Yes! There is a website somewhere that has a tonne of fake os screens - updating/upgrading windows, bsod loop etc.
Run a scary looking one of those, disconnect mouse/keyboard so it can’t be interrupted and let the boss discover it
Quite a few products allow for this home use. Aids with training, familiarisation and locking users into their ecosystem. I’ve been able to do this a few times to help learn complex programs.
Completely legit with Adobe as far as I’m aware - since there is only the one licence available via online check-in so can’t be used on more than one at a time.
Autodesk is similar - used to have an allowance for a training/home use licence (may have been extra), even the common Office 365 corp licence allows for up to 5 installations and doesn’t really care where you install it.
Corp data on a home device or using your own gear for WFH is another story though.
Little red hatchback: Elmo Blue SUV with a big, ugly nose: Gonzo