One of our human tendencies in thinking about changes we wish to make in our conduct and in our emotional responses is to imagine that we can begin anew – and to be repeatedly disappointed. In Jewish religious language, we reinforce that absolute tendency with sources such as Mishna Yoma 8:9 “He who says that I will sin and repent, sin and repent, is not provided with an opportunity to repent.” We demand that our repentance not fail.
However, that mishna actually carries the opposite message. It warns against acquiring a sinful habit precisely because sinful habits are hard to break. Such habits become entrenched as they meet emotional needs. As “R. Huna said: Once a person has sinned a given sin repeatedly, that sin becomes permitted to him” (Yoma 86b and parallels). Bad habits are hard to change.
So, how do we eventually change? One answer is by beginning again instead of beginning anew. Every New Year we follow a period of intense repentance with a new read of the same book, the Torah. Instead of reading a work that will provide a new outlook, we read the same stories and the same laws through our same personality eyes. As we re-read that which we know we discover the new insights that we always knew. This is a message of Simhat Torah. Our souls are like Torah scrolls (Moed Katan 28a) that grow when we return to our true selves instead of by seeking new selves. We improve ourselves in those areas of life to which we are drawn with joy to our truer selves (Rav Kook, Orot HaKodesh 3:124,338) and change our bad habits in slight ways that we do control (R. Dessler, Strive for Truth 2:53). We keep discovering that we can change our habits a bit more. One day that we even discover that we have lost bad habits.
All because we did not strive to begin anew; we strove to begin again.