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Career Shift: 'You're Never Too Old' Success Stories

These 50+ entrepreneurs entered and are thriving in fields that some say are for people half their age

By Gwen Moran

Career advisers say “follow your passion,” but when you hit your 50s and 60s it can sometimes feel as though the ship has sailed on your dream job. But these stories of successful entrepreneurs over the age of 50 prove that it’s never too late to reinvent yourself, even if you hanker to enter what some might consider a “young person’s” field.

Traveling the U.S. as Brand Ambassadors

After Silvana and Allan Clark’s youngest daughter, Sondra, went off to college in 2008, the couple from Bellingham, Wash., got the itch to travel and try something new. Silvana, then 56, had been a writer and professional speaker and Allan, 59, was a trainer of school bus drivers.

They were fans of the Nashville-based charity Soles4Souls, which provides footwear for poor and homeless people in the United States. So Silvana, a writer and professional speaker, approached the nonprofit with an idea: If Soles4Souls would buy the Clarks an RV, she said, they’d drive it around the country, giving free shoes to the needy and promoting the organization.

The Clarks were effectively offering themselves up as brand ambassadors, a type of work usually done by people three decades younger.

“Brand ambassadors are usually spunky, cheerleader-type college students with trim bodies and no gray hair,” Silvana says.

The charity signed on and gave them the titles “Sole Ambassadors.”

“We found jobs as brand ambassadors, even with our semi-firm bodies and a few grey hairs,” Silvana jokes.

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For 19 months, the Clarks lived out of a Soles4Souls-branded RV, traveling to 42 states, never once returning home. After arriving in town, they’d receive shipments of roughly 1,000 pairs of shoes and would sort, organize and distribute them out of the RV.

When that gig ended, they took on new ambassadorship roles by embarking on a 22-city tour distributing hygiene products to tornado victims in the South for Avon’s charitable arm, Avon Cares, out of an Avon-provided van.

These days, Silvana and Allan are driving separate Avon vans around the country, helping the company recruit representatives. They’re paid salaries, plus travel expenses.

“When you’re working with nonprofits this way, there’s a real feeling that you’re helping people,” Silvana says. Being brand ambassadors, she says, “lets us visit places we never would have seen — and be paid for it.”

Jumping Into the Trampoline Business

Rick Platt, 62, had owned a successful scrap metal business in Beverly Hills, Calif., for 12 years when, in 1996, he discovered his employees had carried out a sophisticated embezzlement scheme, leaving him bankrupt.

After a long-fought court battle that ultimately awarded him a seven-figure settlement, Platt felt invincible and started looking for a new venture. In early 2003, after meeting a Las Vegas group of athletes trying to promote a trampoline-based sport they’d invented, Platt decided this was it.

(MORE: Older Entrepreneurs Are Better Than Younger Ones)

Friends told him he was crazy to go into the trampoline business, but Platt disagreed.

So he bought the patent for the athletes' trampoline and got to work, creating what is now known as Sky Zone Indoor Trampoline Park, an all-trampoline playing field in Las Vegas that was an instant hit with kids. In 2004, he began charging $7 an hour and amassed 800 customers in the first month.

Since then, the unlikely playtime and birthday party host has turned Sky Zone into a bouncing franchise business with more than $52 million in annual revenue. The parks now offer “open jump” sessions, parties, corporate team building events, leagues and tournaments, fitness classes and school programs.

“It’s amazing what you can do if you just focus,” Platt says.

Within eight years, Platt has gone from having no experience in the family entertainment sector to owning a company with more than 30 locations in the United States and Canada.

Heading Up a New Fashion Business

When Andie Cohen-Healy of Altadena, Calif., began planning her wedding in 2008 at age 46, she soon grew frustrated. The MTV satellite executive felt the puffy tulle veils and rhinestone headpieces looked like they were created for much younger brides.


“I didn’t feel compelled to do what 25-year-olds were doing,” she says.

Then, Cohen-Healy had an idea — and soon, a fashion business.

A chicken owner, she enjoyed collecting the beautiful feathers her birds molted. Cohen-Healy also loved making crafts. After tucking a few chicken feathers around a silk flower, she quickly realized that she’d created a beautiful wedding headpiece.

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It didn’t take long before friends started asking her to design feathered headpieces for their weddings. “I started waking up in the middle of the night, designing them in my head,” she says.

At first, Cohen-Healy ran her headpiece business as a sideline while working at MTV. But in 2010, she left her job and made the home-based business, The Feathered Head, a full-time effort, selling headpieces and hats through her website, by referral and at craft shows. Its tagline: A Winged Work of Art Will Inspire the Senses.

“I did a complete 180, despite naysayers stating that a total career change at my age was professional suicide!” Cohen-Healy says. “I went from MTV satellite executive to feather artisan and couldn't be happier.”

Her operation is growing steadily; a single show may bring in $1,000 in sales.

The royal wedding of Kate Middleton and Prince William, with its plethora of hats and fascinators (headpieces often made of feathers, flowers, beads or other materials) was a heady time for Cohen-Healy.

Today show co-hosts Kathie Lee Gifford and Hoda Kotbe wore a few of her feathered headpieces and the “wedding of the century” made women more interested in beautiful millinery.

Cohen-Healy is now inspired to encourage others to shift fields and start businesses, even ventures typically launched by entrepreneurs in their 20s and 30s. “It's now vital to me to mentor and inspire other people, particularly women, to overcome their doubts and not let age be an issue,” she says.

The Secret to Their Successes

As bold as these start-ups sound, all of these entrepreneurs hedged their financial risks in key ways that helped them achieve success.

The Clarks negotiated deals to receive salaries and were also given travel expense budgets, which kept their costs down.

Instead of investing only his own money in the Sky Zone locations, Platt adopted a franchise model, where franchisees took on part of the financial risk.

Cohen-Healy built up savings and worked on growing her business for a year while still at her day job before making the leap.

One more thing the Clarks, Platt and Cohen-Healy have in common: the conviction that making the leap was the best decision they ever made.

Gwen Moran is a small business authority and author of The Complete Idiot’s Guide to Business Plans. She has been running her own businesses since 1992 and was a national finalist in the U.S. Small Business Administration’s Young Entrepreneur of the Year awards competition. Read More
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