When I was writing the piece on Asarah be-Tevet, I was also thinking about how humility is a virtue that we really don't understand, don't appreciate, much less cultivate. Even those whose lives are based upon humility, reject it.
Take my colleagues in academia. The scientific method is, by definition, predicated upon the idea that all knowledge is conditional. Absolute certainty is impossible, because all you know is what you've managed to prove to this point with the data at hand. Ten minutes from now, you (or someone else) may totally upend your conclusion in the light of new evidence or a new insight. Of course, you must follow your present conclusion because that's what you've got. What you don't have is the right to be dogmatic. On the contrary, the awareness of the conditional nature of knowledge should instill scholars with humility. Yet, far too many of them are not only dogmatic, they get abusively so.
I fear that rabbis also fall into this trap. This is not the place to get into a long dissertation about the dynamics of Halakhic decision-making. However, as evidenced during the so-called 'Disengagement,' when it comes to non-Halakhic issues- Humility flies out the window. Too many people 'know' what God wants (never mind predicting what will or won't happen). How can they know? You can hope. You can pray. You can approximate. At some stage, however, they need to have the humility to say, 'I will accept whatever God decides.' The message then must be passed on to those who heed them.
In this regard, I think religious society has fallen into the worst aspect of Late Modernity, namely 'Self-Worship.' The Western World worships Man, i.e. itself. A narcissistic culture, an idolatrous culture, has no room for humility, even as a theoretical construct. As the Rov points out in Sacred and Profane, the Greek view of the hero is categorically opposed to that of Judaism. The Greek hero conquers others. The Jewish hero, first and foremost, conquers himself. Obviously, the Torah does not seek passivility in man. However, man reaches his greatest heights when he acknowledges his limitations.
That, too, is part of what lies behind Asarah be-Tevet.