We are near the finish line of the עשרת ימי תשובה (Aseret Yemei Teshuvah) —the Ten Days of Repentance between Rosh Hashanah and Yom Kippur. Each year, I look forward to choosing a personal growth goal, something general enough to guide my interactions with students, teachers, parents, colleagues, and the broader community. By sharing this publicly, I hope it inspires others to reflect on their own growth and adds a layer of public accountability to keep me honest.
At least once a week, I compose the perfect social media post in my head. Sometimes it’s funny. Sometimes it’s biting. Sometimes it’s provocative. It’s always about a topic I care deeply about, something with real-world impact and significance. But each time, after writing it, I delete it.
I am jealous of people who live in outward philosophical purity. These people tend to fall into two categories. Some are rabbis serving in pulpits who have managed to align their personal beliefs with their communal roles so seamlessly that they are able to be their truest selves, both personally and professionally, without compromise.
Jealous.
Then, there are those who prioritize their philosophical purity above all else. They either carve out professional spaces that align with their values, or they are unafraid of facing the consequences when their values conflict with their roles.
Jealous.
This may seem like an odd choice for teshuvah—repentance for not being more provocative or polarizing. But I worry that in trying to balance discretion and authenticity, I end up standing for nothing. Silence is not neutrality. As Rabbi Abraham Joshua Heschel famously said, “In a free society, some are guilty, but all are responsible.” Remaining silent, especially when something needs to be said, isn’t neutrality—it’s complicity.
Here’s an example:
In 2016, we were living in Florida during the election, and my older daughter wanted us to put out a lawn sign for our preferred candidate. (Notice how I’m still hedging?) I had to consider carefully whether it was wise, as someone running a school in a divided community, to do something so public. In the end, we put out the sign. But even then, I said nothing in person or online. Why? I didn’t want to create unnecessary tension in a divided workplace and culture. And yet, I’m 99% sure that anyone who’s ever met me, or spent five minutes researching me, could easily guess my political views. And still, I said nothing.
There’s nothing wrong with not wanting to insert personal politics into a professional setting where it’s not welcome. The question I wrestle with is whether, as a private individual who holds a communal role, it’s wrong to express personal views. Is there a meaningful distinction between what I espouse as “head of school” and what I espouse as “Jon Mitzmacher”? My heart says there should be; my head says that’s wishful thinking.
Pirkei Avot reminds us, “If I am not for myself, who will be for me? And when I am only for myself, what am I? And if not now, when?” (Pirkei Avot 1:14). I cannot reconcile the way I am raising my daughters with my own silence. I cannot advocate for students to be civically active while avoiding the same. I cannot run a school based on deeply held principles and then be afraid to live those values beyond the school walls.
So, my goal for this year is to take a step—to dip a toe into the waters of personal expression. Nothing dramatic is on the horizon, and it’s possible that whatever I do say will yield no ripple or echo. But I’ll take a whistle in the wind over silence. As Rav Kook once said, “I don’t speak because I have the power to speak; I speak because I don’t have the power to remain silent.”
I don’t want to look back and wonder why I chose to say nothing when I had so much to say.
Additionally, during this time of introspection, let me take this opportunity to ask forgiveness for anything I have done – purposely or unknowingly – to cause offense or upset during the last year. I am sincerely sorry and ask for your forgiveness. As you ponder the purpose of this season for you and your family, I hope you find the time for introspection and the inspiration for the teshuvah you are seeking. From my family to yours, wishing you a tzom kal (easy fast) and a day of meaning.
G’mar chatimah tovah.
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