Unique Quality of Moadei Tishrei There is a pasuk in Yeshayahu (58:2) that says, “v’osi yom yom yidroshun”. The Yerushalmi says that the two days of “yom yom” are Rosh Ha’Shana and Hoshana Rabbah. What this indicates is that the very essence of these days is teffilah; and not just teffilah, but to seek out Ha’Kadosh Baruch Hu. This gives us a different perspective of Chodesh Tishrei in general. Another source that sheds tremendous light on the Yamim Tovim of Chodesh Tishrei is a statement of the Gra in his pirush on Safra d’Tzniusa. The Gra says that the Yamim Tovim of Chodesh Tishrei are mei’ein l’asid lavo. (From Audio Recording and Reb Avrohom Twersky)
Simcha of Sukkos The Mishna in Taanis says that there were no greater Yamim Tovim for Klal Yisrael like Tu B’Av and Yom Ha’Kippurim. The simcha of Yom Kippur is, of course, the fact that we are forgiven for our sins. All of our aveiros are wiped away. Regarding Tu B’Av, there are mefarshim who explain that the great simcha was the fact that, because they were finished with the undertaking of supplying wood for the Beis Ha’Mikdash, that could go back to learning Torah. B’derech tzachus u’melitzah it is possible to say that it is both these elements that infuse Sukkos with such great joy. On the one hand, it is the time when we rejoice over the mechilas avonos that was granted to us on Yom Kippur. And, in addition to that, we are through with the heavy involvement of preparing all the mitzvos that takes place during the four days between Yom Kippur and Sukkos and are thus free to return to our learning.
(From Reb Avrohom Twersky)
כי לבי שמח בכל עמלי קהלת ב:י, שכרה של תורה פסיקתא זוטרתא שם
The third quality is Ha’Kadosh Baruch Hu’s relationship to the Torah. It is described in Kesuvim: (Mishlei 8, 30) “and I was [His] delight every day”. The Torah is Hashem’s delight. For an individual’s learning to be a source of blessing and influence others – as the pasuk says, “my words shall flow as dew” – the Torah must be for him as it is for Ha’Kadosh Baruch Hu. A delight. As the pasuk says, ” And I shall engage in Your commandments, which I love”. For Mori v’Rabi, my grandfather, Torah was the ultimate delight. His joy with the Torah was boundless, and he shared that happiness with others. His simchas Ha’Torah was contagious and organically passed on to his students and those who listened to his shiurim. (Adapted from a hesped written about his grandfather, Rav Yosef Dov Soloveitchik zt”l)
“The avodah of Sukkos is to be happy the entire Yomtov. Just be happy, that is all you have to do…It can be a difficult avodah!”
Once, during a seudah on Sukkos, Rav Twersky shared an idea from the Arizal regarding the significance of the minimum shiur of a Sukkah being two walls and one tefach. The two walls symbolize the upper arm and the forearm, and the tefach symbolizes the hand. This is representative of Hashem wrapping His arm around us, kavayachol, as one does to a close friend. I could not help but feel that Rav Twersky wasn’t just saying the words, but that he truly experienced them; that he could really feel Hashem’s loving embrace. (Reb Ari Linder)