Leadership

What do you have in common with Keller, the hit-man hero in a series created by mystery writer Lawrence Block? Perhaps more than you think. In one book, Keller decides he is sufficiently flush to retire and takes up philately to fill his leisure hours. But the stamps he covets prove costly. Soon, the erstwhile assassin resumes whacking people to support his hobby. OK, your line of work is different. But if you retire, you may find the experience just as fleeting.

Business owners may dream of kicking back, all the way back, after years of full-throttle company building. Yet many return to the fray, suffering adrenaline withdrawal and lured by new opportunities. No one has quantified this breed's failure rate when it comes to permanent retirement. But numerous entrepreneurs tell the same tale: "I sold the business and figured I had it made, so I retired. That lasted about three months."

We don't advocate working forever. Still, while planning retirement you should at least consider that it might be of limited duration. A year from now, you'll be driving to the golf course and spot a lunch truck gussied up as a medieval-theme restaurant. Half an hour later, your clubs are in the closet and you're on the phone to your banker.

There's no right or wrong way to take a break, of course. One entrepreneur's dream sabbatical can be the next one's nightmare. But a pause requires a different approach from a true finale. Here's some advice on life between gigs from retirement experts and from entrepreneurs who have actually given it a try.

Reconnect, get healthy, and enjoy

Creston Owen imagined retirement as a boat and several thousand Caribbean sunsets. But in 1994, when he sold his second company, family obligations tethered him to his home in Manassas, Virginia. Owen took a three-month break, including a six-week RV trip. Restless cruising the highways of Pennsylvania and Tennessee, he sketched plans for his next business, Falcon Communications Solutions, launched in 1995.

Owen proposes that entrepreneurs in "transitional" retirement do three things. First, rebuild personal relationships you may have shortchanged, including those with extended family. Second, tend to your health with a diet and exercise regime. "Entrepreneurs don't take care of ourselves," he says. "Take part of that year and cut 20 pounds." Finally, he suggests buying one nice thing for yourself or your family. "The point is that even if you're not at the end of everything, you're at the end of something," Owen says. "Reward yourself."

Reorder your priorities; do some good

Running a company leaves scant opportunity to personally assist immunization programs in Africa or build irrigation systems in rural Latin America. Yet those are the sorts of experiences that change people and supply direction for meaningful lives, according to Marc Freedman, founder and president of Civic Ventures and author of Encore: Finding Work That Matters in the Second Half of Life. "Join the Peace Corps. Live in a part of the world where there's tremendous need," advises Freedman. "This is your chance to lift yourself out of your comfort zone."

Freedman says such experiences challenge entrepreneurs to apply business skills to world problems. Consequently, their next ventures are more likely to have an element of social responsibility. One entrepreneur, Gary Maxworthy, retired from his large food brokerage and joined the antipoverty program VISTA. "He realized that food banks throughout California were handing out canned and processed food while growers were throwing out tons of produce because it wasn't supermarket quality," says Freedman. "So he developed a system that distributes fresh food instead."

Work it

Retirement is murder on your business skills, warns Dennis Pushkin. He should know: Pushkin has retired three times. In 1980, he sold his furniture manufacturing business and, though he was only 31, settled in for a lifetime of boating and fishing. In 1986, he was back with an automobile detailing franchiser. He sold that in 1989, coached kids' sports until 1992, then became CEO of the U.S. arm of a British dry-cleaning company. In 1995, he left to play golf--200 days a year. Not surprisingly, Pushkin was easy pickings when, in 1999, a relative, Andrew Wetzler, suggested they start search-optimization company MoreVisibility.

During each retirement, Pushkin says, his business muscles atrophied. "When you're successful in business, you're in top business condition," he says. "I would be talking to friends who are still in business and thinking, This isn't me. This isn't the way I used to be." Pushkin advises staying in fighting trim by maintaining a role in your former company, consulting, or serving on boards. "You can turn the radar down a bit," he says. "But keep it on."

Know yourself

When Selina Lo retired, in 2002, at age 42, she felt compelled to try something different. "I thought I should develop the artistic me, the craftsman me," she says. So after a decade at technical companies, including Centillion Networks, which she founded in 1993 and sold in 1995, Lo tried jewelry making. She studied metal-smithing and beading. She held two shows of her work in Hong Kong and foisted her creations on friends and family. But it really wasn't her bag. Two years later, Lo joined the start-up team at Ruckus Wireless as CEO. Now she wishes she had spent more time relaxing, reading, watching television, and enjoying "the luxury of home." Lo's advice: "Don't push yourself to do things you think you should do."

Have enough to retire, twice

"There's no one way to rejuvenate," says Deborah Russell, director of work force issues at the Association for the Advancement of Retired Persons. But financial concerns are universal. Entrepreneurs who aren't sure their retirement will work out should plan for a second one as well. That means putting aside money to invest in another business but also "making sure you have a sufficient nest egg in case for some reason that company is not as successful as your last one," says Russell. "If all goes well, you'll add to your retirement portfolio." But you will also be ready, Russell says, for "the world of uncertainty."

Resources

For more ideas and insights on creative ways to recharge, take a look at the following books: Encore: Finding Work That Matters in the Second Half of Life, by Marc Freedman; Don't Retire, Rewire!, by Jeri Sedlar and Rick Miners; and Retire Smart, Retire Happy, by Nancy K. Schlossberg.