Learning with Reb Shlomo (66): Reclaiming the Joy of Yom Kippur

What if Yom Kippur isn’t about the weight of your debts, but the celebration of being completely forgiven—and given a "new loan" to start again?In this moving shiur, Rav Leibish Hundert dives into the radical teachings of Reb Shlomo Carlebach to uncover the hidden Simcha (joy) of the holiest day of the year. Shlomo used to say that spending all of Yom Kippur counting sins is "almost a chillul Hashem." Instead, Rav Leibish invites us into the Kodesh Kodashim (Holy of Holies) of our own souls to experience a connection with the Divine that transcends time, space, and judgment.In this episode, we explore:The Bank Analogy: Why Yom Kippur is the ultimate "reset" for our spiritual ledger.Childish vs. Childlike: Moving past rigid self-criticism to a place of wonder and "newness" (Chadesh Yamenu K’Kedem).The Secret of the Satan: Understanding the Gematria of HaSatan and why the "prosecutor" is silent on this one day.Confession as a Love Song: Transforming the Viduy (confession) from a list of failures into a melody of longing for a Beloved.Whether you are preparing for the High Holidays or looking to heal your relationship with Teshuva, this teaching offers a path to stop hiding from Hashem and start hiding with Hashem.Recorded at Yeshivat Simchat Shlomo, Jerusalem.Recorded Aug 23, 2026.