Episode
The Habits That Hold Us Back [Day 157 - Orchos Tzaddikim | Repentance 14]
- Published
- Jul 6, 2026
- Duration seconds
- 1742
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Summary
In this lesson from the Gate of Repentance ( Shaar HaTeshuvah ), Rabbi Aryeh Wolbe concludes the discussion of behaviors that make teshuvah especially difficult by examining five destructive character traits: tailbearing ( rechilus ), lashon hara, anger, harboring sinful thoughts, and associating with negative influences . These habits are particularly dangerous because they become ingrained over time, making it increasingly difficult for a person to recognize their severity or break free from them. Through practical examples, Rabbi Wolbe demonstrates how even seemingly innocent conversations can lead to misunderstanding, resentment, and broken relationships, underscoring the Torah's call to guard our speech and avoid becoming a "peddler" of negative information. The episode then shifts to the practical work of authentic repentance. Rabbi Wolbe explains that teshuvah requires courage because choosing a Torah life often brings resistance from friends, family, and society. A sincere baal teshuvah must be prepared to withstand criticism, misunderstanding, and even ridicule while remaining committed to Hashem's will. He emphasizes that repentance is not limited to correcting obvious transgressions; it also demands careful study of the mitzvos, honest self-evaluation, and a lifelong commitment to improving the quality and intention behind every mitzvah we perform. The lesson concludes with an inspiring reflection on the privilege of living proudly as a Jew. Rabbi Wolbe shares moving stories—from a recently released hostage whose greatest desire was to fulfill the mitzvah of lulav and later inspire thousands to don tefillin, to individuals who refused enormous financial incentives to compromise their observance of Shabbos. These examples illustrate that mitzvos are not burde…