Despite the trouble I had getting paid for my work for Rock Systems/Airborne Media Group, I really enjoyed being an independent contractor.

1. I could set my own hours.
2. I could still work at home in general.
3. Any travel I incurred would be paid for by the client.
4. I could work on a wide variety of projects, therefore learning a lot.
5. There was a lot of free-lance work in Austin.
6. The money was really good, at least when I got paid.

Downsides:

1. Self-employment tax
2. Less of a guarantee of continuous work. This mattered because of the mortgage, etc.
3. Always having to hustle for more work.
4. Paying my own health insurance.

It was coming up on the end of my current contract. And it was coming up on the date I would have to make my first payment for COBRA to continue my coverage from Coverity.

I could continue to do free-lance, and use COBRA for 18 months, but at that point, I would have to get insurance for me and my family from somewhere.

I also have a professional hobby. I am a part-time musician. I am a member of the American Federation of Musicians. Now, there aren’t too many actual benefits for the musician’s union. I did get two incredible lucrative gigs when I lived in the Bay Area. They more than made up for 18 years of union dues. That had not happened in Austin.

But they supposedly have some kind of health insurance. So I applied.

Turns out it’s not actually a group plan. It’s an individual plan with a hefty discount. I filled out the application for me and my family online.

The next day, a representative from the company called me, and told me that my family was all approved, but I was turned down because of my weight.

Huh.

I asked her what my weight needed to be, and she told me, but then she said that I could not apply for 2 years. And all of the other companies would ask me if I had been turned down in the previous two years, and if I said yes, they would turn me down also (which, of course, would reset the two year clock).

I asked if there was any way at all I could get health insurance. She told me that I had to go 6 months without insurance, and then I could apply for the Texas High Risk Pool insurance. The premiums were several thousand a month, and the deductibles were very high, and the policy did not cover that much.

So. I had COBRA for 18 months. After that, I was out of luck, even if I somehow lost 50+ pounds.

That’s when my free-lancing career came to a stop, at least as a full-time, long-term strategy.