“Are You Retired?” That Question Isn’t Working Anymore

Questions that no longer fit the lives we are living.

“Strangely, when that word appears in the conversation, I feel a little… invisible. I never quite know how to answer.”

I was sitting over coffee with a friend and colleague, a woman who had built an impressive career over many years, when she mentioned that she had been asked the dreaded question at a social gathering.

“So…are you retired?”

In her early 70’s, my friend continues to work, but at a different pace and with a bit more selectivity.

Retirement.

The word feels outdated. When someone applies the label “retired,” they place us in a category that erases the very thing we’re working to build in the Bonus Round, these extra productive years after our traditional careers. It’s the erasure of that emerging sense of self that isn’t borrowed from a job title or an org chart. The word “retirement” flattens all of that into a single past-tense story.

You were something.

Now you’re not.

My friend’s story stayed with me, and then last week I noticed former Labor Secretary and economist Robert Reich describing a nearly identical moment. Writing on Substack, he recalled standing in the locker room of his gym when someone asked him the same question.

“I hate that question,” Reich wrote. “It makes me feel ancient.”

The word retired, he wrote, conjures an image of someone who has been “put out to pasture.”

Two people. Two very different lives. The same visceral flinch.

A Word That No Longer Fits

What strikes me is how easily a single word—retired—can carry so much weight. Reich is hardly out to pasture if you follow his writing, and my friend continues to engage in meaningful work. Yet we rely on a model—retirement—to describe a stage of life that no longer matches the way many people are actually living.

The concept of retirement largely emerged in the late nineteenth and early twentieth centuries alongside industrial work and pension systems. Germany introduced one of the first national pension programs under Bismarck in 1889, and the United States followed with Social Security in 1935. Retirement was designed as a brief period of rest after a lifetime of physical labor, often beginning at age 65, when average life expectancy was not dramatically longer. The model assumed a few quiet years beyond work. Not the twenty or thirty years many people now experience.

Yet the word persists. It sits at the center of our financial planning, our social conversations, our greeting cards. So, when someone at a dinner party asks, “Are you retired?” they’re reaching for the only script our culture has given them. The trouble is, that script was written for a world where people worked in factories until their bodies gave out and then sat on the porch for a handful of years. It was never designed for a 72-year-old who is writing a book, or teaching part-time, or launching a second act that looks nothing like the first.

The Numbers Tell a Different Story

The gap between the word and reality is widening every year. According to the Bureau of Labor Statistics, roughly one in five Americans aged 65 and older now participates in the labor force—nearly double the rate from 1985. Workers aged 75 and older are the fastest-growing segment of the workforce, and their numbers have more than quadrupled since 1964. Many of these older workers are choosing part-time or flexible arrangements and craft a rhythm that blends work and other pursuits in ways that defy the old binary of “working” versus “retired.”

These aren’t people clinging to their desks out of financial desperation alone, though economic necessity is real for some. Many are doing what my friend is doing: working differently. Consulting a few days a month. Mentoring. Teaching. Writing. Volunteering with the intensity and skill of a professional. The shape of their engagement has changed, but the engagement itself has not disappeared.

When the Role Falls Away

For much of our lives we introduce ourselves through our roles. The work we do, the title we carry, the organization we belong to—these become shorthand for who we are. When they fall away, the question of identity returns in a sharper, more personal form.

Psychologist Kerry Burnight speaks to this in her recent book, Joyspan. She writes about the importance of seeing yourself less in terms of your societal roles and more in terms of your qualities and values—your curiosity, your humor, your capacity for connection. We are more than the roles we’ve deeply identified with. The task in this stage of life isn’t to find a replacement title. It’s to discover a sense of self that doesn’t depend on one.

I’ve seen this play out again and again in the Bonus Round workshops we run. People arrive with decades of accomplishment behind them—and a surprising amount of uncertainty about what comes next. The ones who seem to find their footing are not the ones who immediately fill their calendars with new projects. They’re the ones who sit with the discomfort long enough to ask a different kind of question: not what do I do now? But Who am I becoming?

The Search for Better Language

If retirement is the wrong word, what’s the right one? People have been trying a better language. “Third act” has its appeal, but it borrows from the theatre, and in most plays the third act is the final one. It’s when the narrative wraps up and the curtain falls. That’s precisely the feeling most of us are trying to escape. “Encore” works if you’re still focused on work, but it leaves out the people who are building something that doesn’t look like a career at all. After my first Bonus Round article ran last year, a reader (Ken Barry) wrote in the comments that he’d taken to calling it “protirement.” I smiled at that. The instinct is right; the prefix signals forward motion.

Each of these attempts gets something right. What they share is a refusal to accept that this stage of life is defined by what ended. They’re all reaching for language that points forward. But none of them quite name the thing that feels most true to me: that for the first time in human history, millions of us have been handed twenty or more years of healthy, capable living beyond our primary careers—years that no previous generation got to have. Years that are not an epilogue. Years that are, in the most real sense, a gift.

That’s why I’ve come to call this time the Bonus Round. Not a wind-down, not a return to old scripts, but a distinct phase of life with its own questions, its own freedoms, and its own responsibilities. The phrase came to me because it captures what so many of the alternatives miss: that this isn’t the end of the game. It’s extra time that wasn’t on the original clock. And what we do with it is entirely ours to shape.

Back to the Question

So what do you say when someone asks if you’re retired?

Try saying something like: “No, I’m creating a new chapter” or “I’m in my Bonus Round.” Most people will look curious. Some might laugh. Nearly everyone will ask what it means. That’s the point. The conversation will shift. Instead of a polite dead end—oh, that’s nice, good for you—something opens up. We can start talking about what we’re doing, what we’re learning, and what surprises us about this stage. The question stops being about what’s over and becomes about what’s happening now.

So, this week, try a small experiment. The next time the question comes—whether from a stranger, a neighbor, or the voice in your own head—pause before you answer. Notice whether the word retired fits or chafes. If it chafes, try naming what you’re actually in. Your Bonus Round. Your next chapter. Whatever language feels true to the life you’re building.