A swelled head story for you: There was a young man who had a knitted kapelech. He always wondered what would happen if his brains grew and grew and his head got bigger. He assumed he would know that he became brainier if the Kappelech got tight on his head. One day, this young man took a walk in the rain, and in the course of his stroll his Kappelech got quite wet. When the young man sat learning in the Bais HaMedrash later that day, the warmth of the room began to dry the Kappele, and as the kappele dried it shrank because wet yarn, when drying, shrinks quite a bit. Suddenly, an hour or two into his learning, the man felt pressure on his head. His head was too large for his Kappele. He was overjoyed, thinking his brain had finally grown to epic proportions. He did not realize the Kappele he was wearing was too small, not that his head was too big.
When we become Baalei Ga’ava [arrogant] we are being as foolish as this man. We think we are great because we are trying to see if our head fits into a shrunken Kappele – if our actions fit into a small version of who we think we can be. If we had great goals for ourselves, if we believed G-d wants great things of us, then we would realize we have a long way to go before we feel that we are that big.
People think Anava [humility] is feeling worthless. Anava is not about that. It is about self-awareness, knowing how great we can be, realizing how little of our potential we’ve reached, and realizing our friends have their own greatness, their own value, equal to our own. This is why we are told to keep asking ourselves, ‘when will my actions be like the Tzadikim before us.” This question doesn’t mean we should be Avraham or Moshe. It means we should realize we have just as great a potential to live up to, as they had in their own life work.
‘Who am I to do great things?’ is not a humility-based question. It is a lazy question. “I haven’t yet lived up to the greatness G-d is expecting me to do,” is the Anav’s lifeline. Moshe didn’t say, “who am I to receive Torah from Hashem.” He took on his life’s job. Yet, he was Anav M’Kol Adam [the humblest of all men] – by always comparing himself to how much greater he could be.
Rav Dessler, ZT”L in Michtav M’Eliyahu explains that Anava is when you know where your inner self doesn’t coordinate with what a great person you can be, where you see what you need to fix up. However, he warns us that those who are honest about their faults and don’t try to become better are not really Anavim – they are just plain lazy, content to be a nothing. An Anav is a ba’al madrega who is bothered when he isn’t living up to his inner potential and tries to correct that.
If you want to hear a lecturer expound on some of Rav Dessler’s ideas, you can click here: http://www.shemayisrael.co.il/publicat/schwartz/mp3files3/Rav-Dessler.html
and another writeup about Rav Dessler here: http://uberdox.blogspot.com/2012/01/48th-yahrtzeit-of-rav-dessler-ztl.html