Sukkot is called zman simchateinu — the time of our joy.

But what happens when Yom Tov arrives and you don’t necessarily feel that way?

In this special Erev Sukkot shiur, Rav Shlomo Katz and the chevra of Shirat David learn a remarkable Torah from R’ Leibele Eiger that opens up a completely different way of entering the chag. Maybe the joy of Sukkot isn’t something we have to produce or prove. Maybe there is something much deeper taking place simply by walking into the sukkah.

A shiur for anyone who wants to enter Sukkot with a little less pressure, and a little more openness to what this Yom Tov is giving us.
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Chapters

00:00 Opening Dedications and Memorials for the Month of Tishrei
 01:30 Why I'm Giving a Shiur on Sukkot This Year
 03:18 R’ Leibele Eiger’s Teaching on Sukkot as Our Joy Time
 05:31 Comparing Sukkot to Pesach and Shavuot
 07:01 Sukkot as Unity of Giver and Receiver
 15:55 Closing Thoughts and Final Blessings
 22:44 Connecting Sukkot Topics to the Teaching
 25:11 Quote from Rabbi Chanania ben Akashia on Torah and Mitzvot

Rav Shlomo Katz and Rabbi Stewart Weiss explore the concept of Mesirut Nefesh (self-sacrifice) during the annual memorial for Ari Weiss Hy"d, who fell in battle after Sukkot.

Drawing on letters from the Lubavitcher Rebbe and teachings from the Vilna Gaon on overcoming hatred (Sinat Chinam), they redefine heroism not just as physical bravery on the battlefield, but as daily restraint, holding back in arguments, refusing to judge others, and making space in our hearts for every fellow Jew.

Rav Shlomo Katz explores the poignant transition from Hoshana Rabbah into Shemini Atzeret and Simchat Torah.

Citing the liturgical prayers (Ani VaHo Hoshia Na) and Rav Kook’s reflections on domestic holiness, Rav Shlomo teaches how to carry the security experienced inside the temporary hut (Dirat Arai) back into our permanent homes (Habayit), trusting that Hashem seeks us out (Doresh Otanu) and desires an ongoing conversation all year round.

Rav Shlomo Katz explores the legacy of Rebbe Nachman of Breslov on his Yartzeit during Chol HaMoed Sukkot.

Citing stories of Reb Nosson buying an Etrog and teachings from Reb Levi Yitzchak Bender (Siach Sarfei Kodesh), Rav Shlomo emphasizes choosing human warmth over legalistic perfectionism and praying to truly taste, smell, and feel the sweetness of our mitzvot.

Rav Shlomo Katz explores Rebbe Nachman of Breslov’s core teachings in Likutey Moharan during an intimate late-night session in the Sukkah.

He unpacks how to break free from Mochin de-Katnut (the petty, contracted mind) and paralyzing guilt, replace self-persecution with Hitbodedut (personal prayer), and focus on the Nikudah Tovah (the good point) to begin completely anew every single day.

Rav Shlomo Katz explores Rebbe Nachman of Breslov’s vital teaching in Likutey Moharan regarding the spiritual trap of stubbornness (Hit'akeshut) in prayer.

Citing core Breslov Hasidut, Rav Shlomo explains how demanding that Hashem fulfill our requests in the exact manner we imagine is akin to taking something by force. Instead, he teaches how to approach Hashem with genuine supplication and humility (Rachamim u-Tachanunim), surrendering rigid expectations to ask Hashem for what we truly need rather than what we think we want.

Rav Shlomo Katz explores three foundational teachings from Rav Kook directly inside the Sukkah.

Citing Orot HaTeshuva, Moadei HaRe'iyah, and Rav Kook’s commentary on Yaakov Avinu in Midbar Shomron, Rav Shlomo discusses how post-Yom Kippur purification breaks spiritual shackles, why true peace (Shalom) includes accepting partial progress, and how to channel Yaakov's midah to integrate sudden spiritual illuminations into steady daily growth.

Rav Shlomo Katz explores Rav Kook's visionary essay from Moadei HaRe'iyah on how a fragile, temporary hut with thin walls serves as a Migdal Oz (tower of strength). 

Rav Shlomo contrasts modern physical weaponry with the eternal power of divine law, demonstrating how rebuilding the national home in Eretz Yisrael requires spiritual courage, inner security, and beautifying the mitzvot.

Rav Shlomo Katz explores how Sukkot shifts our focus from the sanctity of time to the intrinsic holiness of the Jewish people.

Citing the Zohar’s teachings on the Ushpizin (the seven holy guests) and Rav Kook’s commentary on Mikra Kodesh, Rav Shlomo teaches how to invite divine protection and ancient spiritual mentors into our temporary dwellings and fleeting circumstances.

Rav Shlomo Katz explores the profound distinction between essential love (Ahavah) and affectionate fondness (Chibah).

Drawing on the Tur, Midrashic commentaries, and Rav Kook, Rav Shlomo illustrates how basic survival necessities like manna sustain life, whereas the Sukkah and its surrounding light (Ohr Makif) represent the extra "candies" Hashem gives us simply because He likes us and delights in our closeness.