A Jewish Perspective on Constructive Humility

I recently came across an intriguing quote about humility that is attributed to Rav Avraham Yitzhak Kook from his book Middot HaRa'aya:

"It is impossible to achieve clarity of understanding except through humility. Humility which brings out a person's sadness is improper humility, but when it is proper, it engenders happiness, inner strength, and self-respect."

Wait a moment, I thought that humility had to do with being low and meek, especially considering that a) the word "humility" comes from the Latin word humilitas, and b) the word is associated with "humiliation" in English. For many, the word "humility" has almost a negative connotation, where people who are humble let people walk all over them like a doormat. But the Torah (Numbers 12:3) says that Moses "very humble," or ענו מאד. Moses was a great leader who had to tend to the needs of thousands of Jews. He even stood up to G-d on no less than two occasions! We don't associate great leaders with meekness, so something has to be awry with this view of humility.

Meekness leads to self-debasement, which is an extreme I am sure we would all rather avoid. Arrogance is also an extreme because such conceit leads to a narcissistic, hyper-inflated ego that is not based on reality. Both self-debasement and arrogance are extremes. The former is an extreme of modesty, whereas the latter is an extreme of pride.

So what is humility?

As Alan Morinis points out in his book Everyday Holiness (p. 50), "Humility is not an extreme quality, but rather a balanced, moderate accurate understanding of yourself that you act on in your life. That's why humility and self-esteem go in hand." Humility is a balancing act between one's modesty and one's pride. 

With this definition, connecting humility to something such as happiness considerably makes more sense. Humility brings you self-knowledge, which brings about self-awareness. By being self-aware, you have a healthy, intact ego. You know who you are, from where you came, and to where you are going. Knowing yourself and being honest with yourself means you are not prone to having distorted views about yourself or others. Things such as flattery or other people's approval will have no power because you already know where you are, which means you are less dependent on what others think of you because again, you are already aware. 

A practice I have found to be effective in cultivating such humility is from Rabbi Simcha Bunim of Pshischa. He carried two notes, one in either pocket. The first said "I am dust and ashes (Genesis 18:27)." The second said "For my sake alone was the world was created (Mishna Sanhedrin 4:5)." We balance ourselves between knowing that in comparison to G-d, who is Infinite Oneness, we will not be here that long, and knowing that because we are created in His Image, our lives have meaning because we have purpose to fulfill. This near-paradoxical concept is what keeps me more balanced. I know that I should not pretend to be greater than I am, but not deny that I my self-worth. It is the sort of self-truth that we can all cultivate in order to lead more constructive lives.