In last week’s Parasha, Moshe Rabbeinu is described as “Anav Me’od MeKol HaAdam” (Bamidbar 12:3)–Moshe was very humble, more than any person on the face of the earth. The Mishna in Avos, however, teaches that: “Me’od, Me’od Hevei Shefal Ruach–one should be very, very humble. Why was Moshe only very humble, while Chazal implore everyone to be very, very humble?
Your question gives us an important insight to what humility according to the torah really is. Humility is not that a person says, “I am nothing” or I am bad, worthless, etc.” We see from this quite the contrary. Moshe definitely believed with every fiber in his soul that he was the greatest prophet, of the Jews and that no one would ever be a greater prophet than he was. If he didn’t believe it he would have be guilty of not believing what it says in the holy torah, given by Hashem Himself. the answer is that humility is not to deny that one has accomplishments, or to know where a person really stands. To deny that is foolish, and untruthful, and harmful. It is called shiflus- lowliness, and it is a very detrimental character trait. A person must know his strengths, but on the other hand he still has to be humble. There is a story told about R’ Yecheskel Abramsky, that is was once called to the court to testify about something. the Judge asked him, “Is it true that you are the biggest Rabbi in England” To this he answered, “Yes you honor”. then the judge asked him, “Is that being humble?” To that he answer, “but your honor, I am right now under oath”.
Getting back to our question; humility, known as anava, is the person’s knowing that no matter how great I am, it is nothing in comparison to the greatness of G-d. Moshe Rabeinu knew that he was given the opportunity to see G-d in ways that no one else was able to, therefore he saw G-d’s greatness much, much more than anyone else, this is a fact and he didn’t deny it. It was exactly this tremendous knowledge of H-shem that made Moshe feel so, so humbled. No matter what he would do, he would still see himself as an ant, although taller than his peers, when he is standing next to a giant, that fact that he is slightly taller than the other ants, will not make him feel haughty. He is not busy looking at the smallness of the other ants, rather he is looking at the greatness of G-d, therefore he was the greatest prophet and the biggest anav.
As aside point there is another understanding of anava. That all though I may have great talents, etc. it doesn’t mean that I am essentially better or greater, in my service of H-shem than the other person. For example a person that is very smart has the talent, and the responsibility to do and accomplish more. If he is only going to accomplish what the other person did, or even a little bit more, he will be falling very short of his responsibilities. For example, a person that runs or drives a bike for twenty miles, in a day will feel very accomplished that he used his energy an he made it. However a person with a car that feels accomplished by driving twenty miles, or even fifty miles, and he feels he is “better”, or deserving of compliments and praise making quite a mistake. Therefore even if a person is very accomplished, he has to realize that the qualities that he was given, that made his “accomplishment” more or better than other people, may not be a reason for him to feel better or higher or really greater than others. therefore even though Moshe Rabeinu knew that he was the greatest prophet, he knew that it isn’t reason to him to act haughty in any way or to make himself higher or deserving of more as a result. therefore a person should always feel lowly about himself, in the sense of, ” did I use all of the tools that I was given, and develop muself to my fullest potential, or am I lacking in the service of H-shem”? This thought keeps people from acting in a haughty way.