While I feel happy for him, an artist that's been given recognition for his skill and talent, it also brought up questions of success, failure and how different people react to it. Many entrepreneurs know the phrase, "Fail your way to the top," and it would seem as though that's exactly what he's done.
Most of us are conditioned to believe that failure is bad, and that we should avoid failure at all costs. If I've learned anything from my many artistic endeavors and the Mythbusters, it's that failure is always an option, and you always learn something from it when you do. What did Leo learn when he didn't win? His first nomiation was at 20. Maybe he thought he needed more experience, or more training. Is this what spurred him on to greater cinematic challenges?
Most likely, yes. There are two ways to look at failure, and Leo failed multiple times in a very public forum. I'm sure some actors in the past saw their nomination and subsequent loss as a death knell, thinking, "Well, if I can't win with that, I never will! That was the hardest thing I've ever done!" They take easier, smaller roles and slowly fade away. Others, like Leo, look at it and go, "Well, I didn't win with that, and that was the hardest thing I've ever done! Time to tell my agent to ramp things up."
On the flip side, what if he had won when he was 20? Would he have starred in The Revenant? Would Inception have had as much impact? How many people, upon winning high accolades early on in their careers, use that momentum to just coast along through the rest of their work? They've checked the achievement box, but they're living a One-Hit-Wonder life.
To me, Leo's Oscar win is what happens when you don't let failure stand in your way, no matter how many people are watching. So go out there, try to do the thing, and fail until you win. When you do, party, take a moment to thank those that helped you, then scope out your next challenge.