Think Twice Before Jumping Into Business With a Friend

Never make assumptions about pay and ownership, said Marilyn Goldman, a career counselor with offices in the District and Rockville. Whatever promises are made should be put in writing. "People forget," she said.

Things with his friend can get a bit sticky. "It is so hard to go into business with friends," said Malcolm Munro, a career coach in Germantown. "It's like going into business with family."

You really have to examine the relationship. Can it withstand the pressure? Will you be able to say the tough things that need to be said?

"In a sense, it's a marriage," Munro said. "And if there was the business equivalent of a prenup, that would be wise." Because when the partnership breaks up, "it can be more devastating than when it's just two business partners."

Goldman said success with this depends in part on maintaining boundaries. "Playing too many roles gets messy." If you're going to work for friends, it's best to separate professional everyday activities from the social activities.

Perhaps the trickiest questions of all are those he needs to ask himself, though. What is his personal appetite for risk? How can he mitigate his own exposure?

Anyone considering a leap like this has to take a close look at his or her bank accounts and household cash flow. Can a working spouse cover the gap if the business falls apart? What about benefits, such as health insurance?

Another consideration is how quickly the person could find a new job. To shorten that span, he or she should continue to maintain contacts and professional affiliations in the old field awhile. Poke around and see if there's a possibility of returning to the old job if need arises.

But safety shouldn't be the only concern, Moore said. "After the due diligence is done, it is important to check in with the heart," Moore said. "Life is not just about steering clear of any risks or entering into situations with our heads stuck in the sand. There are experiences that make us feel alive and passionate, and those can be very valuable."