Part of me suspects that Technical Writing is a dying career, or turning into something else entirely. You see contracts now that expect you to be proficient at various programming languages -- well, if I was I'd be a developer and earning proper money, wouldn't I? Or they want you to write white papers and marketing stuff. Again, I'd be wearing a tasteful suit and going to expensive conferences if I'd gone in that direction. I've thought about the later route and tried faking it, but they always want samples. The job requirements change but your past experience is mostly fixed.
(Also, and this is something to go into deeper another time, technology has changed and most modern software doesn't need a shelf of manuals and operating guides. For instance, it used to be that 40 page installation and setup guides were common. Now it's just "Right click to download.")
And I'm course I'm old and that's pretty much illegal in the IT world these days. "Get an intern in and she'll do it for minimum wage. Or we can just set up a forum where users can help each other if they get stuck."
I've thought about chucking it in and doing something else, but how are you supposed to do that in your mid-50s? Whatever happened to all those middling jobs that middling people used to have?