Think of it as a trial "offboarding"

posted by Jeff | Monday, March 23, 2026, 3:10 PM | comments: 0

I have pretty much the best therapist ever. I haven't stuck with one this long ever, and it's because she legitimately helps. The last few months have been challenging for a bunch of reasons, not the least of which is that I got RIF'd in January. I have a lot of runway, but it still makes me uneasy for reasons that are not necessarily logical. But she gave me a different way to look at it.

While I was thinking of the lull in work as a sabbatical, that's hard to do when you can't really nail down when the end is. In many ways, it's not up to me. What I could do is look at this more as a trial "offboarding" run. What is offboarding? It's my new word for "retirement." Something that has been clear to me for a long time is that retirement in the classic sense isn't really what I want. If your idea of retirement is sipping martinis and getting up whenever, I think that sounds terrible. Humans are wired to need purpose and intent. Offboarding is the idea that you leave your lucrative 9-5 to pursue specific things that feed your purpose and desires. That's what I want. Also, I don't want to wait until I'm in my 60's for it. No thanks.

So if I were to look at this break in work as a trial run for offboarding, what would it look like? Well, we're not empty nesters, and not ready to downsize, so I have to take those parts out. For the real thing, those would be steps to take. But what would I do with my time? I've explored this to a certain degree, by trying (failing) to make a documentary, learning lighting design, and being an amateur pinball tech. With a day job, you can't commit to these in the same way. For whatever reason, the thing I landed on without choosing it is building TogetherLoop. It mostly didn't exist two months ago. I don't know if it's a business or hobby or what. What I know at the moment is that working on it is satisfying in a way that few things have been, in a very long time. That's what I want offboarding to look like.

Is that it? No, because I think part of what I want out of that experience is the joy of working with others. That's one of the things I certainly enjoyed most about my job. Making stuff by yourself is gratifying, but it's even better when it involves others. Maybe that's what I'll need at some point, working with an investor-maker type. I don't know. Maybe what I need is a marketer.

The point is that I understand more clearly how what I used to call retirement looks. Even if that isn't near-term inevitable, it's good to understand it now.


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