When you go after the biggest person in the room — the hottest girl, the richest businessman, the toughest opponent, you place yourself on a higher plane, whether you win or lose.
Why? Because you showed what your level is. You show the whole room what you expect of yourself and the platform you belong on — which is the level of the big fish you cast your line for. Even in coming up short, you set the bar of where you see yourself, and that gives everyone no other choice but to see yourself the same way.
They have nothing else to go off of.