I measure my success in many ways.
1. Do I havea loving family. Check.
2. Do I have fulfilling hobbies. Check.
3. Do I have enough money to fulfill my responsibilities and hobby, doing things I love. Check.
4. Do I have as much money as I would want to call myself successful. Not yet.
Tying my success to many parameters I can feel a little successful everyday, and continue to feel lucky, and continue to work toward what I would call a successful startup.
If you feel he's a good role model, then what do we make of him being cast out of Eden by his own board, and then having NeXT going basically nowhere until Apple begged him to come back and bought the company for its OS and as a talent acquisition?
I suspect he's been happier in a certain sense when his actions have been validated by the market, but at the same time, I strongly suspect he has certain other motivations that drive him and he's happy when he acts in harmony with those motivations. The marketplace validating his work is probably just icing on the cake.
That's all just speculation I pulled out of my Ass, of course!
This is even stronger than Pasteur's famous, "Chance favors the prepared mind" - if you are not actually working on a problem, there is no possible way to benefit from serendipity.