From Rabbi Johanna Hershenson

Middah (character trait) of the Month: Humility
Much of November contains the Hebrew month of Cheshvan. Bitter Cheshvan, as it is known in the Talmud, contains no Jewish holidays. After our Rosh Hashanah through Simchat Torah run, it's really okay to have a moment to catch our breath.
This year, as Cheshvan began, I thought about a midrash(rabbinic interpretation) about Mount Sinai. In it, the other mountains stand tall in contrast to Sinai. The rabbis ask why did God choose such a small mountain upon which to give the Ten Commandments. They answer that Mount Sinai's humility is essential, as if to make room for the word of God.
There is a Chasidic story about the Baal Shem Tov visiting a synagogue, but refusing to enter. When asked why, he said that the prayers of the people inside were too lofty and there was no space left for him to enter.
In both stories, humility is linked to space. If I take up too much space, there is no room for you or anyone else. If I take up too little space, what I have to offer is lost.
The Talmud curiously instructs:
Who possesses haughtiness of spirit deserves excommunication. 
And who does not possess haughtiness of spirit deserves excommunication.
Proper humility is about having the right relationship to self, giving self neither too big nor too small a role in your life (Morinis, Everyday Holiness). Sometimes it is appropriate to take space and take charge. Other times not. Knowing when requires experimentation in paying attention and noticing, and then practicing.
For me, going back to graduate school has opened up all sorts of opportunities to practice both aspects of humility - pulling back and stepping forward. 
I am an older student. I have experienced some things in life that my younger classmates have not. Just because I recognize naïveté, doesn't mean it is my place to correct it. Some of my classmates simply need to learn from their own life experiences in the coming years. On the other hand, there are moments in which my work as a rabbi can - and does - provide insight, or a vivid illustration, to competencies in counseling. My classmates appreciate those reflections and learn from them along with me. Pulling back, and stepping forward.
Maimonides wrote a treatise to the Yemenite Jewish community he entitled: "A Dance of Two Companies." Pulling back, and stepping forward. Humility can be a dance, sometimes big and sometimes small, ultimately more flowing with practice.
    

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