Working Extra Jobs for Health Insurance

Jon Boggiano, principal partner of an environmental design training firm based in Charlotte, N.C., works one weekend a month in the U.S. Army Reserve to save his family $15,000 in annual health insurance premiums.

Neil Anderson, a full-time small business consultant in Richfield, Minn., spends an additional 20 hours a week as a FedEx package handler to save thousands each year in health, dental and life insurance.

Val Mallinson, a freelance travel writer and author, puts in 24 hours a week at Seattle grocery chain PCC Natural Markets to keep herself and her husband insured at minimal cost.

Mastering the Digital Job HuntPlay

Welcome to the latest health care hack of the self-employed: keeping a part-time job for the insurance perks.

According to a July report by The Commonwealth Fund, half the U.S. adults who purchase an individual health insurance plan (as opposed to participating in an employer-subsidized group plan) pay monthly premiums and out-of-pocket costs totaling at least 10 percent of their income. Not surprisingly, The Commonwealth Fund found that 73 percent of folks who looked into buying their own health care coverage in the past three years didn't go through with it, mainly due to the pricy premiums.

"The biggest challenge of starting your own business is the health insurance," said Boggiano, 30, who co-founded the Everblue Training Institute three-and-a-half years ago and spends 80 hours a week working on his business.

"Until you reach a critical mass where you have about 50 employees, it's difficult to get a good group rate," Boggiano said.

"With what I'm hearing about the health care debate, I'm just thrilled to be where I am," said Mallinson, 43, who started bagging groceries part-time three-and-a-half years ago and has since worked her way up to an HR position at her employer's corporate office.

"I loaned a friend a boot cast a couple weeks ago when she broke her foot and didn't have health insurance to go get a cast and crutches," she added.

Getting Around Pre-Existing Conditions

Any self-employed person with a pre-existing condition will tell you that getting decent health care coverage is a crapshoot, at best.

Take Kelly Livesay, 46, a full-time freelance copywriter and social media consultant from Cincinnati, who has a "serious vascular issue" that requires a fair amount of medication. She works two 12-hour shifts a week as a health unit coordinator in a hospital ER. Although the pay is negligible, the comprehensive health care coverage is worth the price of admission alone.

"Subpar health insurance would be at least $300 a month with no prescription, no vision, no dental," she said.

Mallinson can relate.

"My husband has had diabetes for 15 years," said Mallinson, who now makes half the income she used to before leaving behind a corporate copywriting career to write travel books like "The Dog Lover's Companion to the Pacific Northwest."

"Even with our good health insurance, we spend about $4,000 a year on medical expenses out of pocket," Mallinson said. "But I can go to bed resting easy that although I'm not earning the same income I used to, I can provide a level of comfort and security for my family. If I had kids, they would be covered too."

Boggiano also didn't want to take his chances on the individual insurance market, as he and his wife hope to have another child and found the cost of plans, including maternity benefits, too prohibitive.

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,