It turns out, Har Sinai wasn’t so small after all.
Young children are taught many songs before Shavuos, including the classic where Har Sinai cries that it is not tall or wide enough to host Matan Torah. But in the end, “From all the mountains, Hashem chose Sinai” - specifically because it was so unassuming. The lesson is that true Kabbalas HaTorah can only be achieved by those willing to submissively adhere to a Divine set of laws and humbly respect the opinions of others. This is why Hashem chose to transmit the Torah on the lowest of all the mountains (Sotah 5a).
For the little kids we can leave it at that, but the rest of us should consider the following question: If Hashem really wanted to teach us to lower ourselves, then why did He choose any mountain at all? If receiving the Torah truly requires submission and humility, then Hashem should have given it in a deep valley, or at least on flat ground. What is the significance of choosing an elevated land, but then making sure it is the smallest of the mountains?
Rabbi Baruch HaLevi Epstein zt”l (known as The Torah T’mimah) has an insightful answer in his work, Baruch She’amar. With the choice of Har Sinai, Hashem taught us that a proper Kabbalas HaTorah requires a balanced approach to this midah. At our core, we must be humble and committed to follow Hashem’s mitzvos and the guidance of our leaders. There is no room for arrogance. However, an abundance of self-effacement can be dangerous when internalized, resulting in low self-esteem. Far from the goal of complying dutifully to the Torah, reduced self-worth and self-confidence can lead to the abandonment of mitzvos. Those who feel devalued and that their actions are meaningless are unlikely to experience any sense of purpose. What would be pushing them out of bed each day to engage in a life of avodas Hashem? It is for this reason that a life of Torah observance requires some degree of elevation, a sense of pride driving each of us to climb higher and higher each day. Hashem gave the Torah on the smallest mountain to teach us humility, but make no mistake - it was still given from the top of a mountain.
The goal of Shavuos is to reaffirm our commitment to the Torah, and aspire to a life of humility and submission that is coupled with a sense of pride and purpose.