Earlier quoted context omitted.
I definitely agree. As a recent graduate, I was constantly plagued with thoughts like that. "Did I choose the right company? Area?" etc. It all comes down to, as you've alluded to, having perspective. I set a goal early in my undergraduate career to be in the very position I'm in today: working for a stable company with a lot of job security, and the ability to use it as a stepping stone in the event I'd like to take…
my grass is already as green as I had always wanted it. Which becomes its own struggle. Once you've hit an optimal shade of green, there is nothing left to do. Half of the enjoyment comes from actively working to make your proverbial lawn grow to be so green. Do you rip it up and start over to relive that enjoyment, or sit back and watch it grow?
(I'm not an entrepreneur, just a software engineer.)