This is the sermon I delivered at Congregation Neveh Shalom on Yom Kippur day, 2025.
Let’s talk about Sukkot. As a rabbi, I like to stay a little ahead of the game, so let’s address the elephant in the sukkah. By the way, that’s the real title of a PJ Library book, no kidding.
Sukkot is not my favorite holiday. Of all the Jewish rituals—wonderfully weird, occasionally random, but always deeply meaningful—the ones related to the holiday of Sukkot are the most cringeworthy to me.
Why, you might ask? What’s wrong with a sukkah? And the answer is, nothing actually. I love building the sukkah and decorating it with paper chains and the fake fruit that once hung in my Nana and Papa’s sukkah. I love the open tent symbolism. I love inviting in our ancestors. It’s the lulav and etrog that make me want to just skip over this holiday and go straight to Simchat Torah.
I know not everyone feels this way, but to me, this particular tradition feels pagan and out of place in a religion that forbids the worship of objects. I didn’t always feel this way. It started when I was in rabbinical school in Los Angeles and the minyan moved outside to the sukkah. When you take the lulav and etrog and then add in a drum circle with students dancing and drumming and chanting a rhythmic beat, shaking said lulav and etrog, suddenly it felt different. This was not my Zayde’s Judaism, and I’ve never been able to shake that feeling, pun totally intended.
Again, this is in no way me telling you to share in my discomfort. I’m willing to bet that each of you has a moment in your life—specifically in your Jewish life—when you’ve felt out of place or off-kilter. Have any of you ever witnessed kaparot, the swinging of a chicken overhead before Yom Kippur to transfer your sins? A bris is a meaningful ceremony, but maybe not the most comfortable for everyone in the room. Well, particularly one person in the room. Or maybe there’s merely a ritual you didn’t grow up with, so it’s not second nature.
Each of us has our own individual comfort level in Jewish living. And each of us has places of discomfort. But here is my Yom Kippur message: discomfort, especially in Judaism, isn’t something to be avoided—it’s something to be explored. And today, on the day that confronts us with mortality, vulnerability, and deep spiritual reflection, it’s the perfect time to talk about it. So let’s get uncomfortable.
There’s a teaching in Pirkei Avot—the Ethics of Our Ancestors—where Rabbi Eliezer says, “Repent one day before your death.” His students respond, “But Rabbi, how can we know what day that will be?” And he replies, “Exactly. Therefore, repent today.”
Yom Kippur, in a way, is that day. Not literally, but it’s the day we symbolically prepare for our death, wearing white like burial shrouds, fasting, removing ourselves from physical pleasure. It’s not meant to be morbid, it’s purposeful. Yom Kippur invites us to be uncomfortable so that we might grow.
The psychiatrist Rabbi Dr. Abraham Twerski was not only a prolific author, his online videos also generated views in the hundreds of millions. In one of his more well-known videos, he muses that we can learn a lot from lobsters. I know, Jews learning from shellfish, it’s weird. But the lobster, whose hard shell protects its soft tissue, cannot grow without the discomfort of pushing against a shell that has become too small. You don’t have to push yourself out of your comfort zone, but if you don’t, you risk missing out on opportunities for personal growth.
Discomfort, in Judaism, has often been the catalyst for transformation. Think of our biblical ancestors. Abraham left everything he knew. Jacob wrestled with an angel. Moses stood up to Pharaoh with shaking hands. None of that was comfortable. But it was holy.
Leaning into discomfort gives us the opportunity to examine our lives without pretense. It forces us to consider how we spend our time, how we treat others, and whether we’re living in alignment with our values. Let’s be real; that kind of honest introspection doesn’t happen on a Tempur-Pedic mattress with a Pendleton Merino throw. It happens in the quiet of fasting, in the ache of regret, and in the uncertainty of change.
With Yom Kippur as our symbolic acknowledgement of mortality, there’s a particular kind of discomfort that’s especially relevant for reflection today, the discomfort of attending shiva.
If you’ve ever walked into a house of mourning, you know the feeling. You fumble for the right words. You wonder if you should attempt to say something profound or say nothing at all. Maybe you didn’t know the deceased. Maybe grief makes you anxious. Shiva offers a variety pack of ways to feel uncomfortable.
However, the mitzvah of nichum aveilim—comforting mourners—is not about saying the right thing. It’s not even about having a close relationship with the person who died. It’s about showing up.
The discomfort we feel walking into a shiva house is a sacred discomfort. It reminds us that presence matters. Our tradition teaches that when we visit a mourner, we remove a fraction of their sorrow. Not all of it, just a little. But that little bit can make all the difference.
Shiva is not designed to be comfortable for the participants. It’s designed to hold grief so that we can process it without distraction, without escape from the sadness. And in that honesty, that rawness, there is deep holiness. Sitting with someone in their grief, even in silence, is one of the most powerful things we can do as Jews and as human beings.
And in many ways, Yom Kippur functions like a communal shiva. A shiva for the soul. A sacred time set aside to grieve our missteps, our losses, and our mortality. We sit together, stripped of distractions, focused on what truly matters.
Just as we would never say to a mourner, “You should be over it by now,” Judaism doesn’t ask us to rush past the discomfort of Yom Kippur. We’re not meant to skip ahead to the break-fast. We’re meant to sit in the stillness. To cry if we need to. To say the hard things, to ourselves and to each other.
You’d think an uncomfortable ritual like this is meant to break us somehow. Not at all. It’s meant to open us. The discomfort of Yom Kippur is not about shame or punishment. It’s about potential. It’s about asking, “What kind of life do I want to live? To whom do I need to apologize? What type of person do I want to be when I exit the synagogue doors?”
We’re not promised comfort in this life. But we are promised meaning. And meaning comes from doing the hard things. From leaning in and showing up when it’s uncomfortable.
That’s why we attend shiva. That’s why we fast on Yom Kippur. That’s why we reflect on death—not to dwell in fear, but to live more fully. We show up for each other in our darkest moments because we know that’s what community is for. And we show up for ourselves on Yom Kippur because we believe that every soul can shine again.
It takes courage to lean into discomfort. To walk into a house of mourning or to walk into a synagogue on Yom Kippur and say, “I’ve messed up. I want to do better.” It takes courage to face the parts of life or the parts of ourselves we’d rather ignore.
But the reason we do it is because we believe it can change us. We believe in teshuvah—in return, in repair, in rebirth. So today, I invite you not to rush past the discomfort. Don’t numb it. Don’t flee it. Sit with it. Learn from it.
Ask yourself: What parts of my life need tending? Who have I avoided showing up for because it felt awkward or hard? Where have I played it safe when I was called to step forward?
And maybe today, as the hunger pangs persist or the confessional prayers grow repetitive, you’ll remember that these moments, too, are holy. They are tools for transformation. They are our people’s way of saying: Life is short. Make it count.
May we each find the strength to be uncomfortable. And in doing so, may we write ourselves into the Book of Life—not only for another year, but for an entire life of meaning, compassion, and connection.
G’mar chatimah tovah.
Rabbi Eve Posen 