The Journey

Getting Health Insurance as a Freelancer

  • The Individual Mandate is no longer in effect as of 2019
  • Clicking the sponsored health care links on Google is bad
  • Individual health insurance that protects your wealth is inexpensive

Disclaimer: This author claims no special experience or knowledge of health insurance, other than the experience of losing corporate provided health insurance and having to buy new insurance (and screwing up a little along the way).

When you talk to someone who likes the idea of leaving their corporate job, two times out of three the person will use health insurance as the reason they can’t do it. When I did it this year, I’ll admit that I was worried about it myself, and back in 2015 when I took some time off, I paid around $300 a month for Affordable Care Act (ACA) qualifying health insurance that basically did nothing for me beyond wealth protection in the case of a really big bill. And it also let me avoid the individual mandate penalty on 2015 taxes.

Fast forward to June 1st, 2019, the first date I would lose corporate coverage, I was prepared to eat the $300 (or more) per month once again. Since I was losing coverage, I went on to try to apply during the enrollment off season. First, I wasted a lot of time by answering questions that could lead to discounts (they won’t for any remotely comfortable income, even if earned earlier in the year). Then, over a period of five days, the site was down and couldn’t even process my application. I thought I might have to eat one month of COBRA insurance for over $600 from my last job. Then I realized that the individual mandate is gone, at least at the federal level.

This is due to the Tax Cuts and Jobs act that was passed in December 2017 and eliminated the individual mandate penalty, effective January 1, 2019. It’d be a good idea to search for any law particular to your state, but nothing stood out as too powerful to me. It’s gone.

I have nothing to say about policy, or whether this is good or bad for the country, but I won’t buy expensive health insurance as a freelancer right after losing most of my income, especially when the site to do it isn’t even working.

After realizing I could just buy insurance from anyone, I got in a hurry and searched Google for “buying health insurance online.” Thinking that the top site was some kind of Kayak-like engine for comparison shopping health insurance, it clicked it. Do not do this. I will not write down the link out of fear that I will help these sites’ rankings, but I will show you a picture of what not to click:

The first website actually looked quite clean and professional, and made it easy for me to answer the few, very reasonable questions. I clicked submit.

Within, and I’m not kidding, 5 seconds, my phone started to ring. That’s when I knew I screwed up. Over the next three weeks, I got hundreds of phone calls and dozens of voicemails and emails. Telling them to stop doesn’t work:

It was pretty bad, but in the end it was only digital communications and not impossible to ignore (if you physically turned a few things off). Still, don’t do it.

In the end, I went to a website of a name I’ve seen before, United Health One, who’s offering non-ACA compliant “short-term” insurance. At first I didn’t understand what that meant, but when you’re buying the insurance you can specify different term lengths, and that seems to be about it. These policies are not ACA-compliant because they do almost nothing for you unless you’re out a lot of money (explaining the term “junk insurance”). But that’s okay for me.

What I really want is wealth protection in case something really bad happens and I owe a hospital $700,000, and thus I went for the highest maximum benefit of $2,000,000. The deductible situation is a little complicated because there are two of them. Under the first one the company will not pay anything, and in the sweet middle ground between the first deductible and second, they will pay some. I wasn’t that interested in that middle spot so I minimized the benefits there.

The UnitedHealthOne website ( almost felt like one of those old school restaurants that offered so many million menu items by sheer combinatorics of the options, which I didn’t like so much. And it annoyed me a little bit that the company name changed from UnitedHealthOne to “Golden Rule” when it was time to buy the policy. But it was relatively easy to make the final purchase, I felt I got what I needed, and it was under $100 a month.

I’ll repeat the disclaimer: I have no idea what I’m doing. Maybe I do rack up $700,000 of medical expenses and then $400,000 of those expenses are denied by “Golden Rule.” Who knows? But I do know one thing: if you don’t click on one of those links I showed you, you can buy health insurance at a very reasonable rate without getting attacked by vultures. Sometimes, that’s all you can ask for.