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Making amends is truly when the rubber meets the road. We have done all this work forgiving others, and now we have to go out there and repair the damage we have done. If we worked on our letter yesterday, and rehearsed our conversation, we might feel ready. Yet pride, fear and procrastination can stand in the way of healing. How will we be received? Is the person going to retaliate? Perhaps we are still pining for a certain outcome, or secretly hoping we can be absolved of our responsibilities? But like Nachman ben Aminadav of the famous midrash, we have to walk through our fears, let go of our expectations, and trust that the seas will part for us.

When it comes to making amends, like with many other things, timing is everything. We should not make amends if our doing so will cause more harm, and, when we do, we need to wait for the right opportunity to present itself. There are cases when making amends is impossible; we are unable to locate the person we have harmed, or that person is now deceased. In these cases, it is possible to have the conversation as a visualization; or, if we know where the person is buried, to go to the grave and read our letter to them. There is also a level of hurt, a level of damage that can never be repaired. If we have caused deep emotional, physical or psychological pain to another being, there might be nothing we can do or say that can heal the pain. But this doesn’t preclude us from taking responsibility and making amends by doing related community service for example. In contradistinction, there are cases where correcting the wrongs we have done can be accomplished immediately. If we stole, can we return what we have stolen or make financial reparations? If we broke a promise can we fulfill it now? If we slandered or affected someone’s reputation, can we publically make a declaration to set the record straight? If there is anything for which immediate repair can be made, we must not delay in taking action.

In the same way, we must seize the right opportunity to make amends when it presents itself. The context of the High Holy Days is such an opportunity. Amends need to be made in person, or, at least in a phone conversation, nothing else will do. Prepared to make amends to the person in your letter, you might want to send them an e-mail or let them know in person (if you meet them at synagogue for example,) that you would like to set up a meeting with them. Tell them why.

As you meet with that person, ask for their listening ear and–if you feel well rehearsed–share with them the words you have prepared. It is also perfectly acceptable to read them your letter instead. Whatever happens next, we are to remain an attentive, humble and authentic listener. The person might share with us their story, the pain they suffered that remained beyond our awareness, and all we are asked to do is bear witness to the suffering we have caused. Now they also might refuse to meet with us in the first place, and, they might reject our amends altogether. That’s OK. Remember that we need not harbor any expectations as to how our apologies may be received; our job is to offer them regardless. Our rabbis teach us that we are to make three humble and genuine attempts. If all three are rejected we are to consider ourselves clear of our duty.

Ultimately, we are to make amends to all the people on our list. Some conversations will be less difficult to have than others, and could take place within the next few months. Others might take us many years to even consider having. There may even be one that will remain beyond our reach in this lifetime. As the famous quote from Pirkei Avot–the Ethics of The Fathers–reminds us: “You are not required to complete all the work, but neither are you free to desist from it altogether.” [Avot 2:21]

Tomorrow, as we all ready ourselves to meet in Synagogue for Kol Nidrei in the evening, I will share some concluding thoughts for our “Days of Awe” retreat. And then we’ll have all day Saturday to be together as a community, and support each other through the transformative experience that Yom Kippur can be.

G’mar Chatimah Tovah, may the Divine seal be for good.