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Nacham: From Regret to Comfort

Yom Kippur 5780

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...

Even our biblical heroes suffered from regret. Shimon Kefa, Peter, is someone who deeply regretted a foolish decision. Although Kefa was committed to Yeshua, his fear made him run away when the soldiers came to arrest Yeshua, and we know he later denied any association with Yeshua three times. Kefa’s actions did not come from a desire to sin, but from impulse, from spiritual immaturity, and ultimately from fear. Upon hearing the rooster crow Kefa realized that he’d done exactly as Yeshua had predicted. Kefa deeply regretted his actions and wept bitterly. Yeshua knew about Kefa’s regret and specifically asked to see him after His resurrection in Mark 16:7. He gave Kefa opportunity to repent and atone. We learn from this that our regrets are not hidden from God and He desires to restore us when we return to Him.

“Return to me, and I will return to you," says ADONAI-Tzva'ot.” (Malachi 3:7)

Unfortunately, regret can also just lead some people to self-destruction, but God wants to use it to lead us toward repentance. It’s important to understand that regret is not the same as repentance. For example, Esav deeply regretted his decision to sell his birthright, but he never repented of his sin.

From Hebrews 12:16–17, “[See to it…] that no one is sexually immoral, or godless like Esav, who in exchange for a single meal gave up his rights as the firstborn. For you know that afterwards, when he wanted to obtain his father's blessing, he was rejected; indeed, even though he sought it with tears, his change of heart was to no avail.”

Esav deeply regretted his godless nature and the consequences of his behaviors but never repented and so was never restored.

Regret focuses on the action that has brought the sorrow and often on the consequences of that action; Repentance involves changing our context so that we aren’t put in a position to make the same mistake again. It involves healing a relationship through apology and reparations where possible. It means changing one’s behavior for the better. It consists of everything that is within one’s power to do to turn away from sin and towards the light. But all of that would still be inadequate when judged based on the ultimate standard of how one could have acted.

Atonement is the process of God picking up where one left off and making up the difference. Judaism teaches that one could never fully atone for a sin, because some residual damage will always remain, so forgiveness and mercy by their very nature transcend rationality. We must rely on God’s mercy. Since the destruction of the Second Temple and the elimination of the sacrificial system, traditional Jews have learned to offer Teshuvah, Tefilah, and Tzedakah (repentance, prayer, and charity) instead. As Messianic Jews, we are further comforted with the knowledge that Yeshua’s atoning sacrifice on the cross was sufficient payment for the debt we owe. In our faith, we can be forgiven.

Two men betrayed Yeshua on the night He was crucified. Judas had worldly sorrow and imprisoned himself within his regret, and his life was ended. Shimon Kefa had godly sorrow, repented, and his life was transformed. We have the same choices those men had. When we face regret, we can let it consume our lives, or we can lay our fault at Yeshua’s feet, turn from it, and let Him restore us.

“Therefore, if anyone is united with the Messiah, he is a new creation - the old has passed; look, what has come is fresh and new! 18 And it is all from God, who through the Messiah has reconciled us to himself and has given us the work of that reconciliation, 19 which is that God in the Messiah was reconciling mankind to himself, not counting their sins against them, and entrusting to us the message of reconciliation.” (2 Corinthians 5:17-19)

“God made this sinless man be a sin offering on our behalf, so that in union with him we might fully share in God's righteousness." (2 Corinthians 5:21)

But let’s go back to regret for a moment as it has a very important role. 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 Nacham (Nun-Chet-Mem). 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, or something we wish we hadn’t said… We’ve let our loved ones down. We’ve let ourselves down. Regret is 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 – today we express our litany of regrets.

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 into stepping stones that take us through repentance and into the arms of the Father.

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. The time you weren’t there for a friend or relative. Or the time you had to admit to your business partner that you hadn’t been fully honest. Maybe it was a small as forgetting a friend’s birthday, but it was an important one. Or maybe you lost your temper and yelled at someone. Whatever it was, have you taken a moment to consider the magnitude of your actions or of your words?

If you’ve really experienced true regret – then 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 regret that births the process of Teshuva, that repentance thing we are all doing here today. There is an author named Brené Brown, and in her book, Rising Strong, she 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 we failed to do.

But, today also 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 blackboard. 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, try to clear our minds of our regret. Erase the slate if you will. But we know all too well that we cannot simply erase our mistakes. We might try to bury our regrets deep down, but they never disappear.

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. It’s about confronting them. Our job, over the next 25 hours, is to express our regret, to turn to God and repent of our failings, so that we can make different and better choices in the coming year. Then we throw ourselves at the mercy of the Heavenly Court, knowing full well that our sentence has already been served through Messiah Yeshua’s atoning sacrifice. We are forgiven.

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?

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 which they carried around with them ever after. We can’t just hit “control z” on a keyboard or the backspace or delete buttons. We can’t simply unsend an email, unfollow a friend, undo the problem. That pain we feel, that heartbreak that happens when we let others down, when we let ourselves down, is the very brokenness that lives on in us as our fair but tough teacher. We carry our Nacham with us. It becomes a part of who we are. It serves as a reminder not to act that way again and that we have a redeeming Father and a loving Messiah.

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

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 instilled in the Jewish people at Sinai. Like the broken tablets, our regret is our reminder of the past, a symbol of how it is never too late to do Teshuva, and a reminder of our Messiah.

Now, let’s take one more look at our past, at the origin of Nacham in our Jewish tradition. The first mention of regret in Torah is not from a human, but from God. In the very beginning of the Noach story, it says: “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]

Wait! Did I read that right? God has regrets?! And 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.

I, like many others, disagree with Rabbi Judah’s assessment. Regret can only occur if you didn’t know something would happen. Therefore, to suggest God had regrets implies God has limits.

Instead, there is an easier way to interpret this verse and retain Hashem’s transcendence. Nacham, which we previously translated as the Hebrew word for regret, actually has another meaning. Ironically, Nacham is also the Hebrew word for comfort.


Odd, right?

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 tradition allows us to see things from a different perspective.

So, how are regret and comfort related? As I said earlier, we do not have to be stuck with regret forever. When we address it, when we repent, we can gain a sense of comfort. Also, 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 Nacham as comfort? What would the Midrash teach us then?

[God declared] “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 He 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 to follow that regret into 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. We must remember them, so we do not repeat them, but we do not need to be anchored by them. Though we may yearn for perfect lives and clean slates, we can find comfort in the holiness of our regret. We remember that like the Ark of the covenant, we hold both our wholeness and brokenness inside.

For when we change our character, when we turn towards Hashem, when we accept Yeshua’s atoning sacrifice for ourselves, our regret transforms into comfort. Though we cannot go back in time, to relive the past, Teshuva allows us the opportunity to change our future. 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, and we will continue to regret choices we make. But we can change. We can choose to do better, be better. And in that, we find comfort.

Today, we don’t just stare at a blackboard full of our regrets. Instead, we should stand here today, comforted by them. At the end of that blackboard 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 (Nacham) by that same potential, by those same possibilities, and by that same sense of direction.

In this New Year of 5780, may we gain the strength and the courage we need to transform our regrets into comfort.

Ken Yehi Ratzon. May it be so.

Tzom Kal. May you have an easy fast.

V’g’mar Chatima Tovah May you be sealed in the Book of Life.




[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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