Yom Kippur: Stop Judging Yourself by Your Worst Moment - Rabbi YY Jacobson

Summary

Rabbi YY Jacobson presents teshuvah—usually translated as repentance or return—as more than apologizing for particular mistakes. It is also an ongoing return to the soul’s deepest source and a way of reconnecting with oneself, other people, and God.

1. Attend to the details without losing sight of the whole

Teshuvah has practical, specific dimensions: acknowledge a hurtful act, apologize, repair what can be repaired, and resolve to act differently. But focusing only on individual “trees” can obscure the “forest”—the deeper experience that gives those actions meaning.

Jacobson describes a movement from the general to the particular and back again: a person’s broad sense of purpose takes shape in daily choices, and those choices can then be gathered into a deeper understanding of that purpose. The goal is neither vague inspiration without practical change nor a checklist disconnected from inner life.

2. Don’t reduce yourself to your worst moment

A story about a man hired to act as a tiger illustrates how people can mistake a temporary role for their identity. When the “tiger” once says “Shalom Aleichem,” it reveals something the costume cannot erase: he is a person, not a tiger.

The lesson is to take responsibility for harmful behavior while resisting the conclusion that a failure defines one’s whole self. Jacobson urges listeners to consider moments when they act from kindness, honesty, or spiritual clarity as evidence of a deeper identity—not to excuse mistakes, but to understand that the self is larger than its worst moments.

3. Address what lies beneath the symptoms

Jacobson compares teshuvah to looking beyond symptoms toward underlying causes. He refers to physician John Sarno’s work on back pain as an example of a theory that some physical symptoms may be connected to deeper emotional distress. The lecture uses this as an analogy: a visible problem may deserve practical attention, but sometimes it also points toward something less obvious that needs to be faced.

Likewise, a person may focus on one mistake or recurring problem while avoiding a deeper sense of disconnection, fear, or unmet longing. The lecture does not dismiss practical repair; it argues that repair can be incomplete if the underlying experience remains unaddressed.

4. Aim toward the highest in people

Drawing on Moses’ words in Ha’azinu—“Listen, heavens … and let the earth hear”—Jacobson says teachers and others should speak to the “heaven” within a person: their ideals and capacity for goodness, rather than only their defensive or reactive side.

He compares this to “crabbing” in aviation: when wind may push an aircraft off course, the pilot aims above or beyond the destination to arrive where intended. Similarly, aiming at a person’s best self can be more effective than appealing only to their current limitations.

5. Teshuvah as a return to the soul’s source

Using the morning blessing Elohai Neshamah and teachings attributed to the Alter Rebbe, Jacobson describes the soul as originating in divine “light” before taking on an individual, embodied identity. In life, a person can experience themselves as separate—from God, other people, and their own deepest self—and become absorbed in seeking security through achievement, attention, recognition, or control.

In this framework, teshuvah is not only regret for sin. It is the continuing recognition of separation and the choice to return toward connection. The soul’s longing is compared to searching for a particular song: other pleasures and achievements may be valuable, but they may not satisfy the deeper longing for unity and spiritual home.

The lecture also interprets ayin not simply as “nothing,” but as “not a thing”: a way of describing the soul’s source as beyond an isolated, self-contained identity. Bittul, in this context, means loosening the ego’s demand to be separate, defended, or constantly validated—not denying that one has feelings, needs, or responsibilities.

6. Anxiety and coping strategies may signal disconnection

Jacobson suggests that anxiety, anger, shame, self-judgment, and the urge to prove oneself can sometimes be understood as signs of perceived separation. People may develop coping strategies to survive and function; some may be quite respectable or even religious. But those strategies can also become ways of avoiding difficult inner experiences.

He emphasizes that the aim is not to condemn oneself for having these reactions. A person can acknowledge an emotion, consider what it may be protecting or expressing, and avoid letting it dictate their identity or actions. Difficult circumstances can sometimes interrupt habitual avoidance and prompt a deeper search for connection.

7. A practical way to respond to difficult emotions

The lecture’s practical guidance can be summarized as follows:

• Pause and breathe. Before rushing into the day or reacting, take time to reconnect with your center. Jacobson presents the morning soul blessing as a reminder of who one is and where one comes from.
• Name what is happening. Notice feelings such as anxiety, anger, shame, or hurt without pretending they are absent.
• Observe rather than argue with the anxiety. Jacobson warns that debating with anxious thoughts can keep a person caught in a loop. The alternative is to watch the reaction with compassion and curiosity.
• Recognize vulnerable parts without letting them take over. He uses the image of caring for an “inner child”: a person may feel overwhelmed or reactive while still having the capacity to support that feeling rather than act entirely from it.
• Ask what lies beneath the immediate reaction. What is the deeper pain or longing? Is it a wish for attachment, understanding, fairness, or connection?
• Choose a next step that supports connection. Consider whether a word, thought, or action will bring greater honesty and closeness—or reinforce avoidance, numbness, or defensiveness.
• Make concrete repairs when needed. A broader spiritual perspective does not replace apologizing, changing behavior, or fulfilling obligations.
• Seek further help or conversation when appropriate. The lecture allows that some matters may require working through with another person rather than handling them alone.

Jacobson offers four “litmus tests” for whether inner work is bearing healthy fruit:

1. People closest to you notice a positive change in how it feels to be with you.
2. Your conclusions do not require rejecting Jewish law or the Shulchan Aruch.
3. You become more humble and devoted, rather than feeling superior to or contemptuous of others.
4. You experience a deeper steadiness and openness, even if pain remains, rather than simply forcing yourself to feel cheerful.

8. Shabbat, prayer, and Yom Kippur

The lecture presents Shabbat as a recurring return of the world to its source, and daily prayer as a small taste of that return. Prayer can offer a pause from the day’s demands and a chance to become present.

Yom Kippur, called Shabbat Shabbaton, is described as an especially intense opportunity for this inward return. Jacobson interprets Kol Nidrei as releasing self-imposed bindings rooted in fear or insecurity, and Neilah as more than the closing of heavenly gates: it symbolizes an intimate inward encounter. The day’s prayers invite a person to remember their deepest identity and choose how to live from it.

Central lesson: Teshuvah means facing particular mistakes while also returning to the larger truth of who one is. It is an ongoing choice to move from isolation and self-protection toward honesty, humility, presence, and connection.

Speakers and sources featured

• Rabbi YY Jacobson — the lecturer and primary speaker.
• Audience members — briefly respond during the lecture; they are not identified by name.
• Rabbi Waxman — cited by Jacobson as the source of the tiger-in-a-zoo story.
• John Sarno — mentioned in connection with a theory about emotional factors and chronic pain.
• The Talmud, Eruvin 13b — cited for the debate between the schools of Hillel and Shammai about whether it would have been better for humanity to be created.
• The Talmud, Shabbat — cited regarding the idea of doing teshuvah throughout one’s life.
• The Alter Rebbe / Baal HaTanya — cited through Likkutei Torah for teachings on teshuvah and the soul.
• The morning blessing Elohai Neshamah — used to explain the soul’s origin and return.
• Moses’ poem in Deuteronomy (Ha’azinu) — cited for the appeal to “heavens” and “earth.”
• The Apter Rebbe, Rabbi Abraham Joshua Heschel of Apta — cited for an interpretation of Moses’ address to heaven and earth.
• Rabbi Ishmael — referenced in connection with the interpretive principles of general and particular.
• Kohelet (Ecclesiastes) — cited for the idea of the spirit returning to God.
• Rabbi Akiva and Rabbi Shimon bar Yochai — referenced in an anecdote about being seen and understood.
• Rabbi Yehuda Halevi — cited for the image of the soul as a harp for divine song.
• Rambam (Maimonides) — mentioned regarding joy in serving God and in connection with the account of Moses.