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How do you know when or if you're ready to retire?

How much do you need to change your identity if you retire from you profession, your career, your job?

Changing our pictures of ourselves is difficult.

One of the first joke-y ads I remember from my childhood was the signature phrase "It's Time to Re-Tire" from the Fisk Tire Company.

Illustrated for magazines by the best commercial artists of the day, including Norman Rockwell, the ubiquitous ads appeared in every glossy magazine and on billboards. It depicted a sleepy little boy in pajamas, carrying a candle in one hand and effortlessly supporting a huge automobile tire over his other shoulder.

"Why's the kid lugging a tire around?" I asked my older brother when I was maybe four or five. I hated not getting the point. "It's a joke," he explained. "Some people say 'retire' to say 'go to sleep' and the company is making it funny by putting a real tire there. Get it?"

I didn't. But I pretended to, since one lesson I'd mastered since I learned to walk was to pretend I understood something even when I didn't. This strategy would buy me time to figure it out for real without being embarrassed.

The play of words on "retiring" to bed and "re-tiring" one's car made the catchphrase useful for the original manufacturer; they used it for decades.

And decades later, the memories have resurfaced and been retread. I've been spending a great deal of time in therapy and in conversation with friends and family discussing the other use of the word "retire."

Here's how I define retirement: it's the action of leaving one's job or profession and effectively stepping away from being defined by a public and easily defined position in the workplace.

That simple sentence was hard for me to write.

Coming up with your own definition of something—a term, a plan, an idea, a concept, a feeling, an emotion, a relationship—makes it "more real," as my students would say. Or, as the brilliant British author Fay Weldon put it, "One must be careful with words. Words turn probabilities into facts and, by sheer force of definition, change tendencies into habits."

My husband retired when he was 65. He loved teaching, but he was ready to be out of the classroom. He's kept writing and editing, with enormous success but never regretted taking off his academic robes. My father, in contrast, worked retail until he was 79; only when his Parkinson's kept him from being able to handle merchandise did he quit.

I'm not sure what I'm going to do. One of my friends, an editor I admire, respect, and adore, suggested I not retire; a colleague told me I should leave "while the going is good—before they physically remove the bookcases from our offices"; an old friend who just left a beloved job after 32 years told me she's having the best time of her life.

An intriguing and inspiring examination about seeing life in a new framework is offered by Druga Larkin, M.D., in a recent book Timeless Vision. A board-crtified ophthalmologist who graduated from the University of Pennsylvania and received her medical degree from Duke University, "Dr. Druga" has been a well-known surgeon and expert in her field for years.

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She started writing her book when thinking about what she hoped would be the useful perspective of "empowered aging" as she considering what she'd be doing as she moved forward. What she did not expect was how personally and abruptly she would be called to answer what she would become when life became different.

"An unexpected injury fractured my dominant arm and forced me to step away from cataract surgery, a role that had defined me for decades. The operating room had been my anchor. Each day, I held patients’ vision in my hands. Surgery was not simply a profession; it was structure, mastery, contribution. It was identity. At first, I framed the interruption as temporary. I would heal. I would return. That was the assumption—and, if I am honest, the safer narrative," Larkin explained to me.

Yet, as Larkin learned, recovery creates space. And space can be clarifying.

"The hardest moment in this process was not managing the injury," Larkin continued. "It was admitting to myself that I did not feel called back to the operating room. That admission hit like a shock to the system. For decades, surgery had been central to how I saw myself—precise, decisive, steady under pressure. To question that role was to question the very lens through which I had measured competence, contribution, and self-worth. Stepping back from the operating room forced me to confront whether I could remain whole and influential without performing that role."

Where is the perforated line between "professional role" and "authentic self"? Changing our pictures of ourselves is difficult, especially when the professional role removes us from pressured and demanding yet surprisingly secure and familiar surroundings.

If I'm no longer a teacher in a classroom, I ask myself, will I still have a voice worth hearing--and will anyone listen? If I no longer make deadlines, am I a writer? What can I allow myself to stop doing while still allowing me to remain me?

"Re-envisioning our selves as we age asks us to distinguish between what we can simply continue to do and what is truly ours to keep doing," argues Larkin, and I agree.

Retirement does not mean withdrawal; it could mean winding down, but it can also mean getting started. It might be time to stop the sleepy-time rituals, the useless tire-carrying, and get a bigger, brighter candle.

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