Shoftim v’shotrim titeyn lecha b’chol she’arecha … You shall set up judges and officers (law enforcement) officials for yourself in all your gates … (Devorim 16:18). 

Moshe Rabbeinu is preparing us to set up a just society. Such a covenantal community requires laws, judges, and a system which ensures that the statutes of the Torah and the needs of the individual are upheld. But like so much of our beautiful Torah, there is that which is explicitly understood and that which is nuanced and contains a spiritual message of everlasting importance. And so, perhaps, in these seemingly straightforward words, the Torah is also teaching us a profound life lesson.

We all make mistakes; such is the nature of the human condition. But our mistakes, our aveiros, do not usually just “appear.” If after we sin, we were to trace our steps backwards, we would see a series of actions, often innocuous and not inherently sinful, which put us on a life direction which culminated in sin. There is the sin and the path which leads to sin. In the process of Teshuva, we often become focused on the sin itself. We take the steps to own our mistakes, apologize, pledge not to repeat – but there is often one step which is forgotten – the need to ask myself one simple question, “how did I get here?” What were the steps which led me to this point? Which behaviors, attitudes, and approaches put me on the path which led to this sinful behavior? After I ask and answer this question, I then must begin the process of creating protective boundaries for myself. It’s not enough to stop sinning. One must identify the factors which led to sin and then create protective fences around those behaviors in order to right the personalistic ship. 

Perhaps, this is the meaning of this pasuk. Shoftim V’shotrim, judges and officers, these refer to protective measures that we create within our lives which help to shut down the roads that lead to negative behavior; b’chol she’arecha, in all of your gates, in everyday life. It is not enough to tackle sin; we need to look within our gates, our everyday lives and try to identify which aspects, approaches of behaviors, may be compromised. But the reverse is true as well. When we are in a good spot in life, when we are performing well, spiritually successful, and happy with who we are, those feelings are also results of earlier behaviors. I need to identify what “works” and places me in a positive trajectory and keep reinforcing.  

As we continue our journey through Elul, we yearn to find true and meaningful Teshuva. If we engage in this Shoftim process, introspect, look not only at sin or success but at the pathways of our lives and devise proactive strategies for success, there is no telling what we can accomplish.