As If for the First Time: Rediscovering Life, Death, and Prayer on the High Holidays©

Rosh Hashanah Evening Day 1 - 5786 - 2025

Rabbi David Baum

Photo By Annie Spratt from Unsplash

Elul, the month leading up to Rosh Hashanah, is meant to be a time of reflection. For me, it was also a time of funerals, and I performed more than usual. For instance, in the span of three days, I performed two funerals; both held in the middle of torrential South Florida downpours.

One in particular has stayed with me. It was on a Friday afternoon, and I was called in just the day before to perform the last-minute funeral. The director insisted that the family wanted to do things by the book, but also, did not know the book. In other words, they were, as we now say, Jew-ish. But their beloved mother, who lived a similarly "Jew-ish" life, insisted on an authentic Jewish funeral service and burial, with an authentic rabbi and all. 

The funeral was small, just nine people in total, including myself, the funeral director, and the Jewish gravediggers, because this is the frumest cemetery in South Florida. 

As I stood there, rain soaking through my suit, I wondered: What kind of funeral is this going to be? I had spoken with the family and learned about their mother, but a formal eulogy for such a small group, in such a setting, felt strange. Instead, I leaned into the rituals themselves: the burial, the prayers, the ancient choreography of a Jewish farewell.

The scene was stark and simple: two shovels standing upright, and a mound of dirt beside the grave. 

And I looked at the simple pine box, as is the custom in Jewish funerals, and thought about the woman inside, who was not especially religious at all. She had not given her children much of a Jewish education, and yet, she had insisted that they fulfill her wishes to be buried in a Jewish cemetery, a frum graveyard in South Florida where everything is done by hand, even the grave digging performed by fellow Jews. 

How would they react to the strange ritual dance they were about to see, a dance that I have led so many times over the last fifteen years that I can hardly count them all up (it’s over 100 for sure). 

What struck me most was not the simplicity of the burial, but the reaction of the daughter. She was grieving, of course. But she was also amazed. Every ritual—placing the casket in the ground, reciting the prayers, lifting the shovel of earth—moved her deeply.

At times, I have to be honest, the words of explanation at funerals can feel a bit repetitive for me. I find myself saying the same things again and again, because each family needs to hear them. But for me, the familiarity can sometimes feel like I’m repeating the words, not really saying them. 

But that wasn’t the case for this daughter. For her, each words and step was a revelation. And then, just as we finished, the rain stopped. A ray of light pierced the clouds. She looked up, her face wet from both tears and rain, and I could see it in her eyes: she felt the presence of God.

That moment reminded me that sometimes we experience God not through polished words or learned rituals, but through raw encounters—when something strikes us as wholly new, even if it is ancient.

The High Holidays call us to look again at life and death, joy and sadness, loss and renewal with renewed eyes. This is a way we do Teshuvah, to return to a place where we recognize God in the world. 

These are realities we live with every day, yet most of the year we rush past them, barely noticing. During the Unetaneh Tokef tomorrow, we will sing these words, in the same tune as last year, but listen to these words: 

בְּרֹאשׁ הַשָּׁנָה יִכָּתֵבוּן וּבְיוֹם צוֹם כִּפּוּר יֵחָתֵמוּן. כַּמָּה יַעַבְרוּן. וְכַמָּה יִבָּרֵאוּן. מִי יִחְיֶה. וּמִי יָמוּת.

On Rosh Hashana their decree is inscribed, and on Yom Kippur it is sealed, how many will pass away and how many will be created, who will live and who will die;

וּתְשׁוּבָה וּתְפִלָּה וּצְדָקָה מַעֲבִירִין אֶת רֽוֹעַ הַגְּזֵרָה:

But repentance, and prayer and charity annul the evil decree.

On Rosh Hashanah and Yom Kippur, we are asked to pause, to see what has become ordinary as extraordinary: the gift of being alive, the fragility of our days, the sacred weight of our choices. In doing so, we recover the capacity to be astonished by what we experience every day, and it makes those very special moments even holier. 

What would it look like to look at these high holidays with different eyes? 

That is what Rabbi Jack Riemer once shared in the name of Rabbi Shlomo Riskin. He recalled the words of the psalmist: Achat sha’alti me’et Hashem—“One thing I ask of God.” But then, the psalmist immediately lists two things: “To dwell in the house of the Lord” and “to visit the house of the Lord.” Which is it? One thing or two?

Rabbi Riskin explained: There are two kinds of worshippers.

Those who come regularly know the prayers fluently. Their strength is familiarity. They don’t have to struggle with the words; they flow naturally. But their weakness is that familiarity can breed complacency. They may recite without thinking, the words spilling from their lips without reaching their hearts.

Those who come rarely face the opposite challenge. They stumble over the words, struggle with the Hebrew, maybe even with the choreography of the service. That is their disadvantage. But their strength is that the prayers feel new, fresh, even startling. Every phrase is an encounter.

So, the psalmist prays for the best of both: the fluency of the regular and the freshness of the newcomer. He longs to be rooted and at home, and yet to be struck with wonder as though hearing the words for the very first time.

That funeral reminded me of this truth. For me, the rituals were familiar. But for the daughter, they were astonishing. And through her eyes, I was reminded of the depth I had stopped seeing.

This teaching echoes a beloved story from the Baal Shem Tov, the founder of Hasidism.

A villager would travel each year to pray with the Baal Shem Tov on the Days of Awe. He had a son who was unable to read and recite the prayers. 

After the boy turned 13, the father brought him along for Yom Kippur, worried that he might accidentally eat on the holiday and sin accidentally. The boy carried with him a flute that he used to play while watching the sheep in the fields.

During the long day of prayers, the boy sat silently. He didn’t know the words of Shacharit, Musaf, or Minchah. He longed to pull out his flute. Twice, he asked his father for permission, and twice he was scolded: you would you be breaking the rules of the holiday. 

Finally, during Ne’ilah, the final prayers of Yom Kippur, the boy could contain himself no longer. He pulled out his flute, raised it to his lips, and blew one piercing, heartfelt note.

The congregation gasped. But the Baal Shem Tov stopped the service, shortened the prayers, and ended Yom Kippur on the spot. Afterwards, he explained: That boy’s note had carried all of the congregation’s prayers to heaven. He had no words, but he had pure intention. Rachmana liba ba’ei—“God desires the heart.” (Talmud Bavli, Sanhedrin 106b).

Sometimes our most powerful prayer is not the one with the perfect Hebrew, not the one that follows the prayerbook flawlessly, but the one that comes from the deepest recesses of our heart.

These stories—of the funeral, of the psalmist, of the flute—converge into a lesson for us on this Rosh Hashanah, 5786. 

We are here today as a mixed congregation. Some of us are “regulars”—we know the service, we know the melodies, we are at home in this sanctuary. Others are “newcomers”—perhaps here only on the High Holy Days, perhaps unsure of the Hebrew, perhaps feeling like outsiders.

The truth is, we need both. The regulars provide stability, tradition, fluency. The newcomers bring freshness, awe, discovery. And all of us—whether seasoned or stumbling—need to find ways to pray with both fluency and freshness.

The danger of regularity is that the words become rote. The danger of novelty is that the words remain foreign. The aspiration of the High Holy Days is to join the two—to know the words deeply, and yet to encounter them as if for the first time.

And so this is my blessing for you, and for me, as we enter 5786:

May we combine the devotion of the regular with the awe of the newcomer. May our prayers be fluent yet never stale, familiar yet always alive with wonder.

When we recite Avinu Malkeinu, may we not only say the words by memory, but feel their power anew. When we hear the shofar, may it not just be another sound we’ve heard every year, but may it pierce our hearts as if it were the very first blast.

Hashiveinu Adonai elecha v’nashuvah—Bring us back, God, to that place of innocence and wonder. We know we cannot return to Eden, but for these Ten Days of Teshuvah, let us sit in its garden. Let us taste again what it is like to pray with awe, to live with wonder, to feel God’s presence as though for the first time.

Shanah Tovah.

Practices for Experiencing Rosh Hashanah and the Ten Days of Teshuvah Anew

In the Sanctuary

• Pause at the door before entering. Whisper: “I am stepping into sacred time.”

• Choose one line of prayer (Avinu Malkeinu, Hayom Harat Olam) and focus on it.

• When the shofar is blown, close your eyes. Feel it in your chest and ask: What is being awakened in me?

Around the Table

• Savor your apple in honey as if it’s your first bite of sweetness.

• Offer gratitude to someone at the table: “This year I’m thankful for…”

• Ask fresh questions: What surprised you last year? What do you hope for in the year ahead?

In Relationships

• Listen to a loved one’s voice like you’re hearing it for the first time.

• Offer softness—approach one strained relationship with curiosity.

• Remember: Each person is created b’tzelem Elohim—in God’s image.

In the World

• Step outside and look at the sky as though it was created today. Say: Hayom harat olam – Today the world is born.

• Take a short silent walk without your phone. Notice what feels new.

• Each evening during these 10 days, ask: What felt fresh or surprising today?