How Does Health Insurance Work as a Freelancer?

Low T Doctor Takes Blood Pressure

Surely you’ve heard the phrase “the grass is always greener,” yes? I dredge up the cliché whenever I give a talk on this whole freelance writing thing I do for a living as most attendees want to quit their day jobs and start raking in the dillions as a writer. I’ve written about it a little here and I don’t want to come off as flippant or simplistic — I just think people should plan moves carefully.

Anyway, I got to thinking about this because of a recent piece on The Billfold. (By the way, if you aren’t reading that site, you should. It’s great and filled with adults writing about money and admitting they don’t understand how finances work, either.) Earlier this month there was a piece titled “Six Lessons I Learned After Becoming a Full-Time Freelancer.” There are some good lessons therein, but I wanted to riff a little bit more a point the author makes, aptly headlined: “Health insurance is impossible and seriously, what do you guys do?”

Maybe it’s just my side of the table — the side where you have to buy your own health insurance — but I really do believe within our lifetime will we see full-time employment no longer guaranteeing insurance of any stripe. But that’s neither here nor there. The fact is if you are freelance, there are still options.

And, guys, they are not pretty.

The author knows more about one popular option, the Freelancer’s Union, which I’ve never used. It has a “totally mediocre” dental plan (most of these plans rarely include dental) and is seemingly among the most expensive at $4,560 a year. Obviously, these numbers will shift a bit depending on your age and all those fun variables.

Obviously, I’m not a lawyer or an insurance salesman, so I can’t tell you where you should go, but I can tell you where you can at least look. I go with BlueCross, which, again, doesn’t include dental, but is a few hundo every two months. But it’s affordable and certainly viable.

You’d also be wise to check out, which has a good reputation, although I’d caution people to stay away from COBRA. As if the name alone isn’t scary enough, it tends to be the most expensive. I got an absurd quote from them when I first went freelance, and I’ve also heard others tell me they were expected to pay something like $500 a month.

So, yeah. If you want to go freelance — do your homework on this stuff!

David Wolinsky is a freelance writer and a lifelong Chicagoan. In addition to currently serving as IFC’s comedy, film, and TV blogger, he's also a comedy-writing instructor for Second City and an adjunct professor in DePaul’s College of Computing and Digital Media. (He also co-runs a blog behind the DePaul class, DIY Game Dev.) He was the Chicago city editor for The Onion A.V. Club where he provided in-depth daily coverage of this city's bustling arts/entertainment scene for half a decade. His first career aspirations were to be a game-show host.

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