One of the most difficult parts of losing a job and becoming an unintentional freelancer is losing health benefits.

While changes to the COBRA insurance program this year make health insurance more affordable after losing a job, it's still no substitute to employer-paid health insurance. In my household, I'm underemployed and working part-time while looking for full-time work after being laid off last year, and my part-time jobs don't have benefits. My wife has gone back to work full-time so we can have health insurance.

In what sounds like an acknowledgment to this fact of life, Elance, a site that matches freelancers to clients, is sponsoring a contest,in which the winner gets his or her health insurance paid for one year, up to $10,000.


The lucky winner will be announced in December.

How do you win such a winfall? Answer the question, "What does the New Way to Work mean to me?"

What they mean, I gathered in an interview with Brad Porteus, chief marketing officer at Elance, is for a business owner or freelance worker to express what freelance work means to them.

For a business owner, "The New Way to Work" could mean being able to afford top workers at a moment's notice. For a freelancer it could mean having the flexibility to work the hours they choose while taking care of their child at home.

For both employer and freelancer, in my view, it means not providing or having medical insurance. That's the good and the bad about being a freelance worker who sets your own hours. You and the employer don't pay for medical insurance, so neither side has the extra expense. The drawback, of course, is no health insurance.

Entry rules are available on the Elance blog. The fun part is that entries can be created in any form (blog, creating an App, photo, video, etc.) and published the best way entrants can find. It can be on a personal blog, YouTube, Facebook profile, or another venue. The deadline for submissions is Dec. 1.

"It's more about flying your flag. We'll find you," Porteus said.

Freelancer Karen Swim, who has worked through Elance for more than five years, plans to enter the contest and thinks it's a great idea as the entire country debates health care. Swim, 45, is single and looking for health insurance, something she admits would be much more difficult if she had children.

"I never get sick. I'm not a big consumer of medical services," she told me in a telephone interview from Michigan. She has family members who are doctors, who she sees for routine care, but is looking for continual coverage for hospitalization. Swim created a health care savings plan for herself for emergencies, but wants long-term care as she gets older.

While it's admirable that Elance is offering a year's worth of health insurance premiums to one winner, it's a bit pathetic that basic access to medical care has to be won via a contest. No other contry in the West could offer such a contest. They wouldn't need to.

The working world may never be the same after the recession ends, whenever that is. More workers -- 37 million -- are independent contractors, part-time or temporary staffers, or self-employed, leading to a larger workforce that works online from home.

Losing health care is just one of the societal fibers being lost. Add in other benefits such as sick time, vacation time and retirement plans that go out the door for the self-employed, and it's stressful work. That's why freelancers should have their fees high enough to cover those extra costs they incur.

Some of the $70 million in payments that Elance is delivering to freelancers this year through more than 60,000 companies must be going toward health premiums, a benefit that many voluntary freelancers realized was going out the door when they quit their full-time jobs to become freelancers.

"There are a lot of people who don't want to be dependent on 'The Man' anymore," said Elance's Porteus. "There's a ton of people who are opting into this lifestyle, and saying 'This is for me,'" he said.

I don't know how many that's true for, but I'll bet most people who were laid off in the past year or so didn't didn't choose contract work as a lifestyle, although it may be a comfortable fit when the unemployment checks stop arriving.

Aaron Crowe is a freelance journalist in the San Francisco Bay Area. Reach him at www.AaronCrowe.net