The Freelancers Guide to Health Insurance, Retirement, and Taxes

This isn't so much a guide as it is a flag to let freelancers know that the flip side of getting to be your own boss is taking care of your own health insurance, retirement, and taxes, three things that can make even the strongest of freelancers gag. But you wanted to be in charge, so take charge!

Health Insurance

If you're already working for a company that provides health insurance, consider continuing your coverage via COBRA, if possible. If you can't afford it or even if you don't already have insurance, start looking at private healthcare coverage before you begin your freelance career. You might also check with the Freelancer's Union, which offers health insurance for freelancers in 30 states.

Plan for Your Retirement

Although many freelancers don't believe the day will come when they will actually retire, go ahead and plan for it just the same. It's easy to believe that you'll always be able to work at a sit down job, but that isn't always the case. Freelancers need to take a hard look at the future and start saving for it immediately. Look at IRA options and other retirement options. You might also be able to get a break on your taxes by opening an IRA. It's easy to ignore the future when you're just trying to scratch out a living but since you're the boss now, it's your responsibility to take care of your employees, even if you're the only one.

The Tax Man Cometh

Yes, the tax man cometh for freelancers too! Whether you do your own taxes or ship them off to an accountant or tax professional, as a freelancer, it's something you have to deal with on an ongoing basis. In fact, you should deal with it every time you get paid by setting aside a certain percentage for your tax bill. And you will have a bill. While you can get a refund earning next to nothing working for someone else, once you start working for yourself, you have to pay self-employment tax. In addition, since nothing was held out of your pay to begin with, you won't get an overpayment refund. Start your freelance career on the right foot by bankrolling the tax money so you won't get in hot water when it's time to pay up. Look at it this way: if you overpay your tax savings account, you can give yourself a refund at the end of the year.

For most freelancers, freelancing is the best job in the world. But for those who think freelancing is equivalent to easy street, a short stint at it will quickly change their minds. Freelancing allows those who choose it to call the shots doing something they love to do, yet it comes with its own set of rules. It's not easy but for some, it's the only way to fly!