Days on the Jewish Calendar: Tishrei
Rosh Hashanah: Part 1
Shofar is a mitzvah, a reminder to do teshuvah, and, deeper still, the way we crown Hashem as King. A look at how these three levels explain a strange detail in the Gemara: why the "ten days of teshuvah" are described as falling between Rosh Hashanah and Yom Kippur, as if neither day were included.
Sukkot: Part 1
Both the sukkah and the four kinds are special mitzvot of the holiday, yet the whole Yom Tov is named for the sukkah alone. A look at what makes it unlike any other mitzvah: it surrounds the whole person, and even turns ordinary eating and sleeping into an act of serving Hashem.
Simchat Torah: Part 1
If Simchat Torah celebrates finishing the Torah, the obvious way to mark it would be learning even more. A look at why we dance instead with the Torah closed and wrapped, and the famous story of a simple Jew who danced as hard as anyone in shul.
Rosh Hashanah: Part 2
On Rosh Hashanah we're supposed to feel like a servant utterly nullified before a king, so how do we spend the same prayers asking Hashem for health, children, and parnassah? A look at the difference between asking for yourself and asking so you're able to serve.
Sukkot: Part 2
The Gemara says that whoever never saw the water-drawing celebration in the Beis Hamikdash never truly saw joy in his life, an odd way to praise something. A look at what separates real simcha from ordinary happiness, and why it's tied to serving Hashem beyond your own understanding.
Simchat Torah: Part 2
Shavuot is when the Torah was actually given, so it would make sense to celebrate finishing it there instead. A look at why that joy is saved for right after Yom Kippur, and how it connects to the three stages of a Jew's relationship with Torah and mitzvot: belief, receiving, and finally doing.
Rosh Hashanah: Part 3
Rashi holds that shofar and the Rosh Hashanah prayers of Malchuyot and Zichronot are so tightly bound that neither works without the other. Two parables, from the Baal Shem Tov and from Rabbi Levi Yitzchak of Berditchev, explain why the shofar blast itself, not just the moment it accompanies, is what awakens Hashem's kingship and His memory of us.
10 Days of Repentence
The Rambam's ruling that teshuvah offered between Rosh Hashanah and Yom Kippur is accepted with special speed opens into an analysis of why the Gemara refers to these ten days in two different ways. Teshuvah is shown to operate on two levels: correcting specific aveiros, and renewing the neshamah's essential bond with Hashem, a bond expressed through kabbalat ol malchus shamayim penetrating all ten kochos hanefesh. Rosh Hashanah and Yom Kippur are explained as the 'head' that sets the course of the whole year, with Rosh Hashanah channeling that hisorerus into a Yid's gashmiyus and Yom Kippur channeling it into his ruchniyus.
Yom Kippur
The Gemara records a dispute over whether Yom Kippur itself forgives, or whether teshuvah is required first. A look at how both sides actually agree more than they seem to, and why the deepest layer of the day reaches the yechidah, the singular essence of the Jewish soul.
The Inner Meaning of Shofar
Beyond the halachic mechanics of tekiah, shevarim, and teruah, and why all nine sounds are blown three different ways to cover every possibility, the mitzvah of shofar is unpacked through Rav Saadia Gaon's ten classic reasons. Chassidus reframes the first three, mitzvah, teshuvah, and kabbalas malchus shamayim, as three progressively deeper levels of a Jew's bond with Hashem, explaining why the Rambam places the teshuvah reason specifically in Hilchos Teshuvah and omits malchus from his halachic code entirely. Mashalim from the Baal Shem Tov and the Berditchever Rav, alongside the remaining reasons tied to Matan Torah, the prophets, the Churban, Yom HaDin, the Akeidah, kibbutz galuyot, and techiyas hameisim, close out the ten, followed by a Q&A.
The Specialty of Sukkot
A longer class tracing the sukkah, the four kinds, and simcha back to the same three levels of connection to Hashem found in Rosh Hashanah and Yom Kippur, plus a Q&A on Chabad minhagim, from why we don't sleep in the sukkah to how the Rebbe chose his esrog.
The Ushpizin of Sukkot
A class on the kabbalistic and chassidic meaning behind the seven holy guests who visit the sukkah, why specifically on Sukkot and not any other Yom Tov, and what it means that the sukkah channels a level called makifim d'Binah, high enough to be true light, low enough to actually change us.
The Specialty of Yom Kippur
A full class on what makes Yom Kippur unlike any other day: the same three-level structure as Rosh Hashanah's shofar, why the Kohen Gadol's ketores needed an extra ingredient only on this day, the real meaning of Ne'ilah, and a walk through the customs of Erev Yom Kippur — kapparot, lekach, malkot, and why eating beforehand accomplishes what fasting does on the day itself.
The Year of Hakhel
Lays out the mitzvah of Hakhel from the Chumash and Rambam: the king reading selected portions of the Torah to the assembled nation on the Sukkos following Shemittah, and asks why Hashem withheld this command until Moshe Rabbeinu's very last day, unlike every other mitzvah tied to entering Eretz Yisrael. Answers that Hakhel exists to let the Jewish people relive Matan Torah once Moshe would no longer be there to anchor that feeling, and connects the specific portions the king read to the three stages of recognizing Hashem's mastery embedded in Shemittah. Argues that Hakhel is unusual in that the mitzvah itself is the resulting yiras shamayim rather than a separate consequence, which is why it can still be fulfilled in some form even without a Beis Hamikdash, and closes with a Q&A on where Hakhel had to take place and who read in the king's absence.