HeyJaredOrthodox Conundrum Commentary
I examine major issues affecting the Orthodox world, without exaggeration or whitewashing. I hope to spark wider discussion, thus enabling Orthodox Judaism to move forward where it excels, and to rectify that which needs improvement.
- Indexed issues, last 90 days
- 17
- Latest publication
- Sep 30, 2026
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- Earliest in this view
- Aug 13, 2026
Latest issues
“Spread Upon Us Your Sukkah of Peace” (opens the original)
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I was prepared to write about New York Mayor Zohran Mamdani’s new public attempts to fight antisemitism, which is akin to an arsonist asking for additional funds for the fire department.That, however, will wait until tomorrow.Orthodox Conundrum Commentary is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.<input class="email-input" name="email" tab
A Purim Shpiel on Yom Kippur (opens the original)
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It would be difficult to find two more dissimilar holidays than Yom Kippur and Purim. Nevertheless, Jewish thinkers and mystics have noted some fascinating associations between the two days that demonstrate a deeper thematic linkage. In light of these connections, numerous Chassidic writers have noted the linguistic similarity of the Biblical name for Yom Kippur - “Yom HaKippurim" - and the parallel formulation, “Yom Ke-Purim" - that is, a day like Purim.These similarities, unsurprisingly, are t
Living in the Sukkah: What Halacha Really Requires, with Rav Chayim Soloveichik (BONUS EPISODE) (opens the original)
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What does it really mean to make the sukkah our home for seven days? In this special bonus Sukkot episode, I speak once again with Rav Chayim Soloveichik, this time about the practical halachot of sitting in the sukkah: when to say leishev basukkah, which foods require eating in the sukkah, working and sleeping in the sukkah, dealing with heat, rain, and other discomforts, traveling on Chol HaMoed, and much more. Along the way, Rav Chayim explains why the goal isn't simply to determine when we'r
The Thirteen Attributes of Mercy (opens the original)
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This post was originally published on September 23, 2023. I’m sharing it again now so that new subscribers can print out the PDF before Yom Kippur. Let me add a brief additional thought that I’m considering this year:Orthodox Conundrum Commentary is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber.<input class="email-input" name="email" tabind
Emphasizing the Good: A Solution or Part of the Problem? A Conversation with Rabbi Judah Mischel (opens the original)
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As Yom Kippur approaches, we naturally think about what’s wrong: our failures, our mistakes, and the ways that we, and the Jewish community as a whole, need to change. Rabbi Judah Mischel challenges us to pay attention to something else as well: the nekudah tovah, the point of goodness in ourselves, in other people, and in the Jewish people. He argues that focusing on what’s going right, magnifying it, and building upon it can be a far more effective path toward growth than constantly emphasizin
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