The Greatest Investment You'll Ever Make [Day 163 - Orchos Tzaddikim | Repentance 20]

The Greatest Investment You'll Ever Make [Day 163 - Orchos Tzaddikim | Repentance 20]

July 14, 2026 · 15 min · Episode 481

About this episode

Rabbi Aryeh Wolbe discusses the importance of Torah study and self-reflection in the context of repentance.

In day 163 of the Jewish Inspiration Podcast, Rabbi Aryeh Wolbe continues exploring the Gate of Repentance in Orchos Tzaddikim . He emphasizes the fourth inspiration for teshuvah: studying Torah, Prophets, Writings, and Talmud with the intent to be awakened and apply its lessons personally. One must ask, “Am I like Abraham or Lot? Jacob or Esau?” and internalize the messages rather than treating them as mere stories. Rabbi Wolbe shares powerful personal anecdotes, including a humbling missed speaking engagement and reflections on how Hashem sometimes uses challenges to prompt reflection. He discusses the fifth inspiration — the awe of the Ten Days of Repentance — urging deep self-examination, genuine change, and seizing the opportunity for closeness with God. The class concludes with inspiring thoughts on emunah (faith), the fleeting nature of this world, and trusting only in Hashem. _____________ This Podcast Series is Generously Underwritten by Peter & Becky Botvin Recorded at TORCH Centre in the Levin Family Studios (B) to a live audience on November 24, 2025, in Houston, Texas. Released as Podcast on July 14, 2026 _____________ This series on Orchos Tzadikim/Ways of the…

Sponsors

Peter & Becky Botvin

More episodes of Jewish Inspiration Podcast · Rabbi Aryeh Wolbe

Explore listener stats, chart rankings, contacts and more on the Jewish Inspiration Podcast · Rabbi Aryeh Wolbe podcast page.