The Most Exciting Chapter Nobody Told You About: Redefining Retirement for Women Entrepreneurs

At 97 years old, she signed a modeling contract. Not a small, ceremonial one. A real one, with a major agency, the kind 20-year-olds spend their whole careers chasing. She'd already had a documentary made about her life, a sold-out exhibition at one of the world's most famous museums, and a reputation as one of the most photographed faces of her decade. None of it had happened while she was building her original business. All of it happened after she closed it.

"I never expected people to know my name," she wrote. "I never expected anything. I just feel things in my gut and I do them." She'd spent over four decades running a textile company with her husband, dressing the White House across nine presidencies. When that chapter ended, most people would have called what came next her retirement. She never did. In her own words, retiring at any age was "a fate worse than death." What she actually built afterward looked nothing like an ending, and everything like the truest version of herself finally getting the floor.

Why We Hate the Word Retirement

The word carries so much dread for a specific, well-documented reason: for most of our working lives, we're taught to answer the question "who are you" with our job title. Psychologists who study this call it identity-based retirement, a term for the very real psychosocial process of losing a self-concept that was fused with a career, then having to search for a new one.

Research consistently finds that people with the strongest professional identities, often the most ambitious, most driven among us, struggle hardest with the transition, and that those who feel forced into it experience meaningfully more distress than those who choose it on their own terms.

That's the trap. The word "retirement" was built around the image of stopping, of a gold watch and a quiet decline, precisely because it was designed for a career structure most entrepreneurs and creatives never actually lived inside in the first place.

What You're Actually Walking Away From

For women specifically, the years leading up to this chapter rarely involved just a career. Many of you built a business while also raising children, running a household that somehow always needed one more thing from you, and, often in the very same season, becoming the primary caregiver for aging parents whose needs arrived without warning and without an end date.

Some of you did all of that while quietly managing the physical and cognitive symptoms of perimenopause and menopause, the brain fog, the sleepless nights, the mood shifts nobody warned you about, layered directly on top of everything else you were already carrying. Sociologists have a name for the caregiving portion alone: the sandwich generation, people simultaneously responsible for children and aging parents, a load that falls disproportionately on women.

This chapter isn't just the end of a career. For many of you, it's the first realistic chance in decades to set down responsibilities that were never entirely yours to carry alone in the first place, and to ask, often for the first time since your twenties, what you actually want your days to look like.

What Retirement Actually Represents for Entrepreneurs and Creatives

If you've spent decades building something, meeting client expectations, hitting someone else's deadlines, shaping your creative instincts around what would actually sell, this chapter represents something the traditional definition never accounts for: the first real stretch of time, possibly in your entire adult life, that belongs to no one's agenda but your own.

That's not a small thing. Time is the one resource every entrepreneur spends her whole career trying to buy back, and this chapter is where you finally get to spend it exactly how you want, creating for the sake of creating rather than because a client, a market, or a mortgage required it of you.

For some women, the most meaningful creative act available in this chapter isn't a painting, a business, or a book. It's stepping in to help raise grandchildren, the people who will go on to shape the future of this country and the world. There's a reason we use the word "create" for exactly that kind of work. Raising a child, at any stage of life, is one of the most consequential creative acts any of us ever takes part in.

What This Looks Like: Redefining Retirement for Women Entrepreneurs

The woman in the opening was Iris Apfel. She and her husband, Carl, ran the textile firm Old World Weavers from 1950 to 1992, a business successful enough to earn a White House contract spanning nine administrations. When they closed it, she didn't stop. In 2005, in her eighties, a costume jewelry collection she'd styled herself landed a show at the Costume Institute at the Metropolitan Museum of Art. In 2014, a documentary about her life reached audiences worldwide. In 2019, at 97, she signed with IMG to model professionally. She worked, by her own description with real relish, until her death at 102.

None of it followed a plan. "Nothing I ever did I expected to do," she said. "It just kind of happened." What she did have, once the business closed, was the one thing the traditional story of retirement never mentions: total creative permission, on a timeline that finally answered to no one but her.

I want to name something plainly here: not everyone gets a White House contract, a Met exhibition, or a modeling deal at 97.

Iris Apfel's specific story is genuinely one of a kind, and I don't want to hold it up as a template you're somehow failing to replicate. What isn't one of a kind is the underlying pattern, closing a chapter fully and then using the freedom that follows to build something nobody assigned you to build. That part is available to you regardless of the scale her particular story happened to reach.

If Iris Apfel's story resonates, please know you're not standing in this chapter alone. You're in the company of an entire lineage of women who did their most original work once the world had stopped watching closely enough to tell them not to. Here are a few of their stories worth following, in their own right:

Mary Kay Ash · Julia Child · Pleasant Rowland · Anna Mary Robertson "Grandma" Moses · Laura Ingalls Wilder · Diana Vreeland · Louise Bourgeois · Georgia O'Keeffe · Toni Morrison · Beatrice Wood

A few more of these stories are being written right now, or were until quite recently, in exactly this same spirit.

Anežka Kašpárková was a former agricultural worker in the small Czech village of Louka who picked up a paintbrush for the first time in her retirement, somewhere around age 50. She spent the four decades that followed covering the doors, windows, and village chapel in bright ultramarine floral patterns, entirely for the pleasure of it, painting until her 90s, having quietly become known around the world along the way.

Helen Van Winkle was 85 when her great-granddaughter posted a photo of her online, not long after Van Winkle had lost both her husband and her son. "I got tired of grieving," she later said, "so I reinvented me." The persona she built afterward grew into a following of millions before her her 97th birthday, and became, for a lot of people watching, quiet permission to turn grief into something entirely their own.

Lyn Slater was 60, a social work professor of two decades, when a photographer outside Lincoln Center mistook her for someone important in the fashion world. What started as a creative outlet grew into a following of more than 700,000, and she's since written with real honesty about both the exhilaration of that reinvention and the burnout that came with it, a good reminder that this chapter doesn't have to be perfect to be real.

Lynn Yamada Davis was a retired engineer, 63 years old, when she and her youngest son started filming cooking videos together during lockdown, mostly to keep his camera skills sharp. Cooking with Lynja grew into millions of followers before her passing in 2024, and by every account, she spent those years doing something that brought her, and a great many strangers, real joy.

What This Means for You

If the word retirement has been sitting in the back of your mind as something to dread rather than build toward, it might be worth asking what, specifically, you're actually afraid of losing. Usually it isn't the work itself. It's the identity, the structure, the sense of mattering that got fused to a job title over decades of building something. Those are real losses worth taking seriously. But they aren't the only available outcome.

In my experience as a life coach, the women who move into this chapter with genuine excitement are almost always the ones who stop asking what they're supposed to do with the time, and start asking what they've always wanted to make, learn, or become, back when there was never enough time to actually try.

When one chapter of your life has come to an end, another one is just beginning. Perhaps it's simply worth pausing here, gently, to notice that the time ahead is finally, entirely your own.

Ready to Design This Chapter on Your Own Terms?

If you're approaching this stage and want it to feel like a beginning rather than an ending, you don't have to figure out the shape of it alone. Book a Free 30-Minute Chat with Asi Efros to talk through what this next chapter could actually look like, built entirely around what you want 👉 Book your free 30-minute chat here

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