A few years ago, my husband, Gary, instituted a two-month paid sabbatical for anyone who has worked at least five years at Stonyfield Farm. The program has been one of our company's most popular benefits: So far, almost 200 employees have taken advantage of it. I am ever hopeful—and ever doubtful—that one day, Gary will be among them.

Entrepreneurs understand in theory the restorative value of downtime, but they are notoriously tough to pry from their companies for extended periods. The reasons are fairly obvious. No. 1 is fear the company won't progress—or may even stumble—without its leader. Others include addiction to the work and to the pace of work, and unease at being separated from the founder's mainspring of identity. Unless the entrepreneur is burned out, persuading him to take off a couple of months or, heaven forbid, six months to a year won't be easy. It's like asking him to become someone else for a while—to stop doing things he loves so he can do things that he and his family might love.

Still, I'm a big advocate of career breaks, both for active entrepreneurs and for serialists between ventures. Full stops are a reminder that life is more than what happens in the interstices of business: They provide an opportunity not just to rest but also to change and grow. Given sufficient scope and thoughtfully managed, a sabbatical can be a life stage unto itself. The entrepreneur, his relationship with his family, and even his company may sustain benefits far beyond those of a mere vacation.

Jay W. Vogt, a Boston-based organizational consultant, is my sabbatical poster boy. It's not just the duration of his leaves that impresses me—it's also how hard he works to make them happen and the importance he invests in them. In 1987, when Jay's business was just five years old, he and his new wife, Stephanie, traveled around the world. The trip took Jay away from his young company for almost half a year. And this was before the Internet. "We fast-forwarded our marriage," Jay told me. "We lived five years in five months. It was an unbelievable gift to ourselves. I still get teary thinking about it."

Then, in 2004, Jay took off another six months to live with Stephanie and their teenaged daughter, Camilla, in Mexico. The couple wound up buying a retirement home there, and Camilla, now in college, has become so enamored of travel that she spent last summer in Senegal and will study in France her junior year. "I look at how transformative these trips were for our family," Jay told me, "and ask myself not how did we do this twice but why we didn't do this more often."

Jay and Stephanie managed to save what they thought the vacations would cost and also accounted for the shoulder times, before and after, when Jay would be winding down and then rebuilding his business. Jump-starting his practice after each sabbatical was easier than he imagined. Before the couple embarked on their world tour, a respected colleague warned Jay that he was committing professional suicide. Instead, "my clients' actual reactions shocked me," says Jay. "There was an almost universal respect and a wistful envy—a sense of 'Gosh, I wish I could do that.'"

Of course, the megatrip is just one way to spend a sabbatical. If the goal is to take a break from business, then holing up in your den to write a screenplay or embarking on a home-improvement spree or training for an Ironman is equally valid. But long vacations are a good way to at least start sabbaticals, because all family members are simultaneously lifted out of their routines. That makes the entrepreneur's reentry into domestic life less jarring.

Jim Garland, founder of a private-jet-cleaning company called Sharp Details, in Dulles, Virginia, contrived a plan whereby he, his wife, and their four kids would visit 30 countries in nine months. They would travel two or three weeks at a time, then settle down for a month of home (as it were) schooling. Away from the familiar, always on the move, the Garlands soon settled into a pattern of no patterns. "We had no 'normal' on the road," says Jim's wife, Carrie. "It would have been harder if he'd taken a sabbatical and stayed home."

Even so, the initial transition was rocky. "I love my family to death," says Jim. "But I went through the withdrawal from my engagement with work to being with my kids 24/7. I asked my wife, 'Are they always this crazy?' "

The problem isn't that entrepreneurs find so much family time onerous but that they and their families have been experiencing time differently. Most company founders charge ahead at warp speed, grappling with one huge challenge and momentous decision after another. Their families progress, too, but they do so according to the gentler rhythms of biology and society. School year follows school year. Another birthday. Another drama-club production. Consequently, when entrepreneurs take months off from work, they are transitioning not just from fast to slow (slower, anyway) but also from making things happen to experiencing life as it naturally unfolds. The result can be more stress rather than less.

Prospects for deepening familial bonds instead of annoying one another improve if the family works out in advance how the entrepreneur will integrate herself. How much contact will she maintain with the office? What will be her role in the household during her months as a civilian? How do her plans for the period jibe with those of other family members? What can the family do that will make the best use of its time together?

Richard Humphrey regrets not having had that discussion in 2007, when he decided to take a year off between companies. After working 80 hours a week to build a product-design firm, Richard wanted to "live all the dreams I had deferred" before launching Kavoo Air, a private air-taxi service in New England. "I assumed Michelle had embraced my dreams," he said, speaking of his wife, "but that wasn't the case. We had a new baby, and she wanted to buy a house and settle down, not go live in France for a year."

The couple compromised with a four-month sojourn in Europe and Tahiti. After that, Richard was largely on his own. He went winter camping, visited friends, and scuba-dived in the Great Barrier Reef. While home, he enjoyed taking his son to the playground and remodeling their new apartment. But he now believes he inadvertently pushed his wife away by "being in her space too much." The marriage is strong, Richard says, but the sabbatical taught him that "our rhythms are different. We were unaccustomed to being together full time. I'd been a workaholic. So my attitude was, 'I'm here—let's do something together!' But she was trying to kick-start her career after the baby, and I had too much time on my hands."

Sabbaticals—too rare and precious to squander—are among those things that, if not done right, probably should not be done at all. Sure, I wish Gary had given the kids and me a few months of his undivided attention back when everyone was still living at home. But it would have been worse if we'd tried and failed—if he'd turned restless or (shudders) used the time to cook up another business.

For entrepreneurs, the desirable outcome of a sabbatical will be rest and rejuvenation, but also a new understanding of how family life unfolds when they're not there to see it. Internalizing that knowledge, entrepreneurs will move in greater synchronicity with their families long after family members return to their own orbits.