The High Holiday season is intentionally daunting. The heaviness of its liturgy is built to pierce our hearts. The shofar’s cries are pitched to startle us out of spiritual slumber. The demand that we make amends with the people around us, one by one, asks for real emotional labor.
Year after year I try to hold onto that framing, and year after year I still end up disappointed in myself. I didn’t do enough of any of the work resulting in an endless tally of what-ifs. This past year the disappointment came with an extra dose of self-blame.
Over the last couple of years, our family has had the privilege of watching my wife lead communities through High Holiday prayer, and it has been a joy. Stepping off the bimah myself has let me spend the holidays with our growing family instead, especially in the kids’ section of shul. There’s a trade-off in that exchange. Most of the time it fills my cup in a different way.
Last year while Lauren led services in Los Angeles, I spent more time building trains in the shul’s kids’ play area (a fixture every synagogue should have) than I spent praying. If I had to put a number on it, I probably prayed for about ten minutes across two days of Rosh Hashanah. Sitting with that afterward, a familiar disappointment crept back in.
I didn’t pray enough. I didn’t hear enough shofar. And I certainly didn’t do the harder work of teshuvah, that elusive act of return the season demands of us. It’s hard enough to hold onto friendships at this stage of early parenting. Asking myself to repair what’s actually broken felt like too much to take on.
Then, I ran into a text that resounded straight from its writing into the present moment. It came from Rav Kook, one of the great Jewish thinkers of the twentieth century and the first Ashkenazi chief rabbi of pre-state Israel. In the opening lines of his work Orot HaTeshuvah, The Lights of Repentance, he names exactly what I was feeling:
This subject of repentance is still a closed book and is in need of clarification.
Given how much ink has been spilled on repentance over the centuries, that admission caught me off guard. We return to teshuvah every year precisely because it’s so necessary and so hard to actually pin down. Later in the same book (Orot Ha’Teshuvah 20, 56), Rav Kook explains why the work matters so much. “Teshuvah,” he writes, “Is the yearning of all existence to be better, purer, more vigorous, and on a higher plane than it is.”
Teshuvah is the engine behind how we move ourselves, and the world, toward where we want it to be. How we approach the work matters to that larger project. Which brings me to the major thrust of his argument: If we’ve established that teshuvah is this important, how are we supposed to do it?
To the degree that a person recognizes his sins, the clarity of the light of repentance shines on his soul. Even though ostensibly he has not yet gained the permanence of repentance in his heart, nevertheless, its light hovers over him, and it is already working to turn him into a new creation. Even those things that hinder repentance, to the degree that the person recognizes them, and does not disregard their reality, their hindrance becomes less powerful and their virulence diminishes. From this the light of repentance begins to shine upon him, and the holiness of the supernal joy already clothes itself in the essence of his soul, and closed gates keep opening before him [my emphasis]. In the end he comes to such a supreme level that all the coils straighten, “Every valley shall be lifted up, and every mountain and hill shall be made low; and the rugged shall be made level, and the rough places a plain.” (Orot Ha’Teshuvah 15, 7)
The first step, in other words, is to recognize your own transgressions. The moment you do, you’re already illuminated. The process has barely begun and almost nothing has actually changed, but a shift has happened, and that shift shows up by you becoming something new. That alone takes a weight off. All it takes to begin is an act of noticing.
We all feel it too, in how some of the usual roadblocks lose their grip once we’re in the work. The inner voice that used to scold you starts to sound different. Self-admonishment becomes self-propulsion.
What strikes me about this passage is how directly it cuts against what our culture usually demands of us. We reward grand, sweeping gestures for the size of the shift they represent. Popular culture loves that story. But real teshuvah, real return, happens in small pieces.
As I sit on the precipice between last Rosh Hashanah and this one, where again, I will be playing with the trains in the back, that’s what is buoying me. Instead of getting down on myself for not doing enough prayer or reflection, Rav Kook reminds me that there’s still time. We don’t need to reach the finish line. We just need to get to the starting line.
As we mark the immensity of what this new year represents, I hope we can sit with that lesson. Earlier in the same book, Rav Kook quotes the prophet Isaiah (Isaiah 66:13) to describe what teshuvah offers those who take it on:
“As a man whose mother comforted him, so will I comfort you.”
The nineteenth-century Ukrainian commentator Malbim reads that verse this way:
It’s like a person who is mourning their distant mother, thinking that she has passed away, only to realize that she is alive and returning to comfort him.
Teshuvah reminds us that we are, in fact, enough. Even in the moment when it feels furthest away, all we have to do is take the first step. The light finds us and keeps us in the work, no matter how hard it gets, or how many train tracks might “distract” us along the way.