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T’shuva and its Processes: As the Jew Turns

September 5, 2019

L’Fi Dati: As I See It

A High Holiday Message from Rabbi Sam Weintraub

Self-assessment, the review of our behavior, outlook and relationships, is something we do all the time. We have family meetings, professional reviews, psychotherapy sessions, etc. Part of normal, regular life is taking stock. Every evening, before I pray the bedtime Sh’ma, I meditate on my past day. What is so special about the t’shuva, the self-reckoning, which is the unique feature of the period around Rosh Hashanah and Yom Kippur?

To begin with, it involves a more fundamental analysis. The very fact that the review we undertake day to day is normal and routine makes it susceptible to distortion. We neatly divide our behavior and qualities—positive, negative, constructive, debilitating—but the fact that the review is squeezed into the hurly burly of daily life makes a deeper look difficult. Often, we assess our conduct as we go over our financial accounts. We check to make sure that the bottom line is secure, that things are going on as they were before, but with no consideration of the values, anxieties and aspirations motivating the whole. So, the review may reinforce fundamental errors.

The t’shuva of Rosh Hashanah and Yom Kippur encourages us not just to note misdemeanors, but to probe for deep, underlying corruptions. Maimonides in particular wrote that in t’shuva we should examine our destructive behavior not just by its external consequences but by the inner sin, the basic personality defect, which first motivated it.

Because of this, the t’shuva of this period will be more upsetting than the discrete feelings of guilt which accompany our usual, quotidian reviews. If we let ourselves be moved by this period, then our normal justifications, even our normal sense of self, is rattled. We feel disquiet, a sense of disorientation that we cannot readily understand or describe. In Rabbinic writings, this stage of t’shuva is called charata or trembling, a visceral, non-rational sense that things are fundamentally askew and cannot go on as before.

This feeling can be frightening but it is also a blessing, a gift. It is a message to us from our Divine Soul that we need to change. It urges us to go back and look at our past, not with our general, time worn categories, but with new urgency and new possibilities. We realize that we cannot just atone for our past. We can also rebuild it. The past is no longer fixed but open, no longer a yoke, but a partner in our growth.

This idea, that we can re-shape our past, is basic to t’shuva. But isn’t time unidirectional? How can we change the past? Rabbi Adin Steinsaltz explains: “What should be remembered is that we are not expected to do t’shuva in a conventional universe. We do t’shuva in a universe that is quite unaware of physical laws, a universe in which the present, the future and the past merge into a timeless duration, a universe in which a lethal arrow is liable to fly back and to be as free of all suspicion as if it had never left its quiver.”

We are able this way to rebuild not only our past, but our personality. This is awesome, but not easy. It requires a willingness to go deeply into ourselves, to visit our dark spaces which first sent forth our sinful behavior. Paradoxically, in going to this murky place we also meet G?d. Kabbalah, Jewish mysticism, imagines this symbolically as sparks of divinity caught within the husks of evil. By penetrating to the sin which caused our destructive behavior, we also encounter the G?d whose Holiness and Light were eclipsed by that sin. So, our confrontation with the sins of the past increases our thirst, our passion for the good. From a zone which earlier contained the seeds of sin, we now find the seeds of virtue. Powers that had served evil are now directed to good. That is why the Talmud teaches that a penitent who has sinned and repented is higher spiritually than a saint who has never sinned. The path of the penitent is fed by the forces of good and evil, of the saint, only the forces of good.

T’shuva then is not only a way to repair ourselves and our relationships, but a path to encounter G?d. Judging by the hundreds who return to Synagogue on Rosh Hashanah and Yom Kippur, that encounter remains important, even in our very secular world.

I look forward to seeing you in Shul on and around the High Holidays. Please join us for services and, to explore beforehand the meanings of t’shuva as well as of the High Holiday melodies, join Cantor Sarah and me for three pre-High Holiday workshops, Sundays, September 8, 15 and 22 at 10:30am.

K’tiva v’Chatima Tova, may you and your families be inscribed and sealed for health and spiritual fulfillment this New Year.

Rabbi Weintraub


Please click here for the Lu’ach and information about High Holidays at Kane Street, or click here to register your tickets for our services.


The new season of our adult education program, Open Beit Midrash, starts on October 29. Click here for more information and to register.

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