In the days and weeks leading up to Rosh Hashana and Yom Kippur, the Days of Awe, the concept of Teshuva (repentance) takes center stage in the Jewish mindset. For an entire month before Rosh Hashana, many rise before dawn to recite prayers and supplications which are designed to arouse the congregation in repentance. These services reach their crescendo on Yom Kippur, a holiday whose entire motif is that of repentance. Yom Kippur is, as Rabbi Jonathan Sacks writes, “the holy of holies of Jewish time. It is that rarest of phenomena, a Jewish festival without food. Instead it is a day of fasting and prayer, introspection and self-judgment when, collectively and repeatedly, we confess our sins.” (Democratized Holiness: Yom Kippur and Moral Responsibility) The questions that arise during this time of the year are many, chief among them: What is the nature of sin? How does repentance go about reversing the consequence of it?

The first encounter with the concept of sin in the Torah takes place with the story of Adam and Eve eating from the Tree of Knowledge, and subsequently being cast out of the Garden of Eden. Rabbi Abraham Isaac Kook, the first Chief Rabbi in Israel during the British Mandate period, offers a fascinating explanation and lesson to this story. Rav Kook teaches that since all of mankind was created in the divine image, we all innately know the proper path to follow and therefore should not be coerced by external forces to go against our true selves. He writes “Adam’s sin was that he was alienated from his selfhood, for he followed the opinion of the serpent and lost himself… and he could not give a clear answer to the question “Where are you,” for he did not know his own soul…”(Orot Ha-Kodesh 3:97). Elsewhere, Rav Kook also expounds on the purpose and process of ideal repentance. He writes, “The primary role of Teshuva… is for the person to return to himself, to the root of his soul.” (Lights of Penitence 15:10). The essence of Teshuva, in the view of Rav Kook, is that a person should realize that they have strayed from their inner self and begin the journey of returning to who they really are.

A beautiful story expresses this very idea. Once there lived a scholar named Rabbi Isaac Yekls of Krakow, who lived in dire poverty. Over the course of a few nights he had a series of dreams in which he was digging for treasure in Prague under the bridge that led to the king’s palace. After the fourth consecutive dream, he decided to set out for Prague to try to change his fortunes. But when he arrived he found that the bridge was always guarded, and he dared not to dig out of fear of being caught and apprehended. Finally, the Captain of the Guards, who had been watching him for some time, asked him of his business by the bridge. Rabbi Isaac told him of the dream that had brought him there. The captain laughed, “Because of a dream, you poor fellow, you wore out your shoes to come here?! Why, if I paid any attention to dreams, I would have had to get going when a dream once told me to go to Krakow and dig for treasure under the stove in the room of a Jew, Rabbi Isaac Yekls.” Rabbi Isaac bowed, traveled back home, and dug up the treasure from under his very own stove. When a person decides that they want to change, they need not travel far because what they are looking for oftentimes is very close at heart.

And so we come to Yom Kippur, a day entirely devoted to Teshuva and returning to our true selves. Part and parcel of returning to who we are involves taking stock and objectively looking at our lives and accomplishments over the past year, and using that to determine where we want to go in the future. In doing this, we must confront both our successes and our failures and make a true assessment of ourselves and our actions. And though it may be unsettling to face shortcomings, it is actually this “head-to-head” encounter that allows us to let go of the guilt and instead embrace the positive. This is why many feel that Yom Kippur and Teshuva have a uniquely therapeutic quality to them. Rabbi Abraham J. Heschel famously said about repentance and Yom Kippur, “We are all failures. At least one day a year we should recognize it. I have failed so often; and I am sure those present here have also failed. We have much to be contrite about; we have missed opportunities. The sense of inadequacy ought to be at the very center of the day… to put contrition another way, develop a sense of embarrassment… It would be a great calamity for humanity if the sense of embarrassment disappeared, if everybody was an all-rightnik, with an answer to every problem. We have no answer to ultimate problems. We really don’t know. In this not knowing, in this sense of embarrassment, lies the key to opening the wells of creativity. Those who have no embarrassment remain sterile”. (Rabbi Abraham Joshua Heschel-Yom Kippur) Teshuva, therefore, is the opportunity to return to a healthy sense of self, imperfect as we are.