We generally consider Chutzpah to be a negative trait. But is Chutzpah all that bad?
Think of it this way – chutzpah is what enabled Steve Jobs to make Apple into the company that it is; Chutzpah is what Elon Musk had when he proposed the idea of PayPal to the world; and chutzpah is what you no doubt used in your life to accomplish your most significant breakthrough.
Chutzpah in the right context is good. Chutzpah is not accepting the status quo; chutzpah is not necessarily doing what everyone near you expects you to do.
A well-known saying in the Mishnah goes like this: "Be bold as a leopard, light as an eagle, swift as a deer and mighty as a lion, to do the will of your Father in Heaven" (Rabbi Judah ben Tema, Ethics of Fathers 5:20). This statement is also highlighted in the first segments of the Shulchan Aruch, the Code of Jewish Law.
The first thing that a Jewish person needs to learn is to be “Bold like a leopard” – translation: have a healthy dose of chutzpah. It allows us to be confident in our Jewishness and not ashamed of it. It allows us to take off work for Jewish holidays even though others are not. It allows us to proudly celebrate our Jewish heritage and not hide it.
One way my Jewish chutzpah is expressed is by walking down the street with a yarmulkah on my head. How do you express your Jewish chutzpah?