CashIn what can best be described as shooting yourself in the foot, the freelance-for-hire Web site Elance has selected a winner in its contest for a grand prize of $10,000 to help pay health insurance premiums for a year -- a guy who works full time and already has health insurance through his employer.

The contest, as I wrote in September, was to do some sort of essay (vidoes won the next three spots in the contest) on the topic of what the "New Way to Work" means. The contest was meant to highlight how important freelancers are becoming to the economy.

But since freelancers don't receive employer-sponsored health benefits, Elance made the grand prize up to $10,000 in health insurance premiums for a year, or the option of $10,000 in cash.

Ben Gran, who freelances on Elance for 10 hours a week, in addition to working 40 hours as a technical writer in Des Moines, Iowa, selected the $10,000 in cash for his winning entry, "Cubicles are the Phone Booths of the Future" because his employer already provides health benefits.

Unlike many freelancers who would need the money for health insurance premiums, Gran wants to quit his full-time job and do more work as a freelancer. For now he's putting his winnings in the bank, he told me in a telephone interview during a break from work, as a cushion for when he quits his full-time job sometime next year.

"I'm trying to get to the point where I can go full-time, self-employed," said Gran, 30, whose pregnant wife doesn't work and stays home with their 18-month-old son . He does freelance work on the side so that his wife can stay home.

Having been laid off myself in June 2008 and looking for full-time work with health benefits since then, I can only offer this advice to Gran and anyone else thinking of quitting a job to be a freelancer: Don't do it. At least not yet. Yes, $10,000 is a good cushion, especially in Iowa, but wait until you're earning close to what you were at your full-time job before leaving.

Gran said he's worked at his current job for about 3 1/2 years, and is making $75 to $100 an hour freelancing on Elance in public relations, speech writing and Web content.

Working in a cubicle is becoming a thing of the past, he wrote in his essay, and the traditional idea of a job is becoming obsolete as more workers accept not having job security. The online workplace is replacing the cubicle.

Gran almost quit his job in June so he could spend more time with his child and freelance from home, but the high cost of health insurance kept him from leaving, he said.

That's what having a kid will do to you, along with the cold slap of paying for healthcare on your own -- keep trudging to that 40-hour-a-week job until you find something better.

Aaron Crowe is a freelance journalist in the San Francisco Bay Area who can be found at www.AaronCrowe.net

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