Q&A: Selling Your Business Without Going Crazy

Are you really ready to move on? Many entrepreneurs think they are. But when closing day arrives, so does heartache. Anne Hartman founded the Truro, Mass., consultancy Working Differently to help baby boomers transition into their next stage of life. We asked for her advice on how an entrepreneur can happily say goodbye to her company.

What are the toughest psychological hurdles for entrepreneurs selling their companies?
One of the ones that I hear often from people who have recently sold is, "How do I tell people what I'm doing? What do I say? I'm standing on the first tee of the golf course and I'm supposed to be happy because I'm playing golf in the middle of the day and somebody says, 'What do you do?' Do you explain it in terms of what you did, is that enough? Or do you explain it in terms of what you're going to do or what you want to do?"

For business owners this is a two-part, anxiety-ridden decision. The first decision is "Should I sell, who do I sell it to, how do I prepare the biz for sale?" The second is, "What am I going to be doing with my time?" Most people don't want to step off the side of the Earth. They still want to be a player. They still want to be doing something with purpose, something that gives their life meaning. [But] often the first decision is postponed and only doubles their workload at a time when they want less work. The danger is the decision will be postponed to a point where, if they're not careful, they will make too hasty a decision.

How should a good planner prepare?
The first step is stepping back and looking at what motivates us. Are we more motivated by the need to lead people, or receiving acclaim, having visibility in the community, or are we more motivated now by the equal need to lead and be visible and by a stronger need to give back to community than was there before?

The next step is to engage family and friends in the conversation. There can be surprises. I had a guy and his wife in a workshop together. He asked about relocation and said, "We're going to be moving to Florida." She looked at him askance—she had no idea he was thinking about this!

Third, begin to explore options even while you're working and trying to sell your business. Go out of your way to reach out to people who are older than you or ahead of you in this decision process and find some role models.

Finally, think about your value in the marketplace if you are going to work. What do you have that the marketplace needs and why?