A derivative of this sermon was delivered at Temple Beth Israel in Steubenville, Ohio on Yom Kippur during Kol Nidre services, at the start of Yom Kippur.

Many of the most dramatic moments in a hospital come when something goes unexpectedly wrong. A surgery gone array, a condition gone undiagnosed, or a patient who just doesn’t seem to be pulling through. The surgeons, doctors, nurses, technicians, and specialists do all that is within their power to help their patients — but sometimes there is nothing to be done.

This was a reality I experienced firsthand last year, while serving as a chaplain intern. I was working in the Palliative Care Unit at a large hospital in New York, meeting with patients who faced serious or life-threatening illness. Medicine could do so much — but not everything. Sometimes it couldn’t do anything at all.

In some of those moments of helplessness, when the hospital could no longer keep a patient alive, I took on a truly difficult role: I, along with a team of specialists far more experienced than myself, would break the news of a patient’s death to a family. We would sit in a meeting room off to the side of a hospital corridor. We would give the worst news to people who wanted nothing but the best for their loved ones.

Reactions would vary tremendously on the part of families. Some would express relief that a loved one’s suffering had ended. Others would cry out in pain at the loss. Still others would grieve circumstances that seemed so unfair. But most family members were filled with regret — not only for themselves, but also for the loved one who had died.

Why so much regret? For some, it was because of errors, or perceived mistakes, made early in life — incidents or challenges that the patient had long known about. But for many, there were a whole host of new regrets they voiced on behalf of their loved ones. These ideas had probably not occurred to the patient while he or she was alive. The regrets only became clear after death itself.

One family member particularly stands out in my mind. She was an aging woman who had spent much of her adult life caring for a son beset with medical problems. When we broke the news to her that her son had died, she cried out “I hope he knows I loved him.” I wanted to know more: “You hope he knows you loved him,” I repeated back to her. “Yes,” she said, “I did everything for him. But sometimes we fought like cats and dogs. It was so stressful. I just wanted the best for him. I really hope he knows that.”

The mother’s regret has long challenged me, not only as a particularly difficult moment in my chaplaincy work, but because of the larger questions it raised. What would this woman’s son have said or done had he known his mother harbored such regret? Similarly, what would this woman have done differently had she known the depth of her own regret?

Most troubling, though was the underlying question: how do we know what our regrets will be until it’s too late?

After much rumination, I’m not sure that we ever truly can. But our tradition provides significant guidance about what we can do to at least work to avoid regrets, most notably on Yom Kippur. Just have a look around.

We sit and stand here today with the awareness that many of us will not eat or drink. Many will not wear finery — and some will choose to avoid luxurious clothing, such as leather. Some of us have chosen to wear white and, on this evening unlike others within traditional circles, it is customary to wear a Tallit [prayer shawl] to services.

In no other time during our lives do we cut worldly ties so sharply. We come to synagogue tonight in a way that in many ways mirrors the way we will enter our final resting places.

This evening we spend a great deal of time time peering into the open aron kodesh — the holy ark that holds our Torahs. But to my professor, Lawrence Hoffman, it is of little surprise that the Hebrew word aron also means casket. For it is to the end of our lives that we look tonight.

We may never know who shall live and who shall die this year. We may not know how or when or why. But on some level we know the answer to the question: what would our regrets be if tonight were our last night on earth?

We symbolically cut ties to the world around us so that our minds can be free and our eyes clear to see our lives as they truly are. In my mind the greatest judgment comes not from the Almighty, but from within ourselves. God may well decide who shall live. But we have great power to decide how we shall live.

I invite you to look upon this solemn evening as an opportunity. For during few other times during your life will you have such power to preempt regrets.

May this Yom Kippur be one full of possibility and hope, the chance to look at our potential regrets. And, God willing, address them in a way that will change our lives.

G’mar chatimah tovah. May you be sealed in the Book of Life and blessed with a year of fulfillment ahead.