Personally I've seen it all (to use characters from my story):
- The small town family lawyer who is miserable and feels screwed that they somehow couldn't or didn't want to swim with the sharks.
- The partner at the firm on his third divorce, with kids who won't talk to him, and living in constant worry of the various legally or morally dubious things they've done. Ulcers, high blood pressure, and substance abuse disorder included.
- The opposite of the other who's stayed in touch with "that guy from law school" who is perfectly happy and content only to look at the other and feel pity for how miserable the other's life must be (and often is).
I know all of them and it's pretty strange... Especially when someone will say "Yeah, XYZ is a great guy and good friend but you know... Don't ever trust him." -or- conversely "Yeah what happened to ABC was strange... Guy kind of flaked out. He seems to be doing ok, I guess."
We seem to be much better at measuring and discussing "success" than actual happiness.
EDIT: typo