One of the most difficult aspects of teshuvah is figuring out what to leave behind and what to carry forward with us. Do we simply write off past failures and press the reset button? Or do we enter into the new year with full consciousness of our failings and preemptively try to address them for the future? We will explore this question through an analysis of the history of Kol Nidre, one of our most famous and confusing pieces of liturgy.