Prompt

In the world today, what is the most important thing we should be thinking about when preparing for Rosh HaShana and Yom Kippur, this year?

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Full length · 14 min · 2026-09-09

What Should We Be Thinking About Most as We Prepare for Rosh HaShana and Yom Kippur?

Opening: An Ancient Question for a Modern Moment

There is something remarkable about the High Holiday season that never quite loses its power, no matter how many times we have lived through it. The days grow shorter, a certain quality of light shifts in the afternoon sky, and something stirs in the Jewish soul — a recognition that we are approaching a threshold. Rosh HaShana and Yom Kippur are not merely items on a religious calendar. They are, according to our tradition, the very hinge upon which existence turns. And yet, each year, many of us arrive at these days feeling underprepared, distracted, or uncertain about what we are actually supposed to be doing — not ritually, but spiritually, existentially, in the deepest chambers of the self.

The question before us today is both timeless and urgently contemporary: In the world today, what is the most important thing we should be thinking about when preparing for Rosh HaShana and Yom Kippur?

It is a question that deserves to be taken seriously — not answered with a platitude or a checklist, but genuinely wrestled with, the way Jacob wrestled with the angel in the darkness before a new dawn. And so that is precisely what we will do here. We will turn to our texts — those ancient, inexhaustible wells of wisdom — and we will listen to what they have to say to us in this particular moment in history.

The sources we will examine span the breadth of the Jewish library: the Talmud in tractates [Rosh Hashanah 16b:12] and [Keritot 5b:28], the legal precision of [Mishneh Torah, Repentance 2:7], the mystical urgency of [Tzava'at HaRivash 39:1] and [Sichot HaRan 21:3], and the gate-opening counsel of [Sha'arei Teshuvah 4:10]. Together, these texts will help us build an answer — not a simple one, but a true one. An answer adequate to the complexity of the world we actually inhabit.

So let us begin. Let us open the gates — because, as we shall see, that is precisely what this season asks of us.

Contextual Foundation: Why These Days Are Different from All Other Days

To understand what we should be thinking about in preparation for Rosh HaShana and Yom Kippur, we must first appreciate what these days actually are — not just liturgically, but cosmically, according to our tradition.

The Talmud in [Rosh Hashanah 16b:12] offers one of the most arresting images in all of rabbinic literature. Rabbi Kruspedai, citing Rabbi Yoḥanan, teaches: "Three books are opened on Rosh HaShana before the Holy One, Blessed be He: One of wholly wicked people, and one of wholly righteous people, and one of middling people whose good and bad deeds are equally balanced." The wholly righteous are immediately inscribed for life. The wholly wicked are immediately inscribed for death. And the middling people — the beinonim — are left in suspension, their fate hanging in the balance until Yom Kippur.

This image is not meant to terrify us. It is meant to awaken us. Because the tradition assumes that virtually all of us fall into that third category — the beinonim, the in-between people. We are not monsters, and we are not saints. We are human beings doing our imperfect best, carrying the weight of our failures and the brightness of our genuine goodness simultaneously. And for us, these ten days between Rosh HaShana and Yom Kippur are not ceremonial — they are decisive.

The Rambam, writing in [Mishneh Torah, Repentance 2:7], crystallizes this understanding with characteristic clarity: "Yom Kippur is the time of Teshuvah for all, both individuals and the community at large. It is the apex of forgiveness and pardon for Israel. Accordingly, everyone is obligated to repent and confess on Yom Kippur." Notice the double emphasis: individuals and the community at large. This is not merely personal spiritual housekeeping. There is a communal dimension to what these days demand.

And this is where the contemporary resonance becomes impossible to ignore. We live in a world of fracture — politically, socially, environmentally, spiritually. We are, as a civilization, a people in the category of the beinonim: not irredeemably lost, but urgently in need of a reckoning. The High Holidays arrive each year as if the cosmos itself is offering us a structured opportunity to do what we might otherwise endlessly defer: to stop, to account, to turn.

The numerical structure of Yom Kippur's prayers, as described in [Mishneh Torah, Prayer and the Priestly Blessing 1:8], is itself telling. While ordinary days have three prayer services and Shabbat and festivals have four, Yom Kippur alone has five — culminating in Ne'ilah, the closing prayer, when the gates themselves are said to be shutting. Five prayers, like the five books of Torah, like the five levels of the soul. Everything about the day is designed to draw us deeper and deeper into encounter — with God, with ourselves, with the people around us.

This is the landscape into which our sources speak. Let us now enter it fully.

Source Analysis: What the Texts Are Telling Us

The Primacy of Intentional Preparation

We begin where perhaps we should always begin when approaching these days: with the counsel of [Sha'arei Teshuvah 4:10], Rabbeinu Yonah of Gerona's thirteenth-century masterwork on repentance. The text instructs us that one of the essential purposes of the Aseret Yemei Teshuvah — the Ten Days of Repentance — is "in order that we be strengthened to increase our prayer and supplications on Yom Kippur and think of strategies for ourselves regarding repentance and its main principles."

The word that leaps out here is strategies. Rabbeinu Yonah is not suggesting that we simply feel bad about ourselves, sigh deeply, and hope for the best. He is calling us to think strategically about teshuvah — to plan it, to approach it with the same intentionality we might bring to any serious endeavor in our lives. In our world today, where we are so accustomed to reacting rather than reflecting, this is a genuinely radical instruction.

What does it mean to "think of strategies for repentance"? It means asking ourselves: What are the patterns in my life that need to change — not just the individual moments of failure, but the structures that make those failures likely to recur? It means not waiting for Kol Nidre to suddenly feel moved, but doing the inner work before we arrive at the synagogue doors. The preparation is itself a form of teshuvah.

Silence as Spiritual Discipline

One of the most surprising and practically powerful teachings in our collection comes from [Sichot HaRan 21:3], the collected conversations of Rebbe Nachman of Breslov as recorded by his student Reb Noson. The text is brief but penetrating: "On the first day of Rosh HaShana, one should speak as little as possible. The Rebbe said that a great leader must be even more careful about this."

In a world drowning in noise — in social media feeds and 24-hour news cycles and the constant chatter of our devices — this teaching lands with unusual force. Rebbe Nachman is not simply offering a pious suggestion about synagogue decorum. He is pointing toward something deeper: the idea that the encounter with the Divine that Rosh HaShana demands requires an interior spaciousness that constant speech prevents.

We cannot hear the shofar — truly hear it, in the way the tradition intends — if we are simultaneously narrating our experience of hearing it. We cannot receive the judgment of the day if we are busy managing our social presentation. Silence, for Rebbe Nachman, is not emptiness. It is the condition of possibility for genuine meeting. And the instruction that leaders — those with the most public voices, the most social influence — must be more careful about this is a striking commentary on the spiritual dangers of prominence.

What does this mean for our preparation today? It means building silence into the days before Rosh HaShana. It means creating, even in small ways, pockets of quiet in which the real questions can surface. What have I done this year? Who have I hurt? What do I want my life to actually look like? These questions cannot be heard over the noise. We have to turn down the volume first.

The Judgment Is Real — and So Is the Hope

Returning to [Rosh Hashanah 16b:12], the image of the three books opened before God deserves deeper contemplation. There is something both sobering and profoundly compassionate about this teaching. The tradition does not pretend that our choices are inconsequential. The books are real. The accounting is real. And yet — and this is crucial — the beinonim, the vast majority of human beings, are not condemned. They are given time. They are given ten days. They are given the opportunity to tip the balance through prayer, teshuvah, and tzedakah.

This is not a picture of a wrathful God eager to condemn. It is a picture of a God who waits — who holds the verdict open, who builds into the very structure of the cosmos a grace period for human beings to find their way back. The question for us today is whether we are using that grace period wisely, or whether we are squandering it in distraction and avoidance.

The Gemara in [Keritot 5b:28] offers a fascinating adjacent teaching. Rav Ami says: "One who desires to know if he will live through this current year or not should bring a lit candle during those ten days between Rosh HaShana and Yom Kippur and hang it in a house through which wind does not blow, and he should watch it." Whether we read this literally or symbolically, the image is arresting: a candle in a sheltered space, burning through the ten days of uncertainty. The candle of the soul. Are we tending it? Are we protecting it from the winds that would extinguish it?

In our world today, those winds are many. The wind of cynicism, which tells us that nothing we do really matters. The wind of despair, which says the world is too broken to be fixed. The wind of distraction, which keeps us perpetually busy with the urgent at the expense of the important. The Aseret Yemei Teshuvah are, in this reading, a sheltered space — a house without wind — in which we can watch our own flame and ask: is it still burning? Is it burning brightly?

The Structure of Prayer as a Map of the Soul

The legal texts in our collection, while seemingly technical, carry their own wisdom. [Mishneh Torah, Prayer and the Priestly Blessing 1:8] describes the five prayer services of Yom Kippur — Shacharit, Musaf, Mincha, Ne'ilah, and the evening Ma'ariv — as a progressive deepening. And [Tzava'at HaRivash 39:1], from the teachings associated with the Baal Shem Tov, offers a remarkable instruction about Ne'ilah, the final service: "Before Ne'ilah, reserve your strength and recite the Machzor in a diminished state of Godly awareness — Katnut."

This teaching is counterintuitive and therefore all the more important. We might expect to be told: save your energy for Ne'ilah so you can pray with maximum intensity. Instead, the teaching acknowledges that by the time Ne'ilah arrives, after a full day of fasting and prayer, we may be in a state of Katnut — diminished consciousness, reduced spiritual capacity. And the instruction is not to force ourselves into artificial ecstasy, but to pray from where we actually are.

This is a teaching about authenticity that speaks directly to our contemporary situation. We live in a culture that prizes performance — including spiritual performance. We can feel pressure to appear moved, to demonstrate the right emotions, to perform our religiosity for others or even for ourselves. [Tzava'at HaRivash 39:1] cuts through all of that. Pray from your actual state. Even diminished. Even exhausted. Even uncertain. God receives the prayer of the tired and the broken just as much as the prayer of the inspired and the ecstatic — perhaps more so.

The Community Dimension: We Are Not Alone in This

[Mishneh Torah, Prayer and the Priestly Blessing 2:19] notes that during the ten days from Rosh HaShana to Yom Kippur, certain communities add special language to their prayers. This seemingly minor halakhic detail points to something significant: the ten days between the holidays are not a private spiritual retreat. They are a communal endeavor, marked by shared liturgical intensification.

References

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