Working Extra Jobs for Health Insurance

Boggiano and his two reservist business partners are insured through Uncle Sam's "phenomenal" military health care plan. But they've found the costs and administrative overhead of purchasing a group plan for their company's two dozen virtual employees unworkable. Instead, they give their staff a stipend they can apply toward the individual plan of their choice, as well as a pep talk about the importance of doing so.

Juggling Both Jobs

For some intrepid independents, holding down a part-time job on top of the full-time business venture can get exhausting.

"The situation makes me happy, but I am tired," said Livesay, the copywriter who doubles as an ER health unit coordinator. "I haven't had a vacation in two years. I do professional blogging and article writing, and you can't fake that. A corporate job pays you for 'hanging out' time. Freelance writing does not."

Then there's the matter of whether to tell your customers about your part-time job, especially if it's entry level or near minimum wage.

"I usually don't venture this information until I get the deal and deliver the work," said Anderson, 50, the FedEx package handler who runs a small business consultancy called The Courage Group. Then again, Anderson says, if a would-be small business owner he's counseling asks for tips on affordable health insurance, he might trot out the details of his part-time employment sooner.

Understandably, not all self-employed pros are so forthcoming with their clients about their mercenary gig.

"For my husband and I to have health insurance, I work 240 hours every quarter at the Starbucks down the street from our house," said a 51-year-old full-time freelance marketing executive in Phoenix who didn't want her name mentioned for fear her clients wouldn't approve.

"Not only am I saving us about $1,000 a month, I'm taking advantage of what I'm learning at Starbucks to see if opening a café of my own could be my next adventure."

But for Melissa, a 25-year-old full-time freelance photographer in Darien, Conn., who didn't want her last name used, keeping her clients in the dark about the 20 hours a week she cashiers at a supermarket chain is easier said than done. Sometimes they turn up in her checkout line.

"There is really no way around explaining it," Melissa said. "Usually people are shocked to see me. They'll ask me how work is going, and I'll say, 'Good. This is just a part-time gig. They have great health insurance.' Once, it actually led to a callback from a company that has given me steady work ever since."

This work is the opinion of the columnist and in no way reflects the opinion of ABC News.

Michelle Goodman is a freelance journalist, author and former cubicle dweller. Her books — "My So-Called Freelance Life: How to Survive and Thrive as a Creative Professional for Hire" and "The Anti 9-to-5 Guide: Practical Career Advice for Women Who Think Outside the Cube" -- offer an irreverent take on the traditional career guide. More tips on career change, flex work and the freelance life can be found on her blog,

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