From Regret to Comfort

Yom Kippur 5777

A blackboard stood in a park in Brooklyn with the question: What is your biggest regret?

For an entire day, New Yorkers opened up about some of the deepest, most intimate parts of their lives. As the day went on, the blank board quickly filled.

“Not saying I love you”

“Burning bridges”

“Not staying in touch”

“Not being a better friend”

By the end of the day, the production team who created this project, noticed a common theme among nearly all of the responses. The regrets people shared were all about chances not taken, words not spoken, dreams never pursued.

Of course, regrets aren’t the sole reserve of New Yorkers. We all have them…  

The origin of the English word regret comes from Old French and means “to look back with distress or sorrowful longing.”[1]  And the word in Biblical Hebrew is nachem. It’s that feeling of disappointment, distress over something we wish we had done, something we wish we had said. Or maybe it was something we wish we hadn’t done, something we hadn’t said. We’ve let our loved ones down. We’ve let ourselves down. It’s those raw, honest feelings that we often try to deny or ignore.  Today, this day of Yom Kippur, is the Jewish people’s collective Blackboard Project equivalent — the litany of regrets.

Today, we recite our communal litany of regrets aloud. Al Chet Shechetanu l’fanecha, for the sin we have committed against you — by hardening our hearts, by speaking maliciously of others, by dishonesty in our work. We’ve lied, we’ve cheated, we’ve avoided responsibility.  And we wish we hadn’t. We regret things we’ve done. But today is about much more than simply listing our regrets for the sake of a social science experiment – we do it for a purpose.  Today isn’t about hiding from our regrets or dwelling in them – it is about transforming them. 

Think for a moment: When was the last time you hurt somebody you loved? The time you weren’t as supportive of your child as you wished you had been.  Or the time you had to admit to your business partner that you hadn’t been fully honest. Maybe you just forgot a friend’s birthday, but it was an important one. Have you taken a moment to consider the magnitude of your actions or of your words?

 If you’ve really experienced true regret — you’ve felt the pain, the hurt, well up in your heart.  It’s what keeps you up at night wishing you had acted differently. It’s what causes tears to well up in your eyes knowing that you’ve said something you wish you hadn’t.  It’s what causes your heart to break and causes you to feel vulnerable. But it is from that same place of heartbreak, sorrow, and of regret that births the process of Teshuva, that repentance thing we are all doing here today. In her book, Rising Strong, Brene Brown writes: “If there is one thing failure has taught me, it’s the value of regret…regret is a fair but tough teacher.”[2]

 Maimonides taught in his guidebook on the process of Teshuva, that in order to fully repent, one must experience regret.[3]  Indeed it is a critical part of the Teshuva process, according to Maimonides, for without regret there can be no forgiveness. It is what allows us to engage in Teshuva.  Today as we atone for our sins for the past year, we accept that we are human.  We make mistakes.  We regret things we have said or done.  And the things things we failed to do. But, today reminds us that we can atone for our regrettable actions and choices; we can seek forgiveness, we can make amends, we can do Teshuva.

At the end of the day in Brooklyn, the production team took an eraser and erased the entire board. They replaced the question: What is your biggest regret? With the words, “Clean Slate”.

The truth is, when we think back to our deepest moments of regret, we face our own personal failings, our own imperfections. We so often wish we can just go back and relive those moments, make different choices. And so we try to forget, clear our minds of our regret.  Erase the slate if you will. But we know all too well that simply erasing our mistakes, won’t make them go away.  We might try to bury our regrets deep down and get stuck in them. But they never disappear — they keep popping up.  They weigh heavily on us.  Because for us, as Jews, the process isn’t as easy as washing away our regrets leaving no trace left behind. Thankfully for us, the process is significantly more meaningful.  We don’t get a clean slate.  A chance to start over as if nothing had ever happened, that’s not what Yom Kippur is about.  Yom Kippur is not about blotting out our mistakes. Yom Kippur is about confronting them, living with them.  Our job then today and in the days to come is to express our regret, so that we can make different choices, better choices in the coming year. We can begin to repair the damage that we have done. To heal the hurt.  If we really think about it, when you erase a blackboard, you can still see remnants of the words, they don’t fully disappear.  We, too, can never fully erase our past, and our Jewish tradition wouldn’t want us to either.

Rabbi Joseph Solevetchik, scholar and teacher of Teshuva taught: “Sin is not to be forgotten, blotted out or cast into the depths of the sea.  On the contrary, sin has to be remembered. It is the memory of sin that releases the power within the inner depths of the soul of the penitent to do greater things than ever before.”[4]  Just as sin is not to be forgotten, so too regret. For it is the memory of regret — of the pain and heartbreak — that propels us to change.

We learn this from incident with the Golden Calf as well. While Moses is up on Mount Sinai receiving the Ten Commandments, the Israelites become impatient.  As they await Moses’ return, they build a Golden Calf, an idol to worship.  Upon coming down the Mountain with the Two Tablets, Moses in extreme anger, throws the tablets down, shattering the Ten Commandments. 

But Moses pleaded with God for a second chance. If the Israelites were capable of making mistakes, and of failures, they too would be capable of doing Teshuva. The people are given a second chance, Moses is given a second set of tablets. He climbs back up the Mountain on the very first day of the month of Elul, the month preceding the High Holy Days.  It is on the 40th day on the mountain, the 10th day of the month Tishre, that Moses receives the second set of tablets. That day, became the very first Yom Kippur, the day of second chances. 

Ever wonder what happened to that first set of broken tablets? [Pause]

Those broken tablets could not be repaired.  But they weren’t thrown away either. The broken tablets were placed in the holy Ark, right beside the second complete set.[5]  Even after our ancestors suffered the consequences of building a Golden Calf, they were given the opportunity to reconnect with God.  But, they were also given the responsibility to never forget their past. The lesson they learned is engrained in those broken tablets: We carry our brokenness with us.  We carry our regret with us. It becomes a part of who were are. No matter how hard we might try to make the past, the hurt, go away, it won’t magically disappear. We have work to do.

 When I look back on the moments of my deepest regrets, the words I wish I hadn’t said, the times I hurt the people I care about most, I feel disappointed and sad. I so wish I could go back in time and undo the pain, act differently. But, I can’t. We can’t. It’s not as easy as “control z” on a keyboard or the delete button.  We can’t simply unsend an email, unfollow a friend, undo the problem. That pain we feel, that heartbreak when we let others down, when we let ourselves down, is the very brokenness that lives on in souls. And while we shouldn’t let it consume us, we still carry it with us as our fair but tough teacher.

In an online forum where people shared their deepest regrets, one woman wrote about the lingering impact of her regret, “The time when I chose not to stop and help a stranger who clearly needed it, justifying my decision with the fact that I was already running late and did not want to take the chance that I would be drawn into something time consuming and filled with drama. The brief look that passed between us has stayed with me.”[6]   That lingering look, becomes our image of regret and it is what opens us up to honesty and compassion.  It is is the source that motivates us to change our ways, to do better, to be better. 

Today is not only a day to examine who we are, but a day to examine who we are becoming. This is exactly the lesson that God instills in the Jewish people at Sinai.  Like the broken tablets, our regret is our reminder of the past, a symbol of how we can learn from our past, a symbol of how it is never too late to do Teshuva.

Let’s take a look at our past, at the origin of regret in our Jewish tradition. We first learn in the Torah about regret, not from a human, but from God.  In the very beginning of the Noah story, our Torah teaches: “God saw how great was humanity’s wickedness on earth, and how every plan devised by human being’s mind was nothing but evil all the time.  And God regretted that God had made humankind on earth and God’s heart was saddened.”[7]

Not only does God have regrets, but God regrets creating human beings!

But why would God regret creating humanity?  We learn from Rabbi Judah in the Midrash: [God declared] ‘It was a regrettable error on My part to have created humanity out of earth, for had I created humanity out of heavenly elements, human beings would not have made mistakes.’[8] 

Rabbi Judah imagines God regretting creating human beings from the earth, capable of failure, of missing the mark. Had God created human beings from heavenly elements, we would have been like angels, infallible, free of any error or mistakes. Angels are merely agents of God, and lack any sort of free-will.  This, according to Rabbi Judah, was God’s regret — creating imperfect human beings.

This is all true, if we translate the Hebrew word, nachem to mean, regret.  But the word actually has another meaning.  Ironically, nachem is also the Hebrew word for comfort. How odd; Most of us, do not experience comfort in our regrets.  In fact, feelings of regret seem in conflict with feelings of comfort.  And yet, our Jewish tradition forces us to see things from a different perspective. How are regret and comfort related? We are not stuck with regret forever. And when we address it, we can gain a sense of comfort.  If we think about it, regret can indeed provide us comfort as it points the way towards a different future, a different ending to our story.

So, what if we were to translate nachem as comfort? What would the Midrash teach us then?

“It was a comfort on My part to have created humanity out of earth, for had I created humanity out of heavenly elements, human beings would not have made mistakes.”

What if God found comfort in creating humanity from earth?

What if God found comfort in knowing human beings aren’t angels?

What if God found comfort in the ability for human beings to make mistakes?

If we read the Midrash this way, we learn then, that God is comforted in knowing that God created human beings, created us, just as we are, capable of making mistakes, capable of feeling regret. It’s a setup — God valued imperfect human beings, God granted us free will.  Free will to disappoint, free will to regret.  And it is that very same free will that is our gateway to Teshuva.

Regret serves as our wake up call to listen to what is deep within our souls, to engage in Cheshbon HaNefesh, the accounting of our soul.  We must account for our mistakes, but we do not need to be imprisoned by them. And also, we must account for that which brings us comfort.   Though we may yearn for perfect lives and clean slates, we can find comfort in the holiness of our pain. We remember that like the Ark of the covenant, we hold both our wholeness and brokenness inside. 

For when we change our character, our regret transforms into comfort.  Though we cannot go back in time, relive the past, Teshuva allows us the opportunity to change the outcome. We can make different choices when faced with the same situations.  We can say the words we meant to say. We can be the friend we wish to be. We can stay in touch. We can be honest with our business partners. We are human and we will continue to make mistakes, regret choices we make. But, we can change. We can choose to do better, be better.  And in that, we find comfort.

But our regrets do not only comfort us. In the words of Brene Brown, “Regret, I think, is a function of empathy.”[9]  The only way to develop real empathy is to make mistakes, to make a wrong turn. We are comforted because our regrets help us to develop empathy towards others.  We become sensitized towards others when they find themselves walking in our shoes.  We, in turn become the source of comfort for them.  For they teach us how to have compassion, how to understand. Through remembering our feelings of pain and brokenness, instead of erasing them, we are better able to feel another’s pain.  We know what it felt like to experience regret.  And we know what it was like to be strengthened by our it too.

Today, we don’t just stare at a blackboard full of our regrets.  Instead, we stand today, comforted by them.  At the end of the experiment in Brooklyn, participants exclaimed their new perspectives, “It feels like where I want to be, where I want to go.” “I feel hopeful.” “It means there is possibility.”  When we do our work called Teshuva, we become comforted by that same potential, those same possibilities, that same sense of direction.

In this New Year of 5777, may we gain the strength and the courage we need to transform our regrets into comfort.

Ken Yehi Ratzon.



[3] Hilchot Teshuvah (Laws of Repentance), 2:2, 9

[4] Mishkan HaNefesh 85.

[5] Bava Batra 14b.


[7] Genesis 6:5-6

[8] Midrash Genesis Rabbah 27:4

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