Should You Retire or Rewire?

Entering midlife brings with it many challenges, opportunities, and questions. Rabbi Rami shares his thoughts following a conversation with Chip Conley for the S+H podcast.

Reading Chip Conley’s new book, Wisdom@Work: The Making of a Modern Elder, I came to the chapter called “Rewire, Don’t Retire” and found myself wondering what retirement might be like. I’ve been working since I was sixteen, and I have reinvented/rewired myself several times, and never once have I thought of retiring. Maybe it was time to at least consider it.

Conley traces the origin of “retirement” to the Middle French “to go off into seclusion,” an idea that appeals to me. Covid was a time of semi-retirement for me in that it took me off the road: I stopped eating out, visiting friends, giving lectures, and leading retreats. Zoom kept my seclusion from being total, but I liked my relative seclusion and have not returned to my old life even when doing so became possible. But I don’t consider myself retired. But I’m not rewiring either.

Chris Farrell of the New York Times writes that work provides older people with “a routine and purpose, a reason for getting up in the morning,” which is why rewiring is better than retiring since rewiring keeps you in the work world.

I love routine. My day is structured around walking my dog, reading, writing, and meditation. But I don’t need work for that. As for purpose, I think that is more inner-driven than work-provided. My purpose for getting up in the morning is to see what happens before going to sleep at night. But I get what he means, and I have no negative judgment toward anyone who chooses to rewire rather than retire. But neither seems a good fit for me.

To paraphrase the French mathematician Blaise Pascal (1623-1662), “All of our problems stem from our inability to sit quietly in a room alone.” This is true because sitting quietly in a room alone causes us to realize the fictional nature of the story we tell ourselves about ourselves. We discover that we are not defined by race, gender, ethnicity, sex, religion, nationality, politics, or any other narrative we humans invent to divide ourselves into different and often warring camps. Sitting quietly in a room alone, we discover that we are no-body and no-thing. And, if we sit long enough, we discover that we are every-body and every-thing all at once. While I find this discovery liberating, many people I know find even the thought of it terrifying. This is what troubles me about both rewiring and retiring.

If your rewiring or retiring is nothing more than jumping into a new story—reimagining who you could be, and what you could do, and then spending your last years bringing this about—you might be better off spending some time sitting quietly in a room alone and freeing yourself of your stories both old and new. Indeed, if you don’t make time to do this, the “new story” you invent will be a variation of the old story and will hardly be new at all.

So, my advice is this: Whether you choose to retire or rewire, make time each day to sit quietly in a room alone and see what is true rather than what you insist must be true.

Roadside Musings

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