How To Be Your Own Boss

Before you strike out on your own, make a game plan and get your finances in order.

Talk about bad timing. Just before Shannon O’Brien left her CEO position, the construction firm where her husband worked went bankrupt. So early in 2008, O’Brien and her husband, Emmet Hayes, both found themselves unemployed.

But instead of rushing back to the relative safety of corporate jobs, O’Brien and Hayes decided to parlay their work experience into start-up businesses. O’Brien, 50, is a former Massachusetts state treasurer who ran for governor in 2002 and who had just resigned from heading the Girl Scouts of Greater Boston. She decided to satisfy her entrepreneurial streak and use her expertise to advise renewable-energy companies on how to fund-raise and cut red tape. Hayes, 58, a former state legislator and director of business development for his bankrupt former employer, joined two fellow veterans of the state capitol to found a law firm that does lobbying and consulting.

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Associate Editor, Kiplinger's Personal Finance