A handsome Taiwanese stray dog, kept well-fed by the local university students. No relation to my jobs.

When you file your taxes as an independent contractor there is a line that is, for people like me, often the trigger for a small bit of reflection. It’s the section where you are asked if you used to be an employee but have been re-hired as an independent contractor to perform the same duties you performed when you were a real employee. Each year I would notice that line, think ‘Yes, I am a real employee’, then realize I still needed to file as self-employed. I’m self-employed? I don’t even own a business. I was working 9–5 for someone else who did.

Now, don’t get me wrong, I was taken on as a contractor. I never actually worked as a W2 employee. But when the end of the year came, paying a massive (to me) amount of extra tax for the privilege of being 9–5 with no health benefits, sick time, or vacation was extremely discouraging.

It felt exploitative. Since the company I worked for ‘couldn’t’ afford to take on real employees and outsourced most positions overseas, the burden of actually giving a crap about the people who worked for them was placed solely on the shoulders of the employees. Get sick? The company doesn’t care, enjoy your unpaid sick days and no healthcare.

I’d like to say that I quit after realizing I was being screwed, but what really happened was that I stuck with it for 5 years until being fired. What can I say, the money was decent and the work was slow.

It’s kind of odd that I was fired. Not odd that I parted ways with the company — they were eager to outsource my work and I made a couple of decent-sized mistakes that made it real easy for them. For an independent contractor, dissatisfaction with the working relationship usually means that you or your client does not renew your contract and you continue on with your other clients or projects.

For me, however, I only had one ‘client’ and that was my boss. They controlled my time and my work. I had no time for other projects or ‘clients.’ I was not even close to evenly matched to my ‘client.’ I didn’t call my own shots in really any way except for where in the world I lived. There was no way I can honestly call them a client — I was their employee, they were my employer. They fired me. That’s how it is.

Losing my job meant losing all of my income and was absolutely devastating. I cried. I fell into a bit of depression, though it is likely the depression was already there. I didn’t know how I was going to support the life I’ve been trying to build for myself.

It seems to be working out fine, though. I luckily found a new job, not quite as well-paying, but willing to give at least give a bit of thought to the welfare of their employees. Healthcare no longer feels prohibitively expensive (insurance!!!) and I get a bit of PTO to use if I am sick or want a few days off.

I’m not really sure what lesson I need to take from this experience. That I shouldn’t be so passive? That you can never trust businessmen? Maybe that I should be putting a bigger premium on the value of my time and that I should be a lot less tolerant of any employer shenanigans. Take it from me, though, and avoid the ‘employee-contractor’ arrangement like the plague. Not only is it probably illegal, but it is not likely to benefit you in the long run.