Often think of the worst-case scenario, the "Eaten By Wolves" factor.
Better to fail spectacularly than do something mediocre.
Earnestness is highly underestimated. It comes from the core, while hip is trying to impress you on the surface.
It's easy to be smart when you are parodying smart people.
It is not the things we do in life that we regret on our death bed. It is the things we do not.
Wait long enough and people will surprise and impress. When you're pissed off at someone and you're angry at them, you just haven't given them enough time. Just give them a little more time and they almost always will impress you.