Rosh HaShanah Evening 5776 – The Holiness of Regret

When our kids were little, we as parents often had to make decisions that were unpopular for our children.  They would whine and complain – why can’t we do it our way?  And we would with same wise words our parents used to say:  “Because we said so.” But they would argue and say, “We live in America – we should all get to vote.”

And I would say: “Fine.  But here’s how it works:  Everyone gets one vote for every year you’ve been alive. Now, let’s see – Ari gets 10 votes, Meredith gets 8 votes, and Eliana gets 3 votes: 21.  Now I say you need to go to bed, and I get … well a lot more votes than you.  I win – Now go to bed.”

But our little kids aren’t so little anymore.  My son just left for college, my older daughter is in her junior year of high school, and we are planning for our youngest daughter’s bat mitzvah in just over a year.  Recently, a new acquaintance asked how old my children are.  18, 16, and 11, I responded.  Wow.  Those are some pretty big numbers.  After a recent family vote the kids shared with me that by the end of 2015, they will be old enough to out-vote me.

We all have the same reaction when we pass these kind of milestones.  Wow – where did the time go?  It seems like yesterday we were gathered here in this very sanctuary to celebrate that boy’s bris, and in what seemed like a blink of an eye, he’s grown and gone.

Of course there’s been so much that’s happened in those years.  We went out to dinner the night before Ari left and sat around reminiscing our favorite stories.  We shared a lot of wonderful memories of times we spent together, on special trips, special occasions, and just funny, silly times on random evenings.

I can’t help thinking that we get one shot at this parenthood thing, and I secretly wonder if I didn’t mess up too badly.  I think about lots of times I didn’t get it right as a parent.  I think about times I pushed too hard, and others when I didn’t push hard enough.  I think about the times I got too angry, and times where perhaps I was too lenient.  I think about the things I should have taught, and the things I tried so hard to impart that probably don’t really matter.

This holy day has many names in our tradition. Rosh HaShanah, the head of the year, is also called Yom Teruah – the day of the shofar blast, and Yom Harat HaOlam, the day of the world’s formation.  But it is also called, Yom HaZikaron, the day of remembrance.  And for so many of us, the walk down memory lane these holy days ask us to take can be a very difficult journey.

I’ve often spoken with people who when they talk about their lives will profess: “I have no regrets.”  I am never going to be one of those people.  Frankly I have lots of regrets.  There are so many times in the course of my life’s journey where I look back with a reasonable measure of embarrassment, regret, and shame.  I think of times as a child when I was deceitful and dishonest.  I think of times as a teenager when I was a striver, and said and did things that were disingenuous, but I thought would make me popular.  I think of times as a young adult when I arrogantly pretended to know more than I really did.  I think of times when I made snap judgments without really knowing the facts, when I made assumptions before understanding the full picture, when I dismissed people because of stereotypes, when I lost control of my emotions or lashed out at those I love.

On this Yom HaZikaron, this day of remembrance, I look back at my life filled with mistakes, and I wonder how it is that with my amazing resume of flaws and imperfections that I am even here this evening – that you are here this evening with me.

But the fact is that regret is good.  In his book How Good Do We Have To Be, Rabbi Harold Kushner remembers that when Charles Darwin shocked the world with his theory that human beings and apes had a common ancestry, someone asked him whether there was still anything unique about the human being.  Darwin thought for a moment and then answered, “Man is the only animal that blushes.”[1]

Almost three years ago on Mitzvah Day, we got our first dog.  We have a joke in our house.  “What did the dog do all day?  He dogged.”  That’s what dogs do.  They dog.  Included in dogging is barking, eating, sleeping, walking around the neighborhood, peeing (sometimes on the carpet), pooping (hopefully not on the carpet), and lots of cuddling.  He’s small, he’s tan, and he’s exactly what a dog is supposed to be.

I was remembering this recently with two b’nai mitzvah students who are celebrating their big day when we read the story of creation.  There’s a very interesting facet to that story.  Each day, after God brings something into being, God stands back and judges it:  “And God saw that it was good.”  This is true for light and land, sun and moon, plants and birds and fish and animals.  But when God creates humanity there are two key differences.  First, God creates us in God’s own image.  More about that in a minute.  But second, God does not declare us to be good.  The quality of our goodness is not predetermined.

Charlie the Wonderdog is created exactly as he is meant to be. There is no expectation that he grows.  Sure we hope he doesn’t pee on the carpet, and yes we wish he wouldn’t bark so much when people come to the door, but ultimately, that’s who he’s supposed to be.  He’s already good.

But there’s a big difference between us and our dogs.  Created in God’s image, we carry with us the ability to contemplate the meaning of our own existence.  We can organize our world not simply by instinct but on the basis of values and moral truths that we can use to modify our behaviors.  We may desire material gain, but we can master that desire by refusing for ourselves that which was not acquired through honest gain.  We may desire love and acceptance, but we can master that desire by refusing for ourselves simple lust and infidelity.  We can set for ourselves a bar based on a sense of what is compassionate and just, on what is generous and fair, on what links us to others in bonds of love and understanding.  And when we fail to meet that bar, we can blush from that sense that we didn’t hit our mark, that we didn’t fulfill our expectations, that we failed, or that we sinned.

If, as we leaf in the book of our lives, we feel no measure of regret, If we can look back through the pages of our memories and see no faults, no flaws, no moments for embarrassment or regret, then we have to wonder if we asked enough of ourselves or did we set the bar too low?  Shouldn’t we expect enough of ourselves that perfection is not easily achieved?

We may choose to set the bar wherever we like, but I believe the Holy One sets the bar higher.  I believe that in creating each of us in the image of the Divine that we are as the Psalmist said: “a little lower than the angels. (Psalm 8:5)”  And we ought to try to act like it.  But when we are not all that we can be, when we do not live as we know we should, should we not feel some measure of regret?

It makes us wonder what does God ultimately want us to be?  The Torah answers us very clearly in the book of Leviticus:  “You shall be holy, for I, Adonai your God, am Holy. (Leviticus 19:1)” It seems that what is asked of us is to strive to be like God, to reach ever higher in how we seek to live.

If God wanted us to be perfect, there would be no need for us to gather here tonight, to compile our חשבון הנפש – our resume of regret, our accounting of fallibility and imperfection before which we, in the fullness of our humanity, naturally blush.

No, ultimately what God wants us to be is not perfect, but holy.  Imagine that each of us is a clay jar or vessel.  All year long, every day, we try to fill that vessel with a collection of acts and deeds that will help us realize that vision of perfection we imagine it is our obligation to pursue.  But it seems that no matter how hard we try, we never are able to fill that jar.  It’s as if our failings create that empty space between our lives as they are, and the rim of that vessel.

But that empty space is not failure.  That empty space is holiness.  Judaism is a tradition that teaches from the beginning that we ought never to worship idols, that God is not something we can see or touch.  God is not the work of our hands, our accomplishments or achievements.  God is not something.  God is no-thing.  Holiness is that empty space between what we are and what we ought to be. And what God wants is for us to embrace not simply what we were able to achieve, but also what we weren’t.

I look back on the moments of my deepest regrets.  I think about how because of my personal failings and imperfections there were times that I not only let down the people I care about the most, I let myself down.  In reflecting on those moments, I feel an overwhelming sense of sadness and anguish.  I wish I could go back and relive those moments, make different choices, somehow undo the damage I caused and fix the pain that I never meant to inflict.  But I can’t.  And I finally realized, as I reflected on my regrets, what that spirit squeezing pain in my chest is truly called:  a broken heart.

When we sit with a broken heart we feel so embarrassed and ashamed.  We often refuse to talk about it, even with those we love and trust the most.  It hurts too much.  We feel too much shame and embarrassment.  We wonder if admitting to what we did that left us so brokenhearted will cause even more separation from those we love and cherish.

But it is when we are most broken-hearted that God is nearest to us.  Tomorrow we will read the famous story of the binding of Isaac.  Abraham in his fervor to show God how perfect is his faith, takes his son, his only son, whom he loves, Isaac, and brings him to the summit of Mount Moriah and prepares to offer him up as a burnt offering.  With his son bound tight on top of the altar he built to perfection, Abraham lifts the knife, when the angel tells him that’s not at all what God wants.  God doesn’t want Abraham’s offering to perfection.  God wants Abraham to be holy. Imagine Abraham’s shame when he finally looks down and sees what he has done.  His heart broken, Abraham names that place Adonai Yireh – God sees, for it is when we are most broken hearted that Adonai Yeraeh – God is seen.

From the horn of the ram that Abraham sacrifices there instead of his son comes the shofar we sound to bring in the new year.  The Shofar’s blasts are not the triumphant sounds of perfection, but the mournful cries of the broken-hearted.

The story is told that the great Hasidic sage the Ba’al Shem Tov would hold auditions each year before Rosh HaShanah to select the Ba’al Tekiah, the one to sound the 100 blasts of the Shofar.  More than being able to make the ram’s horn sound the proper notes, the Ba’al Tekiah had to master the 100 special prayers or Kavanot, so that the Ba’al Tekiah could fill each sound with complete spiritual power to lift our prayers to the Holy One on high.  There was a man who dreamed of serving as the Ba’al Shem Tov’s Ba’al Tekiah, so he studied for two years to master the Kavanot and to perfect his technique.  The day arrived for his audition, and he stood before the Holy Ba’al Shem Tov.  And he froze.  He was so overwhelmed with his need to be perfect that he could not remember a single one of the holy prayers, and could hardly sound a single note.  He was devastated.  He stood before the Ba’al Shem Tov, crestfallen and heart-broken, and lost himself in tears of grief.

“I select you,” the Ba’al Shem Tov said.  “But I completely failed,” the man said. “I could remember none of the kavanot, and I could hardly make a sound.”

The Ba’al Shem Tov explained with a parable:  In the palace of the King, there are many secret chambers, and there are secret keys for each chamber, but one key unlocks them all, and that key is the ax.  The King is the Holy One, the Ba’al Shem Tov explained.  The palace is the spiritual world of God’s domain.  The secret chambers are those essences of God that lead us closer and closer to who we ultimately should strive to be, and the secret keys are the kavanot and mitzvot and holy acts we perform that open those spiritual portals.  But the ax, the key that opens every chamber and brings us directly into the Divine Presence is the broken heart.  It is your broken heart, the Ba’al Shem Tov explained, that will carry all our petitions into the presence of the Most High.  For as Psalm 34 reminds us: “God is close to the broken-hearted, and saves those who are crushed in spirit.”

God doesn’t need us to be perfect.  God needs us to be human.  Fully, profoundly, flawed, and human.

When Moses descends from Mt. Sinai, carrying the tablets of the Ten Commandments he encounters his people celebrating a failure of epic proportion.  Not 40 days removed from their collective encounter with God, the Israelites built themselves a Golden Calf, and in full throated celebration proclaim their fidelity to the God they have fashioned for themselves.  And it breaks Moses’ heart.  And in his broken-heartedness, Moses shatters the tablets and seeks to restore order among the people.  But what happens next is what is most extraordinary.  Moses with his broken heart, is summoned again to the summit of Mount Sinai, and fashions a second set of tablets.

And when he descends with the second set of tablets, he declares words we echo throughout the celebration of these High Holy Days:  “Adonai, Adonai, El Rachum V’Chanun, Erech Apayim, V’Rav Chesed V’Emet – Adonai, a God of compassion and graciousness, slow to anger, abounding in kindness and faithfulness. (Exodus 34:6)”  The midrash teaches that Moses took his new tablets and placed them into the holy ark, right next to the broken tablets.  What is most holy to God, and to us, is both perfection and brokenness.

If we are to be holy like God, then we need to be forgiving like God, not simply forgiving of others but forgiving of ourselves.  God is gracious, accepting, and patient, and so should we be as well. God loves our broken hearts, because it is only when we feel the fullness of regret that we may be inspired to grow, to change, to improve, to be a little closer to a vision of what we could ultimately choose to be.

These are the High Holy Days because these are the days that we embrace our regrets, that empty space inside that makes each one of us a complete and holy vessel. These days are the High Holy Days because when we inhabit our brokenness, we hope that our repentance, our prayer, and our resolve to learn and grow will inspire us to transcend the morass of our embarrassment and our shame.

Henry David Thoreau said:  “Make the most of your regrets; never smother your sorrow, but tend and cherish it till it comes to have a separate and integral interest. To regret,” he said, “is to live afresh.”

As we reflect this Rosh HaShanah on the year and years that have passed, let us indeed make the most of our regrets.  May our broken hearts open the gates to a new year where God will inspire us to find forgiveness, healing, love, and peace.

[1] Harold Kushner, How Good Do We Have To Be?: New York: Little, Brown, & Co., 1996, p. 35.



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2 responses to “Rosh HaShanah Evening 5776 – The Holiness of Regret

  1. Bobbi Kalmanson

    Beautiful and inspiring..


  2. jack kalmanson

    great sermon,thank you. la shana tova

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