What every freelancer should know

9. Get health insurance. I know it's a nightmare. I am a Type 1 diabetic, and trying to find health insurance reduced me to tears. ("So are you trying to tell me that even if I were willing to give you a million dollars a month, you would still not let me join your health plan?" I asked one representative. She said yes and hung up.) But if nothing else, you must sign up for catastrophic coverage. Please. This may sound frivolous -- You've never been sick! You'd rather save money for your one vacation a year! -- but it's not. Sara Horowitz, founder of the New York-based Freelancers Union says this is a crucial investment that way too many freelancers don't make. And it's not just about the risk of going bankrupt over a broken leg: When the time comes (or your budget allows) for you to buy into a better plan, you'll need to provide proof of previous coverage (that is, "creditable coverage") to avoid exclusion periods for preexisting conditions. Those exclusion periods can be as long as a year (or in some cases 18 months), which means if you don't have any sort of previous coverage, you could end up screwed.

Granted, none of this is easy. Horowitz says healthcare options for self-employed workers these days are the worst she's ever seen, mostly because there are very few group plans -- that is, ones that can't grill you about your medical history -- for freelancers. Instead, the majority of options available are individual health insurance policies, which are usually much more expensive than group plans, if they agree to cover you at all.

Still, there are resources out there: Freelancers in New York can buy into the Freelancers Union's group plan (they also have partnered with Golden Rule to offer individual plans in 30 other states -- and have options for dental, life and disability insurance as well). If you're in entertainment or an arts-related field, there's the Actors Fund of America -- you might be eligible for its one-on-one health insurance counseling, or its health insurance workshops (in New York and Los Angeles). If you're not in entertainment, try Access to Health Insurance/Resources for Care or Health Insurance Info, both of which list health insurance information and resources for every state.

And if the process of finding health insurance makes you want to bang your head on the floor, please don't. At least not until you find a plan that covers skull injuries.

10. Open an Individual Retirement Account, better known as an IRA. I know that when you're struggling each month to pay your rent, saving for your retirement isn't a top priority. But listen to this: By starting a SEP IRA, I not only put aside money for retirement but also saved $2,000 on this year's taxes.

There are a bunch of different kinds -- which you can read all about next time you need an excuse to procrastinate -- but the important thing to remember is that, while the government normally gets first dibs on your money (taking bites for federal and state taxes, social security, Medicare and Medicaid), most IRAs let you take a first shot at your cash. You don't have to pay any tax on the money you put in these accounts until you take it out. (The exception is the Roth IRA -- you put in post-tax money but then don't have to pay taxes on the account ever again, no matter how much it earns.)

The catch is that you usually can't take out money from your IRA until you're 59 1/2 (there are other restrictions, too, so do your research). But think of it this way: Would you rather have untouchable money that's still yours and that might have earned something by the time you get it back? Or would you rather write a check directly to the IRS?

11. Do not own a coffeemaker. I know this goes against the wisdom of those budgeting articles (the money you save on lattes could pay for your child's college education!). But it's critical for your mental health to leave the house at least once a day and interact with real, live humans -- even if you are only talking about Starbucks. So here's a compromise: Identify the cheapest drink that you enjoy. Then calculate how much it costs -- in my case, $1.50 for iced tea -- compared to a $100 therapy session in which you talk about how lonely and depressed you are. My guess? That iced tea is a bargain.

12. Consider sharing office space with other self-employed people. This is a good option if you don't want to -- or can't -- work from home. Check out the Coworking Wiki, which offers a directory of co-working organizations around the world. Also, if you've managed to find a cafe with the magic combination of good coffee, convenient outlet placement, acceptable music, wireless Internet and a bathroom that is not totally disgusting, do not, under any circumstances, date the barista.

13. Socialize with other people in your field. This will both help you network and keep you sane. Check out the freelancers' Meetup page, or research local professional organizations (writers can turn to MediaBistro.) Leave your apartment. Get dinner. Wear real pants. Enjoy having people around to complain to -- or even better, celebrate with. And in your deepest, darkest moments, remind yourself of what made you want to be self-employed in the first place.

I realize that might be hard to remember right now, given that it's tax day. If so, forget the philosophical contemplation. Grab a friend and get a drink.

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