How to fail Yom Kippur

Have you heard of a pre-mortem? I learned the concept last year from a wise friend.

Before taking on a project or a mission, you have to ask: how will this fail? You draw out what failure would look like, in detail, and what would cause it. Only then can you plan to avoid it.

I’ve been thinking about that idea in the lead-up to Yom Kippur. What would failure look like there? I’m not talking about the technical questions of the day, whether you’re fasting, whether you make it to shul. I’m thinking about the deep spiritual and existential work of the day.

One popular show – Apple TV’s Severance – offers an unusually vivid window into what that kind of failure might mean.

A failed Yom Kippur is a severed one: a day walled off from the life we actually live, so that our Yom Kippur self and the self who lives the other 364 days never meet.

As I thought about it more, I realized just how right my friend is: We need to contemplate failing Yom Kippur before the day arrives, because a failure you can describe is a failure you can prepare against.

For those unfamiliar with the show: employees of a company called Lumon choose to have a chip implanted in their brains that divides them in two: an innie, who exists only at work and remembers nothing else, and an outie, who lives the rest of life with no memory of the office.

Both inhabit the same body, but they do not know each other, and their personalities, tastes, and loves diverge. The procedure is sold as a kindness. Mark, the main character, chooses it after his wife dies, so that for eight hours a day there will be a version of him who does not know she is gone.

The show is appealing because it hints at a familiar desire: to escape ourselves, our memories, our personalities, to inhabit another self temporarily, one severed from the weight we carry.

But the show’s slow argument reveals that the supposed mercy of severance is actually a horror. A person cut in two is not spared anything – only prevented from becoming whole. Mark and his friends spend much of the second season trying to get their innies and outies to communicate, groping toward some kind of integration.

I hadn’t thought about the show in months (like most prestige TV, there is a years-long gap between seasons, and Season Two ended a year and a half ago). But something happened at the end of Rosh Hashana that brought it back.

During Rosh Hashana I felt spiritually connected. I read the prayers carefully and was able to focus throughout the shofar blowings on what it means that God is king and how we are being called to wake up from our slumber and come closer to God. I almost felt as if I were in a zen-like zone.

I was rereading This Is Real And You Are Completely Unprepared, and I paused (as I always do) at Alan Lew’s suggestion that the most important Jew in history was Sigmund Freud, because he taught us that the invisible matters and is the most real thing of all. Every time I remember this idea I breathe differently. What a notion – at once sobering and freeing.

For a moment the Oval Office, Situation Rooms, G7 gatherings, social media, and the stock market all felt very far away, as if I had briefly stepped outside the register in which “real life” is usually measured.

I remembered that there is a higher dimension, and that this dimension is more real than the one I normally live inside. Over Rosh Hashana, those words helped me approach the machzor with urgency, because I need to live more aware of this, and with deep joy, because I want to live in a world that God runs.

But the second Rosh Hashana ended, I felt the walls I had erected come crashing down.

Yes, it was the news.

In other years my spiritual high might have been interrupted by materialism or silly preoccupations. This year it was the weight of Jewish history. This year it was the weight of Jewish history: Pink’s messages on Instagram. The drama playing out between Macklemore, Ed Sheeran, and Robert Kraft. The new Naza documentary and the gleeful 25-minute ovation from a Venice audience… The Israeli elections and the upcoming midterms.

All of it brought anxiety and fear, and the scramble of what do we do and what plans can we make?

In the days since Rosh Hashana I have felt acutely severed. There was my Rosh Hashana self and my post–Rosh Hashana self. I felt dizzy, as if I were two people. I found myself using my prayers seeking not only to connect to God but to quiet my brain, hoping to recover the clarity and lightness of a few days before. God is king. God is king. God is king.

My dizziness pushed me to articulate a pre-mortem vision of Yom Kippur failure. If we go through Yom Kippur and experience, God willing, spiritual heights and intimacy and tenderness, and then return to an entirely different reality — one of earthy preoccupations, desires and demands — what have we accomplished?

And this failure does not only relate to being consumed by the news. It could be the rat race, the call of careers, or the glittering pull of bigger bank accounts and looking better than our neighbors.

As I see it, there are two ways this could happen:

Failure #1: The outie never enters

We arrive at Kol Nidre having left our actual lives at the door: the fear we have been carrying since the news broke, the envy we are embarrassed by, the marriage that is strained, the failure at work, or the thing we want and cannot say.

Inside, we recite a script about a generic sinner. We beat our chests and say the viduy, but the beating is superficial; it does not pierce us or make us vulnerable enough to admit our true failings. Nothing real was brought in, so nothing real can be addressed.

Failure #2: The innie never leaves

Yom Kippur is transformative. Every word feels like a gift. God feels near. We prostrate during the Avodah and feel the presence of the Almighty. We sing Ochila La’El and our hearts yearn to cleave to God. We confess and reach the place where we understand that we can – we must – turn a new page. We look at one another and feel we are one community seeking purity, and at Neilah we feel the grace of God’s forgiveness.

Then the shofar sounds, havdalah is said, the phone turns on, and the person who wakes up on Tuesday has no memory of any of it. Our Yom Kippur self has stayed behind. It does not show up in how we go to work, speak to our children, or engage with the world.

Either failure is painful to imagine, but the point of a pre-mortem is not just to understand how we can fail but how we can prevent it.

Here too, the show is helpful. The opposite of severance is integration: allowing both selves to speak to each other – not to disappear into each other but to shape each other.

After all, each self has something the other lacks.

Our ordinary self carries the truth of our actual life: our fears, ambitions, resentments, relationships, and compromises. Our Yom Kippur self carries a different way of seeing: mortality, God, forgiveness, responsibility, and transcendence. Neither self should swallow the other, but neither can stand apart. The ordinary self has to inform the Yom Kippur self, and the Yom Kippur self has to shape the ordinary self. We bring our whole unedited lives into the day. And then the day sends us back into those very experiences with a different way of seeing them.

We can see the need for this integration from the way Maimonides codifies what teshuva, repair, looks like. Maimonides defines complete teshuva as the case where a person meets the same situation, with the same opportunity, and acts better than in the past.

Teshuva is not proven by our Yom Kippur self; it is proven on Tuesday, when ordinary life returns and we act differently because we have changed.

We have precious days left before Yom Kippur, and we must use them. Let me offer two practices that can help us prevent failure:

Prepare Your Viduy (Confession)

This is a way to bring your regular self into Yom Kippur. My father taught me that the viduy must be prepared.

Literally: before Yom Kippur, sit down, review the ancient words of the viduy, and write your own confession, in your own words, naming the actual things you are admitting to.

Not “we have sinned,” but the specific habit, the specific misdeed, the specific way you fell short with the specific person.

This is how the outie enters: when you strike your chest on Yom Kippur, you will be striking at something real.

Prepare for the Day After

This is how you keep your Yom Kippur self from staying behind. Consider which commitments you can take on and how to create accountability structures for them. Then write a second page, which this year we can think of as the Tuesday list.

This is the Tuesday that Maimonides was describing. Try to imagine the moments where you know you struggle. Is it the meeting? The group chat? The moment your child interrupts you? The news alert that will surely come? Name three situations that you know are coming and decide now how your ordinary self integrated with your Yom Kippur self will show up in them. This is how the innie leaves. Make small commitments of improvement.

In the show, integration is what the company fears most, because a whole person cannot be managed. Our tradition wants exactly what Lumon dreads.

Yom Kippur is not a day to escape our lives for 25 hours. It is the day we bring our lives before God and then take God back into our lives, and walk out of the closing gates as one person who remembers.