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 Hunt

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.

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