Three questions about the confessions of sin we recite on Yom Kippur - included in all five of the prayers of the day - had been bothering me for years until a conversation with my wife Elana last year opened my mind up to a totally new perspective that sheds light on the whole concept of Yom Kippur itself. Here are the questions:
1 - Why are the words in the confession so generic ("we have been guilty, we have rebelled, we have been unjust, etc.") instead of specific?
2 -How can we confess for all of these things when we clearly haven't committed, let alone repented, for all of them?
3 - Why does the Rambam say that a person who has repented and confessed his error on one Yom Kippur can go back and do so again, despite the fact that he has not wavered in his repentance and has no new infraction to confess?
Overall, there is an even more general difficulty - how can the Rambam say there is a mitzvah for everyone to repent leading up to Yom Kippur? If one committed a transgression and was required to repent for the sin, he or she should do it because of the sin, not on account of Yom Kippur. And if one has not committed a specific sin, what is one supposed to repent for before the Holiday?
These problems are only problems because we assume that the repentance and confession of Yom Kippur is focused on our personal process of self improvement and development. Because we are attempting to understand repentance and confession in that framework, it makes no sense to repeat generic confessions that are unrelated to our individual repentance process.
However, the reality is that the process of repentance we are obliged to go through prior to Yom Kippur is not primarily about correcting our individual sins and flaws (although that is, of course, a wonderful byproduct). Individualistic repentance should be done year round, whenever a mistake has been recognized it must be acknowledged and corrected. There is no need to defer it until Yom Kippur, and it makes little sense for there to be a "deadline" each year for the completion of our self-improvement.
The theme of Yom Kippur is the general awareness of a gulf that exists between a transcendent, metaphysical Creator and His limited, physical and very flawed creations. Our acknowledgment of myriad sins is a manifestation of our awareness of how distant we are from perfection. And our individual and collective repentance at this time, although it certainly serves to improve us and our lives, also serves to highlight the existence of human imperfection in general and to contrast that with the perfection and transcendence of Hashem.
So, although personal development would not necessitate the repetition of confession - what has been rectified is rectified and requires no further discussion or declaration - our past sins, and the sins of others that we have not committed personally, are indeed relevant to our general awareness of the limitations of the human quest to know and serve God. The occurrence of these transgressions in the past, even though they may have been corrected afterwards, still testifies to the reality that we are finite creatures whose understanding and worship of an infinite Creator is necessarily filled with distortions, shortcomings and flaws. These distortions and flaws are what lead us to value the physically pleasurable and the material over the intellectual or spiritual - i.e., to commit intentional or unintentional transgressions.
This approach is clearly supported in the Torah, where we see that one of the main purposes of the Order of the Temple Service was to cleanse and atone for the Sanctuary itself, which "dwells among the Jews amidst their impurity". In other words, the very notion of human beings standing before and worshiping God must be recognized as paradoxical and deeply problematic. We cannot take it for granted; rather, we must realize that the very institution of a Sanctuary or of a way of life or system of Mitzvot that allows human beings to approach the Almighty is almost an absurdity given our physicality and consequent intellectual and moral limitations.
This "absurdity" can only be "tolerated" provided that we are well aware of the difference between our flawed conceptions of God and His worship on one hand and the ultimate reality on the other hand. We demonstrate our awareness by repenting and confessing individually and communally on Yom Kippur, all the while affirming the transcendence, uniqueness and inscrutability of Hashem throughout the prayers. Indeed, a close examination of the Temple Service, especially the entry into the Holy of Holies and the pronouncement of the ineffable name of God - and the linking of those activities, fascinatingly, to the fasting and repentance of the nation - reveals that this distinction between our limited and distorted understanding of metaphysical truth and the awesomeness of metaphysical reality itself is what is being emphasized throughout the process. To confuse the two is either to denigrate the Creator or to arrogantly lift man onto a pedestal of which he is not worthy.
(I do not mean that Hashem is unsatisfied with man's existence and wants us to feel bad - after all, He created mankind the way that it is. What I mean is that Hashem instructs us to recognize the degree to which we fall short of true knowledge and perfection, for our own sake, so that we bear the proper perspective in mind.)
On Yom Kippur, our personal process of repentance becomes the window through which we perceive the abiding reality of our own humble position in the universe and recognize the tremendous kindness bestowed upon us by our Creator. We acknowledge that despite our inability to truly know Him or live by His wisdom in the absolute sense, and despite our harboring countless illusions and distortions in our view of ourselves, our world and our God which, by pure justice, should be intolerable, He nonetheless grants us "forgiveness" and "atonement", the opportunity and the tools to engage in the lifelong process of striving for an ideal which we never more than partially attain.