Yagon and Teshuvah: True Remorse vs. Self-Pity

Full Summary

This shiur explores the concept of yagon (remorse/sorrow) in teshuvah from Rav Moshe Cordovero's Tomer Devorah. The primary question addressed is what constitutes proper yagon: should one feel bad about what they did to Hashem (ה׳), or about their own spiritual losses? The speaker analyzes a passage that compares the pain of sin to losing money - just as losing money causes distress, so too should one feel distress over spiritual damage. However, the critical distinction is made that true yagon must focus outward on the relationship with Hashem, not inward on personal losses. The shiur examines three possible interpretations of proper yagon: 1) A combination of regret for harming Hashem plus regret for personal spiritual loss, 2) Pure focus on what was done to Hashem, or 3) Sorrow specifically about the damaged relationship and loss of connection with Hashem. The speaker strongly argues against the first interpretation, noting that depression and self-focused sorrow are counterproductive to teshuvah. A fundamental teaching emerges from the text that yagon of the neshama (soul) is more effective than physical suffering in arousing Divine mercy. The Tomer Devorah explains this through the concept that Hashem has three partners in creating man, but the neshama belongs entirely to Hashem. Therefore, when the neshama experiences genuine spiritual anguish, it awakens Divine compassion more than physical pain, which doesn't directly involve Hashem's portion in man. The shiur draws an analogy to divorce proceedings: losing a car in divorce causes personal distress, but losing the shared home represents the loss of relationship itself. Similarly, bodily suffering represents personal loss, while spiritual anguish of the neshama represents the damaged relationship with Hashem. True teshuvah requires focusing on this relational damage rather than personal spiritual deficits. The speaker emphasizes that most requests for forgiveness, both to Hashem and between people, are actually self-centered - focused on how one appears or feels rather than on the harm caused to the other party. Authentic teshuvah demands shifting focus from 'what I lost' to 'what I did to Him' and 'how I damaged our relationship.' The text concludes by stating explicitly that one should not be distressed over worldly losses, but only over sins and damage to one's service of Hashem, reinforcing that proper yagon must be relationship-focused rather than self-focused.