Tackling health insurance coverage as a freelancer

One of self-employment's trickiest puzzles: not going broke at the doctor's office.

The moment you decide to start freelancing full-time, you have a million other decisions to make. How will you structure your time? How will you find new clients? How will you pay for healthcare?

This month’s issue of The Freelance Series is, I’m sad to say, a uniquely American one. Here in the US, the easiest way to acquire and maintain healthcare coverage (past the age of 26, when you fall off your parents’ plan) is to work a full-time job. Your employer might not provide good insurance, but it’s insurance nonetheless, and you’re less likely to drain your life’s savings should a medical emergency occur. When you make the decision to freelance, though, you simultaneously make the decision to ditch employer-sponsored medical coverage in favor of nabbing your own.

I love the freelance life, and I hope I get to live it until the day I retire. But I’ll readily admit to anyone who listens that the health insurance options available to freelancers totally suck. I’m saying that as someone who doesn’t require frequent medical attention, too; for those with chronic illness or other long-term health concerns, a lack of steady insurance can bring them to the edge of physical or financial catastrophe. Most of us who freelance, then, are stuck between a rock and a hard place.

I can’t make self-employed healthcare coverage options suck any less, but I can at least describe some of their pros and cons as a freelancer who’s carefully considered (and tried) most of them. Here’s the scoop on not going broke at the doctor’s office.