The key to Repentance

A spiritual tool to achieve lasting change, even after Yom Kippur is over

By: Rabbi Dovid Samuels

So Close

It says in the Torah[1]: For the mitzvah that I command you today is not too difficult for you, nor is it far from you. It is not in the Heavens, that you say, “Who will ascend for us to Heaven and get it for us, and teach us and we will do it?” Nor is it on the other side of the sea, that you say, “Who will cross the sea for us and get it for us, and teach us and we will do it?” Rather it is very close to you, in your mouth and in your heart to fulfil.

The Ramban explains that this mitzvah is referring to the mitzvah of teshuva, repentance, which was being discussed in the verses just before this one. This means that the mitzvah of teshuva is very close to us; not just close, but karov meod – excessively close to us.


The Meshech Chochma[2] explains using a fundamental principle learned from the Chovos Halevavos that the Creator, when He made the world, made it that everything that was most necessary for survival was produced in abundance and required little effort to obtain. For example, the most vital thing for a person is air – oxygen – and Hashem made it that air is very easy to access and it is found in abundance. After air, a human being needs water, and so Hashem made it that water is in great abundance and it is also very easy to access, although more difficult to obtain than air. After water, food is vital for our existence, but less so than air and water. Therefore, although it is in abundance, it is still harder than water to access. After that we have things like housing which, although the resources are in abundance, more effort is required to build a house than to produce food. Likewise, a child immediately upon birth is dependent on mother’s milk for survival and the mother, in most instances, is able to produce this milk for her child’s survival instantly, in abundance, with minimal effort. Only when a person pursues the things which are not critical for his survival – the “extras” over that which is necessary – does a person encounter more difficulties in obtaining those things, and he will find that they are harder to achieve and in less abundance.

Default Setting

The default state of man is that he knows what is right and wrong and that he knows what is beneficial or dangerous to him and his health, as this knowledge is critical to his survival. If a person would only remove all of his foreign desires from himself, he would find, carved in the depths of his being, pure love for that which is good. This is the default status of man: that, within him, the most critical and vital knowledge is in the most abundance. Chazal[3] teach us that the soul of a person will testify against him on the Yom HaDin – the Day of Judgement; that the soul itself will feel the iniquity that was performed by the body while it was alive. This is because his soul will feel the effects of the sins that he did while he was alive and the contrast between that default state of pure goodness and the foreign state of following false desires will be extremely noticeable. We also have a default understanding of G-dly awareness, to know that there is a G-d who created everything, and that is engraved in our soul. With this idea, the Meshech Chochma explains why the Torah refers to the mitzvah of teshuva as very, very close to a person. It is the default setting and it is engrained inside of us; and it is in abundance with easy access, as it is critical to our (spiritual) survival. To obtain air one needs only to open his mouth, but to tap into the concept of teshuva one need not even open his mouth. It is the default setting of the Jew; to be able to access the relationship that always exists between Hashem and His children.

A Tzaddik for your Thoughts

We find an example of this in the story in the gemara in Avoda Zara 17a regarding Rebbi Elazar ben Durdaya who transgressed many aveiros, but when it came time to repent he put his head between his knees and cried out until his soul left him. At that moment, a Heavenly voice came out and proclaimed that Rebbi Elazar ben Durdaya was invited to life in Olan Haba. Rebbi, upon hearing this, cried, and said there are people who can acquire their World in many years, and there are people who can acquire their World in one moment. Then Rebbi said: “Not only is the repentance of a Baal Teshuva accepted on High, but he is also called Rabbi!” Now, all this man did was put his head between his knees and cry out to Hashem and his repentance was accepted; so much so that he was invited into the next world. More than that, he was referred to as Rabbi, because he taught everyone else how to do the mitzvah of repentance, and how easy and natural it actually is. A Jew is naturally close to Hashem, but the act of sinning distances him from his Creator, but the thoughts of repentance, going back to the default setting where a Jew is close to his Creator, removes that distance created by sin. Teshuva is the resetting and returning, coming back to the close relationship that we naturally have with our Father in Heaven.

Breaking the Habit

This is all good if a person dies amidst teshuva, like in the story up above of Rebbi Elazar ben Durdaya who died in the middle of his repentance, but for us – who are hopefully still alive after our expressions and thoughts of repentance – how can we be sure that our behaviour and habits will change after our repentance? After our teshuva we remain in a dangerous position of potentially sliding back into the same behaviours that got us into trouble in the first place. How do we change, and stay changed after teshuva?

Rav Tzadok HaKohein teaches us[4] that when a person does teshuva, a Divine light envelops him and it brings down Heavenly help from Above to aid him in changing his ways that he should not slip back into his old behaviour. But Rav Tzadok asks: how come we see so many people pouring out their hearts in repentance, but falling back into their old habits immediately afterwards? To this he answers that, at the time when a person is performing the mitzvah of teshuva and is, as mentioned above, relying on Divine assistance in this holy task, there is a powerful mekatreig – prosecutor – who attempts to restrict and block the Divine influence assisting his repentance. So, how does one avoid this mekatreig – this prosecutor? He answers that the simcha and security a person feels when repenting, stemming from the knowledge that Hashem will definitely accept his repentance, is the antidote to this prosecutor’s efforts to stop the Divine assistance. With the mekatreig out of the way, the Divine influence from the mitzvah of teshuva will allow this person to change and break free from even his most ingrained habits and behaviours.

As the Baal HaTanya writes[5] that the fact that we make a brocha in Shemoneh Esreh that Hashem is gracious and abundantly forgiving, we are showing our absolute belief that He will accept our repentance. For, if there was any doubting this, we wouldn’t make that brocha, as we don’t make a brocha in a situation of doubt.

Impossible? For us

Taking this idea a step further, the Me’or Einayim[6] explains that whenever a person is attempting to arouse Divine assistance and bounty, there exists this prosecutor – mekatreig – to see whether the person is in fact a valid recipient of this bounty from Above. This is like a person asking for a loan. The bigger the loan, the more he will be scrutinised by the lender if he can be trusted, and the more guarantors will be needed to secure the loan. Likewise, when we do teshuva, and we are expecting to arouse Hashem’s assistance in making sure that the repentance is full, pure, and long-lasting, there is a very strong mekatreig that scrutinises us, the hopeful recipients of Heavenly influence. And to break habits, we are in need of a lot of Divine assistance. Knowing this, that we are relying on so much help and we are fighting against the scrutiny of the mekatreig, the only advice is to pray. To daven to Hashem that He remove the impediments, that He grace us even if we do not deserve it, and He shower down Heavenly help to allow us to break the heavy shackles of habit.

This teaches us that a fundamental aspect of teshuva is prayer. By applying both the words of Rav Tzadok and the Me’or Einayim together, a powerful and critical tool in our repentance is praying with joy; joy that Hashem listens to our prayers, that He answers our prayers, and that He wants our repentance to be true and long-lasting. With our joy and trust that Hashem will help us in our repentance, the mekatreig will be bypassed and we will truly change, even after Yom Kippur is over.

Still, so close

Even though teshuva is so close to us – even inside us – we still need to daven from the depths of our hearts that the teshuva is received on High appropriately, and that the prosecutors against us receiving Divine help are silenced. As we embark on the mitzvah of teshuva, we need to know that to uproot our prior behaviours and to change our patterns and habits is a massive endeavour. It is far above us to achieve this alone, and the only way to effectively succeed is to have help from Hashem. We need to pray to our Father in Heaven for help in this mission, for without His assistance it is an impossible task. With this in mind, Hashem should answer all of our tefillos, that we have help from Above to really change, to break our habits, and return to our default settings: a true and everlasting closeness to our Father in Heaven.

  1. Devorim 30:11-14
  2. Parshas Nitzavim
  3. Taanis 11a
  4. Tzidkas HaTzaddik (129)
  5. Iggeres HaTeshuva chpt. 11
  6. Parshas Chayei Sarah

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