Lessons on The Essence of Sukkot
Returning to the Land
The Sukkot holiday is full of mitzvot (good deeds), including the mitzvah of the lulav, the four species. Our Sages say that the four species are similar to weapons - the lulav is similar to a sword, or perhaps a rifle, the etrog maybe to a grenade. In any event, the Sages intend to tell us that there are spiritual wars and there are physical wars, and Man in this world must confront various pests and ward them off.
Rabbi Zalman Baruch Melamed | Tishrei 14 5782
Absence makes the heart Grow fonder..
The “3 Festivals” (or “R’galim”) have connections between them- such as the ‘Hekish’ (connection) between Pesach and Succos.
Rabbi Avraham Berk | Tishrei 13 5782

Taste the Tree Like the Fruit- Sukkot as a Microcosm of Eretz Yisrael
Rav Kook points out that just as most of the tree is roots, trunk, branches and leaves, despite the fact that the goal is the fruit, similarly most of life is preparations (e.g. eating, dress, work, cooking, raising children), and often one doesn't even achieve his goal. Does that mean that he wasted his life?! The basic question is, if most of life is "tree", and I want to have meaning in life, I have no choice but to find a way to have "taste" in the tree, not just in the fruit. This was the original plan in Eden, and is meant to be the ideal lifestyle, as expressed in the Etrog where the tree tastes like her fruit. Eretz Yisrael is likened to Sukkot, where even the secular/mundane/"tree" has meaning/taste/holiness, and it's all a mitzva.
Rabbi Ari Shvat | Tishrei 23 5781

Sukkot, Emunah & Cherophobia: Solving the Fears of Happiness
Sukkot is the climax of agricultural success, but also brings with it the anxiety & nervousness regarding the upcoming season. The Sukkah represents the clouds which precede the rainy season, & are the time when God judges us regarding rain. Cherophobia is a common problem where happiness & accomplishment are accompanied by fear: After I've achieved my goals, there's a feeling of emptiness- What do I do now?!". Also, we ask like Kohelet, "Why am I still not happy?!". There's also the fear that I may lose or someone will take away what I've achieved. Also the fear "what if people reveal that I'm really not so talented?". Sukkot are termed in kabbala: "The Shade of Emuna", that only God has absolute success, & only He can provide security regarding past & future.
Rabbi Ari Shvat | Tishrei 21 5781
Succot
Rabbi Berel Wein | Tishrei 12 5781

The Strength of a Sukka
Rabbi Stewart Weiss | Tishrei 12 5781

MOVERS & SHAKERS
Rabbi Stewart Weiss | Tishrei 14 5779
