Working Doubletime

Having two (or more!) careers is ultrademanding, but the rewards can be just as great

own destiny.” And for black folks, she adds, that must be a priority.

Thompson is the quintessential multicareerist. This dynamic entrepreneur can be found in his Boston office Monday through Wednesday running the Summit Group Inc., a 15-year-old conglomerate that includes a computer systems integration company, an engineering services firm and six food franchises (four Subways, a Dunkin’ Donuts and a TCBY).

On Wednesday evenings, Thompson trades his business suit for a Delta Air Lines pilot’s uniform and spends the next three days flying the skies between the U.S., Mexico and the Caribbean. He returns home to his family on Saturday afternoons, turning his attention to his home and community (he’s on the national board of directors of the American Cancer Society, among other things). On Monday morning, it’s back to Summit, where, in addition to serving as chairman and CEO, Thompson dons a legal hat serving as in-house counsel.

That’s in an “ideal” week. The fact is, Thompson can’t always control his flight schedule, and conflicts do arise. Luckily, with more than 70 employees, he’s able to do much of his managing for Summit on the phone and on the run if necessary. It’s a pace Thompson concedes is not for everyone, but he is unsympathetic to those who claim generally that having more than one job is too much, too hard or too hectic. “We all have the same 24 hours, and if you take a look at what you’re doing, you’ll probably find you’re wasting a lot of it,” he says. “If financial success is a priority for you, if it’s way up there on the list, you’ll make the time.”

Now 46, Thompson was always a multilevel achiever. In high school, the Orangeburg, South Carolina, native was an Eagle Scout, honors student and star athlete. The first African American from his state to receive an appointment to the U.S. Air Force Academy in Colorado, Thompson completed jet pilot training, got his college degree and entered law school during his 11 years in the service. In 1980, he left the Air Force to fly for Delta, relocating to Boston where he received his law degree.

Summit began as a tax-planning firm. Thompson, who started with a bar exam buddy who was a hospital administrator, speculated that between pilots and doctors they’d easily establish a strong client list. He was right. He was also lucky. It wasn’t long before one of his clients asked him to invest in a shopping center with a group of doctors. He did, they turned it over in 18 months, and all made a sizable profit. That, says Thompson, “gave me the cash to do other things,” which, over the years, have included numerous real estate investments and several diversified businesses — some created, some acquired. His current companies grossed a combined $3.7 million last year.

There are two primary questions that people like Thompson always get: Why do you do it? And how do you do it?

Thompson’s responses to both are surprisingly simple.

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