Last week, during a prison chaplaincy visit, I got into a discussion on Teshuvah with a group of inmates. One of them had a paperback English translation of Shaarei Teshuvah, a treatise on Teshuvah by 13th century sage, Rabbi Yonah of Girondi. There he cites a Talmudic discussion between Rabbi Eliezer ben Yaakov and the Sages regarding the following question. If one confessed a sin on Yom Kippur and did not repeat the sin during the following year, may that sin be mentioned the following Yom Kippur. While the sages prohibit one from bringing the sin back up, Rabbi Eliezer ben Yaakov recommends it.
What drives these two opinions? How do we apply this wisdom in our daily lives?
The sages are concerned that repeated focus on past sins can drag a person down and paralyze them, preventing further growth. Rabbi Eliezer believes that keeping an eye on past indiscretions can help prevent arrogance, the root of all sin.
Practically, the Rambam and other Halachic authorities encourage it but do not require it. Clearly the solution lies in finding a balance. The Rebbe framed this in terms of compartmentalization. We should designate certain times (such as reciting Shema before bedtime) for introspection on our imperfections. Knowing what I am capable of will keep me vigilant and humble. However, we should free ourselves from these thoughts during all other times to avoid paralysis and melancholy. While I am busy with the rest of my day, serving Hashem must be with joy and alacrity.
Chassidus offers one additional insight to solving this dilemma.
They once asked a drunkard why he kept drinking, knowing that it was going to not end well. He explained that each time he takes a drink he becomes a new man; that man also deserves a drink…
Ideally, as we progress through life, we grow and develop spiritually. The new me finds deeper ways to return to Hashem that I was incapable of previously. So, rather than keeping me down, the new Teshuvah is the symptom of a higher striving. This is rather more liberating than paralyzing.
As we approach Yom Kippur, I wish us all to have a meaningful day, filled with connection and at-one-ment.
Shabbat Shalom
Rabbi Mendel Rivkin