I have found a few things to be helpful to me personally in cultivating the trait of humility:
1. Going on a hike, going to the botanical gardens, seeing the ocean, going to the zoo—any experiences in nature—really have the power to show me the greatness of Hashem as Creator, and consequently remind me of my place in the world. Often, these experiences are powerful in the moment and don’t last past a few hours or days, and we forget our place in the world soon after. Hanging up pictures of those sights or looking at your album or pictures periodically can help you “relive” that experience.
2. The Rambam counts as one of the 613 to “cling to Chachamim and their traits.” I don’t think that the Rambam is advocating stalking your teachers or Rabbis, but I think the idea is that we are influenced by the people around us. Surrounding ourselves with people who have the trait of humility can help us develop that trait within ourselves.
3. I find that if I think about the words that I say in davening, i.e. that Hashem, is a Melech, Gibor, Gadol, etc., it is helpful in reminding me of my place in the world. Rosh HaShana and Yom Kippur davening are jam-packed with tefillot that discuss these themes, but if we try to stop and focus on our daily davening (definitely a struggle!!), it’s there too.
Finally: Cultivating a character trait is definitely hard work. I think that it is a lifelong endeavor, and there’s no simple “quick fix.” I do, however, believe that a person can make great strides in working on this trait (or any other) and becoming the best that she can be.
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