What if the most important Jewish holiday isn’t the one you think it is? And what if the rituals you grew up with are the very things holding you back from a more meaningful holiday experience?

In this eye-opening episode of In Such a Time: Conversations on Jewish Life, Leadership and Meaning, Rabbis Jonathan Jaffe and Leora Londy dive deep into the High Holidays—unpacking personal childhood memories, family legacies, synagogue culture, and the surprising ways that stress, boredom, confusion, and even teenage flirting have all shaped their connections to Rosh Hashanah and Yom Kippur.

Together, they challenge the dominance of guilt and atonement-centric themes, ask if fasting might eclipse the deeper purpose of Yom Kippur, and reflect on the difference between simply showing up for holidays and truly making Jewish life meaningful year-round. With stories ranging from bike-filled streets in Israel to behind-the-scenes synagogue preparations in the US, this conversation invites you to rethink what it really means to celebrate, atone, and renew.

Key highlights include:

• Rabbi Londy’s powerful early memory of visiting hospital patients on Yom Kippur—and learning Judaism is as much about action as about prayer
• Rabbi Jaffe’s honest admission of a “problematic” relationship with the High Holidays and the secrecy of prayerbook traditions that left him bewildered as a child
• How the narrative of fasting can undermine the intention of Yom Kippur, leading to hunger over holiness
• Why Jewish education models may sow seeds of alienation and how context is everything for spiritual connection
• The contrast between Jewish observance in Israel and America, and how cultural immersion (or isolation) shapes the seasons of meaning
• Honest reflections on disappointment, optimism, and the practice of forgiveness—both with others and oneself
• The ritual and symbolism that follows Yom Kippur—like building the sukkah—as powerful metaphors for doing and becoming

Whether you’re a lifelong synagogue-goer or someone who only peeks in on the High Holidays, this episode will challenge your assumptions, spark some laughter, and just might inspire you to embrace the holidays in a new way.

Episode Overview with Timestamps:

• 00:00:00 – Intro and episode setup
• 00:00:54 – Childhood memories: nerves, stress, and meaningful action
• 00:03:14 – Growing up fidgety, confused by synagogue traditions
• 00:06:11 – “Wow”, “Ouch”, and “Oops”: What Jewish prayer really means
• 00:08:25 – Why the High Holidays don’t represent the whole Jewish experience
• 00:09:59 – Communal responsibility and the value of atonement
• 00:12:42 – Jewish education, missed opportunities, and lasting impressions
• 00:15:30 – The problem (and machismo!) of fasting on Yom Kippur
• 00:20:15 – The power of preparation: Behind-the-scenes and in Israel
• 00:25:46 – The difference environment makes: Jewish life in the diaspora vs. Israel
• 00:28:01 – The unexpected optimism of Yom Kippur—do we ever really “finish”?
• 00:29:33 – Vulnerability, forgiveness, and the beauty of trying again
• 00:31:22 – Ne’ilah in Israel, the joy at the close of the holiday
• 00:34:21 – Sweet rituals: Symbolic foods and building the sukkah
• 00:35:12 – Final blessings & takeaways for a meaningful High Holiday season

Ready to be shocked—and renewed—by the High Holidays? Tune in now!