Kol Nidrei Sermon 2025
Rabbi Laurie Zimmerman
Congregation Shaarei Shamayim
October 1, 2025
Congregation Shaarei Shamayim
October 1, 2025
“Turning from Regret to Comfort”
Jacob is alone in the desert. It’s the middle of the night, and he can’t sleep. He keeps thinking about his brother, Esau. Tomorrow he will reunite with him, after being apart for twenty years. He is afraid. Esau had wanted to kill him after Jacob tricked his father into giving him the blessing instead of Esau. He prepared. He sent huge gifts of cattle to appease his brother. He divided his camp in two so that even if one were destroyed the other might survive. He prayed to God.
And then, out of nowhere, a mysterious figure grabs him. They wrestle all night long. Jacob gasps for breath. He grunts. He refuses to let go. It’s unclear who this mysterious figure is. The Torah says it’s an ish—a man, but we do not know what that means. It could be an angel, or his conscience, or God. Jacob seems to be fighting himself, trying to come to terms with how he deceived Esau.
Tonight is Kol Nidrei, a time in the year when we are supposed to wrestle with ourselves, with who we are, with the decisions we have made. We consider our actions in the past, and how we want to move forward in the future. We ask ourselves: When do we take a risk and when do we use caution? How do we care for our own needs while also caring for others?
When we make decisions, sometimes we act out of jealousy, hatred, or anger. Or we are self-righteous or arrogant. We know there is a right and a wrong choice, and we choose the wrong one. But often we are confronted with decisions that are messy and complicated. Sometimes there is no clear right or wrong, or there is but we cannot see it at the time. Our vision is clouded by our love for another person, or we make decisions out of fear and anxiety, or we repeat patterns from our past.
We cannot know what the consequences of our decisions will be, and that makes decision-making feel impossible. Regret takes over. We wish we had chosen the other path. We wish we had known what was on the other side.
*****
My friend, Jon, was recounting his move to Philadelphia from Ann Arbor. “It took my wife and I three or four years to decide whether to move to the east coast. All my siblings live out there, and one of my sisters who is disabled needed my care. I wanted to be closer to them. There was loss in any decision we made, because we loved our community in Ann Arbor. But I thought it would be good for my daughter to be near her cousins. She was already in sixth grade when we decided to move. If we stayed until she finished high school we would be much older. It was now or never. We did it — and it was really hard.”
Jon continued: “Our daughter had such a hard time. Being a new kid in seventh grade made her miserable. She left behind so many friends. This past winter we discovered that she had developed an eating disorder. It was serious. We had to hospitalize her. I was heartbroken, and I felt so guilty. I felt like I had caused the eating disorder, that I was responsible. I thought about moving back.”
As we talked I sensed how much he, like Jacob, had wrestled with his own decisions. Jewish tradition teaches us to be deliberate in making decisions, and to weigh our options carefully. We are supposed to consider derech eretz (human decency), chesed (kindness), and anavah (humility) when making a decision. Yet even if we do, sometimes our values come into conflict. Sometimes how we apply the value is unclear. Sometimes values are only one part of the decision.
“We really deliberated,” Jon said. “It took us three years to decide. We talked, made spreadsheets, went to therapy, visited the different cities. We got to a point where we just had to make a decision. The process was too long and too hard.”
He continued: “Finally, we made our decision, but looking back, I don’t know if we made the right choice. I know that it might have been better if we had never left Ann Arbor. But I really feel that there comes a point when you have to accept your decision and make the best of it. The life you have chosen becomes stronger, and the life you did not choose recedes into memory. You adapt. I didn’t lose the feeling of regret, it’s always with me, but things began to feel a little less dark.”
*****
As dawn approaches, Jacob and the mysterious figure are still wrestling. Jacob won’t give in. He’s trying to work out his relationship with his brother, and his parents. His mother had pressured him to deceive his brother, Esau. He knew it was the wrong thing to do, but he did not want to go against her wishes. She had told him it was for the well-being of the family. She believed that he, and not Esau, was meant to carry forward the covenant. He wanted her love, so he obeyed. The consequences were unbearable. He had gone into exile for twenty years and never saw his mother again. He regretted his decision. And now, after all this time, he was going to reunite with his brother tomorrow. He felt anxious.
The mysterious figure realizes that Jacob is not going to give in, so he strikes Jacob in the hip. Jacob is wounded. He feels the pain. But still, he won’t let go. He hangs on and demands: “I will not let you go unless you bless me.”
The mysterious figure asks, “What is your name?”
“Jacob,” he answers.
The mysterious figure replies: “No longer Jacob. From now on you are Israel, because you have wrestled with God and with human beings, and you have endured.”
Jacob wrestles with his fear and guilt. He is blessed because he faces these feelings honestly and directly. He wrestles and he won’t give in. He turns his pain into blessing. He endures.
*****
My friend, Amy, endured for years when she was taking care of her parents, who lived in Rochester. “My dad was diagnosed with Alzheimer’s in 2012. My mom was his caretaker. Managing the illness was complicated enough, but my father was mean and abusive. He would only allow my mother to care for him. One day my mother fell apart. She had a breakdown, and she never recovered. Eventually she developed a psychiatric condition that presented as, or maybe was, dementia.”
Amy would travel back and forth from New York City frequently. “It’s like I was watching my parents fade in real time,” she explained. “They were alive but not really there. They couldn’t make rational decisions anymore.”
Amy had to make impossible decisions. “There were no good options. My brother was useless. My aunt barely helped. It was all on me.” She decided to put her parents in different facilities. “You only have the information you have at any one time. Nothing was clear. Separating my parents – I wondered, do I have the right to do that? It was so sad. But just because it’s hard and painful doesn’t mean it’s not the right thing to do. I thought that it would give my mom another chapter in her life, to be free from my father’s control, and she deserved that.”
Amy continued, “I don’t regret most of what I did. But I do regret how little time I was able to spend with my husband. He never complained or criticized, but it wasn’t fair to him. I had to quit my job; I was always in Rochester. Even when I was here my head was somewhere else. And my kids. My daughter has Down Syndrome. They both got too little of my attention. I was emotionally unavailable to them.”
Eventually, Amy found some compassion for herself. “I learned that you have to go easy on yourself, tell yourself that this is hard and I’m doing the best that I can. It’s overwhelming, and there’s no right answer. What seemed right a year ago is no longer the case. But how could you possibly have known?”
*****
The sun comes up, and the mysterious figure vanishes. And Jacob, now Israel, limps across the river toward Esau. He carries with him a new wound from a night of wrestling, as well as his blessing.
Jacob names the place Peniel, meaning “Face of God,” because, he says, “I have seen a divine being face to face, yet my life has been spared.” Perhaps the divine being was in the wrestling, in the struggle, in coming to terms with his past.
*****
We all carry wounds from the complexities of the difficult decisions we make. The question is what we can do with those wounds — our regret, our distress over actions we took and actions we did not take, our pain from living with the consequences.
In Biblical Hebrew, the word for regret is nacham. It implies a sense of sorrow, disappointment, and distress. But it also has a second meaning, which is comfort. Regret and comfort could seem like opposites. The medieval philosopher, Rashi, teaches that nacham really means a shift in perspective or a turning of the heart. With regret, we turn away from a previous decision. With comfort, we turn away from grief and towards consolation. Both regret and comfort require that we open our hearts, which have been closed by fear, grief, and pain.
We cannot change the past, but we can shift our perspectives, and we can turn our hearts. We can open space for change and in that space embrace growth. Jon and Amy, our patriarch, Jacob, and all of us can heal from our wounds by shifting our perspectives and turning our hearts.
As we grow older we are continually faced with difficult decisions. Sometimes there are no good options and doing the right thing is unclear. Our values only get us so far. We research and plan and do our best, but we cannot predict what is on the other side.
Like Jacob, we carry our wounds with us. And like Jacob we also carry our blessings with us. The blessing of being able to emerge from dark times. The blessing of healing.
We are sustained by our fierce commitment to others. By our strong sense of compassion. By caring for ourselves. By the wisdom of past mistakes. By seeking guidance and deliberating. By our moral compass.
On this Kol Nidrei may our regret turn to comfort, and may we walk into the new year with open hearts.
G’mar chatimah tovah—may we be sealed for life.
Tue, October 28 2025 6 Cheshvan 5786