Freelance Finance

I’ve been told I’m hard to surprise. I’ve alway wanted one of those great surprise parties, one you have no idea is coming, one that brings together all your favorite people, favorite foods and favorite expensive gifts.

But when it comes to bills, I hate surprises. What I hate more is that—even though I know it’s coming—our health insurance payment catches me off-guard every time. It’s like I have some sort of internal calendar malfunction. Payments should be monthly. Period. Quarterly bills are like freeloading friends: You can’t get rid of them and they come around just often enough to tick you off and drain your checking account.

It’s hard enough that as an independent worker you don’t know what you’re getting paid each month (or if you’re getting paid, for that matter). This makes it particularly challenging to to know how much you can and can’t spend each month on various bills and expenses. So yesterday, I said, “Enough!”

I set up yet another money-market savings account online. This one is designated for health insurance payments and setting aside bucks for a health savings account (HSA). If you have not heard of an HSA, it might be a good idea to look into them NOW. Kind of like an IRA for your medical expenses, an HSA works with a high-deductible (meaning low monthly premium) health insurance plan that lets you save money in a tax-exempt (yup-exempt) fund to cover your medical expenses. But more on HSAs at a later date.

What I really wanted to do was “pay” my health insurance premium monthly, so that when the bill came due quarterly, the money was already set aside. Again: this is nothing more than a mind-over-wallet game, but the clearer Muck and I are about what needs to come out of our account each month, the easier it is. So if the system isn’t working for you, create your own system, I say. But again, discipline. This only works if you transfer a third of your total quarterly payment to the account every month. I have now done it once. Uno time-ohs. We’ll see how this all plays out in the months to come.

Health insurance is hands-down the most annoying (and expensive) thing about being self-employed. Luckily, as our numbers grow, so do our options. A few we’ve found helpful are:

1. EHealthInsurance lets you search for insurance plans by zip code and compare all available plans in your area.
2. Working Today: Sited by Fast Company as one of “25 Social Entrepreneurs Who Are Changing the World,” Working Today provides New Yorkers with affordable life, health and disability insurance that they can keep no matter where they’re working. Says FC: “More than 30 million individuals are now employed in nontraditional arrangements as freelancers, contractors, and temporary workers in industries ranging from media and technology to domestic child care and taxi drivers, and all indicators suggest that these numbers are increasing.” More information about Working Today can be found at the Freelancers Union site.
3. Muck recently came across HealthMarkets, a company specializing in providing insurance for individuals, self-employed, hourly workers and small businesses. They don’t offer coverage everywhere. (Sorry, New York, but you’ve got Working Today anyway.) Seems like an interesting company, but I can’t speak for their rates, because they do not—unlike EHealthInsurance—allow you to get a quote immediately online. You answer a few basic questions and then “a licensed insurance agent in your area” will contact you. No thanks. Not my bag, but for those who don’t mind insurance agents calling…