R. Joseph B. Soloveitchik, Days of Deliverance, pp. 9-10:
Why should man be modest, shy, humble? Particularly, why should successful man be humble? He has the right, prima facie, to be proud of himself, to be arrogant toward those who have failed in life. In fact, man is inclined to be arrogant, to be impudent and aggressive. He is inclined to reach for things that are above and beyond his legitimate reach. Human arrogance is, of course, the consequence of victory; the feelings of self-assurance and self-righteousness that accompany success result is pride and arrogance. However, human pride and arrogance disappear the very moment man becomes aware of his vulnerability and of the suddenness with which fortune changes. In other words, the awareness of human vulnerability is cathartic, cleansing; it is an awareness that ennobles man and has a redemptive impact upon him. Humility is the expression of that awareness.
Humility is not only a moral virtue; it is a good practical rule. We read in the Megillah:And Mordecai walked every day before the court of the women’s house, to know how Esther did, and what would become of her (2:11).
Had Mordecai abandoned caution and adopted the attitude of the arrogant fool, had he let everybody know that he was related to the queen, he would have commanded their respect. However, had he been proud and vain, had he boasted that he is a relation of the queen, the whole miracle would not have happened. The miracle was made possible by Mordecai’s caution and humility. He was silent, humble; he was waiting for something to happen. He knew that the more fantastic the success story, the more vulnerable man is and the more intense is the need for prayer. Vulnerability of man is proportionate to his greatness. The greater the success, the more vulnerable he is. Mordecai knew that as Esther climbed up to the very heights of success, the deeper became the abyss into which she might plunge. Because of Mordecai’s humility and because of his awareness of vulnerability and caution, the great miracle happened. In sum, vulnerability leads to humility, humility to caution, and caution leads to success.