The Power of Yom Kippur & Ascending the Spiritual Ladder

Everyone has shortcomings and mistakes that require teshuva, the spiritual repair known as “repentance. The possibility of teshuva was granted to the world as a gift, and comes from profound Divine compassion. The way teshuva actually works is something that defies logic or human comprehension. Teshuva is also counted as one of the constant mitzvot that is incumbent upon everyone. King Solomon says, “For there is not a righteous man upon the earth who does good and does not sin.” (Eccles. 7:20)

Let’s say that a person completely breaks something belonging to another. According to halacha, in most cases, a replacement would need to be purchased, since the original is irreparable and lost. This is not the case with teshuva, which involves the ability to fix the actual thing broken in the first place.

According to the Talmud, if one’s teshuva is based on fear of sin, then the deed is considered unintentional. However, if one does teshuva and returns out of love, the misdeed itself is transformed into merit, and actually counted as a mitzvah. How is this possible?

The possibility of such a transformation comes from HaShem’s compassion on the world. Our sages identify the great potency of teshuva as coming from the fact that it preceded the creation of the world, when everything was good and perfect. If it would have come into existence after creation, it would have been irrelevant, since when something is broken beyond repair, that should be it. Yet, regarding the damage caused by our actions, HaShem preceded the illness with the cure. He created a world dependent upon teshuva, since there is “not a righteous man upon the earth who does good and does not sin.” In order for the world to function, teshuva needed to predate creation so that the moment a person damages or destroys something, a remedy is already waiting.

There is also one day of the year when HaShem repairs the past and purifies us, erasing all that is undesirable. The essence of the day itself atones not only for many intentional sins, but even for certain things done by someone who is completely unaware it is Yom Kippur and does not observe the day!

Yet, according to Rebbe Nachman, teshuva is ongoing. It is usually understood that when you know you did something wrong, as long as you take upon yourself not to repeat it, the issue is considered closed. However, Rebbe Nachman explains that teshuva is not a one-time event. An even higher level of teshuva is required, despite the fact we already did teshuva on a particular action. We need to return to it again and repent on yet another level.

On Yom Kippur, there is a special mitzvah to confess, and there are ten different times we confess wrongdoing in the order of the day’s prayers. According to Jewish law, we not only verbally confess transgressions of the current year, but from the previous year as well, despite the fact that we already repented last year on Yom Kippur. This Yom Kippur there is still a mitzvah to do teshuva again by confessing anew everything that happened in the past.

Why do we have to dig up the past and confess all over again, particularly when we already did teshuva for it? Rebbe Nachman explains that when you verbally admit, “I sinned, I transgressed,” etc., it is very difficult to say these words with a completely pure heart. In other words, teshuva must be done on our first teshuva, when our hearts were less pure.

This is alluded to in the verse, “They honor me with their lips, but their hearts are far from Me.” (Isa. 29:13) When you admit your wrongdoing and take upon yourself to be better, you become worthy of kavod HaShem, [a level where you are encompassed in the honor of HaShem]. Kavod HaShem is attained through nullifying your ego and being concerned solely for the honor of heaven. When teshuva is done from this place, honor is “restored” to HaShem.

Still, the rest of the verse says, “…their hearts are far from Me.” Even when you already did teshuva, repentance is still necessary for your previous teshuva, since it was done only according to your understanding of HaShem’s greatness at the time. When you ascend to a higher level afterwards, your mind becomes more purified, and you comprehend HaShem’s greatness at a completely different level. Even if you initially understood that HaShem is extremely great, your conception was still limited, since if you had understood at a higher level, you wouldn’t have transgressed in the first place. Relative to your current more spiritual level, your previous understanding is now considered “physical” because it limited the greatness of HaShem in your heart and mind.

To illustrate, say an ordinary person is sitting in synagogue and someone passes by and unintentionally trips over him. The one who tripped immediately says, “I’m so sorry! It was an accident!” Contrast this with another scenario. Instead of an ordinary person, this time he accidentally trips over an important person so forcefully that that person falls off his chair. Now, a completely different level of apology is needed, since not only is it a more distinguished person, but the force of the blow is much stronger than in the previous example.

This is similar to our situation with HaShem. To the extent we realize His greatness, we understand that every transgression has a much deeper impact than initially thought. Likewise with our example, the level of requesting forgiveness is much different between the insult of an ordinary person, or someone who is greater. Likewise, the more you understand the greatness of HaShem, the more you understand how even a seemingly small thing is an insult to His honor. The request for pardon must be commensurate with our current level of understanding. As we progressively raise ourselves up, we will experience an increased understanding of the enormity of our misdeeds. They now will require a new teshuva, demanding more of our heart and mind.

Teshuva becomes even more subtle the higher you ascend spiritually, since it will begin to involve the thought process itself. A level can be reached where the teshuva is not so much on the transgression anymore, as our actual thought and misconception that HaShem is limited in some way. We may intellectually understand the idea that HaShem’s greatness is unlimited, but our hearts are not yet sufficiently purified to feel it. We may say the words by rote, as described in the verse, “With their lips they honor Me,” but our heart doesn’t comprehend the true meaning of God’s limitless nature, thus, “…they are far from Me.” To the extent we are unable to understand the infinity of the Divine, we are in effect placing a limitation on the honor of HaShem in our hearts and minds. This is what requires teshuva. For this reason, according to Rebbe Nachman, in order to progress step by step up the spiritual ladder, one must constantly hold onto the attribute of teshuva.

The entire dynamic of teshuva is intrinsically connected to the world to come, when it will be completely Shabbat—all teshuva. The connection between Shabbat and teshuva is alluded to in the verse, “…and you shall return to the Lord your G-d…” (Deut. 30:2) “You shall return” is v’shavta, the same Hebrew letters as the word, “Shabbat.” When will this return happen? It will occur in olam haba, the world to come, when it will be only Shabbat. Olam haba is defined as a progressive attainment of knowledge of HaShem, where each of us will perceive HaShem at our own level. And then, every time you come to a greater level of understanding, teshuva will be required on your previously more limited understanding. The nature of olam haba is the continual attainment of a greater understanding of HaShem. We will then fulfill the verse, “…and you shall return to the Lord your God.” Shabbat and teshuva will be one.

The profound connection between Shabbat and teshuva is quite relevant today. We rest on Shabbat, but what is our true purpose on this holy day? Any thoughts of our own wrongdoing must be brought to a state of rest so there will not be even a hint of improper deed or a damaged world on Shabbat. However, while Shabbat is a time of teshuva, it is not a time of confession. It is a time for spiritual ascent and elevation. So how is teshuva done without confessing? On Shabbat, teshuva is based on understanding rather than confession; it is accomplished when you come to a higher understanding of the greatness of HaShem and then do teshuva on your previous understanding. This is what will define our olam haba, but we can also attain this now on Shabbat. Such is the power of Shabbat, and this opportunity recurs every seven days.

Generally, when a person senses the seriousness of their situation after doing something wrong, teshuva is done with a broken heart. But there is another aspect to teshuva not commonly discussed. We witness on Yom Kippur how some people appear sad and may even weep in their efforts to do teshuva. They find it difficult to greet others during the course of the day, since they think it will detract from the seriousness of the holy day. However, truthfully, Yom Kippur should be the happiest day of the year, since it is a day of total forgiveness. We confess, and HaShem forgives and erases all of our undesirable deeds. We can dance from joy the entire day that such a thing is occurring. This positive attitude should also be conveyed at home to our families every year. Who needs to eat on such a day? We are like people in olam haba who have no need to eat or drink. This joyful attitude has practical relevance as to how to experience Shabbat as well, since teshuva and Shabbat are deeply connected.

Rebbe Nachman gives further definition to teshuva. When you want to embark on the path of teshuva, you need to be expert in the “going.” Two types of expertise are needed here: One in the running (ratzo) and one in the return (shov). This concept is alluded to in the vision of the prophet Ezekiel [1:14] where he describes how the angels were “running and returning,” as they served and praised HaShem.

The same concept applies to us. In the evening prayer, we say the blessing of hashkiveinu, where we ask, “…and remove the satan from before us and from behind us.” Sometimes when you begin something new in your quest for holiness, you experience such great enthusiasm together with expectations far beyond your actual capabilities. This is merely another strategy of the yetzer hara to set you up for a big fall when you don’t meet your unrealistic expectations. This is what is referred to in the verse, “Remove the satan from before us and from after us.” “Before us”—before we charge ahead to accomplish our goal. “Behind us”—afterwards when we fail to meet our expectations, and everything comes tumbling down where we are unable to do the things even within our power. A person needs tremendous Divine compassion at this point.

Failure to achieve a desired result after unrealistic expectations (or even realistic ones), should be your signal to guard yourself against becoming weak or falling. When you start something with good intentions and desires, be happy with whatever you accomplish; don’t fall into frustration or despair. It helps to know this in advance, when you are “running.” Then afterwards, during the return, you will be able to protect yourself from falling into a low place, and you’ll be able to renew your strength once again. If it didn’t go this time, so try again with more realistic expectations.

There is yet another aspect to the concept of “running and returning.” Rebbe Nachman explains that it is a zechut when you are able to both enter and exit an endeavor in the right way. King David describes running and returning in the verse, “If I ascend to the heavens, You are there; if I go down to the depths, You are there.” (Psa. 139:8)

The first section of the verse refers to when you undergo a spiritual ascent and feel as if you were in heaven, close to HaShem. This can happen after teshuva or when you see how much HaShem helped you beyond your wildest expectations. Yet King David sharpens the idea further as if to say, “Listen well, if you go to heaven, You are there.” There meaning not here. In other words, HaShem is still far from you. You need to come yet closer to HaShem, since He is “over there,” far away, so don’t bask in the feeling that you have already arrived at the ultimate level. Even if you ascend to heaven, know that it is still far from you. Strengthen yourself and your good aspirations to strive even higher, since you haven’t yet “made it.” There is still much more work ahead to come closer to HaShem.

The second part of the verse refers to when you experience a fall so great that you feel as though you’ve fallen into a pit—into sheol—a place much deeper in the earth from where people normally walk. You can become saddened even without a specific reason. The yetzer hara works overtime to give you a feeling of worthlessness. He can convince you that you’ve completely fallen into the lowest of depths, with no ability to pick yourself up. King David writes that this is where HaShem says, “Here I am. I am here in the deepest pit together with you. Let’s ascend together.”

You can say, “Ribono shel Olam! I made a mistake, but You are here with me wherever I have fallen. I want to raise myself up.” HaShem will immediately give you the strength to ascend. You can feel HaShem in this way, and derive strength to get up again. This is the way of teshuva.

Don’t let the temptations of the yetzer hara drag you into feelings of worthlessness and despair. The yetzer hara will give you a good feeling at first, only to trip you up later by making you feel like nothing, draining you of the strength to stand up. Rampant thoughts fill your mind: “You really messed up this time. Don’t you know yourself already? You’ll never change, so who do you think you are to try to get up again…” Don’t become overly emotional or despair out of proportion, since if despair doesn’t exist, according to Rebbe Nachman, then it doesn’t exist regarding any fall or failure.

Now it can be understood why expertise in “running and returning” is needed. Progress must be made step by step. While you are running and ascending, appeal for Divine compassion that you shouldn’t fall, but if you do, that you have the strength to get up immediately again and again. This is the wondrous expertise that Rebbe Nachman is teaching us.

The secret of teshuva was created before the creation of the world out of Divine compassion. Because of this, we have the ability to strive continually to come closer to HaShem. Know that HaShem is always waiting for our teshuva.

Hashem should help each of us to return in teshuva shleima. We should merit to feel Hashem’s closeness throughout the entire year, and draw all good influences upon ourselves, the Jewish people, and the entire world. For this will be how we will bring the complete redemption and the beit hamikdash very soon, in our days. Amen. ♦

Translated and adapted from a talk given from Tsfat to a group in Sydney, Australia. Lesson based on Likutey Moharan 6.