Isn’t this the basis of zomb100? Where his work life was so shit that when a literal zombie apocalypse happened he finally started living the life he wanted. And it wasn’t that he dreamt of survival and shooting dead people, just a bucket list of cool things to do.

Anyway, I can relate.

This manager at least decides to park it rather than doubling down which honestly already puts her better than many.

I like how Pathfinder 2E does it. A 20 brings your result one tier higher. A 1 brings your result one tier lower. With a high enough base expertise, you can still succeed when rolling a 1, just not as awesome as you normally are. And a 20 isn’t a guarantee against really strong foes.