I interrupt my half-completed follow-up "Matrix" essay to share some things that emerged in a conversation with a friend last night. He was talking about someone he worked with whom he perceived as arrogant, and I said, "Guess what? It is OK not to be humble, you know."
Then the following information came through:
Humility is not something you can achieve. Those who pursue humility as a goal end up with a counterfeit. Real humility is something that sneaks up on you. If you are not humble, then be OK with that and don't pretend otherwise. That is the beginning of true humility -- to not care about maintaining an elevated self-image. If you feel pride and superiority, and then try to stuff it down and pretend it isn't there, you will end up feeling even more superior as you congratulate yourself on your humility.
If I may offer a suggestion, see pride and superiority merely as symptoms that you are not seeing the truth of yourself and others. Symptoms, that's all. Nothing to be ashamed of. Arrogance harbors its own cure. Eventually, only one thing can happen to the tower of pretend virtue we build. Something "humiliating" will happen, something that strips away our pretenses and reveals our naked self.
If you aren't sure whether you are humble or not, here are a few clues. If you are gratified when someone says you are humble, you are not humble -- you are just good at faking it. If you are offended when someone says you are conceited, then you are conceited. Both these responses point to an inflated self-image.
If, after reading the "suggestion" paragraph above, you feel a desire to demonstrate that you are in fact "seeing the truth of yourself and others," then you are not humble either. Underneath the inflated self-image of the arrogant person lies self-rejection, self-diminishment, for which the inflation seeks to compensate. The humble person is rock solid in self-love. The humble person does not care if she is humble or not. Humility is not something you can cultivate. It is a side-effect of something else.
Sometimes a humble person might appear arrogant, because he is very sure of his gifts. I once knew a very humble massage therapist. When someone asked her, "Are you good at what you do?" she would reply, "No, I'm great!" And she was, and she knew she was, and she had no need to pretend to be humble. Modesty is only humble when you aren't sure.
I could conclude this piece by saying, "So, if you want to be humble...", but if you want to be humble, then already you are heading away from humility. Instead, seek to be truthful. You might end up humble as a result, but you won't even notice.