The Power of the Month of Cheshvan featuring Rabbi Pill

In this episode, I sit down with Rabbi Pill to explore the power of Mar Cheshvan and discover that it’s not a spiritual lull at all, but the time when we’re meant to integrate the inspiration of Tishrei into everyday life. We discuss how Jewish time moves in an upward spiral, and how Cheshvan shifts us from “gadlus ha’mochin” (expanded consciousness) to “katnus ha’mochin” (constricted consciousness), when serving Hashem without emotional highs becomes the real avodah. Drawing from Torah, Kabbalistic, and Chassidic sources, we reflect on how our service counts most when the excitement fades, and how the letter Nun—representing both falling and divine support—reminds us that every descent can become the beginning of an ascent. We also connect Cheshvan to the Flood and the dedication of the First Temple, showing how this same month can hold both darkness and revelation. On a practical level, we talk about yearning honestly for renewed connection, resisting the urge to escape discomfort, and carrying even one small piece of Tishrei forward—whether a mindful bracha or a focused moment in tefillah. The message is that Cheshvan invites us to bring Hashem into our work, family, and daily routine, turning quiet consistency into true transformation.

Join the Conversation! 
Be part of our growing community—join the Shema Podcast for the Perplexed WhatsApp group to share feedback, discuss episodes, and suggest future topics. Click here to sign up.

Get the Companion Guide: The Power of the Months
This free resource outlines the spiritual focus of each Hebrew month — including its mazal (zodiac sign), tribe, Hebrew letter, body part, and unique avodah. It also includes suggested actions you can take to align yourself with the energy of the time. Click here to download and keep this month-by-month guide as a tool for your own growth and reflection.
 
The Power of the Month of Cheshvan featuring Rabbi Pill