Shabbat Shuvah – Parshat Vayeilech (Deuteronomy 31)
5 Tishrei 5786 (9/26/2025)
by JRC member Linda Mathias Kaskel
Welcome to Our Season of Return
Here we are on Shabbat Shuvah, the Sabbath of Return, we stand in the sacred space between Rosh Hashanah and Yom Kippur, between who we have been and who we are still becoming.
These Ten Days of Awe call us to the practice of teshuvah, literally it means “return” and is often translated as “repentance.” The text can offer us examples on how we can approach teshuvah, both as individuals and as community.
This Shabbat takes its name from the opening words of the Haftarah: Shuvah Yisrael—Return, O Israel. Throughout the portion, the prophet Hosea calls out disconnection and wrongdoing but ends with the promise that sincere return leads to healing, wholeness, and renewed relationship with God. He reminds us of that teshuvah is not a single act but a lifelong journey of growth.
The title of this week’s Torah portion, “Vayeilech,” (Deuteronomy 31) is translated from the Hebrew meaning “and he went.” The parsha mirrors this season of transition. Though it is one of the shortest portions in the Torah, it carries immense weight. Moses is preparing for his final day, Joshua is preparing to step forward, and the people are preparing to enter an unknown future.
Moses Teaches Us that Teshuvah Begins with Humility
The parsha begins with Moses acknowledging: “I am now 120 years old; I can no longer be active. Moreover, God has said to me: You shall not cross the Jordan” (Deuteronomy 31:2). Moses recognizes his limits and accepts that his leadership and his life are ending. Rather than seeking personal honor or clinging to power, he is motivated by a desire to serve the greater good and fulfill the Divine plan. His example shows that true humility—releasing control and empowering others—is not weakness but a form of holiness. Even as he steps aside, he offers the people reassurance: “Chizku v’imtzu—Be strong and courageous,… for God goes with you; God will not fail you or forsake you” (Deuteronomy 31:6).
As Rabbi Deborah Waxman teaches, “Power in Judaism is not centralized—it is shared. Authority is earned in community, and humility is the foundation of leadership.” Similarly, Rabbi Jill Hammer, in The Jewish Book of Days, reminds us that “Teshuvah is not only turning back—it is letting go. We let go of who we think we must be to become who we are meant to be.” In our own lives, we are called to notice where we cling too tightly, where we need to release control, and how embracing humility can open the door to new possibilities.
Moses and Joshua Teach Us that Teshuvah Requires Courage and Community
Moses then turns to Joshua and before the entire people, he says: “Be strong and courageous, for it is you who shall go with them into the land. …” (Deuteronomy 31:7). We can almost sense Joshua’s anxiety about stepping into leadership. The command is not: Be perfect. The command is: Be brave. Throughout the parsha, reassurance is repeatedly offered: “ Be strong. Be resolute. I am with you.” This reassurance echoes into our own practice of teshuvah.
Teshuvah requires spiritual courage. Rabbi Toba Spitzer, in her book God Is Here, reminds us that faith is not about certainty, but about the courage to live by our values even when outcomes are unknown. It is not only about apology, but about choosing to live differently afterward, even when that path is difficult.
Teshuvah is also rooted in justice. As Rabbi Danya Ruttenberg in On Repentance and Repair, writes, teshuvah is a process of transformation that calls us to take accountability, repair relationships, and commit to ethical action not for recognition but simply because it is right.
Teshuvah requires a certain softness. Rabbi Rachel Barenblat (the Velveteen Rabbi) reflects on this theme by noting that true strength is not about hardening ourselves, but about softening—opening our hearts to hope, vulnerability, and renewal. Strength and compassion are not opposites; they are partners.
Teshuvah is also grounded in hope. Rabbi Jonathan Sacks (z”l) taught that to be Jewish is to resist despair and to strive toward a better world. Even Jewish time itself models this truth: each day and every holy day begins in darkness and moves toward light. This rhythm assures us that no matter how difficult the past, transformation and renewal are always possible.
Teshuvah is not only individual, but also communal. In Deuteronomy 31:12 we encounter the commandment of Hakhel, the public Torah reading, held once every seven years “gather the people—men, women, children, and even the strangers in your community that they may hear and learn.” This ritual affirms that Torah belongs to everyone, regardless of gender, age, ability, or status.
Teshuvah also means repairing the collective harms of our world. Rabbi Tamara Cohen teaches that our tradition affirms that every person is created B’Tselem Elohim—in the image of God. That belief calls us toward a more expansive and inclusive vision of teshuvah, one that makes space for the voices of Jews of color, disability community members, trans and nonbinary Jews, and all those too often pushed to the margins.
Teshuvah deepens through compassion. Rabbi Sheila Peltz Weinberg teaches, “the soul of community is compassion. Teshuvah that does not expand our compassion is incomplete.” True return must be more than personal change—it must become a communal act of compassion, healing, and renewal that embraces us all. Just as teshuvah on the individual level requires courage, so too does communal teshuvah. It takes courage to widen the circle, to face painful truths, and to imagine a more just and compassionate community.
Teshuvah, as Rabbi Rachel Weiss teaches, is the shared work of returning to who we truly are and to what we most deeply value.
Torah as Song: Carrying Our Tradition Forward
As the parsha nears its end, God commands Moses: “Write down this song and teach it to the people” (Deuteronomy 31:19). The sages understood “this song” to mean Torah itself. This verse is the final of the 613 commandments. It is an invitation to write our own Torah not only as a sacred text but as a living melody that must be sung anew in every generation.
Rabbi Jonathan Sacks (z”l) explained that Torah is called a song because no single voice can carry it alone. Like harmony, it requires the blending of many voices, each one unique and essential. Jewish life is infused with music. We do not read Torah, we chant it. We do not pray; we daven and sing. Each generation must find its own voice in Torah, bringing it to life through justice, compassion, and renewed interpretation.
The Message of Teshuvah: There Is Always a Way Back
Perhaps the most comforting message of Parsha Vayeilech is God’s promise: “I will not abandon you. I will not fail you.” This is not only for Joshua—it is for all of us. In Reconstructionist theology, God is present in every act of courage, compassion, and return.
Rabbi Mordecai Kaplan taught: “Salvation is not otherworldly. It is found in striving for goodness in this life, in this world.” Teshuvah is not just about seeking forgiveness, it is about becoming partners in building a more just and loving world. Each morning during Kehillah, here at JRC, our youngest students sing joyfully about building a better world, one person at a time. Perhaps we can learn from them that teshuvah begins with small acts of kindness.
In Conclusion: Shuvah Yisrael – Return, O Israel
The messages of this week’s Torah and Haftarah portions complement one another. Moses says: You can do this. You can walk forward, even without me. Hosea says: You can return. You can begin again.
As we stand in this sacred time between Rosh Hashanah and Yom Kippur,
Let us bless the Source of Life,
the Wellspring of Courage and Compassion,
who calls us to return together
and to build a just and loving world.
May we find the courage to walk new paths
and the strength to seek justice with open hearts.
May we soften into compassion
and meet one another with humility and care.
May we be guided by hope,
as each day turns from darkness to light.
May we find the strength to heal what is broken
within ourselves and within our world.
And may we, through our actions and our love,
write new verses of Torah together.
Shabbat Shuvah Shalom. G’mar Chatimah Tovah.
Texts
• Deuteronomy 31:1–8
• Hosea 14 (Haftarah for Shabbat Shuvah)
• Mishnah Yoma 8:9 – Personal vs interpersonal atonement
Source Citations
1. Rabbi Jill Hammer
Hammer, J. (2006). The Jewish Book of Days: A Companion for All Seasons (pp. 291–293). Jewish Publication Society.
• Referenced for insight on teshuvah as “letting go” and spiritual transformation.
2. Rabbi Danya Ruttenberg
Ruttenberg, D. (2022). On Repentance and Repair: Making Amends in an Unapologetic World (pp. 7, 27–34, 95–98). Beacon Press.
• Referenced for her framework of real teshuvah as a process of justice and transformation.
3. Rabbi Toba Spitzer
Spitzer, T. (2022). God Is Here: Reimagining the Divine (pp. 5–6, 111–113). St. Martin’s Essentials.
• Cited for her Reconstructionist theology about God as a presence in courageous, values-based living.
4. Rabbi Deborah Waxman
Waxman, D. (2018). Evolving Ethics: Reconstructionist Perspectives on Power and Responsibility. [Podcast episode]. Hashivenu: Jewish Teachings on Resilience. Reconstructing Judaism.
Available at: https://hashivenu.fireside.fm
See also: Waxman, D. (2021). “What Comes Next? Building a Progressive Jewish Future.” In Evolve: Groundbreaking Jewish Conversations. Reconstructing Judaism.
Available at: https://evolve.reconstructingjudaism.org/what-comes-next/
• Used for understanding shared power and communal responsibility in Reconstructionist Judaism.
5. Rabbi Tamara Cohen
Cohen, T. (2014). Yom Kippur: Vidui for a Violated World. Ritualwell.
Available at: https://ritualwell.org/ritual/vidui-violated-world/
See also: Cohen, T. (2012). Elul: Forty Days of Teshuvah. Ritualwell.
Available at: https://ritualwell.org/ritual/elul-forty-days-teshuvah/
• Used to highlight feminist and justice-centered approaches to communal teshuvah.
6. Rabbi Sheila Peltz Weinberg
Weinberg, S. P. (2007). Let Us All Breathe Together: Reflections on Living, Healing, and Wholeness (pp. 84–86, 119–120). Jewish Lights Publishing.
• Cited for teachings on compassion as a spiritual and communal value in teshuvah.
7. Rabbi Jonathan Sacks (z”l)
Sacks, J. (2010). Covenant & Conversation: Deuteronomy – Renewal of the Sinai (pp. 205–207). Maggid Books.
• Referenced for teachings on Moses’ humility and spiritual leadership.
https://rabbisacks.org/covenant-conversation/vayelech/torah-as-song/
8. Sfat Emet (Rabbi Yehudah Aryeh Leib Alter)
Alter, Y. A. L. (1997). Sefat Emet: The Language of Truth (A. Rosenthal, Trans., Vol. 5, pp. 175–176, Parashat Vayeilech). Jewish Publication Society.
• Used to support the idea that courage is acting in holiness without clarity or certainty.
9. Rabbi Mordecai M. Kaplan
Kaplan, M. M. (1934). Judaism as a Civilization: Toward a Reconstruction of American-Jewish Life (pp. 382–385). The Macmillan Company.
• Cited for his theology of salvation and teshuvah as this-worldly ethical striving.
10. Rabbi Adin Steinsaltz
Steinsaltz, A. (Ed.) (n.d.). Hosea: Section Preface 8. In Steinsaltz Introductions to Tanakh. Sefaria. https://www.sefaria.org/Steinsaltz_Introductions_to_Tanakh
Tanakh: The Steinsaltz edition. Koren Publishers Jerusalem [Publisher].
• Cited for Hatorah.
11. Rabbi Rachel Weiss
• Cited for Teshuvah – from her sermon on Rosh Hashanah morning 2025