Gen X’s Retirement Strategy? Start a Small Business

Many professionals work to achieve such an opportunity, but Dindal found the role unfulfilling. In 2015, without a plan for what she might do next, she walked away from the only profession she’d known.

“There was a lot of corporate red tape, bureaucracy and politics,” Dindal recalls. “It just wore me down.”

Dindal was fortunate to have saved enough to last about a year with whatever her new venture might be. She and her partner turned to retail, launching a boutique clothing store online that became the first of four ventures Dindal has launched in the past decade.

Besides e-retail, Dindal is a content creator with 6 million followers on TikTok, a following that paved the way for Dindal to become a standup comic who goes on tour under the stage name, the “Real Slim Sherri,” making colorful observations about Gen X.

Dindal’s personality has earned publicity for her and her businesses, including appearances on “Good Morning America” and “Live with Kelly and Mark.” Dindal now has the flexibility to scale back working when she likes while ensuring her adult son and two younger daughters have a stronger financial foundation than she did.

“I’m trying to build a legacy for my children,” she says. “There were times in my life I needed help and didn’t have that.

Professional networks can boost your business.

Buhrdorf of ZenBusiness notes Dindal’s success demonstrates that individuals can become entrepreneurs later in life.

“There’s a myth that you need to work for someone to be secure. That's just not true,” Buhrdorf says. 

Many Gen Xers have spent more than 20 years on a specific career path and can rely on that experience to start their own company.

That’s the path Sara Trujillo, 60, of Westchester County, New York, chose in 2013 to launch her public relations firm after serving as vice president at DBA Public Relations, where she led campaigns for companies ranging from Amazon to Toshiba.

Trujillo has leaned on prior connections and her knowledge promoting consumer products with a tech twist. Recently, she has branched out to other sectors to grow her business.

“Keep learning new skills that spark your curiosity and strengthen your capabilities” is advice Trujillo offers would-be small business owners. She plans to work another seven to 10 years and has modest goals. 

“One goal is to make improvements to my home so I can age in place comfortably and securely,” she says. “Staying engaged with work also enables me to travel and to have the means and flexibility to support my daughters in their future endeavors, should they need it.” 

Core customers can sustain your small business.

Judd Wiggins, 55, and Mark Taylor, 56, took a different approach in opening Savannah Square Pops. Wiggins is a “recovering attorney,” as he likes to joke, and Taylor previously was a systems administrator for a psychiatric office.

When they met in Birmingham, Alabama, they shared a bond over careers they deemed unfulfilling. So, they went all in on an idea Wiggins conceived of years earlier after trying a gourmet buttermilk-flavored popsicle at an office event. Another popsicle brand had a foothold in Birmingham, so the couple turned to Savannah, a city they enjoyed visiting that has a strong tourism base.

The store opened in 2015 on Martin Luther King Jr. Boulevard, which is in Savannah’s historic district but removed from most of the established restaurant and retail favorites. Wiggins and Taylor brought their products to farmers’ markets, weddings, community gatherings and birthday parties to gain customers.  

Failure was not an option.

“We sold a historic home; we cashed out our 401(k)s,” says Wiggins. “We had pushed all the chips in the middle of the table. There was nothing left to do except to make this succeed.” 

That commitment helped Savannah Square Pops find its core customers. A parent attending a birthday party that the duo catered asked if they could create events for Girl Scouts. Juliette Gordon Low, founder of the Girl Scouts, lived in Savannah, and hundreds of troops visit the city each year. In 2025 alone, Savannah Square Pops held more than 250 two-hour events for girl scout troops, who often turn into repeat customers during their Savannah visits.

“This is the house that the Girl Scouts built,” says Wiggins, who estimates 20 percent of their business is attributed to the scouts’ business. “Without them, we wouldn’t need this kind of space.”

A known commodity at this point, the popsicles are now offered at various local restaurants — sometimes for adults in an alcoholic drink — and are shipped nationally. With so much success, retirement isn’t on the agenda.

“We’re going to keep doing this until we can’t [anymore],” Wiggins says.