Chag HaSukkos is a Yom Tov meant to commemorate the manner in which Hashem displayed His love for the Yidden by protecting us from the harmful elements of the desert. The following famous question is asked by the Tur. If these events played out in the spring, why then don’t we celebrate the Yom Tov in Nissan rather than Tishrei? Another point to reflect on is the seemingly mystifying Medrash that refers to Sukkos as "ראשון לחשבון עונות" when in reality, “Rishon” is actually several days earlier?

     The Chiddushei Harim of Ger, R’ Yitzchok Meir Alter zt”l, explains as follows. A main proviso of the mitzvah of Sukkah is "למען ידעו דורותיכם". To realize and internalize what Hashem did for us, but not just we must internalize this, but all generations as well, need to be cognizant. The ideal time to really focus on this is when our heads and hearts are clear and pristine. Now, after the Yimei Hadin, we have a fresh slate and a clear mind. Whereas by the time Nissan rolls around, our minds aren’t as clear to think and thank properly.

     Similarly, while sitting in the Sukkah, the shade of Hashem, we can make a cheshbon, a proper reckoning, of our madreigos and prepare for the entire year. Hence,  Sukkos is indeed a Rishon to make a cheshbon of our aveiros. 

     The Gemara (Sukkah 53a) brings down from Rav Yehoshua ben Chananya who said that whilst celebrating the Simchas Beis Hashoeiva, we saw no sleep in our eyes. The obvious question arises, how can one see himself sleep?

     The Chasam Sofer zt"l offers an insightful thought. A person can be wide awake yet find himself in a deep slumber, numbed to any form of inspiration. This was not the case in the Bais Hamikdash. Rav Yehoshua ben Chananya was making a profound statement: we were never idle but rather, we were constantly mesmerized and taken by the holiness of the Simchas Beis Hashoeiva. We were therefore spurred on to grow closer to Hashem. Because sitting by idly or remaining stagnant is like sleeping through life while awake. So let us reflect on Hashem’s infinite kindness, make the proper calculations on the first day of reckoning, and wake up from our slumber. With this we will do teshuva shelaima m’ahava, and be zoche to an abundance of  beracha, nachas and be zoche to sit in the Sukkah of the Leviyasan all together in Yerushalayim.