"Someone handed me a check that set me for life," recalls serial entrepreneur George Jacobs, "and I was miserable."

The year was 1998, and the check was for $20 million. Jacobs, 50 years old at the time, had just sold American Limousine--the largest limo company in the country--to Carey International. But something felt wrong. With the lucrative check in hand, he walked the streets of his native Chicago for an hour and a half. "I should've been overjoyed," he says, "but I wasn't."

What ailed Jacobs that day--and for the next seven years--was the entrepreneurial equivalent of postpartum depression.

"I have seen so many people go into such deep depression after selling," says Judith Glaser, an executive coach and communications specialist who has counseled many entrepreneurs through transitions.

Postpartum Blues

The misery, she says, often increases when founders stay aboard to run their former businesses. That's because new management often takes the business in a different direction.

For founders, says Glaser, this is like someone "taking your child and performing plastic surgery on it. You believe they're destroying the beauty of this thing you've spent your whole life creating."

That's why Jacobs, for all his money, was blue for the next seven years. He stayed aboard, hoping to serve "as a buffer" between new management and his longtime staff. He remains proud of the work he performed in that role. But he does not recall the period fondly. "It's miserable when you're your own boss, and all of a sudden you're working for someone else. You're hurt. Your company is your child," he says.

How to Move On

To escape the postpartum blues, "You have to give yourself a different framework for your dreams and aspirations," says Glaser. For most founders, their company was the vehicle for their aspirations. With the company out of your control, you’ll need a new vehicle.

"You have to give yourself a different framework for your dreams and aspirations," says Glaser.

For serial entrepreneur Rick Stierwalt, finding a new vehicle was quite literal. After selling his first company, Concord Holding Corporation, in 1996, Stierwalt began returning weekly to his native Indianapolis--to train as a race car driver. He was 40 at the time and realized that it was "now or never" to pursue an ambition he'd first hatched as an eight-year-old.

"It was as hard a job as actually working," he recalls. "Thursday you practice, Friday you qualify, and you race Saturday and Sunday. Plus you really need to stay in shape. I raced at same tracks where I almost got killed going well over 100 miles per hour."

Acting on Your Next Ambition

By having another ambition to throw himself into, Stierwalt avoided the postpartum blues. And when he was ready to return to the business world, he was newly inspired. He even restructured his childhood list of ambitions, in anticipation of future transitions.

Based on the categories he saw in a goals list for AOL founder Ted Leonsis, Stierwalt reclassified his own list into categories such as "personal," "charitable," "travel," "financial," and "egotistical." Today he is the CEO of ATPA, the second largest third party administrator of employee benefit plans in the country.

And he is well prepared for his next break in the action.

As for Jacobs, his story, too, has a happy ending. During his seven years of misery, he realized that he'd be most fulfilled if he were in charge, once again, of his own limo company. In 2006, he cofounded Windy City Limousine and Bus. Today, Windy City is an $18-million company. Its customers include the Chicago Bulls, Harpo Studios, and the Make a Wish Foundation.

"I never considered a different business," he says. "This is what I know and love. And I’m good at it."