Teshuvah: Softening Our Hearts
Staying Open amidst Our Challenges — especially Israel/Palestine
Rabbi Zelig Golden — Erev Rosh Hashanah Sermon 5787
The Master Key — A Broken Heart Opens the Gates
One year, Rabbi Yisrael ben Eliezer, the Ba’al Shem Tov, asked Rabbi Zev Kitzes, one of his senior disciples, to blow the shofar for Rosh Hashanah. He instructed him to study all the kavanot—the mystical intentions associated with the shofar—so that he could meditate upon them while blowing. Rabbi Zev applied himself to the task with joy and trepidation: joy at the privilege, and trepidation at the immense responsibility. He studied the kabbalistic writings on the multifaceted significance of the shofar and what its sounds achieve, and prepared a sheet of notes with the essential kavanot so he could refer to them when the moment came.
Finally, Rosh Hashanah morning arrived. Rabbi Zev stood on the bimah surrounded by Torah scrolls and a sea of tallit-draped bodies. Across the room stood his master, the Ba’al Shem Tov, his face aflame. An awed silence filled the room in anticipation of the piercing blasts of the shofar. Rabbi Zev reached into his pocket—and his heart froze. The paper was gone. He searched his memory, but panic had emptied his mind. He could remember nothing. He had failed his teacher and the sacred task entrusted to him. With tears in his eye, Rabbi Zev lifted the shofar and blew. Then he sat down, avoiding his master’s eyes.
After the prayers, the Ba’al Shem Tov found him sobbing beneath his tallit. “Gut Yom Tov, Reb Zev! That was an extraordinary shofar blowing today.” “But Rebbe…how?” The Ba’al Shem Tov answered: “In the king’s palace there are many gates and doors, and each has its own key. The kavanot are like those keys, each opening another chamber in the supernal worlds. But there is one master key that opens every door and reaches the innermost chambers of the Divine palace. That master key is a broken heart.” (Adapted from a Hasidic tale, “The Master Key.”)
Hayom Harat Olam - What is Birthing for Us
Rosh Hashanah is Hayom Harat Olam — the day the world is born. And on this day of birth, our tradition turns the question toward us: What is asking to be born in us this year—and what needs to soften for that birth to be possible? Sometimes we know exactly what needs to change, but often we don’t. Or we do know somewhere deep down, but fear, habit, and identity - coverings over our true heart - make it hard to feel and know. I know this from my own life.
In my high school graduation speech, I urged my classmates to “take the road less traveled— follow the heart rather than power, prestige, and money.” Ironically, eight years later I graduated from law school and stepped onto a path that offered me exactly that. Fighting for organic farmers as an environmental lawyer was meaningful. Yet underneath, I was depressed, confused, and lost.
Beginning around 2004, I entered psychedelic-assisted therapy. Slowly, I peeled away layers of fear that had led me and tethered me to law — a certain version of success. Part of me felt a different calling. Over three years, I slowly cracked open. As that shell dissolved, I could feel my truth - a longing to weave wilderness, Judaism, and build sacred community. By 2007, I embraced my calling and vision for Wilderness Torah and leapt — because my heart was open enough that I could hear what I already knew. Looking back, the deepest transformation was that something around my heart had to break — the fear and certainty about who I was supposed to be. Only then could I hear what was trying to be born.
Teshuvah: Nothing More Whole than a Broken Heart
I believe, as our Passover story teaches, the greatest danger is not our hearts breaking, but our hearts harden. Pharaoh’s tragedy is not what he does. It’s his heart hardening again and again.
The Kotzker Rebbe, Rabbi Menachem Mendel of Kotzk of Poland, offers the seeming paradox: Ein davar shalem yoter mi-lev shavur — “There is nothing more whole than a broken heart.” And the prophet Ezekiel, speaking to our ancestors out of devastation and exile, imagines redemption in similar language: “I will give you a new heart; I will remove the heart of stone…and give you a heart of flesh.” (Ezekiel 36:26)
A heart of flesh. Vulnerable. Touchable. Because it can be touched, it can be hurt. Perhaps this is why heartbreak can become a doorway. Sorrow can crack through our armor. Grief can make us bitter and closed—but when we allow ourselves to feel sorrow, something that has become stone can soften.
The Talmud teaches, Rachmana liba ba’i — “The Merciful One desires the heart.” (Sanhedrin 106b). God is looking beneath performance, achievement, identity—beneath all the ways we present ourselves—to the inner place from which we actually live.
Torah gives us this extraordinary command: U’maltem et orlat levavchem — “Circumcise the covering of your heart.” (Deuteronomy 10:16). Because the heart does become covered over: armored by fear, numb with shame, defended by certainty. In the language of our mystical tradition, kelipot—husks— accumulate around what is most alive within us. The work of teshuvah - spiritual return - is to loosen those coverings so that we can feel and become reachable again.
The Palestinian-American poet Naomi Shihab Nye writes in her poem Kindness: “Before you know kindness as the deepest thing inside, you must know sorrow as the other deepest thing.” Or in the prophetic words of the late Dolly Parton, “If you want the rainbow, you gotta put up with the rain.”
That is the mystery. Sometimes sorrow is what breaks the shell. It reveals what we truly love, makes us permeable again, and from that softened place, compassion, forgiveness, and real change become possible. Maybe teshuvah does not begin when we decide to change, but when our heart softens enough to be changed.
The Test of the Open Heart - Israel/Palestine
The real test of this teaching is whether we can practice it precisely where our hearts are most likely to harden. For many of us in Jewish community, there is no greater test than Israel and Palestine.
I think back to living in Israel during the 2014 Gaza war: hearing Palestinians tell of olive groves destroyed and boys arrested by Israeli authorities; a knock at Bonna Haberman’s Jerusalem door freezing us with fear of news of her son fighting in Gaza; circling and holding hands to bless pita with Palestinians and Jews at a West Bank olive tree planting when suddenly air raid sirens blast, no shelter to hide in, Iron Dome intercepted rockets overhead; standing in Jerusalem at the 2001 Sbarro bombing site, remembering the Israeli lives lost there.
And now, nearly three years after October 7, we continue to live with devastating loss and trauma in Gaza and Israel. However we understand this conflict, wherever our sympathies and convictions lie, can we stay rooted in our values and remain connected by allowing ourselves to feel the heartbreak together? Not to surrender conviction. Not to pretend we agree. Not to solve the conflict tonight. Simply to refuse to close our hearts to one another’s sorrow and hopes.
If we can keep our hearts soft here, together in our pluralistic Jewish community, on the issue that stands to tear us apart most easily, then perhaps we can learn to stay together through almost anything. Perhaps that is the deepest teshuvah.
Shofar — The Heart Beneath Words
And when words run out, Judaism gives us a language beneath words.
The shofar does not explain or argue. It cries. It calls from somewhere deeper than language. I hear the voice of my Rebbe, Reb Zalman Schachter-Shalomi ztz”l, reminding us of the krechtz—the deep groan that rises from beneath words. And I hear the shofar as the great krechtz of Rosh Hashanah—the cry of the breaking heart.
Tekiah —- A cry for help.
Shevarim – – – wailing with brokenness.
Teruah - - - - - - - - - uncontrollable sobbing - shattering.
Tekiah Gedolah ——— a greater wholeness, spacious enough to hold our brokenness.
Maybe this is why the broken heart is the master key. When the heart breaks open, we become reachable again—by one another, by the suffering and beauty of this world, by our own truth, by God. The shofar is the sound of the heart breaking open.
On the hardest questions—the devastation in Israel and Palestine, conflict with friends and colleagues, struggles in marriage, even the conflicts within ourselves—we may not resolve everything. But what if we can meet one another in the heartbreak? What if that itself is part of the way through?
This brings to mind the Parents Circle–Families Forum (PCFF), a joint Israeli-Palestinian organization of over 800 bereaved Palestinians and Israelis, all of whom have lost immediate family to the conflict. Despite their profound grief, the members choose a courageous path: to transform their pain into a force for reconciliation, dialogue, and peace. If those who have buried their kin can sit together and refuse to let sorrow harden into hatred, then surely we can stay open to one another here.
Chevrutah or Journal Reflection Invitation
Take five minutes to explore the following questions, from the heart. No fixing, no advice—just sharing from the heart.
Why does my heart harden?
How can I soften my heart for some birthing to be possible
