Yom Kippur 5759 - '98

Outline Vol. 2, # 47

by Rabbi Yaakov Bernstein

This issue has been dedicated in honor of the recent yahrzeit of I. H. Bernstein -- Yitzchak Tzvi ben Shimon Menachem Nachum Halevi, by his grandchildren. Passed away 26 Elul 5726 -- Sept. 26, ‘65.

Chodshei Hashanah Vol. 2, Part 30

Every year, the following issue comes up: The self-examination of Yom Kippur seems very difficult. Regret and embarrassment over our mistakes make us cringe at the thought of facing up to the past.

Rebbenu Yona in Yesod Hateshuva deals with this issue succinctly: A person should not tackle the past and bemoan all his errors. If he were to do so, he would become ashamed and not be able to improve himself. Rather, he should see himself as a new-born individual, with no connection to the past -- neither merits, nor errors. He enters with a clean slate, and can start fresh, without being burdened with a disturbing past. If approached in this way, a person will feel released, as if he has just unloaded a heavy weight.

Strangely, though, the same author wrote the contrary, in another work: A basic requisite to Teshuva is to be bitter over one’s mistakes. Only in this way can a person change fundamentally; according to the level of the bitterness, is the degree of the change of heart. (Sha’arei Teshuva, First Gate, 13.)

Which is the important aspect, to regret the past, or to avoid past errors and turn over a new leaf?

The Test

The Talmud (Sanhedrin 107) states that Dovid Hamelech (King David) erred in having asked to be tested. He was punished by having to face a test too difficult to withstand, until he saw the error in his having made such a request. Originally he said, "Examine me, Hashem, and test me; refine my insides and my heart." (T’hilim [Psalms 26:2].) Later, he reversed himself: "You have tested me, and found nothing suitable; muzzle my mouth that it not transgress." (Ibid., 17:3, according to Rashi’s commentary to Sanhedrin)

Rav Yitzchak Hutner (Pachad Yitzchak, Rosh Hashanah, 7) shows that the Talmud’s statement cannot be taken literally. Dovid Hamelech could not have completely regretted having asked to be tested, for the original request is a verse that remains in the book of T’hilim (Psalms 26:2): "Examine me, Hashem, and test me; refine my insides and my heart."

Rather, Dovid Hamelech came to the realization that a prayer expressing concern precede a desire to be tested. Only one who truly realizes the dangers inherent in being "tested" may merit to withstand the "test."

Complete Teshuva

In Hilchos Teshuva, Rambam states the ideal, complete repentance. If a person returned to the same situation to which he had succumbed to temptation, under the exact circumstances, but this time withstands the temptation -- only in such a case has complete Teshuva been fulfilled. (Hilchos Teshuva, 2:1) Surely this is difficult to understand. Would a person ask for such a thing to happen -- after having succumbed to temptation, to request to be faced with the same temptation again, in order to overcome it? Perhaps he will fall to temptation again! Surely he would be much better off running away, and not encountering such a test...


If we are to improve our ways, the important aspect ought to be to change our direction. Why focus on the negative aspects of the past? On the other hand, if we do not examine our blunders, the likelihood of returning to them is great. It is similar to the contemporary question of reforming criminals. Some say, why focus on punishments? Simply set them on a new path and release them. Experience shows, however, that convicted criminals are likely to return to their former ways.

Ideally, the past would be uprooted entirely. The criminal would have to come to a deep conviction of the seriousness of his crimes; in order to be reinstated as a law-abiding citizen, observable procedures indicating his remorse would have to be confirmed.

That is the ideal. In dealing with our own, self-initiated improvement program, though, it is not always practical to deal with the past head-on.

In Hilchos Deos (2:2), Rambam writes that if a person has acquired a bad habit, he should go to the other extreme. Eventually, he will become accustomed to living without the habit entirely. Then he can return to a median path.

We imagine that this aspect comes first and foremost: Relinquish the bad habit until you no longer think of it. There may come a time when we will be able to directly deal with every aspect of the past, and come to terms with it; until such time, however, ‘turning over a new leaf’ retains priority.

In fact, Rambam seems to state this clearly. After the ‘complete Teshuva’ which we discussed above, he writes: "What is Teshuva? He forsakes his error, turns his thoughts away, decides not to act in such a manner again..." Only after this, does the Rambam mention the need for regretting the past. (Hilchos Teshuva, 2:2)

Rabbi Yaakov Bernstein
11 Kiryas Radin
Spring Valley, NY 10977
Phone: (914) 362-5156
E-mail: [email protected]

Good Shabbos!

Text Copyright © '98 Rabbi Yaakov Bernstein and Project Genesis, Inc.

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