You keep count of my wanderings; put my tears into Your flask, into Your record. (56:9)

This verse is reminiscent of the central metaphor of Rosh Hashanah – that God keeps a record of our “wanderings.” The Jewish path of behavior is called halakha. I imagine that wandering might represent our straying off the path of halakha.

The High Holiday amidah, in a section called “unetaneh tokef,” suggests that through teshuvah, tefillah, and tzedakah – repentance, prayer, and giving, we might lesson the severity of the decree against us. The first two items on the list, repentance and prayer, go hand in hand with tears.

In order to repent properly, one has to virtually break one’s heart. If we have committed some kind of harm against another person, in order to make amends we need to absolutely feel the pain that we caused. An apology should be felt in the kishkas … we have to feel as if we caused a rip in the fabric of another person’s universe, which is precisely what we did when he committed the harm. The tears are the tearing of the fabric of our own universe experiencing the pain of the other.

Prayer is only effective for the purpose of lesson a Divine decree against us when it pours forth from a broken heart. Prayer is meant to be a transformative experience. We ought not to ask for a gift on a silver platter, but rather ask the Divine Blessed One to help us realign ourselves and become the person created in God’s image that we were meant to be. These are the tears that I shed in the process of changing my fate, that I’d like to be entered into the record.