blogs/rabbigoldberg

You can tell a lot about what people value in a life 

from what they choose to highlight when it ends. 

As a rabbi, I have the privilege and responsibility 

to attend more funerals than the average person, 

certainly of my age. And what they say 

about resume virtues versus eulogy virtues 

is absolutely correct. 

While at times people do talk about 

a person’s professional accomplishments, 

there is usually much more focus on a person’s role 

as a parent, spouse, friend, and neighbor.

 

While I’ve never seen this myself, 

I read years ago that the Frank Sinatra song My Way 

is among the most frequently played or quoted songs at funerals. 

The song celebrates those, usually men, 

who live life on their own terms 

with bravado and fierce independence. 

Among the song’s lyrics is a line about regret: 

“Regrets, I’ve had a few, but then again, too few to mention.”

 

The sentiment is not unique to this song. 

Indeed, our culture sometimes tells us 

that regret is a, well, regrettable emotion, one to be avoided. 

No regrets, sometimes people say. 

Another iconic entertainer, the French chanteuse Edith Piaf 

famously sang “je ne regrette rien,” I regret nothing. 

The idea here, to the extent there is one, 

seems to be that we should not focus on the past 

and instead just plunge ahead to whatever the future will bring. 

 

But Jewish wisdom, psychological research, and common sense 

all confirm that this is bad advice. 

 

Like the fast that many of us undertake today, 

regret may be unpleasant to experience 

but can nonetheless be an important tool 

for personal and spiritual growth. 

Regret forces us to confront the ways 

in which we can be the source of our own suffering. 

So, we need regret if we intend to make our futures 

better than our pasts, 

as wrenching as that process can be. 

And so, we need Yom Kippur, our holiday of regret.

 

Over and over again today, we repeat our list of confessions, 

which is arguably just a list of regrets. 

And the weeks and days leading up to this moment 

encourage us to engage in a process of teshuva, 

which is about acknowledging our regrets 

and then doing whatever we can to make things right.

 

One of our tradition’s most important stories of regret 

lies just beneath the surface of Yom Kippur. 

Do you remember the story of the Golden Calf? 

When Moses is delayed in coming down from the mountaintop, 

the anxious people prevail upon Aaron to make them a Golden Calf, which they precede to worship. 

God becomes incensed at this apostasy

 and plans to destroy the entire people. 

But Moses intercedes, 

offering reasons why that would be a bad course of action. 

 

Hearing this, God regrets what God had planned

–v’yinachem Adonai, the Torah tells us. 

While the people would be punished, 

they would not be entirely destroyed. 

 

Hearing this, the people go into mourning, 

removing their fancy clothes to express regret for their actions. 

And then, after 40 more days on the mountain, 

Moses returns with a new set of tablets 

and a renewal of the covenant that had been breached

between God and the people.

 

So, what we have in this story 

is a broken relationship followed by mutual regret. 

Both the people Israel and God look back on their past actions

–the idolatrous worship 

and the plan to destroy the people, respectively–

and wish they had acted differently. 

Moses then brokers a reconciliation, 

enabling both sides to restore and repair their relationship. 

 

Quite tellingly, the rabbis associate this episode with Yom Kippur. According to tradition, 

Moses returned to the mountain on the first of Elul 

and came down with the new tablets 

40 days later on Yom Kippur. 

The 13 Attributes of Mercy we recite over and over again today 

also emerge from this story of breach, regret, and reconciliation.

 

Our Yom Kippur is likewise the culmination of a process 

when we express our regrets 

and then find a new way to move forward. 

Yom Kippur is the day of second chances, for us, 

and, it would appear, even for God. 

And if God is capable of such regret, 

of realizing that a course of action was unwise 

and then finding a better way, 

then surely we are as well.

 

So, what regrets does Yom Kippur invite us to experience? 

For his recent book about regret, 

the author Daniel Pink conducted an international study 

where thousands of people submitted their regrets. 

On this basis, Pink identified four basic kinds of regret 

that cut across domains of life

 such as romantic relationships or career. 

Let’s consider each one in turn and see how these basic regrets 

also show up in the Al Cheit, 

the list of sins we recite again and again on Yom Kippur.

 

First, there are what Pink calls foundation regrets, 

which are failures of foresight and conscientiousness, 

where we fail to lay a foundation for future thriving. 

These happen when we fail to attend 

to our health or finances or education 

and end up paying the price later in life. 

In the mahzor, we confess sins of eating and drinking; 

of disrespecting the parents and teachers 

who tried to set us up for success, but whose warnings we ignored; and of confusion of the heart, where we did 

what was easy and fun in the moment 

instead of what would have been better in the long run.

 

Second, there are boldness regrets,

 the mirror image of foundation regrets, 

where we failed to take an opportunity or risk 

that might have changed our lives for the better. 

These are the choices–usually a choice not to do something–

that leave us wondering: 

What If? 

What if I had taken that job, asked that beautiful stranger out, 

moved to a new city? 

 

This shows up when we confess to the sin 

of being stiff-necked or stubborn. 

This was how our ancestors behaved 

when they worshiped a calf of gold 

instead of trusting in Moses and God. 

And it is how we also behave 

when we only see what is right in front of us, 

and not the amazing possibilities waiting 

just to the right or left of the path we thought we were on.

 

Third, there are moral regrets, 

when we do something 

that goes against our sense of right and wrong: 

when we hurt others, flout communal norms, or act unfairly. 

While this was the smallest of the four categories of regret 

that emerged from Pink’s study, 

moral regrets unsurprisingly make up 

a good chunk of what we confess in the mahzor: 

sexual immorality, wronging others, violence, fraud, 

bribery, swearing falsely, breach of trust, and more.

 

Finally, there are connection regrets, 

which result when a relationship frays or rips 

and we are left holding the tattered pieces. 

This too comes up in Al Cheit, 

mostly in sins involving how we speak to one another: 

mocking, idle gossip, talebearing, and other behaviors 

that strain relationships among people.

 

What are we to do with this wide range of regrets, 

present in both contemporary research and our ancient liturgy? 

 

One strategy affirmed by both Pink’s research and Jewish tradition 

is confession: 

saying what we’ve done in speech or writing, 

which concretizes our emotions into specific language 

and thereby makes them feel less overwhelming. 

Such confession is a major step in the process of teshuva, 

as laid out by Maimonides in his Laws of Repentance, 

the benefits of which have also been confirmed 

by psychological research.

 

More broadly, we can invite our regrets to become our teacher. 

Pink suggests that these four basic types of regret 

(foundation, boldness, moral, and connection) 

reveal through their opposites what people really value: 

stability, growth, goodness, and love.

Regret enables us to learn from our mistakes and set out on a better way. 

 

The mahzor alludes to this concept: 

“Sarnu mimitzvotecha,” we say: 

“We have turned away from Your mitzvot and Your goodly laws, 

and it wasn’t worth it!” 

With the benefit of hindsight, maturity, and experience, 

we can look back and realize just where and why we went wrong, 

as difficult as that can be to admit.

 

In that spirit, let me join Pink’s regret survey 

and share one of my regrets with you. 

Years ago, I had a friend with whom I was very close, 

at a time in my life when I didn’t have so many such friends. 

But, as circumstances enabled me 

to develop more and different friendships, 

I left this person behind. 

 

We rather suddenly ended our friendship, 

not because anything specific had happened, 

but, frankly, because I had more and better options. 

I regret this deeply: 

I could have found a way to maintain what I had 

even while I gained new friendships. 

 

As I thought about this recently, 

I decided to reach out to try to re-establish a relationship, 

especially after a quick internet search revealed 

that this person’s father recently passed away. 

I haven’t heard back yet, but I hope to. 

I have no idea whether this person has totally forgotten about this, 

r if he wakes up every morning angry at how I abandoned him. 

I hope one day to make things right. 

And I’d like to think that I learned my lesson. 

I now make an effort to stay in touch with certain friends 

from earlier periods in my life 

that it would be easy to just let slip away.

 

The Hebrew term for regret reveals a key aspect of this emotion. 

That word for regret is related to the word for consolation. 

Regret and consolation are similar emotions. 

In both, we look back on the past with the benefit of time 

and feel differently now than we did then. 

That course of action felt right at the time, 

but we now realize the error of our ways. 

That loss felt devastating at the time, 

but we now realize that there can be life even after loss. 

When we experience both regret and consolation, 

we reframe something from the past that can’t be changed 

in order to feel differently about it in the present.

 

The regret of Yom Kippur and the consolation after grief 

come together in the Yizkor service. 

As we think about those we’ve lost, 

perhaps regrets come to mind: 

times when we were not our best selves toward those who are gone, times we were too busy with other things 

we thought were more important 

to spend time with the people we love, 

times we got into stupid arguments that we shouldn’t have. 

While the deceased may have had few regrets worthy of mention, 

the finality of death might produce plenty of regrets 

among those left behind.

 

But, perhaps with the benefit of time, 

we can reach a third emotion: self-compassion. 

We can temper the stringency of our desire for self-improvement 

with the same compassion that we extend to others,

but too often forget to give ourselves. 

 

And, because one of the messages of Yom Kippur 

is that it’s never too late, 

we can ask forgiveness even of the dead. 

Our tradition teaches us that the souls of the departed 

are never too far away; 

they hover just beyond the confines of the world as we know it.

 

So, as we recite prayers of Yizkor in a moment, 

let us summon up those regrets. 

Let us speak them in our minds and hearts. 

And then, let us turn to the spirits 

of those who no longer walk this earth 

and ask their forgiveness. 

But most importantly, 

let us turn those regrets into our teacher, 

inspiring us to change our ways in this new year and beyond.

 

We turn to Yizkor on page 569.