Question

When doing Teshuvah, what is the first step; giving up the sin and improving ... or regretting one's sin and being sad that one did it?

Answer

Rav Yechiel Schlesinger, director of Yeshivat "Kol Torah", deals with this question in a famous article and he concludes as follows:

"It is first of all necessary to abandon the sin and improve one's conduct, precisely by rejoicing, and without thinking of the past which can cause pain or sadness. It is advisable to concentrate on the joy of being free from sinful conduct after having distanced oneself from the sin. The pain that the memory of the past can generate will come next."

This can be explained as follows: "If we cultivate regret, pain, and anguish before distancing ourselves from the sin, we will sink into a destructive feeling of pointless suffering. We may think that we lack the strength to be able to escape the sin since we are filled with sadness and pain. We will then be dominated by pain and we will lose the desire to get to work as we will feel weak.

This is why we should first approach the Mitzvah to give up the sin with joy and in doing so, we will become aware of our power and independence. Then we will regain confidence in our ability to completely change our behavior and we will feel great satisfaction. Only then will we be able to focus on remorse and pain. At that point, these feelings will not make us sink, but on the contrary, lift us up and lead us to aspire to repair our past, to "run" towards Hashem. We will feel so strong that was able to dominate our Yetzer, to have conquered evil by using our free will, that our pain will be nothing in comparison. "

The words of the Rav are similar to those of Rabbeinu Yona (Shaarei Teshuva 1st part, letter 11): "Man who is entangled in sin should begin by abandoning it while the one who occasionally sins, and who thus approaches the process of abandoning sin with ease, must regret is sin first, since abandoning it is easy for him".