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A Spiritual Toolkit for Difficult Conversations

Sermon delivered Yom Kippur morning, 5778.

Naming the problem: For the Sin of Avoidance

Later this morning, together in one voice- we will again recite the words of “Vidui”— the liturgical centerpiece of Yom Kippur.  In a moment that is intensely personal while simultaneously communal, we will name our rough spots, our shortcomings, and our faults.

For the sin we have committed with our words, we ask forgiveness.

For the sin of speaking maliciously of others, we ask forgiveness.

Our tradition has much to say about the power of speech, and much of our confession on this Day of Atonement focuses on what we have said.

However, when it comes to that which was left unsaid, the tradition is consequently silent.

I’d like to add one more “Al Cheit” to my prayer for this morning, and I suspect that I am not alone in feeling guilty of this:

Al chet sh’chetanu l’fanecha b’hi’maniut.

For the sin of avoidance.

For not saying what could, or should have been said.

For not speaking openly and honestly with those I love.

Al chet sh’chatanu l’fanecha…

For the ways in which I have lowered my eyes instead of meeting the gaze of someone whose viewpoints challenge me.

For the times I changed the topic.

And perhaps most offensively— for the relationships I simply don’t have, with those whose views are different than my own.

Over the course of the year gone by, it seems that hard conversations have become even more difficult to have.  If I were to ask, by a show of hands, how many of you sat around a dinner table at some point this year, hoping the conversation wouldn’t turn to “what’s going on in our country”, how many of you would raise your hands? Who sat quietly, unsure how to respond, when someone else was attacked for an opinion? Or elsewhere, who has sat among groups of Jews wondering: do these people really support Israel, or do they criticize her? Or, chas v’shalom (God forbid), do they care too much about Palestinians, or too little?[1]

But, maybe, — you are sitting here thinking to yourself,

“Well, actually- not really that often.”

Sitting in the cocoon-like protection of our echo chambers, it’s so much easier to wring our hands with like-minded people, and to share the finely crafted opinions of commentators who think as we do.It’s much harder to sit with complexity— and it seems that we have abdicated our ability to live with opinions that are different from our own.

In the spring of 2016, at the height of the presidential campaign, The Wall Street Journal created a real-time news tracker by collecting trending news stories on Facebook. The tool offered a side-by-side look at conversations on current events from differing political perspectives. The results showed that social networks create “echo chambers,” in which users see posts almost exclusively from like-minded friends and media sources.

The divide was striking.

In the same country, on the same website, at the same moment, millions of people were split into two distinct camps,each one seeing the same issue in a profoundly different way.We are drawn to the news outlets and stories that reflect our world view, and we tend to discount or disregard dissenting opinions. And while it’s popular and not wholly untrue to blame social media—we are just as guilty of constructing these echo chambers in our lives off-line, as well.

A recent study[2] presented 200 participants with two choices: they could either read and answer questions about an opinion they agreed with, or read the opposing viewpoint.

The topic was same sex marriage.

If the participants chose to read the opinion that they already agreed with, they were entered in a raffle to win $7.If they chose to read the opposing viewpoint, they could win $10. 63% of participants chose to stick with what they already believed,forgoing the chance to win the larger sum of money.This was true both for people who were pro-same sex marriage, and those who oppose it.

In a slight variation on the first test—researchers asked participants to rate how interested they were in learning about alternative political viewpoints,as compared with activities like“watching paint dry”, “sitting quietly”,“going for a walk on a sunny day” and “having a tooth pulled”.

The answers do not surprise:listening to an opposing viewpoint isn’t quite as bad as oral surgery,but it’s trending in that direction.It’s certainly not as highly rated as a leisurely stroll in the sun.

The study concludes:“People on the left and right are motivated to avoid hearing from the other side for some of the same reasons: the anticipation of cognitive dissonance and the undermining of a fundamental need for a shared reality with other people [are just too much to bear].”[3]

They call it “motivated ignorance”. In other words— we are choosing to not to hear. As a society, we are just not engaging.

Consequences of Avoidance: Polarization and Estrangement

I believe we are suffering from our avoidances.

We are carrying psychic loads that threaten to break our backs and our hearts—and most of us, don’t really know how to stop. We avoid consciously, and it turns out- we avoid subconsciously as well.

Jonas Kaplan, a psychologist at the University of Southern California compares it to our body’s immune system:

“The psychological self is the brain’s extension of that way [in which the body works to protect itself]. When our self feels attacked, our brain is going to bring to bear the same defenses that it has for protecting the body.”[4]

The consequences of these patterns of avoidance are significant: On a national level, we see the polarization.The “us” and “them” mentality. The polarization is geographic— as more people choose to live in state and even communities where their neighbors are more likely to share their political views. “The polarization is personal: Fully 50% of Republicans would not want their child to marry a Democrat, and nearly a third of Democrats return the sentiment”[5]  It seems that inter-party marriage is the new interfaith, or interracial marriage.


Avoidance doesn’t happen solely in the political realm.We experience it in our families,in our closest constellations of relationships as well. The consequences of avoiding difficult conversations and challenging interactions hits on a deeper, more personal level.  It results in grudges and familial estrangements, and in the toil of carrying that emotional load.

It’s often the conversations we don’t have that we spend the most psychic energy on:

… not telling our friend that they disappointed us, that they weren’t there when we needed them most.

… not telling our parents that we worry about them, or that we cannot be there for them in the way they expect.

…not telling our sister that we are hurt, or that we miss her, or that we are concerned about her health

…not telling our children that we cannot afford to pay for an experience they want to have, or that we are worried about the choices they are making

Relationships can be complicated. Our family constellations are complex. Many of us have lived with loss and fractures in our families, estrangements and bereavements,as well as new additions:  new lives and new loves that bring with them their own set of considerations. Like you, I have complex relationships within my own family. I can promise you that your complexity in relationships is universal.  And so often, the tensions arise, and the feelings are hurt,because we avoid the tender spots, and just don’t talk about it.

These avoidances are so common,that even our biblical ancestors were guilty of them:

Isaac and Abraham never did speak again after their experience together up on Mt. Moriah.

Our ancestor Jacob was said to have tzaar gidul banim, a complex relationship with his children and his parents—or more literally, “big tzuris with his children”.

Even God is culpable.

Just as Abraham and his son never find the words to reconnect after the Akedah, God is also silent in Isaac’s life, going forward.

These are difficult conversations, for us all.

Why we avoid: Naming Disagreements & Conflict

We learn quickly, from a young age,that if we have nothing nice to say, we should say nothing at all. Many of us are conflict-averse: we’d rather not engage, telling ourselves that it’s easier to say nothing at all.

“What’s the point of it anyway” we wonder— remembering the stubbornness of one relative, or the intransigence of a particular friend?

“Who wants to get into an argument”, we say? We assume there will be conflict.We avoid the possibility of disagreement, because sometimes, we just don’t know how to disagree.

Somewhere along the way, we came to believe that disagreement was bad. We came to assume that the Jewish value of “shalom bayit” meant a “quiet home”, instead of a home of peace and wholeness, where matters of grave importance could be discussed respectfully.

However, our Jewish tradition offers us another point of view—the idea of the makhkoket l’shem shamayim: the disagreement that is for the sake of heaven.

Perhaps you’ve heard of Rabbi Hillel and Rabbi Shammai— two of our Talmudic sages, who never agreed.

If Hillel said right to left, Shammai said left to right.

If Hillel said up, Shammai said down.

They didn’t even try to pretend to agree— but  that’s exactly the point. You see, despite their disagreements, they never stopped talking. It is recorded in Pirke Avot:

Every disagreement (mahloket) that is for the sake of Heaven will continue to exist but one that is not in the name of Heaven will not continue to exist.

And what is a “disagreement that is in the name of Heaven”? The kinds of disagreements as existed between Hillel and Shammai. It makes you wonder—what made their disagreements so special?

The rabbis answer:it’s the fact that they never ceased to be engaged in communicating with one another. And what’s more, that they continued to love one another. Despite their intellectual differences and legal disagreements,they did not refrain from being in relationship:

Although Beit Shammai and Beit Hillel are in disagreement on the questions of (marital and personal status), Beit Shammai did not, nevertheless, abstain from marrying women of the families of Beit Hillel, nor did Beit Hillel refrain from marrying those of Beit Shammai. This is to teach you that they showed love and friendship towards one another, thus putting into practice the Scriptural text, “You shall love truth and peace.” (Zechariah, 8:16).[6]

One of the crucial pieces of this loving and complicated relationshipis that neither were afraid to change. Both of their opinions are recorded— even the one that did not prevail. We often attribute this to our traditions’ respect for the minority opinion, but it goes deeper than that: it was to teach the generations to come that no one should persist in an opinion when they realize they are wrong.[7]

In other words, Hillel and Shammai continued their dialogue in the service of (attaining) the truth.

When the truth became known one would not continue to insist (on their opinion), and they would accept in joy the correct opinion that had been clarified…Because from the onset, they did not intend to disagree other than for the sake of Heaven.[8]

They assumed best intent.

If Hillel could admit when he was wrong, so can we. Rabbi Shammai lives on in our Jewish memory

not because he was right, but because he was loving, and dedicated to both peace and truth.

The spiritual challenge of this day then becomes, answering to this sin of avoidance. How do we have difficult conversations?

There has been much written on how to have difficult conversations— everywhere from Harvard Business School to our own tradition.  We aren’t doomed to the lifetime of silence between parent and child that Abraham and Isaac experienced. We needn’t resign ourselves to our echo chambers and silos. We have another chance, to say the things that are hard to say, and to listen to things that may be hard to hear.   I think this is as true for the friend at our dinner table with deeply different politics from our own, as it is for the parent or sibling we have been avoiding a hard conversation with.

Today is a day for self-reflection and honesty: I am terrible at this. My best friend lovingly calls me the Queen of Avoidance. It is one of pieces of relationships that I struggle with most. Sometimes it does feel easier to carry the psychic load myself—  to keep the worry, or the fear all to myself. And I do it, despite my best intentions- and despite “knowing better”. I suspect I’m not the only one. But as I have learned from some of the wisest people I know: it’s never really worth it. We are only as “sick as our secrets”— or as sick as the grudges, misunderstandings, and unanswered questions that we shlep from place to place.

And so, with the wisdom of those who have thought and written extensively on this topic behind me, I want to offer you a spiritual toolkit, for having difficult conversations in the year ahead.

  1. First: we have to ask ourselves, what are we willing to risk, for the sake of “heaven”—for the sake of relationships? What, if anything, would you really have to give up in order to have these conversations?

  2. Then, can you assume best intent? With the depth of incivility that we see played out on the national stage, I fear we have taken on a permanent posture of defensiveness; assuming that those whose opinions differ from ours seek to harm us. I think that we have forgotten how common the human need for love, understanding, and comfort is. If we can engage in dialogue assuming, unless proven otherwise,that the other has only best intentions,it opens up the possibility of really hearing another point of view.

Also in our spiritual toolkit: curiosity.

  1. Be curious, not certain. When we find ourselves with an opportunity to be in relationship with someone whose views differ from our own, or to read something that holds up an opposing opinion, can we proceed with deep curiosity and not certainty?

These conversations will be hard work. They will require much of us:

  1. To be aware of our bias and our privilege.

  2. To be humble.[9]

  3. To lean into our own discomfort. That’s why they’re called “growing pains”

And, finally: a word about boundaries and self-care. There may be some conversations that cannot be had.

There may be relationships where the silence is the healthiest option after all.  I am sure that many of us can think of examples where this is true. Even our sages knew this, teaching that we are obligated to speak when we are likely to be heard, but it is also our obligation to choose silence, when we are not likely to be heeded.[10]

My teacher, Rabbi Larry Hoffman’s voice echoes in my mind— he reminded us constantly that “learning” was all well and good, but really, learning implied something transactional. It’s the acquisition and application of a skill, or an idea. Instead, he always encouraged us to “find out”.

Finding out—really discovering?

That is something worthy of our time and attention.

To find out, is to take the path of asking hard questions,  and then closing your mouth and opening your mind to really hear the answers.

To find out, is to discover, by practice- what it means to listen It’s to uncover what it means to be at peace in your heart when someone else’s truth is different from yours.

In this year ahead, I want to invite you all into a personal challenge, to which I am holding myself:

Let’s have the difficult conversations this year.

Let’s not let misunderstandings cloud our relationships.

Let’s talk about it. Really, deeply, talk about it.

[1] Thanks to Paul Kipnes for this gem of a sentence.
[3] “I just choose not to listen”: Why Trump Supporters are Tuning Out The Scandals” Brian Resnick. Vox. May 18, 2017.
[4] “I just choose not to listen”: Why Trump Supporters are Tuning Out The Scandals” Brian Resnick. Vox. May 18, 2017.
[5] ibid.
[6] Babylonian Talmud, Yevamoth 14b
[7] Mishna Edoyot, chapter 1
[8] Yayin Lavanon, Avot 5:17
[9] Based on work of 9Adar Project:  5 steps of #MyFeetYourShoes: (a.) Be aware of your bias, (b.) Have humility that you may not know the full story; (c.) Have respect for possible other interpretations; (d) Listen/read other interpretations with deep curiosity; (e.) engage in constructive conversations with those that you are in disagreement with.
[10] B. Talmud Yevamot 65b


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