High achievement is probably most difficult because of how humiliating it is. The path requires many moments where you let go of who you are right now, confident that you can be someone better tomorrow. 

Often times I feel like I'm quite sharp. I may go months feeling like I'm reiding a high horse. But these moments are always followed by some wakeup phase where I learn that I'm not special. Or I shouldn't even say learn. It's more of an acceptance. Because all along I was riding a high horse, why?, because I knew I wasn't special. Riding the high horse was like someone leasing a luxury vehicle to signal something.

Lately I've been much more open to just not trying to act sharp. Not trying to signal that I know secrets to things and that people should listen to me. It's been a existential breath of fresh air. 

I remember one time I was at someone's house when it started storming outside. It was the kind of thunder without any rain. We went out there to watch and listen. What the guy said was "I love nature. You look at something like lightning and go, fucking humans aren't shit!"

Anytime I get high horsey about things like words or code or whatever I might be into I love to refresh by visiting things that make humans puny. Usually out in nature. We all should really not take things so seriously. Take it honestly and put in good work? Yes. But it's not holy.

However, I also think that humility can result from high achievement and confidence as well... though it is rare and difficult. Narcissism is a beast on its own and it is on my list of things I want to understand more. I would say that narcissisms and over confidence are correlated and narcissism and humility are inversely related. 

I want to believe that with work - humility, confidence and the ability to recognize failure and learn from it is achievable.