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Career Shift: A Couple Manages Island Properties Together

When their industries flattened, Dann and Gail Jackson moved to their dream spot and began successful second acts in real estate

By Anne Miller | October 3, 2013

Dann Jackson, 60, and his wife Gail, 62, met as children near the Jersey shore and dreamed of returning to the seaside one day.
 
In the 1980s, the couple fell in love with their version of paradise, Bald Head Island, N.C. It’s a quiet locale where the Cape Fear River empties into the Atlantic, about 60 miles northeast of Myrtle Beach, S.C. Ferries provide the only access from the mainland and golf carts are the only vehicles allowed.
 
Hatching a Plan to Live Seaside

In the 1990s, just as they became empty nesters and their industries declined — Dann was a textile executive and Gail was an airline customer service supervisor for Piedmont and US Airways — the couple hatched a plan to move to their favorite island.
 
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They’d earn their real estate licenses, sell their 4,600-square-foot house in Greensboro, N.C., switch careers and start working together selling and renting properties along the North Carolina vacation coast.
 
A Change in Plans

Things didn’t work out quite so neatly, though.
 
Dann earned his license in 2000 and moved three years later to neighboring Southport, N.C., where he got a job working for a company that handled real estate on the island. Meanwhile, Gail stayed on at US Airways in Wilmington, N.C., 45 minutes from Bald Head Island. The couple maintained a long-distance relationship until 2004, when Gail earned her real estate license and retired from the airline.
 
Then the Jacksons moved to Bald Head Island full-time where they lucked into a dream opportunity: taking over a small island vacation property management company.
 
The real estate firm Dann had been working for owned another business that managed eight vacation rentals on the island. So the company agreed to let Dann focus on those properties and then to buy the subsidiary outright.
 
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“You know how they say timing is everything?” Dann says. “The timing was perfect.”
 
The Couple's New Life Working Together

Bald Head Island had fewer than 200 full-time residents and its property owners valued leaving their rentals in the hands of neighbors they trusted. The Jacksons were an ideal match.
 
In their new life, the couple markets the real estate, finds renters, handles the contracts and supervises the cleaning and maintenance staff. Serendipitously, some of the Jacksons’ skills from previous jobs — management, customer service and bookkeeping — have contributed to their success.
 
They’ve more than tripled the business and now manage 40 to 45 properties. The Jacksons envision their son, Shane, who is their operations manager and lives nearby with his wife and children, eventually taking over. (Their daughter Cari lives in New York City with her husband and kids; as a former US Airways employee, Gail gets free flights from Wilmington, N.C., to visit her.)
 
During the beach resort off-season, the couple spends mornings in their real estate office accompanied by their 155-pound mastiff, Ellie Mae. Then they adjourn to the country club for exercise and lunch, work a little more and ultimately wander home past spectacular waterfront views. Sometimes, they take their boat to the next town for dinner, bringing Ellie Mae along for the ride.
 
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Once spring arrives, the Jacksons jump into overdrive, renting and prepping their properties. Things reach a manic pitch during the summer high season months of June, July and August, when they clock more than 14 hours a day at the business.
 
“We don’t see ourselves really wanting to retire,” Dann says. “We’re fortunate to be doing something that we really enjoy and that is rewarding. And we’re doing better than we ever have in our lives. I think we’re going to be one of those couples who are going to stay in business together for a long time.”
 
Gail adds. “There’s no reason to give it up.”
 
Advice for Starting Second Acts Together

The Jacksons offer these tips for other couples seeking to follow their model and start second acts together:
 
Be honest about your ability to work jointly. Dann and Gail acknowledge that not all couples can work side by side — and those who aren’t cut out for it may face marital woes. “We just happen to be compatible enough to be able to be together all day long and go home together at night too,” Dann says.
 
Have a vision and stick to it, even if things don’t always go according to plan. The Jacksons say their worst time as a couple was when they were living apart, but keeping their end goal in sight pulled them through.
 
Go all in. With their kids grown, the couple didn’t feel overwhelming pressure to work like mad to rake in a substantial income. But they knew they couldn’t succeed by going only halfway.
 
“We just went for it,” says Dann.

Anne Miller is a freelance writer and editor. She has written for media outlets including Next Avenue, The Wall Street Journal and Slate.com.