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Regret – Yom Kippur 5776 Sermon by Rabbi Saks September 23, 2015 – 10 Tishre 5776

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Yom Kippur 5776

September 23, 2015 – 10 Tishre 5776

Congregation Bet Ha’am

Rabbi Jared H. Saks



In a December episode of This American Life, I heard the childhood story of Elna Baker and her four siblings, including her younger sister Julia, and how their father, Gary, handled bad behavior in their house. In one incident, where Elna whacked her sister in the head with a broom, Gary decided to conduct a trial, which he videotaped. The premise was to see if Elna was guilty, but the truth was that he knew that she was. The trial was an opportunity for Elna to confess, which she never did. Ultimately, her mother decides that maybe she didn’t do it on purpose, that maybe she was just foolish.

Elna, now an adult, still holds a lot of regret for having gotten away with hitting her sister. As adults, Julia has repeatedly told Elna that she forgives her, but she continues to regret what she did, especially because she got away with lying about it. “Some regrets just never go away… People tell us that they forgive us, we try to forgive ourselves, and we still know we did wrong. We hurt somebody. And it was real.”[1]

The Talmud tells us that there are four things that God regrets every day.[2] How can God regret? “Regret implies that one now knows something that one did not know before; that one’s earlier decision or deed was flawed or ill informed.”[3] If God is omniscient, then regret cannot be something that God does. But still, our tradition teaches us that God has regrets. Among the four things that the Talmud indicates God regrets is exile, our living outside the Land of Israel.

The Lubavitcher Rebbe taught that when we regret, it is about something that we desired to do in the past, but today do not desire to have done. For God, it’s the opposite, in a way. God desires what was – the Garden of Eden, our ancestors’ life in the Land of Israel – and regrets that those things don’t exist now. Still, God both desires our living exile and doesn’t at the same time. God desires that living in the Diaspora gives us fortitude, that it enables us to be a light to the nations. But at the same time, God regrets that we are scattered and disunited as a people. It is this regret that inspires us to try to work towards perfecting the world. Because of this, God’s regret is a valuable aspect of our relationship with God.

Our tradition tells the story of Rabbi Susya on his deathbed, a story many of you have probably heard before. Rabbi Susya is crying and his students ask what he regrets about his life, since he is such a pious and exemplary man. He says that if God were to ask him why he wasn’t more like Moses, he would say he wasn’t given Moses’ leadership qualities. If he were asked why he was not more like King David, he would say that he did not possess King David’s skills as a poet. And if he were to be asked why he wasn’t more like Rabbi Akiva, he would say that he was not as wise as Rabbi Akiva. However, if God were to ask Reb Susya why he wasn’t more like Reb Susya, he wouldn’t have an answer. We usually see this story as one of being our true selves, but Rabbi Stuart Grant teaches that Reb Susya questions his accomplshments and regrets missed opportunities.

Some Jewish belief holds that we are exactly where we are supposed to be right now, facing what we need to face, connecting with the people with whom we are meant to connect. The Rabbis teach us that everything is in God’s hands except reverence of God. Even if this isn’t entirely satisfying for us theologically, it means that everything we’ve faced until now can be put to good use to handle now. Regret empowers us to do better now, even if we can’t change the past.

Rabbi Brooks Susman teaches that Yom Kippur reminds us that there are two types of sins: those of commission and those of omission. Sins of commission are the ones where we’ve made poor choices in the past. Sins of omission are the ones where we failed to act and this failure had a negative impact on us and on others. We have to accept that the past has occurred and that we cannot change it. When we accept the sins of omission in the past, then we are empowered to make better choices in the future.

In his song My Way, Frank Sinatra sings, “Regrets, I’ve had a few…” and if that’s where the lyric ended, it would be fine. But it’s not. The full line is, “Regrets, I’ve had a few. But then again, too few to mention.” The thing is, regret is the key to forgiving and being forgiven. Most of us, I hope, have not had only a few regrets. “If you don’t have regrets, it means you haven’t [messed] up. It means you haven’t had your heart broken. It means you haven’t been bloodied. It means you haven’t failed.”[4] Good judgment comes from experience; experience comes from bad judgment. It is regret that enables to make better choices moving forward. The thing is, Frank Sinatra has it all wrong. Going through life doing it our own way, not having regrets about our choices, never trying to do it better in the future, means that we live without the opportunity for becoming better people, for reconciling with those whom we’ve hurt or who have hurt us, for offering and finding forgiveness.

Too often, though, the message we get is one of ‘no regrets.’ In the Jonathan Larson’s musical Rent, in the finale, the company sings, “There is no future / There is no past / Thank God this moment’s not the last. / There’s only us / There’s only this / Forget regret – or life is yours to miss / No other road / No other way / No day but today.”[5] But here, too, as much as I love the show and this song, the message is wrong.

One of my favorite books, which was given to me when I was in high school by my 7th grade Language Arts teacher, Diane Kasiski, is Lois Lowry’s, The Giver. It is the story of twelve-year-old Jonas, who lives in a seemingly utopian world. He receives his life assignment as decided by the elders and becomes the Receiver. He is to be mentored by the book’s namesake, the Giver, so that he can hold all of the memories of the world. It is the Giver’s task to transmit all of the memories of the past to Jonas, the new Receiver. At first, Jonas thinks he’s only there to receive the personal memories of the Giver.

The Giver explains to him that it is the memories of the whole world, generations and generations, that have to be transmitted to him. Jonas is confused. “‘Do you mean not just us? Not just the community? Do you mean Elsewhere, too?’ He tried, in his mind, to grasp the concept. ‘I’m sorry, sir. I don’t understand exactly. Maybe I’m not smart enough. I don’t know what you mean when you say ‘the whole world’ or ‘generations before him.’ I thought there was only us. I thought there was only now.’”[6]

At the Maine Conference for Jewish Life, Lois Lowry said that this is one of the book’s most important lines. Many of us were taught that there’s only us and there’s only now. Many of us are still teaching it. But it’s not true. Jonas learns the truth about his world and this untruth he was taught. There isn’t only us. There isn’t only this. We cannot forget regret. It is the key to finding forgiveness and offering it. G’mar chatimah tovah, May you be sealed for blessing in the Book of Life. Shanah tovah.



Chabad.org. Regret. http://www.chabad.org/library/moshiach/arcticle_cdo/aid/144583/jewish/Regret.htm.

JewishValuesOnline.org, “What does Judaism say about regret…” www.jewishvaluesonline.org/115.

Larson, Jonathan. Rent, 1996.

Lowry, Lois. The Giver. Boston: Houghton Mifflin Company, 1993.

Meek, Miki (Narrator). (2014, December 5). 541: Regrets, I’ve Had a Few [Radio broadcast episode]. In Ira Glass (Producer), This American Life. Chicago: PRX, the Public Radio Exchange.

[1] Miki Meek (Narrator). (2014, December 5), 541: Regrets, I’ve Had a Few [Radio broadcast episode]. In Ira Glass (Producer), This American Life. Chicago: PRX, the Public Radio Exchange.

[2] Babylonian Talmud, Sukkah 52b.

[3] Chabad.org, Regret, http://www.chabad.org/library/moshiach/article_cdo/aid/144583/jewish/Regret.htm.

[4] 541: Regrets, I’ve Had a Few.

[5] Jonathan Larson, “Finale B,” Rent, 1996.

[6] Lois Lowry, The Giver. Boston: Houghton Mifflin Company, 1993, p. 78.

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