What is ‘situational retirement’—and should you give it a try?

As an operative researcher for luxury retail companies, I spent my career grabbing onto one corporate contract after the next, like a tree-swinging retainer monkey. But in a tariff-distressed industry, those contract “branches” grew further and further apart until I was left hanging. Then a colleague experiencing a similar work gap said, “Well, I guess we’re retired.”

I’ve been called a lot of things in my life, but nothing prepared me for the word “retired.” I’m a freelancer, so no one is coming to my house with a gold watch as a reward for loyal service; I have no desire to move south; and I don’t play golf. My equally self-employed friend Roland had a suggestion: Why not consider myself “situationally” retired—that is, retired until the phone rings.

It’s funny how one word can make or break your spirit. I was crushed by “retired” because the concept is foreign and frightening. But adding “situational” made it comfortingly familiar. After all, for us freelancers every corporate contract is situational; you might even say that situational is my superpower.

A friend who’s spent decades in a grueling C-suite position still can’t bring himself to retire, despite vested stock and a strong financial footing. Happy or not, he remains in the grip of his job, unable to let go of a role he believes defines (and so ultimately confines) him.

I’ve been an outside observer of corporate America long enough to understand his struggle, although it is not my own.

Redirecting your energy

As an independent contractor working for different companies, each with its own ecosystem, I constantly adapted my work persona to fit each unique corporate culture. Fluidity is what stabilized my career and so the loss of a fixed identity was not my retirement problem. My issue was displaced energy.

Whether writing a history of plaid for a fashion CEO or helping the VP of design at a boutique hotel chain find just the right urban neighborhoods for expansion, every project required a tremendous amount of advance work.

From sleuthing out relevant reference resources to searching for subject-specific experts, my research work was as fascinating as it was fun. I rarely left my desk yet built a national network of specialists and accumulated wide-ranging knowledge that often dovetailed, making every project a little easier. When the work slowed—and then stopped—my detective skills had nowhere to go.

I can’t remember how long I was in that uncomfortable standstill until Roland’s use of the word “situational” got me moving. To kick off “Project Retirement,” I went on my usual research prowl.

Every day, about 11,400 Americans turn 65—the traditional retirement milestone—fueling a busy and lucrative media market spanning content, publishing, and podcasts. But the most valuable operative research is not about finding the most information. It requires you to find the right information—information that is directional, that you can build upon, that can help steer your project to a successful conclusion.

Redefining retirement

For me, the initial guiding principles came from the YouTube channel Small Retired Life and Raina Vitanov’s practical yet inspirational attitude. Her conversation about being rebellious enough to redefine and rebrand retirement broadened my understanding and freed me to choose my own norms and values. But the most significant contribution was her observation that in retirement, “Productivity is not the conversation.” Using the Roland method, I added a word and had a revelation: Transactional productivity is no longer my conversation.

The time between contracts used to feel borrowed; now I own it. And all that research joie de vivre that I enjoyed over my corporate years is mine to use as I like. Sit next to me if you want to talk about the architecture of Shaker communities, art in ’80s New York, or the difference between Ivy style and preppy fashion.

I also started a side gig in a small boutique where I once shopped whenever I needed to outfit myself for a rare visit into corporate America. Because I’ve never had a structured straight job, I find the work to be fresh and interesting. It’s also rewarding because I get to use decades of style research on real live women, many playing out their own life-shifting issues through the lens of their wardrobes.

Although I’m not sure I can pull off being an introvert cosplaying as an extrovert for more than my customary two workdays a week, I might give it a shot. Because now that I’ve got the hang of it, situational retirement can be whatever I want it to be.

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