Simon Jacobson: 'The music of Judaism is what I’m looking for, not just the mechanics'

Simon Jacobson: 'The music of Judaism is what I’m looking for, not just the mechanics'

Author: 18Forty May 4, 2026 Duration: 46:13
Rabbi Simon Jacobson describes his childhood years as being shaped by his nature of being a “skeptic and a seeker.” As he grew older, he began to study other traditions, eventually returning to a deeper study of Hasidic thought, where he found “the music of Judaism.” As he continued his studies, he became a close disciple of the Lubavitcher Rabbi, serving as one of his oral scribes. 

Rabbi Simon Jacobson is the founder of the The Meaningful Life Center, an organization dedicated to sharing the wisdom of the Torah to people of all backgrounds. He is the author of Towards A Meaningful Life

Now, he joins us to answer eighteen questions with Rabbi Dr. Benji Levy on Jewish mysticism including its emphasis on action and how Pnimiyut HaTorah [inner dimensions of Torah] is a taste of redemption.

Here are our questions: 
What is Jewish mysticism?
How were you introduced to Jewish mysticism?
In an ideal world, would all Jews be mystics?
What do you think of when you think of God?
What is the purpose of the Jewish people?
How does prayer work?
What is the goal of Torah study?
Does Jewish mysticism view men and women the same?
Should Judaism be hard or easy?
Why did God create the world? 
Can humans do something that is against God’s will?
What do you think of when you think about Moshiach?
Is the State of Israel part of the final redemption?
What is the greatest challenge facing the world today?
How has modernity changed Jewish mysticism?
What differentiates Jewish mysticism from the mysticism of other religions? 
Does one need to be religious to study Jewish mysticism?
Can mysticism be dangerous?
How has Jewish mysticism affected your relationships with yourself and with others?
What is a Jewish teaching that you always take with you?

What does it mean to live a meaningful life? How do we navigate doubt, find purpose, or understand suffering? 18 Questions, 40 Mystics explores these profound human inquiries through a distinctly Jewish mystical lens. Hosted by Rabbi Benji Levy, this series from 18Forty engages in deep, personal conversations with a diverse global community of thinkers-including rabbis, kabbalists, artists, and teachers-each deeply immersed in mystical tradition. The format is elegantly simple yet expansive: eighteen core existential questions posed to forty different voices, yielding a rich tapestry of perspectives drawn from ancient wisdom and contemporary experience. Listeners will encounter discussions that weave together spirituality, daily practice, and the inner dimensions of faith known as pnimiyut. This isn't about abstract theory; it's about the practical and soulful insights that arise when earnest questioning meets lived spiritual knowledge. Whether you're well-versed in Jewish texts or simply curious about the intersection of mysticism and modern life, each episode offers a unique point of reflection and inspiration. The conversations are intimate and revealing, designed not to provide monolithic answers but to illuminate the many paths toward understanding. Tune in for a journey that is as much about the questions we all share as it is about the diverse, thoughtful responses from those who have dedicated their lives to contemplation. This podcast serves as a rare gateway into the minds and hearts of today's leading mystical practitioners.
Author: Language: English Episodes: 79

18 Questions, 40 Mystics
Podcast Episodes
Devori Nussbaum: 'I see God as this one coherent frequency of truth' [not-audio_url] [/not-audio_url]

Duration: 36:58
For Devori Nussbaum, Jewish mysticism is the study of the soul behind the psyche, a transformative framework that integrates the profound spiritual truths of Chasidut [Hasidism] with insights of psychotherapy to foster p…
Jeremy Tibbetts: 'Being a spiritual seeker is not in vogue' [not-audio_url] [/not-audio_url]

Duration: 37:33
For Rabbi Jeremy Tibbetts, Jewish mysticism is all about turning inwards: both individually and religiously. While he did not grow up Orthodox, Rabbi Jeremy was exposed to Hasidic teachings for the first time at eighteen…
Shlomo Katz: 'Today's idol worship is self-persecution' [not-audio_url] [/not-audio_url]

Duration: 42:28
To Rabbi Shlomo Katz, the song of Torah is the most natural gateway into Jewish mysticism. A spiritual disciple of Shlomo Carlebach, Rabbi Shlomo believes that our greatest challenge today is that we lack the courage to…
Tonia Chazanow: 'Every soul has a story' [not-audio_url] [/not-audio_url]

Duration: 26:31
Tonia Chazanow believes everyone deserves to have access to Jewish mysticism because it is a tool through which each person can discover and understand the divinity in their own life and help others find theirs.Tonia Cha…
Ora Wiskind: 'The presence of God is everywhere in every molecule' [not-audio_url] [/not-audio_url]

Duration: 28:34
As someone who has always been “anti-rational,” Dr. Ora Wiskind finds a world of deeper connection in Jewish mysticism. In particular, she is drawn to the study of Hasidism as a pathway to integrating spirituality into d…