One of the beautiful ideas behind Rosh Hashana and Yom Kippur is the notion that we need to reflect, review, and rethink who we are and what we have achieved in our lives. We should never see who we are and what we have created as the ultimate expression of who we ought to be. There must always be a gap between who we are and who we ought to be, between reality and our aspirations. When our aspirations are fulfilled, there must be something wrong with our aspirations.

This is the fundamental idea behind teshuvah and its challenge to us – to embark on a process of self criticism and self reflection. To embrace teshuvah is the ultimate aspiration of our humanity, for the highest level that humans can achieve is not one of fulfilling all our values, but of constantly maintaining a tension in which goals serve as a foundation to evaluate the lives we have created and to challenge us to move forward and beyond.

An expression of this idea is found in the Biblical depiction of heroes, all of whom are imperfect. We are never given a hero who embodies everything. Sometimes it’s embarrassing. The biblical heroes seem too human – permeated by too much imperfection. The Bible is teaching us that being a hero doesn’t mean that one is devoid of imperfections; it means that one must do something about those imperfections.

By elevating these people to be our ideal, it challenges us to emulate them. You are going to fail like Moshe or Avraham. You are going to sin like David. There are going to be multiple dimensions of your life, whether it’s in your worship of God, with your spouse, or with your children, where you’re not going to be who you ought to be. Welcome to the human story. Our religion has no fantasies about human beings. It has aspirations from human beings.

For human beings to embody the aspiration of self criticism and reflection, it is not only the individual who must be open to change but also the societies within which we live. People around us often want us to remain who we are are. People don’t want us to change. They have gotten used to and comfortable with our imperfections, for it gives legitimacy to theirs.

Some Rabbis in the Talmud were deeply worried about the social pressure to maintain mediocrity and lock everyone within the status quo of their failings. As a result, in Tractate Baba Kama 94b we find the following teaching:
It once happened with a certain man (thief) desired to repent and make restitution (to those from whom he stole). His wife said to him: Fool, if you are going to make restitution, even the clothing which is on your back would not remain yours. He consequently refrained from repenting. It was at that time that it was declared: If robbers or usurers are prepared to make restitution, it is not right to accept it from them, and he who accepts its does not obtain approval of the Sages.
A thief’s desire to complete his or her process of self-correction by making restitution is clearly understood and valued. The problem is that this standard may inhibit them from beginning the process. A lifetime of harm cannot be erased and as a result may lock us in our imperfections under the argument that one can never really begin again. “Fool, if you are going to make restitution, even the clothing which is on your back would not remain yours.”

In response the rabbis teach that we have a responsibility towards each other to enable these new beginnings. A Jewish society is one where we make sure that reflection, self-criticism, self-evaluation, and the ability to accept new horizons and new ideas are things society fosters and encourages, even at a high cost. We are individually responsible not to merely refrain from hindering each other’s growth, but that we must be willing to forgo what is rightfully ours in order to ensure that our fellow citizens will grow and change.
A Jewish society is not simply characterized by a high level of kashrut or Shabbat observance. A Jewish society is one where we allow others to do teshuva, where we are not threatened by others’ desires to move in a new direction. A Jewish society is one which understands that to be fully human is not to accept our failings; to be fully human is to aspire to overcome them.

Shana Tovah to us all.