Why do we celebrate the mitzvah of Sukkos? The commentators state that the Zohar refers to the Sukkah as צלא דמהימנותא, the shade of trust. This depiction of the festival teaches us that throughout Sukkos we are building trust in HaShem. Nonetheless, we must wonder why we focus on the theme of trust and faith specifically on Sukkos?
The answer to this question is that we celebrate Sukkos as a commemoration of our having left Egypt and entering an uncultivated wilderness where our very existence was constantly in the balance. HaShem, in His kindness, provided us with Manna, a well and Clouds of Glory to protect us from the elements and from our enemies. Our leaving Egypt was essentially a transition of our leaving our “homeland” and entering into the unknown. When we are in transition, we need to bolster ourselves with great stores of faith in HaShem.
Sukkos, then, is a time for toil, both in faith and in Torah study, as we culminate the festival with Simchas Torah, rejoicing over the Torah. The Gemara states יגעת ומצאת תאמן, if you toiled and found success, believe it. It is noteworthy that the word תאמן equals in gematria the words זה סכת, this is Sukkos. When we truly toil in our faith in HaShem and in our Torah study, we will be guaranteed success.
Have a wonderful Yom Tov and a Great Shabbos!