18Forty Podcast25 Maalis 2025

Sylvia and Simon Jacobson: How Different Generations Talk About Jewish Life [Divergence 1/6]

Our Intergenerational Divergence series is sponsored by our friends Sarala and Danny Turkel.

This episode is sponsored by an anonymous friend who supports our mission.

In this episode of the 18Forty Podcast, we talk to Rabbi Simon Jacobson—a leading rabbi in the internet age who previously worked closely with the Lubavitcher Rebbe—and his mother, Silvia, who was born into a Chabad family in Europe nearly 90 years ago.

Together, they have witnessed and experienced the development of the Chabad movement and the Jewish People over several historic eras. In this episode we discuss:

How has Chabad managed to maintain continuity over wildly different generations and historical contexts?
What can the mystical notions of tzimtzum, concealment, and revelation teach us about parenting?
How has the way we talk about “trauma” evolved over generations?

Tune in to hear a conversation about how we can transmit tradition to our children with confidence and rootedness in order to find a dwelling place for God in every generation.

Interview begins at 11:15.

Rabbi Simon Jacobson heads The Meaningful Life Center, called a “Spiritual Starbucks” by The New York Times, which bridges the secular and the spiritual through a wide variety of live and online programming. He is the author of the best-selling book Toward a Meaningful Life, a William Morrow publication that has sold over 400,000 copies to date. Rabbi Jacobson is a speaker, educator, and mentor.

Sylvia, Simon's mother, is the matriarch of the Jacobson family.

References:

Kabbalah and the Rupture of Modernity: An Existential History of Chabad Hasidism by Eli Rubin

Toward a Meaningful Life by Simon Jacobson

“Tzomo Lecho Nafshi”

The Count of Monte Cristo by Alexandre Dumas

Vanity Fair by by William Makepeace Thackeray

The Algemeiner

“Rabbi Simon Jacobson Appears on Larry King Live | June 1994”

The Way of All Flesh by Samuel Butler

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