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Kol Nidrei is one of the most powerful tefillos of Yom Kippur. What is the significance of Kol Nidrei? On a purely halachic level, it is one form of hataras nedarim, nullification of a vow. Why does this play such a central role as we are about to enter Yom Kippur? There are different approaches in the meforshim to this question. The Rav zt”l developed the following idea[i].

The Rav explained that the central idea behind hataras nedarim is the declaration of remorse, of charata, for having made the vow.

Through the recognition that the original act was in effect a mistake, the vow is nullified retroactively. The Torah provides the authority to change his intention of vow from willful to accidental on the basis of his present understanding rather than on the basis of his state of mind at the time the vow was spoken.

We see that charata is essential to hataras nedarim.

The Rav goes on to explain that this is exactly the idea behind teshuva. The central part of teshuva is charata, we are acknowledging that the sins were done impulsively. I was not thinking when I did the aveirah. If I were thinking clearly at the time, I would not have done the aveirah. The aveirah does not reflect my present value system. This is what we are doing in the process of teshuva. So, when a Jew is hearing and reciting Kol Nidrei, he should be thinking that just like a person has the ability to have full charata to be matir neder, a person also has to have full charata for one's aveiros and in that way to do teshuva.

This is a very powerful message. A Jew has to say to himself- How can I have possibly done that aveirah?! Hashem, I must not have been thinking clearly when I did that aveirah. Hashem, please, I am doing teshuva now. I was not thinking clearly. As the Rav writes, “The way I acted does not represent my present value system. Please accept my teshuva just like the Torah gives the authority of hataras nedarim.” Had I known then what I know now, had I been thinking then like I am thinking now, there is no way I would have even done the aveirah.

This is a beautiful p'shat. Based on this p'shat, Kol Nidrei takes on a broader, more far reaching significance. The words of Kol Nidrei focus on hataras nedarim, but the message of Kol Nidrei focuses on doing teshuva for all of one's aveiros.

[i] This can be found in many places of the Rav's writing. One is 'Rabbi Soloveitchik on the Days of Awe' page 73-74, 116-117.