How do you know your skill is degrading? Could it be the old "the more you know, the more you know you don't know"?

Not in my case. My company hasn't allowed me to settle into a steady type of work/language/stack. I used to be an expert in other systems/tech, but they outsourced and downsized those. So now I'm always working on different languages/systems/etc. I'm basically an entry level with 10 years experience and an MS who gets a bad rating because I'm slow.

I can relate, although I have fewer years of experience. I've switched from one sub software industry to another. My past experience is not valued or at least doesn't count as much. Which I understand. Small and medium companies want a person who knows their stack and who needs only a few weeks to adjust to the company but not someone who needs a full month or so of study to learn their stack. There isn't a lot of demand for generalists in my experience, which again is understandable.

I guess my point is that one has to think carefully about their career path and what they want to do beyond "Write code and build stuff".

> entry level with 10 years experience

This sounds like a toxic work environment. Get out while you can!

That's the thing. I think they purposely make people a jack of all trades so it's more difficult to leave (everyone wants an expert). I don't really have any options to leave (put in a few resumes, had an interview, but my location sucks for decent IT jobs).