AI Summary
5 min readThe Teshuva of Coming Back to Yourself
Rabbi YY Jacobson, a prominent Chabad lecturer and teacher, has recently shifted how he shares Torah—moving from intellectual exposition toward raw personal vulnerability. In conversation with host Dovid Bashevkin, he describes a late-in-life transformation that forced him to confront the gap between his external success and his internal disconnection. The episode explores what teshuva (return) actually means when you move beyond the institutional frameworks of yeshiva and into the messy reality of family, marriage, and the self.
Two Layers of Teshuva
Jacobson draws on a discourse from the Alter Rebbe (Rabbi Schneur Zalman of Liadi, 1745–1812) to distinguish between two levels of teshuva. The outer layer is the familiar one: regret for specific sins, resolutions to change, asking forgiveness. But the inner layer, he argues, has nothing to do with transgression at all. The Gemara says "all your days should be spent in teshuva," which seems odd—wouldn't it be better to simply stop sinning? The Alter Rebbe answers that teshuva is the soul's natural posture, not a response to failure.
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What you'll learn
- 1 (00:07) **Episode Introduction & Host Welcome** - Host Dovid Bashevkin introduces the episode and the annual Teshuva series, thanking sponsors Daniel and Mira Stokar.
- 2 (09:56) **The Two Layers of Teshuva** - Jacobson distinguishes between the outer layer (repentance for sins) and the inner layer (the soul's posture of return).
- 3 (15:02) **The Shift from Intellectual to Embodied Judaism** - Jacobson describes his personal journey from intellectual achievement to confronting his own emotional blockages.
- 4 (19:57) **Discovering the Blocked Heart** - Jacobson details the painful process of discovering his own disassociation and beginning deep emotional and spiritual work.
- 5 (26:43) **Criticism of the New Vulnerability** - Jacobson shares how his shift towards vulnerability was met with criticism from those who preferred his old, more intellectual style.
- 6 (29:02) **The Trap of External Validation** - Jacobson discusses the addictive and ultimately unsatisfying nature of seeking validation from views, likes, and praise.
- 7 (32:21) **The Liberating Power of Letting Go** - Jacobson explains the freedom that comes from being willing to give up all external success and validation.
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Show Notes
In this episode of the 18Forty Podcast, we talk to Rabbi YY Jacobson, one of the foremost online teachers of Torah, about how each of us can find the moshiach inside of us by experiencing Hashem’s infinite love and presence in the present moment.
In this episode we discuss:
—Why has there been a shift in the way we approach publicly sharing Torah?
—What is the nature of the Torah approach to vulnerability?
—What are we trying to achieve with our own teshuva?
Interview begins at 5:02.
Tune in to hear a conversation about the burden of having to exist outside of infinity.
Rabbi YY Jacobson is a Chabad rabbi, teacher, and scholar of Torah and Jewish mysticism. He is the founder and dean of TheYeshiva.net, where his classes reach thousands of students around the world. A sought-after speaker, Rabbi Jacobson draws on Torah, Chassidic thought, Kabbalah, and Jewish philosophy to explore contemporary questions of faith, spirituality, relationships, and Jewish life.
References:
The Dance of Teshuva by David Ebner
Likkutei Torah
Ben Porat Yosef
The Trauma of Everyday Life by Mark Epstein M.D.
To Live with an Open Heart: Tanya through the eyes of a Psychotherapist by Devorah Leah Nussbaum
Talmud Daily
Tzidkat HaTzadik
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