You win by trying. And failing. Test, try, fail, measure, evolve, repeat, persist.
I think that any time reality doesn't match your expectations, it means that marketing was involved.
If you can raise money, you're never going to have trouble getting a job.
That's why there's lots and lots of kinds of hot sauces, and not so many kinds of mustard. Not because it's hard to make interesting mustard - you could make interesting mustard - but people don't, because no one's obsessed with it, and thus no one tells their friends.
The habit of doing more than is necessary can only be earned through practice.
Discomfort brings engagement and change. Discomfort means you're doing something that others were unlikely to do, because they're hiding out in the comfortable zone. When your uncomfortable actions lead to success, the organization rewards you and brings you back for more.