[dottjt]

I've tried this, it didn't seem to work. I think half the challenge is remembering to even put them on your keyboard in the first place - because if you miss it once, then it's completely out of mind.

For context, I guess part of the issue is that I'm moving from my desk a lot and coming back.

[mubou]

Do you feel like overengineering?

Look up some python computer vision tutorials and train a model to detect you wearing glasses vs. not wearing glasses. Run that on a Pi and hook up a smart plug or displayport switch between your monitor and pc so that it only turns the monitor on once it detects you're wearing the glasses :)