Vayeilech & Yom Kippur

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Repentance – A Practical Guide & Important Pointers

By: Rabbi Barak Bar-Chaim

Yom Kippur is the most effective time to cleanse and purify ourselves. The repentance process is the modality through which this cleansing is achieved. In his Laws of Repentance, it is clear from Maimonides that there are two distinct categories from which we are required to repent: 1) sinful action and activity we have performed (such as speaking badly about others, acts of dishonesty, theft, transgressing the laws of Shabbat, eating things prohibited by the Torah, and all other forbidden activity), and 2) repentance for negative character traits or beliefs we have developed (such as laziness, anger, a lack of true faith, jealousy, and similar internal flaws).

There are four main parts of the repentance process: 1) stop performing the forbidden activity, 2) regret the performance of the negative activity coupled with a sense of embarrassment, 3) accept upon oneself never to perform the activity again, and 4) verbally confessing and detailing one’s sins before God, verbally expressing one’s remorse and shame, and verbally stating that one will no longer engage in the forbidden activity.

The entire repentance process must be performed with complete truth and sincerity. It is, of course, ideal for us to completely repent for every negative character trait, faulty philosophical view, and negative action performed, but this is a daunting task. Rabbi Yisroel Salanter suggests that every sin can be divided up into various aspects. We should begin our repentance process with the aspect of the sin that is easiest for us to correct, and then perform the four steps of repentance on that specific aspect. Rabbi Salanter explains that if one does this sincerely, one is considered (in the eyes of the Torah) to be a person who is completely repentant. Ultimately, we should work to correct every aspect of our sins, but we should begin with truth and sincerity on the easier aspects.

I remember someone once asked me: “Rabbi, how can I honestly repent and tell God I am going to keep Shabbat this year on Yom Kippur? I live far away from my parents, and I am going to drive to their home on Shabbat. I honestly do not intend to keep Shabbat!” I explained to the person that, while there are aspects of Shabbat they were not ready to observe at the present time, they should repent and work on other aspects of Shabbat. For example, they could refrain from driving to the mall on Shabbat, from doing business on Shabbat, and from turning lights on and off at home on Shabbat. They could honor Shabbat by wearing special clothing, attending synagogue services, and in various other ways.

Let us use this precious time to consider and analyze our actions and character traits. Let us find aspects that we can transform completely, thereby achieving the cleansing and purity that Yom Kippur offers!