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Repentance: Theory and Practice

  • Harav Yaakov Medan

Adapted by Immanuel Meier

Translated by Jonathan Ziring


How is Forgiveness Possible?

On Shabbat Shuva we read:

Yet even now, says the Lord, turn back to Me with all your hearts, and with fasting, weeping, and lamenting. Rend your hearts rather than your garments, and turn back to the Lord your God. For He is gracious and merciful, slow to anger, abounding in kindness, and renouncing punishment.  Whoever knows shall repent and regret, and it shall leave after it a blessing, a meal offering and a libation to the Lord your God.  (Yoel 2:12-14)

When the prophet promises forgiveness, is it based on “mercy” or “concession”? While mercy is a fine attribute, it would seem that the attribute of concession involves injustice and dishonesty. Ramchal expressed this in Mesilat Yesharim (chapter 4):

And this is what Moshe, peace be upon him, said: “The Rock, whose works are perfect, whose ways are all those of justice, a God of faithfulness, with no crookedness…” (Devarim 32:4).  Since God desires [a world of] justice, it would be a violation of justice to turn a blind eye either to merit or to misconduct. Consequently, if there is meant to be justice, He must repay each person in accordance with his conduct and the results of his actions – both for good and for bad, with the strictest of precision. This is what Chazal said: “‘A God of faithfulness, with no crookedness, righteous and upstanding [is He]’ – for the righteous [as well] as the wicked.” This is the standard, He judges everything, and for every sin He punishes and there is no escape.

How, then, can God forgive the sinner and not give him the punishment he deserves?  The Maharal explains that when a person repents, it becomes clear that the sin was never a part of him, of his essence. Therefore, he succeeds in shaking off the sin, and he can be forgiven for it.

This can be compared to a car's chassis that was damaged in an accident and lost half of its market value. If a person sells the vehicle without informing buyers of the defect, the sale would be considered deceptive and therefore would be invalid. However, if the headlight doesn’t work, there is a piece missing that is not part of the car’s “essence.” The seller will have to compensate the buyer and pay for a new headlight, but the sale will not be voided. In other words, repentance makes it possible to completely sever the sin from the sinner’s essence.  This severance becomes clear upon the sinner's complete turning away from his sinful paths.  

But there is still a nagging question: practically, how do we go about regretting sins and atoning for them?

Practical Guidance

Can a person decide overnight to set out on a new path? We commonly use the expression “to turn over a new leaf.” The implication is that it doesn’t matter that the previous leaves or pages were scribbled on or filled with obscenities.  When the old pages are covered, only the new one will be before our eyes. However, if we don’t examine the scribbled pages and take the time to erase them, we can assume that the new page will soon be as scribbled on as the previous ones. But again, how do we erase and restore the pages? Can any of us truly regret all our evil actions from the past year? Can we do this every year?

I doubt it. But I am convinced that each of us can, though with no small amount of effort, make a fundamental change in two, three or four things in our lives. Some things we change should be in the realm of holiness, Torah study and prayer, and others in the realm of ethics, integrity, loyalty, righteousness and justice.  

Each of us can identify a small number of defects, and decide to take it as our task for the coming year to remedy them. If we do this, we can stand before God on the day of mercy as penitents and pray for ourselves and our nation, that we should all have the strength and ability to repair ourselves.

One who decides to undertake this challenge will have to establish checkpoints throughout the year, maybe on Yom Kippur Katan (the day before Rosh Chodesh) every month.  He will then assess whether he is succeeding in his task, coming close to it, or, God forbid, remaining stagnant or moving away from it. At each assessment, he will have to determine what he must do to improve his performance.  Come the next Yom Kippur, he will evaluate where he succeeded and where he did not, what he should continue to work on and what he can add to his mission for the subsequent year.


In anticipation of the holy day, we should remember the vidui, confession, which is the primary mitzva of the day. True confession is not trivial. The words of vidui are too general and vague; as such, there is a concern that by saying them we add the sin of insincere confession to the list. The author of the Chayei Adam sensed this, and added a long list of specific sins in alphabetical order. But what is the point of reciting a list of sins written by someone else, even if the author was a great and saintly person?!

We all must devote time to dig through our past and make a list of all the sins we remember. We should arrange them alphabetically and say them along with the vidui in the siddur. How many times were we careless when driving? How many times did we “steal” another car’s turn at the intersection? How many times have we ignored asher yatzar (the blessing made upon exiting the restrooms), and so on?

The recognition of sin is an important step even if we cannot get ourselves to the point of total remorse. However, it is an important step only if we have a real desire to improve, even if we know that right now we cannot expend so much emotional energy on our endless sins.

The Ten Days of Repentance

A final point: Logically, the Ten Days of Repentance should have been at the end of the year and not the beginning, as they repair last year’s sins.  They are like a makeup test to improve our grades for the year that just passed.

Yet, the Days of Repentance are put at the beginning of the year. Repentance is return to, not returning from. Its essence is not an escape from sin, as important as that is, but a return to God. We begin the new year by saying how essential it is to return to God, to be close to Him, without having our sins separate us from Him.