While I have been flying solo in my business full time for a number of months now, the time has come for me to find health benefits. I knew it was going to be a complicated process, but the last few weeks have left my head spinning in a way I haven’t experienced since my first big party weekend as a freshman in college.

In the past for me the choices were simple: what does the company’s flex benefits offer and which one is the furthest from an HMO because I refuse to be told who I can and cannot see for my personal care? Now, I have the same myriad of choices but with more complex details and of course a far heftier price tag since I am insuring myself and not part of the corporate herd. What makes the choice even more anxiety producing are the horror stories you hear about from Michael Moore’s movie Sicko (while he does tend to the dramatic there is a lot of scary truth in there) and from some firsthand accounts from personal colleagues. How’s a savvy self employed woman to choose?

First I will set my philosophy out on the table. I believe in today’s world in the US you cannot afford to be without health insurance. While I am a big alternative care person, I still follow traditional medical practices as well and am damn sure that I am not going to roll the dice hoping I never encounter an illness or accident. I think the mindset that “I don’t need insurance because I am healthy” is a recipe for disaster. I like to think I am still young (upper 30’s) and healthy, but that doesn’t guarantee that I won’t get in a car accident, get diagnosed with a disease, or incur an injury when I am out hiking, biking or kayaking. And, any one of these scenarios spell mega bucks and could in one fell swoop bring my personal financial life down like a house of cards. I’m not alone in this thinking as Tina at Money $mart Life shares:

Unless you work for a company that has a group insurance plan, health care insurance can be astronomical. In fact, more and more people do not have insurance at all because smaller businesses cannot afford the benefit, and getting insurance on your own becomes a choice between keeping a roof overhead or having a health coverage.

For the self-employed, the problem can be even more pronounced, since you are already struggling to make enough to pay the bills, without the guarantee of a regular paycheck. So, how to get insurance for the self-employed is a stressful issue.

In a nation like the US people really shouldn’t have to choose between food and a roof or health insurance, but then that’s a different post for another time. While I am a very practical and detailed person, I firmly believe in my heart that I shouldn’t have to choose a career I hate in a corporate cube simply for the benefits. That is like staying in a toxic marriage just because you like the house. Not a life strategy.

That means it is down to looking at options. Based on my research there are several broad options:

  • Traditional PPO type coverage
  • HMO coverage
  • High Deductible Plans combined with HSA’s

Things for the self-employed are not as bleak as you might think. Anne at Web Worker Daily says in “Health Insurance Outlook for Soloists”:

But the health insurance outlook for the self-employed is not as bad as you might think. If you are reasonably healthy, you might be surprised how cheaply you can arrange coverage, especially if you choose a high-deductible health plan. And now that health insurers are looking for growth beyond their bread-and-butter large group policies, you could see even better rates as those insurers compete for your health coverage dollars.

She goes on to offer great tips for those seeking health insurance in her article as well as links to a realm of individual first hand experiences with health coverage.

Besides the dizzying array of choices (I could probably be declared legally insane from trying to read and compare all the charts and coverage) I feel stressed by the fact that I feel like “what aren’t they telling me?” It only takes one perusal through real-life stories like those of this BlogHer Contributing Editor who wishes to remain anonymous to give you heartburn:

I’ve been self-employed since 1996 and have had an uninterrupted medical insurance policy with Blue Cross. With the exception of one year when symptoms dictated fairly extensive testing (a couple of ultrasounds, a couple of MRIs) but discovered no ongoing medical issue, my health care needs have been limited to annual appointments for well woman care, including a mammogram. With the exception of one year, there have been zero prescriptions.

Over the years, the premium has had “normal” annual increases, 14%, 19%, 13%, 18%, etc, one year 30% but another only 8%.

This year the premium increased a full 81%. Attempting to apply salve to a gaping wound, Blue Cross’ notification letter switched the premium from quarterly to monthly — I guess they thought I might not catch on.

This Open Thread is very illuminating as well and illustrates just how complex this process can be.

As I see it this health insurance decision isn’t just “for now” but also a look to the future and anyone following the election knows that the future is a big question mark depending on which way the political tide turns. So I can’t say I have arrived at any golden solution for myself yet and I’m not sure there even is one. Regardless, I need to choose an overall best fit policy in the very near future.

How about you? What have been your experiences? And, what angle of this challenge would you like to see me write about in upcoming posts. My experiences are fresh and I would love to delve more into this topic but want to approach it from an angle that would be of most benefit to you, the reader. Let me know by posting in the comments.

Paula Gregorowicz is the Comfortable in Your Own Skin(tm) Coach and you can learn more at her website www.thepaulagcompany.com and blog www.coaching4lesbians.com .