like, well… a phoenix), I’m ready to hand over the keys (in January) to the land owners after a 39-year land lease expires.

But don’t cue the farewell music just yet. I’m not done. I’m simply changing costumes.

The truth is, I’ve never been good at the traditional notion of “retirement.” It’s always sounded more like a medical diagnosis than a life stage. (“I’m sorry, sir, you’ve come down with retirement. It’s terminal.”) For people who work with ideas, creativity, and relationships, there’s no clean break between doing and being. Our curiosity refuses to clock out.

For knowledge workers, the problem isn’t that we can’t stop working — it’s that we’re finally doing the work we actually want to do. That’s a hard thing to walk away from.

According to a recent Northwestern Mutual study, only 44% of Millennials expect to retire by 65 — and one in five believe they’ll never retire at all. Not because they can’t, but because they don’t want to. Retirement used to be a reward for surviving work. Now it often feels like an interruption to meaning.

The Industrial Age version of retirement made sense when work was mostly physical — when your back gave out before your spirit did. But for today’s thinkers, makers, and mentors, the mind keeps evolving. Our operating system updates itself every few years. We’re not winding down — we’re just switching from “production mode” to “wisdom mode.”

So tonight, as I raise a glass to The Phoenix Hotel, I’m also toasting to its namesake: rebirth. I’m letting go of one chapter to make space for what I can’t yet imagine. The first half of life is about creating your résumé. The second half is about creating your eulogy — not morbidly, but meaningfully.

I don’t want to stop working. I want to keep awakening.

In a culture that worships youth and productivity, it feels almost rebellious to say: I’m not retiring, I’m rewiring. My business card may change, but my curiosity won’t. If anything, it’s louder than ever — like a slightly eccentric friend who refuses to leave the party.

So here’s my toast: to the Phoenix, to midlife mischief, and to the beautiful trouble of staying curious at any age.

I may be 65, but I’m not done dancing with my next act.

-Chip

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