Why Yom Kippur is my favorite Jewish holiday

This story originally appeared in Hey Alma.

I get a lot of odd looks when I tell people that my favorite day of the Jewish year is Yom Kippur.

As Jewish holy days go, Yom Kippur exists at the complicated intersection of community observance, intense liturgy and heavy-hitting ritual expectations that can be - and for many people, is - a perfect storm of anxiety, pressure and guilt.

From the traditional fast to the powerful language of the readings, Yom Kippur can bring up complicated feelings and unpleasant associations. There's a reason that there is such a growing movement to expand and adapt the rituals of Yom Kippur to be more inclusive and oriented towards growth - from designing a meaningful Yom Kippur seder for people in recovery from eating disorders for whom fasting would not be healthy to the reframing of the confessional accountings of the liturgy to also include the acts of goodness performed by the individual and the community.

As someone who struggles with anxiety and depression, and who has a history of disordered eating and a chronic pain disorder, I spent years experiencing Yom Kippur as something miserable and exhausting. I couldn't take in the melody of Kol Nidre or the radically intense language of the readings in Isaiah - all I could focus on was the intrusive thoughts reading me litanies of everything I'd done wrong, on the tempting reminders of my years of restricted eating, of how much my body hurt after hours of sitting in uncomfortable synagogue chairs.

For a long time, I wanted to just stop observing Yom Kippur altogether. But even when it was a terrible day, I felt like there was a potential for a meaningful experience that was just out of my reach.

The rituals and liturgy of Yom Kippur center heavily on the concept of teshuvah. In the context of mainstream teachings and conversations, teshuvah is most commonly translated as atonement or repentance. The idea of repentance is deeply embedded in Yom Kippur readings and traditions (and prayer books!), from the confessing of individual and communal sins to the framing of the Yom Kippur fast as a way of enacting punishment for the last year of harmful actions (which has, as far as I'm aware, literally no basis in traditional Jewish teachings at all).

But literally - and traditionally - translated, teshuvah means returning.

In "This Is Real and You Are Completely Unprepared," one of the most widely accessible but deeply transformative books on the practices and teachings of the weeks leading up to and through the High Holidays, Rabbi Alan Lew (z"l) frames teshuvah not as a yearly practice of spiritual reflection and repentance but rather as a journey of transformation and awakening. It's not a journey that begins with Kol Nidre and concludes with Neilah, or even one that begins on Rosh Hashanah and concludes on Yom Kippur. Rather, it's a constant, unending process that begins, and then begins again, with the intake of each new breath. For Rabbi Lew, the spiritual work of Yom Kippur is not about a litany of one's sins or making it 25 hours without your usual coffee intake (in fact, if I remember correctly, he doesn't assign any particular virtue to fasting on Yom Kippur at all; it's simply another avenue for connecting to internal and transformative work).

For Rabbi Lew and the teachers and Jews his work inspires, the work of teshuvah is about the difficult, radical and sometimes deeply terrifying journey of returning to the places inside ourselves where we lock away pain and grief and suffering, and to open them up, exposing them to clean, healing air. "Our suffering," Lew writes, "the unresolved element of our lives, is also from God. It is the instrument by which we are carried back to God, not something to be defended against, but rather to be embraced."

To put it another way, quoting the late poet Mary Oliver: "Someone I loved once gave me a box full of darkness. It took me years to understand that this, too, was a gift."

My brain is a loud place; it always has been. I have vivid memories of being very small, maybe 6 or 7 years old, and lying awake at night because the inside of my brain simply wouldn't stop talking, counting the glow-in-the-dark stars on my ceiling in an attempt to lull myself to sleep. As I got older, my constant inner monologue shifted from a running recap of my everyday activities to a low, buzzing roar of catastrophizing and anxiety.

Over the course of my life I've become someone who always needs to have some kind of sound present, whether it's an audiobook or a podcast or just a recording of ambient coffee shop noise. Silent contemplation and reflection have always been - for me, at least - simultaneously a white whale of inaccessible inner work and an absolutely terrifying concept (you want me to just sit there? In a room? With my thoughts? By myself? No thank you!). But my introduction to this concept of teshuvah as a practice of returning to those frightening places and seeing what they have to teach us, how acknowledging them as parts of ourselves can help us to grow, shifted something in the way I approached the anxious, constantly humming rumble of my inner voice.

I wasn't starting a meditation practice anytime soon - I'm still not, much to the ongoing despair of some of my wonderful former colleagues in the Jewish mindfulness field - but the rituals of Yom Kippur offered me an avenue to explore those parts of myself within a space that felt safe. Sitting in community and allowing the voices of a congregation to spill over me allowed my brain to duck inside myself and follow now-familiar paths to the places it's hardest to return to, hardest to explore.

On Rosh Hashanah, 10 days before Yom Kippur, we read a section of Bereshit in which Hagar, Sarah's handmaid and the mother of Ishmael, is alone in the desert, out of water for herself and her baby. She's certain that they've lost all chance for survival, and, broken-hearted, she puts the child down and walks away from him, so that she doesn't have to watch him die, and bursts into tears. God hears her weeping, and opens her eyes - and suddenly she can see a well of water before her. Both she and the baby survive.

In a commentary on this Torah portion that appears in the Reconstructionist machzor, Rabbi Reena Spicehandler notes that the text doesn't say that a well appeared in front of Hagar, but rather that she was suddenly able to see it. When we are trapped in a place where all we experience is fear, or despair, or hopelessness, we aren't able to see the possibilities or openings around us, whether that's a new opportunity or a literal life-saving spring of water. We can only see those possibilities when we open our eyes to them, or, sometimes, when someone opens our eyes for us.

The season of teshuvah, of returning - and with it, the spiritual work that makes Yom Kippur so meaningful - is about undertaking the journey through the places of fear and despair until we can find the wells that open us up to everything around us that offers us a chance at renewal. Yom Kippur, for me, is about fully dedicating my heart and mind to that journey, year after year, prayer after prayer, breath after breath.

For me, it couldn't be further from suffering. It's the first delicate notes of the melody of Kol Nidre, as a congregation of hundreds holds its breath in perfect unison. It's the first sip of water in a desert, pure and sweet. It's a returning to the broken places, where we can still find the endless possibilities of wholeness.