A Gap Year at 60


Episode 56 | Mystic, Connecticut

Three cups of Nespresso. Bad hair. A porch with a view of the water that I couldn’t stop looking at. This is what passed for a morning routine in Mystic, Connecticut, and I have no complaints.

The sunrise didn’t materialize. The clouds were thick and milky and the sun apparently decided to take the morning off, which I respect. I sat in the Adirondack chair anyway, coffee in hand, and spent about an hour talking to myself about what I’m doing with my life. Which is either very healthy or very concerning, depending on who you ask.

The AI Scripts, Officially Released

I brought printed scripts to New England. Multi-page documents, shot lists, narration notes, the whole thing. ChatGPT and I had built out a detailed plan for how to cover Mystic, Newport, the coast. Mystic Pizza, the aquarium, the art museum, interviews at the seaport. Two days in Mystic done properly.

I sat on this porch and looked at those sheets and looked at the water and let them go. Mentally, completely, and without much grief.

This is not a travel show. I don’t have a production team. I have a camera, a recorder, and a year that I decided to spend driving around the country when most people my age are thinking about where to golf. The AI scripts would be a fine road map for a different project. This isn’t that project. This is me, documenting what I’m doing, hoping a few people find it interesting, and trying not to manufacture something it isn’t.

The Amtrak went past twice while I was working through this. Apparently that stretch of track is one of the busiest in the country. I found that oddly comforting.

The Gap Year I Never Took

When I was backpacking through Europe in my late twenties, mostly solo, I kept meeting people taking gap years. Between high school and college. Between college and work. Between a couple years of work and a graduate degree. I admired it every time. The deliberateness of it. The decision to stop and look around before moving on to whatever came next.

I never did it. I had a business. I had a life that required showing up. I took summers in Europe when the lighting work slowed down, two weeks here, three months once, and I treasured every bit of it. But a real stop, a genuine pause, a year of not requiring myself to be anywhere in particular? That didn’t happen until now.

So here I am. Sixty years old. Sitting on a cottage porch in Connecticut watching a lobsterman pull traps in the harbor, and calling it a gap year. Is it really a gap year if you’re sixty? I’m not totally sure what it is. It’s not retirement, I’m not built for that. It’s not a vacation, it’s too intentional for that. It’s more like permission. Permission to slow down, to look around, to figure out what comes next without forcing the answer.

I don’t have the answer yet. That’s probably the point.

John Anderson and the Art of Still Showing Up

I keep coming back to the concert the night before.

John Anderson is eighty years old. During Roundabout he brought his wife Jane out to the side of the stage and danced with her during one of the musical interludes. I got a little bit of it on camera, zoomed in from the back of the theater, and it was one of the more genuinely sweet things I’ve seen on this trip. They’ve been married since 1997, the same year I got married. He made it work. I made it ten years.

He told a story from the stage about the time the band went to see Spinal Tap in the theater and slowly realized they were watching a documentary about themselves. He told it better than I’m telling it here. The point was that they were who they were, not big shots, not legends in their own minds, just a progressive rock band that wrote some songs and kept going.

That’s it. Keep going. At your own tempo, in your own direction, with the people you love if you’re lucky enough to have them there.

I’m 60. He’s 80. He’s still got his voice. I’m still trying to find mine.

The cottage had four Adirondack chairs on the porch. If you were sitting in one of them that morning, I’d have been glad for the company. We could have watched the lobsterman and not talked about anything that mattered and that would have been exactly right.

Rhode Island next.

The Author

I visited all 50 states at 60. Now I am chasing the light and story through all 63 national parks, some with my cat Penny! The journey continues - follow along.

The Journey Continues

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