Reflect, repent, but don’t berate yourself

Virtually all Jewish holidays revolve around an historical event. And our mandate on each holiday is not merely to remember that such an event once occurred, but to reenact that event and relive it annually ourselves. For example, at the Pesach seder, we eat bitter herbs and matzah, recline, drink four cups of wine, and more, all toward the goal of ultimately feeling as though we ourselves are marching triumphantly out of Egypt. On Sukkot, we literally move our tables, and often even our beds, into our own portable tabernacles to feel our closeness with and dependence upon God. Yom Kippur is anomalous in that it seems to lack any historical context. There is no reenactment, no fun foods to eat, or dramatizations to keep the kids (and the grownups!) awake and engaged. It is too austere and solemn a day for that, a no-frills day to spend hunched over in prayer, beating our chests for our wayward behaviors.
But maybe not.
Though the Torah never explicitly links the observance of Yom Kippur with any specific moment in history, the date on which the Torah commands us to observe Yom Kippur is way-too-coincidental for it to be merely a coincidence. If one calculates the chronology, as Rashi does in his commentary to Exodus 33:11, it emerges that the tenth of Tishrei, the date of Yom Kippur, was the very day on which Moses came down from Mount Sinai with the second tablets! The giving of these tablets was God’s way of signifying to the Jewish people that He had forgiven us for the most egregious sin in our history, the Sin of the Golden Calf. Clearly, there could hardly be a more appropriate phenomenon to invoke on Yom Kippur, as we beg God to forgive us for our sins. That is certainly true, but I posit that the significance of the connection is far more profound.
I would suggest that just as on Pesach, we relive the Exodus from Egypt, and on Sukkot, we reenact our dependence upon God in the Wilderness, on Yom Kippur, we take on the persona of Moshe Rabbenu and re-experience the most intense Divine-human interaction that has ever taken place.
I used to envision the giving of the second tablets as God essentially throwing up His hands much as the exasperated parent of an incessantly begging 3-year-old might, and saying, “Fine, I’ll give you another set of tablets.” However, an examination of the biblical narrative reveals that nothing could be further from the truth. God did not dismissively hand over the second tablets with a frustrated divine eye-roll. Quite the contrary. He chose to bestow the second tablets in the midst of what was arguably the single greatest moment of divine revelation in the history of the world. The verses describe how God placed Moses in the cleft of a rock, personally protected Moses by covering his face with His own divine hand, and then removed His hand so that Moses could glimpse God’s back (Exodus 33:21-23). Never before or since has a human being been granted such intense, up-close access to the Divine. In fact, the experience is so altering that Moses’s face literally glows in its aftermath, such that he must wear a mask when interacting with the Israelites afterwards (Exodus 34:29-35).
And the content of what God reveals about Himself during this interaction is unsurpassed in its intimacy. At Sinai, God revealed of Himself by sharing His laws, but here, during the revelation accompanying His granting of the second tablets, He discloses His Thirteen Attributes; in other words, here He reveals His qualities, His personality, so to speak!
This encounter of intense closeness and intimacy with the Divine, then, is the historical experience that we strive to recreate every Yom Kippur.
The climax of Yom Kippur when the Temple stands is when the High Priest enters the Inner Sanctuary, where the Divine Presence is most intensely concentrated — the singular day of the year when this is permitted. And this experience of approaching God is not unique to the High Priest. I would suggest that the practices of Yom Kippur are designed so that each and every one of us feels as though we are Moshe Rabbenu glimpsing God from the cleft of a rock.
Throughout the prayers of the day, we repeatedly cry out God’s Thirteen Attributes of Mercy. This is not merely at attempt to invoke a magical formula guaranteed to vouchsafe divine pardon, but rather a recreation of the moment when these attributes were revealed on this very date all those centuries ago.
More strikingly, the most prominent mitzvah of the day is refraining from food and drink. We tend to think of this as expressing our desire to be angel-like, to remove ourselves from physicality and focus on our spiritual essences. However, one of the miraculous aspects of Moses’s time in Heaven was “lechem lo achal u’mayim lo shatah — He didn’t eat bread or drink water” all 40 days (Exodus 34:28). I am convinced that our fasting on Yom Kippur is part of our aspiration to transform ourselves into Moses encountering God on this day. Similarly, we refrain from wearing leather shoes – just as Moses was instructed by the Burning Bush, “Shal ne’alekha me’al raglekha — Remove your shoes from your feet” (Exodus 3:5). In fact, the Talmud (Berakhot 62b) derives from this verse a general prohibition against ever wearing shoes on the Temple Mount. Shoes must not be worn when in the presence of the Divine, and the Divine is intensely present everywhere on Yom Kippur. Likewise, marital relations are forbidden on Yom Kippur, which is strikingly reminiscent of the fact that Moses separated from his wife since he could receive prophecy at any moment (and of the fact that before the giving of the Torah, all Jews were instructed to refrain from relations with their spouses in preparation for their encounter with God — Exodus 19:15). Clearly, our observances of Yom Kippur do in fact re-enact an historical event, just as Passover recreates the Exodus and Sukkot reconstructs the Wilderness experience. On Yom Kippur, we recreate and relive the most intense Divine-human interaction.
This perspective transformed my own experience of Yom Kippur. It is no longer a somewhat depressing day of self-flagellation. Yes, introspection and repentance are a key component. But they are not the end-goal. They are rather critical steps along the way to being equipped for and worthy of what the essence of this awesome day is truly all about — an incredible opportunity to experience an intense sense of closeness with God.