Yom Kippur D’var 5784

בס״ד

Presented in-person at Tremont Street Shul’s lay-led minyan, Cambridge, MA
for Yom Kippur Shacharit, 5784 (2023)

When I was asked to speak for the HHDs, my first thought was “Of course! Yom Kippur!”…followed 2 minutes later, internally, by “OMG… what in the world do I have to say about Yom Kippur?”

Later that day I had an Inigo Montoya moment and realized 5-10 minutes is not NEAR enough time to “Let me explain…
No, there is too much. Let me sum up!” 

(I think if there had been a sequel, Inigo might have gone on to be a kabbalist since he was from Spain with his affinity for mystical experiences and epic journeys…)

Lol… anyway…

So, what on earth possessed me to not consider the introvert ramifications of agreeing to speak this morning?

Because I love Yom Kippur! 

No, I don’t mean the fasting, the arm-numbing hours of holding a heavy machzor, or any other restrictions that characterize the day. It’s the connection. 

I haven’t always understood why, exactly. It has historically been an indescribable embodied experience for me. I still can’t say I really have answers, but I’d like to offer some texts and ideas that may provide some context and I’ll let you experience the metaphors however they sit with you.

As I have heard my teacher and friend Reb Marcia Prager say - Keep what you find meaningful and let the rest just float away.


For the kabbalists, mystical experiences weren’t an ever-present state of being. They understood that these experiences are not sustainable indefinitely. It is the peak experiences; the moments of intense kavanah and elevation interspersed between stretches of the mundane - or existence on a slightly lower rung - that is actually sustainable. It’s these occasional highs and lows at regular intervals with the majority of experiences averaged somewhere in between that makes up the mystic’s healthy spiritual heartbeat. 

Yom Kippur is a day built into our calendar when such kavanah might be obtained. 

We read in the Zohar that on Yom Kippur the gates of mercy are opened and malachim carry our words directly to the Blessed Holy One - kind of like a Divine love letter passed between Tiferet and Shechinah. 

Kabbalistic texts also talk about the five levels of the soul. The highest and deepest of which is known as “yechidah” or point of unity. This point is only felt and accessible one time a year - on Yom Kippur - when we reach the closest connection to our essence, the point of oneness.

In parallel - Yom Kippur was the only point in Jewish time that the Kohen Gadol was allowed into the Holy of Holies - the place where the Divine touches the Earth - the point of unity between Above and Below.

The Kohen Gadol’s primary obligation in the Mikdash is the once-yearly avodah. The Talmud stipulates that there can only be a single qualified Kohen Gadol for this unique function on this particular day. Every aspect of the Kohen Gadol’s life both in the week of preparation prior and throughout the entire year, keep him in a constant state of mindfulness towards his devotion to the Divine. Even Jeruslaem itself is given the status of “mikdash” so that the Kohen Gadol is always residing physically and metaphorically within its walls.

So too, on Yom Kippur we fast, we pray, we strip away anything and everything that may distract or hinder our singular devotion on the Achat B’shanah; the pivotal day in our religious calendar. 

Yom Kippur is also called the “Day of Forgiveness” and is thought to be the day that Moses descended from Mount Sinai with the second set of tablets after being forgiven by God, representing the opportunity for second chances. In most cases, everyone deserves a second chance if they are contrite enough to ask for it.


Looking back to the liturgy of last night, right after Kol Nidre, we find an interesting section from the book of Numbers where God forgives the Israelites for succumbing to their fears. 

It begins with God’s pronouncement of forgiveness:

“And there shall be atonement for the whole community of Israel, and the stranger dwelling in their midst – indeed, for an entire people that has gone astray” (Numbers 15:26). 

Then it brings Moses’ request for forgiveness, which actually came before that:

“Grant forgiveness, then, for the transgression of this people, as the abundance of your love demands” (Num. 14:19) 

and then God replies,

“I grant forgiveness, as you ask” (Num. 14:20).

Forgiveness is given, we ask for it, and it is granted again. This section of the liturgy becomes the model of the process we are engaged in over Yom Kippur: forgiveness has been granted; we ask for forgiveness, and we are forgiven.

So, if we were already forgiven last night after Kol Nidre, what are we doing ALL DAY today? What are the other 4 services for? Why are we STILL fasting??? 


The 5 sets of services (evening, morning, Musaf, afternoon, Neilah) correspond to the 5 levels of the soul, culminating with yechidah at Neilah. We ascend through each level in the aforementioned process of seeking forgiveness.

The most effective, restorative, and healing apologies take time. They take time and open, honest conversations between those involved. Even though the Divine is ready and quick to forgive us - like any loving parent, partner, or friend - we must be clear and sincere in what exactly it is that we are apologizing for. 

The process is just as much for us as it is for the one injured, and I might argue that it is ourselves, as vessels of Divine light, that we have both injured and need to heal in this act of Divine reconciliation. It is cathartic to bear one’s soul to a safe person; one that you know already forgives you and is patiently and lovingly holding space for you to clear the air and verbalize it so there is no misunderstanding between either of you at all. 

As we ascend through the four services following the Divine’s statement of forgiveness, we plead, explain, and pull away layer upon layer of sins, excuses, and a plethora of complicated feelings; being brutally honest with ourselves as the Divine holds space - holds the gates of Mercy open for us - as our apology and longing for connection flow through until finally - at Neilah - if we have been earnest in our conversation and dug deep within to uncover the spark of light we all carry, as the shofar sounds there is nothing left but Divine connection as we stand as our truest selves - for a brief, timeless moment - at that point of unity.


As I implied earlier, this point is not easily accessible, so what does one do if this doesn’t happen for us this year or if it doesn’t resonate in some way? I mean - life happens. We all read Unetaneh Tokef... What do we do when we feel too broken to connect?

Photo: Kintsugi, Jan. 2024

The rabbis teach that when Moses shattered the first set of tablets, he preserved the fragments and placed them within the Ark, alongside the second set of unbroken tablets. This midrash reminds us that brokenness possesses a unique holiness. The Japanese have even made this into an art form; transforming what might otherwise be discarded and worthless into a treasured piece of priceless beauty… something to embrace. 

The Zohar teaches us that Tiferet, the Heart of the Sefirotic tree, is the perfect balance between Chesed and Gvurah; between love and judgment. We mirror Below what is Above. As we continue on this day-long journey together, may we keep in mind that there exists a Torah of brokenness, alongside a Torah of wholeness, and both coexist within our own hearts.

May we look kindly on ourselves as we remember that we are already forgiven. May we be held in the Divine Womb of Understanding surrounded by Supernal Chesed, cradled by That which is "Rav Chesed v’Emet" – "overflowing with love that is truthful, and a truth that is loving.”… and know that the forgiveness we seek is already within ourselves to find. 

In that Makom of safety and acceptance, may we be open to avodah and connection at the gates of Mercy.

כן יהי רצון

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Tisha B'Av: A Journey into the Mystical Depths of Suffering and Redemption