Having a job that requires Windows is not what I would call self-inflicted.
I'm eyeing up a shift to apple when my current hardware fails me, but it's impossible for me to just go Linux.
I really wish free(libre) tools existed that allowed you to do your work. Hopefully they will in the future, I am sure someone has tried/is trying to build them.
Wine is getting better and better, but it's still not perfect yet. I am so wishing that they figure out a way to get modern MS Office working, and then I feel like a lot of people's only reasons for staying on Windows would suddenly disappear.
Sounds like we're back to self-inflicted then? If you're self-employed supposedly that software suite was your decision.