"looking stupid" seems like a poor abstraction for two other things: 1) failing to come to terms with your own insufficiency, and 2) being willing to do things that others are not doing. I think separating them out helps us realize they are separate skills, and this way, those of us who are not naturally talented at them are more likely to pick them up.

Another helpful thing would have been examples. What were the stupid questions he was asking in college?