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What can a fragile sukkah teach us about what it means to feel held? On the first day of Sukkot, Rabbi Alex Braver contrasts the Torah’s image of the all-encompassing clouds of glory with the vulnerability of the sukkah itself. Precisely because our shelter is never perfect, he suggests, what we create and offer one another becomes all the more precious.

After Yom Kippur, how do we begin living the life we said we want to live? On the second day of Sukkot, Rabbi Becca Weintraub reflects on the physical mitzvot of the holiday (building the sukkah, holding the lulav and etrog, and immersing ourselves in ritual) and asks what practice we might carry with us once the hag is over.

What does it actually mean to do teshuvah? On Shabbat Shuvah, Rabbis Felicia Sol, Alex Braver, and Becca Weintraub together discuss the many ways Jewish tradition imagines the work of return. They remind us that there is no single path into teshuvah and invite us to discover which doorway might help us enter the work this year.

As the gates of Yom Kippur begin to close, how do we turn infinite possibility into choices about how we will actually live? In his Ne’ilah sermon, Rabbi Alex Braver explores what courage looks like in a moment of profound uncertainty. Drawing on the Torah’s command to “choose life,” a rabbinic parable about paths that wind through thickets and clear ground, and the Israelites’ fear while waiting for Moses at Sinai, he challenges the idea that courage always means choosing quickly and decisively. Sometimes the braver act is to resist panic, make room for uncertainty, and hold one another through the discomfort of not knowing what comes next. Teshuvah asks us to believe that other choices remain possible and to cultivate the inner strength to recognize them. As the gates close, Alex calls us toward a quieter, harder kind of courage: the courage to remain open, stay in relationship, and preserve the possibility that something new can still emerge.

Yom Kippur confronts us with mortality so that we might learn how to live. In her Ne’ilah sermon, Rabbi Felicia Sol reflects on Yom Kippur as a rehearsal for death and on the urgency and clarity that can emerge when we remember that our time is limited. Drawing on Jewish teachings about revelation, multiplicity, and a “heart of many rooms,” she invites us to resist a world organized around certainty and purity tests and instead cultivate hearts spacious enough for disagreement, questions, complexity, and truths larger than any one of us can hold. And yet, for all the possibilities before us, there is one thing we do not have infinitely: one life. As the gates close, Felicia calls us to cross a gesher L’hayim, a bridge to truly living with dignity, justice, peace, moral grandeur, spiritual audacity, love, connection, and pride in who we are.

In her annual Yom Kippur letter to her children, Rabbi Becca Weintraub reflects on the creativity children bring to figuring things out and what that can teach us about Judaism. Also retelling the story of Rabbi Yishmael entering the Holy of Holies and unexpectedly being asked to bless God, Becca explores what happens when the carefully prescribed way of doing something gives way to an encounter no one could have prepared for. Yishmael must respond in his own way, drawing on a blessing that only he can give. Becca shares that there is no single way to practice Judaism, connect with God, or bring our gifts into the world. Her blessing for her children and for all of us is to hold onto the imagination to say “but maybe,” discover new possibilities when we feel stuck, and remember that each of us has blessings that only we can offer.

What might become possible if we loosen our need to be certain? In his Yom Kippur morning sermon, Rabbi Alex Braver begins with the ancient ritual of the Kohen Gadol, the High Priest, and an oath intended to ensure that every detail of the holiest service of the year would be performed exactly right. In a moment filled with purity tests, loyalty oaths, and demands for certainty, he asks whether doubt might instead open us to encounters that surprise us, transform us, and even bring blessing. On Yom Kippur, perhaps teshuvah begins by putting down some of what we think we know and listening for what might emerge.

What if doubt is not the opposite of faith, but the opening through which transformation becomes possible? In her Yom Kippur morning sermon, Rabbi Felicia Sol explores two radically different rabbinic visions of the High Priest entering the Holy of Holies. In one, a system built around precision and certainty leaves the High Priest and the elders suspicious of one another and weeping alone. In another, Rabbi Yishmael encounters an unexpected God who calls him by name and asks him for a blessing. Felicia suggests that doubt can create the spaciousness to imagine God, ourselves, and one another differently. A question creates a “maybe.” A maybe creates possibility. And possibility makes room for change. Teshuvah begins in that opening between what is and what could be.

In her Kol Nidre sermon, Rabbi Becca Weintraub begins with the exhausting calculations many Jews make about when it feels safe to reveal who we are—and asks what becomes possible when, for these 25 hours, we no longer have to hide. Through the names Ivrim, B’nai Yisrael, and Yehudim, Becca explores the multiplicity built into Jewish identity itself. An Ivri can stand apart, cross into new territory, and carry hope for what has not yet come into being. Yisrael holds questioning alongside faith. Yehudi joins gratitude with responsibility for ourselves and one another. Yom Kippur does not ask us to become one thing, she teaches. It asks us to become honest: to uncover ourselves, make room for all that we are, and step into the year ahead whole.

On Kol Nidre, Rabbi Felicia Sol reflected on what happens when fear, shame, polarization, and communal litmus tests pressure us to hide or to reduce Jewish identity to a single story. Drawing on three ancient names for the Jewish people (Ivri, Yisrael, and Yehudi) Felicia explores the fullness of our inheritance. We are boundary-crossers willing to stand against the tide. We are wrestlers who refuse easy answers and strive toward what is upright. And we are a people called to gratitude, truth, responsibility, and repair. At a moment when so much is projected onto Jews from the outside and so much is contested within our own community, Yom Kippur asks us to stop hiding and remember who we are, alive in all our complexity, struggle, responsibility, beauty, and possibility.

On Erev Rosh Hashanah, 25 years after the attacks of September 11, 2001, Rabbi Felicia Sol remembers the nearly 3,000 lives lost and reflects on BJ’s experience of that devastating day and its aftermath. From trying to reach members and loved ones to gathering for interfaith prayer and supporting first responders, Felicia recalls a city and community forever marked by those 102 minutes, inviting us to hold in memory all those whose lives were taken or irrevocably changed. Zikhronam livrakha. May their memory be for a blessing.

On Erev Rosh Hashanah, Rabbi Becca Weintraub reflected on the Jewish experience of time not as a straight line or an endless circle, but as a spiral. Each year we return to the same holidays, prayers, rituals, and sacred moments, but we do not return as exactly the same people. Drawing on Rabbi Joseph Soloveitchik’s teaching that we “remember deliberately, anticipate responsibly, and act precisely,” Becca invites us to bring the lessons of our past and our hopes for the future into the choices we make now. Even the round Rosh Hashanah challah can become an image of this spiritual journey: not simply circling back, but spiraling upward. As we enter 5787, may we return to the places we have been before as people who have changed, and who are still becoming.

Rabbi Alex Braver offers a blessing for renewal in all its forms. Some of us enter the new year amid exciting changes; others face new challenges, losses, or absences; and some may feel stuck, longing for change that seems far away. However we arrive at these Days of Awe, may we meet change with courage, recognize the possibility of newness within ourselves, and make 5787 a year of “good newness.”

What does it mean to be an American Jew at a moment when our deepest commitments can seem to pull us in opposing directions? Beginning with BJ’s founding in 1825, Rabbi Felicia Sol traces the intertwined histories of American democracy and American Judaism and the freedoms that allowed Jewish life here to become diverse, creative, and chosen from love. She then turns to the challenges of the present: rising antisemitism, threats to democracy, debates over free speech, Israel, and a polarized culture that continually demands we “pick a side.” Felicia offers another model: covenantal belonging. Belonging does not require agreement, and disappointment does not release us from responsibility. America is unfinished. Jewish life is unfinished. Our task is not to walk away when either falls short, but to remain in relationship, demand more, repair what is broken, and continue to build.

On Erev Rosh Hashanah, Rabbi Felicia Sol reflects on the threshold between the year that has ended and the one that has yet to be written. Drawing on a Talmudic teaching about giving thanks for the past and crying out for the future, she invites us to look honestly at what has been without allowing it to control us and to bring our moral and spiritual imagination to the future we still have a role in shaping. Let the new year and its blessings begin.