YY Jacobson: The Teshuva of Coming Back to Yourself

Main Ideas

• Teshuvah is more than repentance. Rabbi YY Jacobson distinguishes between its external dimensions—regret, confession, and correcting wrongdoing—and its deeper meaning: “return.” At its core, teshuvah is the soul’s longing to return to closeness with God after experiencing itself as separate.

• Anxiety can reflect spiritual separation, not simply personal failure. Jacobson describes the soul as rooted in divine infinity, while everyday life can make worth and safety seem dependent on achievement, approval, or religious performance. Teshuvah involves recognizing that pain and choosing trust, love, surrender, and connection.

• Intellectual religious knowledge is not the same as embodied experience. Jacobson recounts a life of Torah learning, teaching, and public success alongside anxiety and emotional disconnection. Through personal work, family relationships, and healing, he came to see that religious ideas had not fully reached his emotional and bodily experience. He now wants to teach Torah in a way that is lived and felt, not only understood.

• Praise and criticism can both reinforce dependence on approval. Jacobson says that compliments and criticism once affected the same fragile “shell” of identity: praise temporarily reassured him, while criticism threatened him. He is trying to become less dependent on either and to assess his words honestly—correcting mistakes when needed without treating a mistake as proof that he is worthless.

• Family struggles can reveal what achievement hides. A spouse or child may not be moved by public accomplishments or impressive religious ideas; they may be asking for genuine presence and emotional openness. Jacobson presents close relationships as a form of revelation because they challenge people to meet one another beyond their roles and reputations.

• Parents can respond to a child’s struggles in two stages:

  1. See the child’s pain without treating it as a verdict on the parent. A child’s difficulties do not automatically mean the parent has failed. The immediate task is to offer affection and support rather than react from shame or unmet expectations.
  2. Consider what the child’s struggle may uncover in the parent. A child may bring unresolved or disowned parts of a parent’s own experience into view. Jacobson compares this to children finding the hidden afikoman: what families conceal can eventually be exposed. The response should be curiosity and connection, not blame or rejection.

• This generation’s religious work includes turning inward. Jacobson argues that Jewish communities have built strong institutions and traditions, often in response to real historical threats. With greater security for many people, there is now more opportunity—and a need—to address anxiety, emotional wounds, and inner disconnection. He sees the task as transmitting Judaism not only through institutions, words, and rituals, but also through lived relationships with God and other people.

• The “walls” of anxiety may not be the whole reality. A story attributed to the Baal Shem Tov describes people overcoming walls and obstacles to reach a king, only to discover that the walls were an illusion. Jacobson uses this as a metaphor: fear, shame, and anxiety feel real, but they may exist within a much larger “ocean” of divine love and presence. The point is not to stop at the temporary rewards of self-work, but to keep moving toward deeper connection.

• Religious life is presented as relationship, not merely information. Jacobson describes Torah study, prayer, and mitzvot as opportunities for closeness with God. He also suggests that authentic conversation—whether within a family or elsewhere—requires presence rather than an effort to impress, manipulate, or obtain reassurance.

• The host’s closing reflection emphasizes responsibility and openness. David Bashevkin says that 18Forty aims to make room for sincere religious growth and difficult questions. He acknowledges that some episodes may have left listeners confused or uncertain, apologizes for that, and says the project will continue trying to present Jewish perspectives and create space for discussion.

Sources and Speakers

Speakers

• David Bashevkin — host and interviewer; also speaks in the closing reflection.
• Rabbi YY Jacobson — guest and principal teacher in the interview.

Works, Teachers, and Other Sources Mentioned

• Rabbi David Ebner, associated with the collection The Dance of Teshuva
• Rabbi Shneur Zalman of Liadi, the Alter Rebbe, especially Tanya and Likkutei Torah
• The Baal Shem Tov
• The Maggid of Mezritch
• The Talmud, including passages from Shabbat and Sanhedrin
• Pirkei Avot
• Ben Porat Yosef and Toldot Yaakov Yosef, associated in the discussion with Rabbi Yaakov Yosef of Polnoye
• Maimonides (Rambam), including Mishneh Torah
• Mark Epstein, The Trauma of Everyday Life
• Devorah Leah Nussbaum, To Live with an Open Heart: Tanya through the Eyes of a Psychotherapist
• Kesher Nafshi, an organization discussed in connection with supporting families
• The 18Forty project and its Talmud Daily initiative