12. Making the High Holidays Matter: Practical Ideas for Rosh Hashanah & Yom Kippur

How do you create a High Holiday experience that is authentic, engaging, and meaningful for Jews at every level of observance?In this pre–Rosh Hashanah conversation, we get practical about what actually works: structuring services, creating meaningful learner experiences, using niggunim, stories and humor, making Tashlich accessible, and thinking differently about the role of the High Holiday sermon. The discussion explores a central question for every Shliach: Are we giving the sermon we want to give—or the sermon the person sitting in front of us needs to hear?We also turn to Yom Kippur and discuss how to move the day beyond guilt and obligation toward relationship—helping people recognize that simply showing up reflects an existing connection with Hashem and asking how we can help deepen it. Along the way, we share practical ideas for Kol Nidrei, Yizkor, the Avodah, Neilah, Napoleon’s March, and keeping people engaged throughout the day.And underneath it all is a reminder for Shluchim themselves: people reflect the energy we bring. When we are comfortable, inspired, and genuinely grateful for the privilege of Shlichus, that authenticity becomes contagious