The sages of our tradition have been quick to note the subtle and mystical parallels that connect the joyous holiday of Purim and the most serious day of the Jewish year, Yom HaKippurim, translating Yom HaKippurim as “the day that is like Purim“, Yom K’Purim.  Once, Rabbi Larry Kushner was dramatizing the climactic moment of the Purim story for a rapt audience of pre-schoolers. “What shall I do?” he asked them, in his best Queen Esther voice, as he recounted the options available. “If I don’t go and see the king then bad things will happen to my people and I will feel sad. But if I do go to see the king without being invited I might get hurt myself and then I would feel really bad about that, too! Oh, what shall I do?”  Suddenly, a little boy called out from crowd, “Quick! Be someone else!”

How tempting it is to have that option in life! “So sorry, officer, that wasn’t me speeding. Regretfully, you must have me confused with someone else.” There are various choices we have when it comes to facing the difficult moments in our life.  Examining our actions that have caused us regret is one of the toughest moments! We would much rather be someone else than lay claim to the mistakes we have made or own up to the good deeds we have neglected to perform. However, facing our regrets is the hard work we are called to do at this time of year. When we are called to account on Yom Kippur for our deeds before our community, ourselves, and, ultimately, the Holy One, we cannot simply pretend we are someone else. Each of our actions inscribed in our Book of Life is written by our own hand. All the masks that we wear during the year are removed on Yom HaKippurim and we stand revealed, spiritually naked.  There is nowhere to hide. We are who we are.  We have done what we have done.

Examining our regrets is painful.  We see all too clearly the most sensitive and tender parts of ourselves–our flaws and shortcomings, our imperfections and failings; those parts of ourselves that we endeavor to keep hidden, even from ourselves. But these uncomfortable, embarrassing aspects are part of us, too, and must be accepted if we seek atonement and at-one-ment. Only if we look at our regrets with honesty and compassion will we be able to move forward in our lives.

A hard-edged punk rocker was lying in the hospital and his

situation was looking very serious, indeed. The nurse takes one look at him, sees what terrible shape he is in, and asks him, “Is there anything you regret?” The punk rocker sighs and says: “Well, there were a lot of drugs. A lot of drinking. A lot of fights. A lot of women. (Sigh) I regret everything else.”

Regrets: We all have them.  There is no way around it. If you want a life of no regrets you basically have two options: either you have to be a tzaddik, a completely righteous person, or have no conscience at all. Not many of us can aspire to option number one and none of us, I imagine, would want to aspire to option number two. That leaves most of us with the very likely reality that we will experience the pangs of regret at various times in our lives. How we deal with that regret, however, makes all the difference!

Our rich tradition has given us Yom Kippur–this day of soul searching– because our wise ancestors understood that we are imperfect, that we are fallible human beings. We aren’t saints. We mess up. And we feel bad about those things when we have missed the mark. And that, in fact, is good! That is part of being a human being, too. Feeling regret means that we are sensitive souls who are upset and disappointed when we don’t live up to the image we have of ourselves or when we let others down. Feeling regret about our behavior suggests that we are motivated to do better; to act differently next time around so that we can be better. Regret is a healthy and integral part of our lives when it serves its purpose to help us grow and to move us towards more positive actions. For you see, when we gather together on this holy night/ day, we should not only focus on who we are, but on who we are becoming; who we are meant to grow into.

Regret, from the Old French, means to weep fervently over something that evokes great distress in us. This definition pretty well captures the feeling we experience when we have acted in ways that embarrassed or shamed us, or when we have hurt someone or when we have failed to fulfill our best intentions and responsibilities. Acharatna is the Aramaic for regret, which many of us may be familiar with from Kol Nidre: “kolhone acharatna v’hone,” where the prayer speaks of ‘all those things we regret.’ ‘Gret,’ bewail, and ‘charat,’ the modern Hebrew for regret, even share the same ancient roots, where the ‘g’ and ‘ch’ can be interchanged. But the most remarkable discovery that my research revealed about the origins of the word “regret” was the close association between the Hebrew word for regret, “charat,” and the Hebrew the word “charadah,” meaning fear. From this linguistic connection, we can also sense that, at a deep, primal level, much of our relationship with regret is driven by fear.

Yom Kippur offers us a unique opportunity, not to run in fear from our regrets or to hide from them, but to befriend them in the safety of our communal embrace. It might seem like a crazy idea, but each regret, when listened to, has a lesson to teach us, a gift to share with us about who we are and what is important to us.  If we regret hurting someone’s feelings, we see that we value being sensitive to others. If we regret not taking a vacation, we understand that caring for ourselves is important. If we regret not fulfilling our responsibility to give tzedakah, we appreciate that making a difference in the world is a significant concern for us. It is up to us, however, to extract the tender learning embedded within the hard shell of life experiences so we can gain valuable insights that will help us grow. Through the litany of confessions that punctuate our services, we invite our regrets into our hearts so that we may truly pay attention to the lessons they are trying to communicate to us while we still have time to do something about them.

Our tradition talks about two qualities of teshuvah. One is teshuvah ila’ah, higher teshuvah, and the other is teshuvah tata’ah, lower teshuvah (from Meta-Parshiot by Rabbi David Wolf-Blank z”l, 5755,

p. 128). Teshuvah Tata’ah, the lower version, involves looking back on our lives, correcting mistakes, rebalancing things that are out of synch and repairing the broken places. This Teshuvah process is often motivated by a sense of lack or bitterness. Tonight/ Today, I have been focusing on Teshuvah Ila’ah, the higher version of teshuvah, which is about moving forward with joy and delight, and transforming ourselves into the people the Holy One wants us to become.

This is how it works: Yom Kippur is a dramatic enactment of our own deaths and then rebirth, where we can experience our finitude without actually having to die. We don’t eat or drink, we don’t work, we completely remove ourselves for a 26 hour period (btw, 26=the value of God’s most holy name) from everything that defines us as a human being in this world. This critical and cathartic ritual is a precious gift to us so that we can examine our regrets before the end of our lives…. And, as a part of the process, we forgive and ask forgiveness. This is called selichah, and is the focus of our work during the month of Elul. Then we make amends. We do the repair work, called mechilah, that is the centerpiece of our work during Rosh Hashanah. On Yom Kippur, we are engaged in kapparah (related to Kippur), where we are called to return to our divine essence in love. We experience in our kishkes the limits of our earthly existence and feel the urgency of time compelling us to do the inner-work that will bring us a sense of completeness and wholeness….  And, then, we may begin to perceive our own power to transform our regrets about the past into powerful opportunities to learn and grow in the future. We can’t undo what we have done, or bring back opportunities that we have missed, or always fix what has been broken, but by facing our regrets willingly, with love and joy, we aspire to reconnect with the ideals that led us to experience regret in the first place, recommitting ourselves to those deeply-held values that make each of us who we are and who we are meant to be.

The most powerful word of the High Holy Days is “Nu”–N-U. You can hear us uttering “nu” constantly in our prayers this time of year: Ashamnu, bagadnu. Avinu, Malkeinu. That “nu” ending signifies the first person plural–we, us, our. Everything  that we do on these holy days is communal. I’ll let you in on a little secret: Though our regrets are uniquely ours, even they are shared by one another.  That sense that we are all in this together gives us the strength to tackle these difficult issues.

Bronnie Ware, a hospice nurse in Australia, spent several years working in palliative care, counseling the dying and caring for patients in the last weeks of their lives. Her experience has revealed the most common regrets people have at the end of their lives. (see http://www.inspirationandchai.com/Regrets-of-the-Dying.html)

The top 5 regrets expressed by the dying are by no means surprising.  But they afford us the clarity of vision and the wisdom now that people often gain only at the end of their lives. These are the regrets: 1. I wish I’d had the courage to live a life true to myself, not the life others expected of me. 2. I wish I hadn’t worked so hard. (more by men, of course) 3. I wish I’d had the courage to express my feelings. 4. I wish I had stayed in touch with my friends. 5. I wish that I had let myself be happier.

What are the underlying values related to these regrets, and how might we recommit to our highest selves, tonight/today, on this Yom Kippur?  1) By living with courage to be our true selves and not compromising simply to please others 2) By spending our time according to what is of greatest importance to us and allocating our time in line with our values and priorities 3) By living with an awareness of our feelings and honoring those emotions by expressing them honestly from the heart whenever necessary 4) By living a life that embraces friendships and community involvement so that we will always remember that we are a part of something much larger than ourselves 5) By choosing a life that is fulfilling and brings meaning and a deep sense of happiness to us.

The regret within us this Yom Kippur has the potential to be transformed into lessons that blossom in unexpected ways, bringing us to see those blemishes as portals to our own growth and learning.

The great Dubner Maggid, a disciple of the Ba’al Shem Tov, the founder of Hasidism, often told this story about a king who owned a most magnificent ruby, flawless in every way. He loved to watch the way that light sparkled in the ruby and cast beautiful patterns across the room. One day, however, there appeared a horrible crack, right on the face of that most precious jewel. The ruby was ruined. The king was beside himself with anguish and did not know how to repair it. He conferred with all his wise advisors and sought solutions from far and wide, but no one could devise a way to fix that crack. One day, a young man appeared at the palace and announced that he could solve the king’s dilemma. While the king was rather suspicious of the lad’s claim, he felt that he had nothing to lose. He gave the young man 26 hours to restore the flawless ruby to it’s former glory. As the time drew near, the king became anxious and could hardly contain himself. At the appointed hour, the young man appeared and placed the ruby gently and lovingly in the king’s trembling hands. The king’s eyes grew wide and a tear rolled down his cheek for the ruby, though no longer the same, was even more beautiful than before. It still sparkled and refracted the light into brilliant patterns across the room, but there, in the middle of the ruby, the boy had carved a gorgeous rose. And the ugly crack was now transformed into an elegant stem for the flower, cascading across the face of the jewel.