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A Hopeful Future for Midlife Entrepreneurship

Read the inspiring stories of these three entrepreneurs, then submit your own story of entrepreneurship to Next Avenue

By Chris Farrell

Carline Bengtsson, age 59, retired in September 2019 after a nearly 27-year career as an engineering program manager with Medtronic, the global medical technology company headquartered in Minneapolis. She launched her for-profit social enterprise Dine4Dinners in June 2020, despite the pandemic. "I would say I got the idea on my way out the door at Medtronic," she says.

Two side-by-side photos of midlife entrepreneurs. Next Avenue, second act business
From left, entrepreneurs Bev Jennings and Carline Bengtsson  |  Credit: Bev Jennings/Carline Bengtsson

The idea for her venture came from connecting the dots. The first dot was how she and her Swedish husband Lars Johan Georg Bengtsson loved to entertain at their home. Carline Bengtsson would cook her "mosaic" recipes that reflected her Jamaican roots, growing up in St. Paul, Minn., visiting Scandinavia with her husband, working at Medtronic's European headquarters in Switzerland, trips to Asia, and elsewhere.

Bengtsson is self-funding Dine4Dinners and its payroll is "me, myself and I," she chuckles.

When her husband passed away in February 2012, she wrote a cookbook with the encouragement of friends that included her mosaic recipes. "Carline's Fork & Cork: Simply Delish!" was published in January 2015.

The other dot reflects her experience cashing in her remaining 19 recognition points from Medtronic. The points are typically turned into gift cards, retail items and the like. Hers went to support the nonprofit food organization, Feed My Starving Children. She learned that her 19 points would feed one child for 19 weeks.

"That was my 'aha' moment," she says. "I need to use my cooking to give back."

Bengtsson is self-funding Dine4Dinners and its payroll is "me, myself and I," she chuckles. She is hired to come into the home of the host giving the dinner (or some other meal) with guests. She sets the table and cooks one of her mosaic meals.

Key to the enterprise is one-quarter of proceeds go to a food charity organization chosen by the host. She's currently booked through August, 2022. She also raises money for food organizations through events and partnerships. "It's about paying it forward," Bengtsson says. "It has worked well."

The Swelling Ranks of 50-plus Entrepreneurs

Bengtsson is part of a large, growing and yet still deeply underappreciated movement: The swelling ranks of 50-plus entrepreneurs, new small business owners, solopreneurs and self-employed. According to figures compiled by the Kauffman Foundation, about one-quarter of new entrepreneurs were ages 55 to 64 compared to nearly 15% in 1996.

Self-employment also increases with age. In "Contract Work at Older Ages," three economists found that among those with any work activity, the share of self-employment as the main job is under 20% for workers below age 50. The share rises to 25% for ages 55 to 59; 46% at ages 65 to 69; and 68% for those ages 75 to 79.

Age even plays a critical role in the exclusive club of high-octane venture capital backed businesses. In "Age and High-Growth Entrepreneurship," four economists focus on the founders of "growth-oriented" firms, the kind of companies that have large economic impacts and are often tied to improving living standards. These corporate dynamos are popularly associated with youth, such as Evan Spiegel, founder of Snap (Snapchat's parent company) or Jack Dorsey, co-founder of Twitter. But conventional prejudice is wrong — deeply wrong.

"We find that age indeed predicts success, and sharply, but in the opposite way that many propose," they write. "The highest success rates in entrepreneurship come from founders in middle age and beyond."

Think about that for a moment.


Of course, the vast majority of new businesses and social enterprises started by 50-plus entrepreneurs aren't transforming ventures. They're mostly self-funded with self-employment popular, and a handful of employees at most. The enterprise provides a paycheck to help pay the bills and provide purpose in the latter stages of life.

The Pursuit of a Dream

"Older Entrepreneurs are brashly stepping into the start-up ethos," writes Kerry Hannon in her book, "Never Too Old To Get Rich: The Entrepreneur's Guide to Starting a Business Mid-Life." "Some, admittedly, have been elbowed into opening a business after a corporate downsizing or an early retirement package. Others have been drawn into it by burnout, or the desire to pursue a dream or return to a childhood passion."

Jennifer Dorr, age 54, pursued her dream not long after she and her husband moved from New Jersey to Pinellas County, Florida some four years ago. He could do his business remotely and she took on some part-time work to get to know the community and decide what she wanted to do next.

"My husband said, 'aren't you bored yet?'" Dorr says. "I said, 'I think I am going to start a business.'"

Dorr had a lengthy career in the beauty industry. She decided to open a women's upscale clothing store that specialized in meeting the needs of locals rather than depend on tourists. She had briefly owned a small business when she was 28 years old, an entrepreneurial experience that came in handy.

A midlife business owner standing outside her shop. Next Avenue, second act business
Jennifer Dorr  |  Credit: Jennifer Dorr

She found a roughly 1,000 sq. ft. downtown retail space in Dunedin some ten minutes from her home. She came upon the space on a Wednesday and the application to the owner was due on Friday. She drew on her earlier experience to quickly draft a business plan.

She didn't get the space initially, but she did when financing fell through for the business picked ahead of her. Citrus Styles opened for business in October 2020.

Dorr works six days a week and is having a blast. "I hit the ground running," she says. "The business is doing great."

Stories like these still aren't highlighted enough in the entrepreneurial ecosystems that have developed in most metropolitan areas and towns around the country over the past quarter-century.

That's the experience of Elizabeth Isele, a pioneering advocate for older entrepreneurs. Among Isele's many initiatives is founding or co-founding the Global Institute for Experienced Entrepreneurship and SeniorEntrepreneurshipWorks.

When she first started talking at conferences and gatherings about people starting their own business when they were 50 years and over back in 2012 "people would look at me like I was a raving lunatic," she laughs. "A lot has changed. But not enough."

The experienced-worker-turned-entrepreneur has a comparative advantage over their younger peers. First and foremost, they have experience to draw on. Their experience allows them to tap into their creativity and practical wisdom to solve problems for customers.

Risk Taking is Even More Important Than Resilience

Older entrepreneurs typically have some financial resources to draw on to start their business, although the biggest commitment is time and energy. They have developed networks they can rely on for guidance and support that boosts the odds of longer-term success.

If we really want to get the economy working for people of all ages, then society and public policy should focus more on unleashing the experience and the accumulated human capital of older entrepreneurs-to-be.

"Even more important than resilience, they're willing to take risks," says Isele.

Beverly Jennings is a risk taker in her 60s. She worked in various management positions at health care behemoth Johnson & Johnson for more than three decades, with her last position as head of global supplier diversity & inclusion.

She had the idea for her business while working at J&J, but with her demanding job, she put off working on it until she retired in October 2019. She started Jacksonville, Fla.- based SEE Company the following year. (SEE stands for See Everyone Elevate.) The pandemic didn't deter her at all.

"I always said there will be time when I retire from J&J," Jennings says. "I'm building a business from scratch and it's enjoyable."

Jennings is self-funding the business, although she says she has interested investors in the wings. SEE currently is comprised of two major initiatives. The first is a focus on providing business advice, coaching and consulting to help firms grow while cultivating diversity and inclusion. Many of her clients are women-owned and minority-owned businesses.

Her other venture is a collaboration with a group of women-owned businesses and organizations that recently launched a collection of high-end clothing for women, with an ambition to expand its offerings into other parts of the clothing trade, including men.

"This will be a global brand," Jennings says. "That is the intention."     

To quote from the band Chicago, we're at "only the beginning" when it comes to mid-life and late-life entrepreneurship. That prospect is one of the most hopeful economic and social messages to emerge in recent years. If we really want to get the economy working for people of all ages, then society and public policy should focus more on unleashing the experience and the accumulated human capital of older entrepreneurs-to-be.

In something of a virtuous cycle, their businesses and social enterprises will provide an income and meaning in the second half of life; they'll hire younger generations; and they'll teach them the start-up ropes "shortening the learning curve of younger people," says Isele.

Taken altogether, with 50-plus start-up owners in the vanguard, entrepreneurship in America will grow and expand. Sounds good, doesn't it?

What's Your Business Story?

Every business has a story — and if you're running a business in your 50s or 60s we want to read yours. We're seeking personal essays about your second-act businesses.

From April 18, 2022 through May 31, 2022, readers may submit a 500-word original essay about their experience starting and running a business after age 50. The Next Avenue editorial team will select 6 essays, representing a diverse collective of voices for publication on the site this summer.

We're looking for insightful essays that discuss why you started your business and when, what's surprised you, your biggest challenges, your greatest joys, and what advice you'd offer others thinking about starting a business after 50.

Learn more and submit your essay here.

Editor’s note: This article is part of America's Entrepreneurs, a Next Avenue initiative made possible by the Richard M. Schulze Family Foundation and EIX, the Entrepreneur & Innovation Exchange.

Photograph of Chris Farrell
Chris Farrell is senior economics contributor for American Public Media's Marketplace. An award-winning journalist, he is author of the books "Purpose and a Paycheck:  Finding Meaning, Money and Happiness in the Second Half of Life" and "Unretirement: How Baby Boomers Are Changing the Way We Think About Work, Community and the Good Life." Read More
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