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RH 1 -  5786 |Rabbi David Wolkenfeld

09/25/2025 01:17:45 PM

Sep25

The Holiday of Failure

One of the ways that technology has addled my brain is that I find it nearly impossible to do household tasks unless I’m listening to a podcast. This is often very annoying for members of my family who sometimes expect to tell me things or ask me questions while I’m washing dishes. It also doesn’t always align with my goals of efficiency since often I’ll hear something interesting and want to look up a fact online or I will finish putting away the groceries and stand in the kitchen doing nothing until whatever it is that I’m listening to comes to an end. But I do get to listen to a lot of podcasts along with a lot of audio shiurim and I have been returning, in conversations with others as well as in my own mind, over and over again to a recorded discussion from last spring between New York Times columnists Ezra Klein and Ross Douthout about religion and public life and mysticism and politics. 

Ezra Klein is secular, liberal and Jewish. Ross Douthat is a conservative and a Catholic and the author of a recent book with the subtitle, “Why You Should Be Religious." They had a lot to talk about.  To me, the most compelling and memorable moment in their conversation occurred in the first half of the interview when Klein complained to Douthat about the ethical lapses of religious Americans in the context of the morally fraught political moment in which we live. 

Douthat’s response was brief and to the point: Have you read the Bible? It’s not a story of God’s people living up to the demands placed upon us. It’s a consistent and persistent story of failure. 

Later in the conversation Klein shared his skepticism that any ancient religion that has existed for centuries could possibly retain any significant truth claims. The compromises and shifts that were necessary to survive and even thrive under various repressive empires surely washed away whatever piercing and transformative truth the religion may have once possessed. In Klein’s words, “a religion that took that truly seriously would end up being very incompatible with ruling regimes and would have a lot of trouble from them.”

And again Douthat responds with sharp insight: “...the Hebrew Bible, is a story where the Jews are failing your tests…You’re like: Well, if this religion was really from God, they probably wouldn’t all become idolaters. And they’re like: Ezra, here’s our holy book. It’s all about how we became idolaters.”

The failure of religious individuals to live up to the demand of their religion, discredits religion to Klein whereas for Douthat, since the natural inclination of most people is to think of ourselves in flattering and self-justifying ways, the existence of a religious tradition that records and preserves a record of our own failure, holds it up to us, and demands that we do better surely must contain a Divine spark. People would not invent such a challenging and chastising super-ego on our own.

Their conversation then goes in a different direction, but I have been mulling over this exchange for several months and, especially, leading up to Rosh Hashanah, I have thought about the implications of this basic observation. The Torah is a record of our failure. Tanakh - the Scriptures -is an account of our failures and inconsistent loyalty to God. The liturgy of the Yamim Nora’im - these days of Awe are a litany of our frailty, inconsistency, and sinfulness. 

And that record of failure, on Rosh Hashanah, is transformed into a source of hope.

Rav Menachem Froman z’l, the mystic educator and peace activist,  expressed a more whimsical version of Douthat’s observation.

For many years I have said that I have two proofs for the existence of God: 1. The media fills the world with so much nonsense, and yet there are still intelligent people. This is a sign of God. 2. The religious community looks like it does, and talks about God like it does, and yet despite this, there are still some people who believe. This is a sign that there really is a God..

Rav Froman asserted that we cannot observe the Divine spark right now at the center of a beautiful and well ordered society in which we are surrounded by messages of truth and exposed to role models who exemplify the right and the good. The spark of the Divine is discernable in the darkness that exists in the absence of truth and beauty. The Divine spark is observable when  we look to one side or another and see too few role models of piety and decency and kindness and integrity and yet we still decide to seek out God.

The Rosh Hashanah liturgy is filled with references to the lack of role models to inspire us and educate us properly and to our personal failure to be worthy exemplars of who the Torah wants us to be in the world. But on Rosh Hashanah, that litany of failure is transformed into hope.

אַתָּה זוֹכֵר מַעֲשֵׂה עוֹלָם וּפוֹקֵד כָּל־יְצֽוּרֵי קֶֽדֶם. לְפָנֶֽיךָ נִגְלוּ כָּל־תַּעֲלוּמוֹת וַהֲמוֹן נִסְתָּרוֹת שֶׁמִּבְּרֵאשִׁית. כִּי אֵין שִׁכְחָה לִפְנֵי כִסֵּא כְבוֹדֶֽךָ. וְאֵין נִסְתָּר מִנֶּֽגֶד עֵינֶֽיךָ:

“You recall the deeds of those who walk the earth today, and You attend as well to the conduct of generations past. Before You, all that is hidden is laid bare, the countless secrets stretching back to the dawn of creation. For before the throne of Your Glory there is no forgetfulness, and nothing is concealed from Your sight.”

This passage from the Zichronot portion of Rosh Hashanah Mussaf emphasizes the penetrating scrutiny of God to which we are subjected. Our good intentions do not impress God and neither is God moved by outward displays of piety. We stand before God, in the words of the Selichot, דלים וריקים -impoverished and emptyhanded.  

In the poignant coda to the Unetane Tokef prayer, we recall just how unsteady and unreliable human beings are:

אָדָם יְסוֹדוֹ מֵעָפָר וְסוֹפוֹ לֶעָפָר. בְּנַפְשׁוֹ יָבִיא לַחְמוֹ. מָשׁוּל כְּחֶֽרֶס הַנִּשְׁבָּר. כְּחָצִיר יָבֵשׁ. וּכְצִיץ נוֹבֵל. כְּצֵל עוֹבֵר. וּכְעָנָן כָּלָה. וּכְרֽוּחַ נוֹשָֽׁבֶת. וּכְאָבָק פּוֹרֵֽחַ. וְכַחֲלוֹם יָעוּף:

“A human being begins as dust and returns to dust. Life is risked in the struggle for daily bread. We are like fragile shards of pottery, like grass that withers, like a flower that fades, like a passing shadow, a vanishing cloud, a wind that blows by, dust scattered in the air, and a dream that slips away. כַחֲלוֹם יָעוּף”

The Torah and scripture records the persistent failure of the Jewish people to live up to the expectations of the Torah, and the rabbis and scholars who crafted our liturgical experience on the Yamim Nora’im ensured that we would come before God at this sacred time of year in full recognition that we have not done all that we can or should do, but rather approach God דלים וריקים - impoverished and empty handed. They crafted a holiday experience designed to undermine our self-confidence and complacency by reminding us of the unreliability and transience of every human commitment that is no more than a חֲלוֹם יָעוּף a dream that slips away.

But the religious experience on Rosh Hashanah and the Yamim Nora’im is one of faith and hope. 

Perhaps no word in our liturgy expresses the hopeful potential of this season than למענך “for your sake” which first appears in the Selichot prayers a week before Rosh Hashanah. It  grounds our pleas and requests and even demands  in God’s own faith in us and God’s own desire that the world be a place of justice and kindness and bounty. We repeat the word in Avinu Malkeinu that we recite today and through Yom Kippur עֲשֵׂה לְמַעַנְךָ אִם לֹא לְמַעֲנֵֽנוּ if you cannot act on our merit, at least act on behalf of Yourself. And the word returns in the Selichot recited at Yom Kippur Ne’ilah prayers. 

The machzor agrees with Ezra Klein’s critique of religious people. We have not lived up to the demands of the Torah. We are not as kind or as honest or as reliable as we should be. But the machzor holds a mirror to our faces and invites us to try again and to have faith in God’s patience in our ability to learn and to grow. The Torah is not an opiate that teaches complacency, but a source of insistent encouragement to moral excellence and spiritual virtuosity. 

No moment on the Yamin Nora’im captures this dynamic more than the Haftarah on Yom Kippur which is the opposite of an opiate. When we are already feeling hungry… and proud of ourselves. We are already feeling thirsty…and pious. We are already feeling tired… and forgiven. The Haftarah says: 

“Is such the fast I desire? A day for men to starve their bodies? Is it bowing the head like a bulrush And lying in sackcloth and ashes? Do you call that a fast?...

No, this is the fast I desire: To unlock the fetters of wickedness, And untie the cords of the yoke To let the oppressed go free; To break off every yoke.”

Nothing I ever say could possibly be as controversial or as edgy as the Haftarah that our tradition itself selected for Yom Kippur. The Torah is not an opiate. The Torah has the potential to wake us up. 

I’ve mentioned before how Sefas Emes, the great Hasidic philosopher of the turn of the last century, writes that we must rejoice on Rosh Hashanah because the potential for renewal itself is renewed each year on this day. We don’t rejoice because we are good, but because we can become good. We don’t rejoice because of what we are, but because of who we can be. 

But for many of us our faith is not only challenged by the behavior of religious individuals who fail to live up to the Torah’s demands of ethical excellence.  In the aftermath of the twentieth century, in the aftermath of too many tragedies, big and small, far and near, the benevolent protection of God is so hard to perceive. 

But disappointment in God, even anger at God, can be expressions of the truest faith. One can only be disappointed if we expected something different. We can only be angry at someone who deviates from the established norms that define a relationship between two parties. In the words of Rabbi Sholom Carmy, “it is precisely  the religious believer, alive to the Creator’s goodness, who is most prone to be unspeakably  distressed by the world’s imperfection and depravity.”

One of the details of the Laws of Rosh Hashanah as they appear in the Shulhan Arukh is the preference for a prayer leader who is at least thirty years old. Rabbi Moshe Isserles, in his Darkhei Moshe, explains that one cannot make it to age 30 without encountering heartbreak and one cannot lead a community in prayer on the Yamin Nora’im unless one’s heart has been broken.

A heart that has been broken, whether by acts of God or by disappointment in other people, and has healed enough to rise in song and prayer, can sustain a congregation in this moment. The Passover Seder “begins with degradation and ends with praise” - “Our ancestors were slaves unto Pharaoh in Egypt and God has brought us close with service of God.” So do the Yamin Nora’im. We begin with recognition of how others have disappointed us, and how we have disappointed others and ourselves. But in this season, and on this day, we find a path forward with hope in the possibility of becoming something better.

I wish all of us a day of honest introspection and honest confrontation with God. And in the merit of that hard work, and as a result of that hard work, I wish you all a Shanah Tovah.

 

Thu, October 23 2025 1 Cheshvan 5786