Elul looms large. As the summer wanes, this Hebrew month presents us with the enormous possibilities of teshuva, or repentance.

While the practice of asking for forgiveness from God is part of the daily prayers, during the month of Elul we are meant to take this to an entirely new level – by turning to every person in our lives, and to God, and asking for forgiveness for all the ways we have failed in the past year. It is perhaps one of the most powerful, terrifying and purifying religious practices.

But the sages differ on how one should engage in this practice, and what its dangers and limitations are. Rabbi Jonah of Gerona, a medieval scholar, posits in The Gates of Repentance that the first principle of teshuva is, “One must ask oneself: ‘What have I done? What have I become?’” This initial act of reflecting on who we are and what we have become in the last year is only a beginning. The hard part is turning to those we are closest to, whom we might have hurt (and who hasn’t hurt someone this year, even unintentionally?), and saying to them: “Please forgive me if I have hurt you in some way.” Whether the pain we caused was known or unknown to us, just saying these words can open up the path for reconciliation, but such direct interpersonal encounters can also open a floodgate of difficult responses and realizations.

But the ancient sages who edited the Babylonian Talmud tractate of Yoma were very much aware of the complexities of this practice of asking for forgiveness. They knew that if we were really to take the practice seriously, difficult questions would emerge: How many times do I have to ask someone to forgive me? What if the person I need to ask forgiveness from has died? Is it always the right time to ask for forgiveness? Experienced as they were with the same human frailties that we struggle with, the sages taught us some guiding principles which, even today, may help us best navigate Elul: • You need to ask someone for forgiveness at least three times; • If need be, ask rabbis and friends for help in a difficult situation; • Even if the person is deceased, you should go to their grave and ask them and God for forgiveness; • Repentance isn’t always possible and we cannot force another person to forgive us; Don’t wait until the night before Yom Kippur to ask someone to forgive you. And don’t wait for a time when it might get easier – because it probably won’t.

As the famous rabbinic dictum in Mishna Pirkei Avot, repeated in the liturgy, teaches us, “Repent one day before your death. But how do we know when the day before our death will be? We don’t, and thus we should repent every day.” (Shabbat 153a) All of these questions and challenges become the focus in Elul, an entire month of engagement with our most difficult relationships. All of them call for examination, all of them call on us to rethink and repair them.

Even the most perfect and righteous need to examine their deeds.

As Rabbi Jonah of Gerona wrote, quoting Ecclesiastes: “‘There is not a righteous person on earth who does [only] good and does not sin’ (Eccles.7:20). However, [the righteous] subdue their evil inclination 100 times. If they have succumbed to a sin once, they do not repeat it, to prevent becoming loathsome in their own eyes; and so they repent.”

(The Gates of Repentance, The First Gate) It is this process of teshuva now which will enable us to better engage with the deep spiritual challenges of the month that follows, Tishrei.

The more work we do now on heshbon hanefesh (accounting for one’s soul), the greater will be our joy, because we will be living our most important relationships – and our entire lives – closer to the best vision we have for ourselves.

■ Rabbi Rachel Sabath Beit-Halachmi, PhD, is the national director of recruitment and admissions and President’s Scholar of the Hebrew Union College- Jewish Institute of Religion. She teaches at the Shalom Hartman Institute of North America.

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