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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.
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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.
