Exit Strategies for Corporate Dropouts

Work nine to five -- then from five to two

Once you decide to make a move, there's inevitably a pause before you can follow your muse. Corporate dropouts concede that one of the most difficult things is to maintain the same level of enthusiasm for the job you're about to leave as the venture you're about to start. The little things, such as staying a bit later to finish a project or going out for drinks with coworkers, tend to fall by the wayside. Ian and Shep Murray, brothers who left the worlds of public relations and advertising to start a whimsical clothing company called Vineyard Vines, admit that clock-watching became the norm. "You work your job from nine to six, and all you want is for six o'clock to come so you can work on your business," he says. "That's when our day began."

Of course, it's not unnatural for achievers to wonder if they can pull off doing both the day job and the dream indefinitely. "Can we enjoy the security of six-figure-plus law-firm jobs and start a business on the side?" Finger asked himself. Ultimately, though, he realized that "the only way things get done is if you give it 100%. And if we tried to balance working at the law firm and the business, neither one would get a fair shake."

Corporate dropouts forget that the relationships they've built are part of an entire career story that they take with them. It's important they speak with their employer when going through the transition.

Turn on the warning lights

Dropouts also need to manage their exits carefully. "They sort of forget that these relationships they've built, the positions they've held, are part of an entire career story that they take with them," says Lisa MacKenzie, who left what was then Cunningham Communication in 1993 to start her own marketing firm. "So it's incredibly important for them to have a conversation with their employer when they're going through the transition."

Graceful exits aren't just a matter of honor -- or even of keeping doors open. They're good business. MoPho's Dyer keeps in touch with the people he used to work with because, he admits, his company could be using Warner Bros. content in the future. Plus, he adds, "You don't want to mess with the 900-pound gorilla." SeamlessWeb's Finger gave his law firm ample warning before he left, fully aware that his fledgling business idea depended on 900-pound gorillas like his employer as clients. Finger first presented his business plan to a senior partner as a friend's idea. Three months later, he again broached the subject, adding that he was thinking of leaving the firm. The soft sell worked, and he was able to circulate the plan in the firm, which ultimately became a beta client. In fact, the partner's initial enthusiasm was "one of the impetuses for us going through with it," says Finger.

Coworkers are a constituency that must be managed as well. Ellerton was already well into her fitness-club plan when she took a job with Arch Insurance Group in October 2003 to help overhaul its IT infrastructure, a post she accepted with the understanding that she planned to leave in a year's time to pursue her idea. But Ellerton "didn't advertise [her short horizon] within the company," she says. "I didn't offer it upfront, because what I was doing in the company was not incredibly popular." She knew that if she were viewed as a short-termer, her work might have been met with more resistance. "I still treat it today as if I'll be here for a career," she says.

Who are you?

Dropping out brings with it trepidation -- and not just with finances. "There's very much the identity that goes along with being part of a corporation, and that's a little scary to give up and wear workout clothes all day," says Ellerton. That's why it helps to have a partner. While Ellerton will be doing her yoga alone, SeamlessWeb's Finger and Appelbaum, MoPho's Dyer and Moloney, and the Murray brothers of Vineyard Vines all made tandem leaps. In the weeks leading up to their departure, Shep Murray would call Ian several times a day pretending he'd quit. When Shep actually gave notice, Ian understandably didn't believe him. When Shep finally did, though, Ian went straight to his boss and did the same. For the brothers, scraping by, even failing at their own thing, was no worse than toiling in quiet desperation. Says Ian: "There's always going to be a job out there if you're coherent and can put a sentence together."