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Ashikaga Yoshimasa was a shogun, living in the 15th century. One of his favorite possessions was a Chinese tea bowl. A story suggests that he accidentally dropped it on the floor, and immediately It shattered into many broken pieces.

He was beside himself. Distraught, the shogun picked up the shards and sent them to China for repairs. But even after many attempts, it could not be repaired. He then approached local craftspeople, hoping for some way to make his treasure whole.

It took a while, but the craftspeople returned the bowl to him. It looked somewhat different than before, but it was beautiful. In repairing the bowl, The artisans created a new art form, named kintsugi. Translated as golden joinery and still popular today, its artisans mend areas of breakage with powdered metals. It does not try to patch them up or blend them so that they aren't noticeable. From a Philosophical perspective, kintsugi seeks to highlight an object's imperfections. ...

Tonight and tomorrow, we engage in a kind of golden joinery. Like those artisans, we highlight our cracks and fissures - our mistakes - as we acknowledge them and even concentrate on them. Over the next 24 hours, we come across many prayers, songs and meditations that focus on this theme.

Earlier, we heard the hauntingly beautiful melody of Kol Nidrei. Its words focus upon all of our vows that we have been unable to fulfill. During repeated utterances of ashamnu, we gently point our chests as we name the sins that we have committed.

We admit to God that indeed, we have made mistakes: Adonai, we are arrogant and stubborn, claiming to be blameless and free of sin. In truth, we have stumbled and strayed. We have done wrong.

In fact, this is a major theme not just of Yom Kippur, but also throughout the previous month of Elul. We think about our actions - and inactions - of the past year and consider what we could - and should - do differently.

But Yom Kippur takes this theme and distills it into a concentrated, intense experience. We fast so that we inflict ourselves with discomfort. And we are uncomfortable, as we engage in the difficult and possibly painful task of looking at our mistakes, some of action, and some of inaction.

We jump to the past and say: If Only: If only I took better care of myself ... If only I spent more time with my children ... If only I was nicer to my spouse ... If only I took that risk. These if onlys then transport us back into a counterfactual reality from the present: What would be different if you had tried to heal that relationship? How would you feel if you did attend that life cycle event, made that phone call, wrote that letter? What might your life be like if you took that new job opportunity.

Yom Kippur is full of If onlys. It is a Day of Atonement precisely because it is a day of regret.

...

Edith Piaf was one of France's most widely known singers. Perhaps best known for La vie en rose, she recorded a song toward the end of her career which was almost as popular; Non, Je Ne regrette Rien.

No, nothing of nothing
No, I don’t regret anything
Neither the good things people have done to me
Nor the bad things, it’s all the same to me.

...

In his recent book, The Power of Regret, Daniel Pink writes, ...few credos blare more loudly than the doctrine that regret is foolish—that it wastes our time and sabotages our well-being.

Many of us think that regret might seem ... forgive me ... regrettable. Dwelling on the past, focusing on the negative ... why bother? Regret can add to unhappiness, or even worse, despair. Shouldn't our focus be on happiness and blessing?

We hear this message everywhere: From Edith Piaf to Bob Dylan, and dozens of other popular song: our modern culture steers us away from regret. The late Justice Ruth Badger Ginsburg said: Waste no time on regret. You may have seen pictures on the Internet of people with a ‘no regrets’ tattoo on their skin.

And It may seem like a wonderful creed to live by: No regrets!

Regret should sometimes be avoided, especially when it is sets us speening on a feedback loop of unease and pain. Just as Lot's wife looked behind her and instantly transformed into a pillar of salt, repeated cycles of regret can stultify our path forward.

...

But regret can also moves us forward. It makes us feel worse today, but helps us do better tomorrow,

Daniel Pink teaches that when you feel regret, you can do one of three things:

1 - You can try and ignore it, burying the feeling. 2 - You can feel it deeply, which may lead to wallowing and even more despair. OR 3 - instead of it leading to even more bad feelings, it should lead to constructive thinking. And then doing.

Regret requires self-awareness, honesty, pointed thoughtfulness, and then a change of course. The travesty isn't to live with regret; it's letting yourself surrender to the feeling of regret. Or, to put it Jewishly: Regret is the beginning of Tshuvah.

Regret is not only necessary, but holy.

...

There's a great Chinese proverb:

The best time to plant a tree was 20 years ago.  The second best time is now.

Our regret helps us remember that we should have planted a tree. And then, it motivates us to get some seeds, go outside, and put your fingers in the soil.

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Tomorrow afternoon, we will come to this reading in our Yom Kippur machzor:

Feel bad, It won't kill you. Use these feelings as a catalyst to make amends, so long as doing so doesn't inflict more pain. Do something positive that will help offset the damage you have caused.

It's easy to regret that you did or did not do something, and then to simply feel sadness. It's far harder to feel the regret, and then give yourself the permission - and the motivation - to do better, to be better. Plant the tree.

...

A midrash from Pirke D'Rabbi Eliezer discusses God having some problems with creation:

When the world had not been created there was God and only God. It occurred to God to create the world. But as God began to outline the world, God noticed that it would not stand. What is this similar to? To a king who wishes to build himself a palace. If God had not outlined Their foundations, entrances, and exits on this earth, God could not begin to build. Therefore, God outlined the world. But it did not stand until God created t'shuvah.

The conjoined concepts of regret and t'shuvah are necessary parts of creation.

God is a metaphysical kintsugi artist. The cracks don't weaken creation - far from it - they help hold creation in place!

God created the world and its creatures and nature and us - not despite our limitations and mistakes - but because of them. Leonard Cohen understood this: There is a crack in everything: That's how the light gets in.

...

Our intentional regret during this most holy day of Yom Kippur brings out these cracks. And through prayer, t'shuvah, and righteousness, we make them beautiful. We make them holy.

Rabbi Linder