This post is dedicated in merit that Hershel ben Etya Sarah have a yeshuah.
In Rav Chaim Feuer's commentary on Iggeres haRamban: A letter for the Ages he mentions Rambam's explanation on the words "Be very very humble..." (pirkei avot 4:4) with the following story, "A pious man was once asked for a description of his happiest moment. He replied, 'I am poor. Once, during a trip, I was assigned the lowest hold in the ship, next to all the luggage. While resting, one of the wealthier men came down and because he didn't "see" me, dumped his waste on me. He laughed and returned to his cabin. Apparently, I was so low in his eyes that he judged it fair to treat me in a demeaning fashion. When he left I wondered at the strength of his obnoxious behavior. After further contemplation, though, I was overjoyed to discover that I felt no personal affront at his actions. In that moment, I discovered that I had reached a level of genuine humility."
This story isn't justifying poverty and humiliation as a means to an end. Rather, humility gives one the spirit of indifference to circumstances, especially unjustified ones, which would cause normal people to blow up in a fire of indignation. I'm not advocating for asking crazies to toss their cookies on you but if they did would it be as monumental an experience if there was no ego to prick?
When it comes to ego and self worth, the differences in meaning are often blurred. Ego needs public approval; self worth doesn't. Jewish history's classic example is the Novardock yeshiva of the early 1900s. Not only was it the largest mussar (ethics) yeshiva in Europe, its methodologies were unique. The students would put themselves in purposely demeaning situations; they'd don patched or shabby looking clothes; they'd walk into convenience stores and ask for cake. If one allows himself to appear a little loony in the eyes of others enough times, essentially he unchains himself from the terrors of public disapproval. One of the students at the Novardock yeshiva explained that the exercises were meant to show the discrepancy that exists between fear of other peoples' opinions and the actual reality, which is that no one cares as much as we imagine they do. By using the above methodology, coupled with the yeshiva's learning schedule, the Alter of Novardock (elder of Novardock) succeeded in building young Jews into courageous men who could stand tall in the wake of social instabilities such as the Bolshevik revolution or World War II.
In his sefer (book) on Shmirat haLoshon, the Chofetz Chaim speaks about the protection that a humble attitude provides against the temptation of loshon hara. After all, in the morning prayers we say, "On the heels of humility comes fear of Heaven" (Proverbs 22:4). The Chofetz Chaim also quotes Deuteronomy (8:11), "Watch yourself lest you forget Hashem, your G-d" as a warning to rude people. A man who offend his friends with comments like, "What did you eat for breakfast Jerry? Your breath smells like a dead fish!" while laughing and slapping his knee is presumably pretentious. Since G-d flees from the quality of arrogance the Torah places people like this in the same category as those who serve strange gods i.e. they are the definition of self serving. Naturally, the two cannot coexist. This is why Chofetz Chaim specifically advises these fools to squash their pride and save their souls.