A free account is required to play audio and download files.
No community start suggestion yet.
Should teshuvah begin with regret for the past or resolve for the future? Rabbeinu Yonah teaches that occasional sins require charatah first, while habitual sins demand azivat hachet first - you cannot properly regret what you're still actively pursuing. The approach resolves apparent contradictions in the Rambam (רמב"ם)'s sequence of teshuvah.
This shiur analyzes a fundamental teaching from Rabbeinu Yonah regarding the proper sequence of teshuvah (repentance) based on the nature of one's transgression. The Rav explains that there are two distinct paths to repentance depending on whether the sin was committed occasionally (derech mikreh) or habitually. For occasional sins - where a person doesn't seek out transgression but fell due to a moment of weakness - teshuvah must begin with charatah (regret). This involves genuine remorse accompanied by yirat Shamayim (fear of Heaven), not merely feeling bad about one's actions. The sequence follows 'modeh v'ozev yerucham' - first confession/regret, then abandoning the sin. The person must strengthen themselves with Divine fear so that even if the same temptation returns with equal force, they will resist.
Looking for the full summary?
Full access is available to members of the TUF Alumni Association or the Yam Hagadol Foundation.
Already a member? Let the admin know!
Looking for the full transcript?
Full access is available to members of the TUF Alumni Association or the Yam Hagadol Foundation.
Already a member? Let the admin know!
Dedicate a Shiur in Mussar
L'ilui nishmas a loved one. In honor of a simcha or yahrzeit. As a zechus for a refuah sheleimah. Your dedication helps carry Rabbi Zweig's Torah to learners around the world.
Up Next in this Series
Why does Rabbeinu Yonah reverse the normal order of teshuvah for habitual sins, requiring one to first commit to stopping before expressing regret? For ongoing transgressions, genuine regret is impossible while maintaining intent to continue sinning. The shiur applies this principle to interpersonal offenses, showing how even forgiven wrongs may still require teshuvah to God.
What type of yagon (remorse) leads to effective teshuvah - sorrow over personal spiritual losses or over damaging the relationship with Hashem? The Tomer Devorah's teaching that neshama-pain awakens Divine mercy more than physical suffering reveals that authentic teshuvah requires focusing outward on relational damage, not inward on personal deficits.
Why does Rabbeinu Yonah require da'agah (worry) as a separate principle of teshuvah beyond regret? The shiur develops that the heart and eyes act as 'sarsur aveirah' - not mere conduits but active intermediaries that influence sin. Each requires its own repair: the heart through brokenness, the eyes through tears that serve as 'dam ayin' - a sacrifice from the sinning organ itself.
Why does the Rambam place free will exclusively in Hilchos Teshuva rather than Yesodei HaTorah? The shiur argues that teshuva begins not with correcting specific sins but with recognizing that free choice grants us ability, not right—we must abandon the arrogance of self-centeredness and reposition Hashem at the universe's center. Only then can we achieve immediate closeness to Him.
Why is vidui (confession) the central mitzvah in Hilchos Teshuvah, rather than teshuvah itself? The Rambam distinguishes between teshuvah (establishing a prospective relationship with Hashem) and vidui (achieving kapara for the past). Vidui transforms the focus from self-improvement to recognizing Hashem as the "baal davar"—the injured party—and communicating directly to Him, which is what undoes yesterday's aveiros.
Why does the Rambam locate the essence of teshuvah in vidui (confession) rather than behavioral change? The shiur explores how vidui works even for shogeg (unintentional sin), showing that confession restores relationship with God even when one has pushed Him out of one's world. The connection between vidui and todah (thanks) reveals the deeper meaning of confession.
What does kapara really mean—erasing the sin or restoring the sinner? The shiur builds on Rambam Hilchos Teshuvah 1:3 to argue that kapara is not about making sins disappear but about going forward in a relationship with Hashem. The story of Yishmael read on Rosh Hashanah—"ba'asher hu shom"—teaches that the din focuses on who we are now, not on fixing the past.
