A certain amount of overconfidence is an integral part of being a healthy, thriving human being. People who are depressed have more accurate self-assessments than healthy people. Humility exposes a person to a lot of unpleasant, aversive feelings that can convince them that their energy is not being well spent, making it hard to continue investing at a high enough level to achieve much.
I think it's good to learn the ideas and skills of humility. I think it's important to recognize that it's unpleasant to find out that we're wrong, and we have a natural tendency to avoid unpleasant things, so we have to consciously and actively compensate for our tendency to preserve our own mistaken assumptions. However, I wonder if it's really healthy to internalize humility, to give up a subconscious way of thinking associated with high functioning and adopt a subconscious way of thinking that is associated with depression.
Ideally we'd all have such unassailable emotional security that we wouldn't be bothered by an accurate degree of humility. In reality, I think we have to fake it, and I think a lot of the people preaching this gospel of "you shouldn't feel bad when you find out you're wrong" are faking it too. But that's okay. Our full being is a combination of our messy human psyche that isn't designed for the things we try to use it for and the conscious ideas by which we interact with it. Sometimes these parts are compare to an elephant and a rider — the tiny rider on top is the part of our mind that we consciously control. I think it's okay if that's the only part that really practices humility.