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I've heard stories that Steve Jobs can often be a condescending asshole. I'm certain the same is true for other highly accomplished folks as well; if condescension were linked to confidence, wouldn't highly accomlished individuals such as this be amazingly generous and helpful?

I think the bit about superiority may be true: it is a way to demonstrate superiority, but I don't believe that immediately indicates low confidence.

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Some of the most successful people are very insecure. That's one of the factors that drives them relentlessly forward - the fear that everyone will find out their not actually good enough.

I think "drives them relentlessly forward" is a part of the conversation we're missing out on. Useful feedback can come from anywhere, even an asshole. Waiting for insight from only expert communicators seems like a way to slow down one's progress.

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