As the High Holidays approach, Jews engage in the practice of “cheshbon hanefesh,” an “accounting of the soul” or "self-inventory." I’d like to put in a plug for making such activity a regular practice throughout the year. Many of us engage in various self-improvement activities, but how many of us regularly pause to take stock of how we are actually doing relative to weeks, months, or years ago, and where we are deficient?

Human beings naturally gravitate towards looking at what we do well and patting ourselves on the back instead of looking at our “sins” or character defects. Reflecting on the latter is uncomfortable! But we still need to clean out the things that are blocking us off from our true potential. After all, stacking self-help techniques on top of a shaky foundation is not a recipe for long term success. Sooner or later, that pain and negativity will come to the surface and need to be dealt with.

The unfortunate reality is that many of us wait until external circumstances, usually negative ones, force us to take an honest look at ourselves. At that point, it’s often too late. It takes time to clean up trouble. And if we’re lucky enough to work through an issue successfully, we learn and get better, but frequently we’re only getting back to par. Waiting too long to perform introspective accounting can lead to bigger and bigger setbacks.

The most common blockers keeping us from performing a real cheshbon hanefesh stem from fears and resentments. Resentments come from bitter feelings as we relive old wounds over and over. Usually, we perceive those grievances to have been caused by other people, institutions, or even society. One can only imagine how these old hurts have kept us from achieving our full potential. Underneath most of these resentments is fear – the fear that something we have will get taken away or that we won’t get something we really want. To understand what the underlying fear is, it can help to list our resentments in the following format:

  • Who or what am I resentful toward?
  • What is the perceived wrong?
  • What part of my being is affected? E.g., self-esteem, my ambitions, my financial, emotional, or physical security, a relationship?
  • What is my part in the situation? e.g., Where am I acting out of fear? Where am I being self-seeking or selfish? Where am I being inconsiderate? Where am I being dishonest? And last, but not least, what will I do differently next time?

One of the transformative parts of doing an inventory like this is sharing it with another trusted individual. This is best done with an individual who will keep our confidence, but will also hold us accountable, like a confidant, a mentor, a life or business coach, a rabbi, or anyone we feel comfortable confiding in.

When working with an accountability partner or even within a group, it’s important to let the other person/s know if you’re looking simply to share/process the resentment (“vent”). Other times, you may ask for verbal feedback, or you may want to be held accountable for taking some corrective action by a certain date.

As a result of this exercise, we may find that we have wronged somebody, or that we are complicit in the very thing upsetting us. Sometimes, we may need to do teshuva to make amends on our part. That may be simply a conversation to clear things up. Often, animosity, negativity, and discord melt away and relationships are repaired; we are unblocked, and new possibilities present themselves.

Once we have moved past our internal blockers, cheshbon hanefesh asks us to think honestly about where we are in our growth. What are the signs of our growth? What does success look like in a particular department of our life? In areas where we feel stuck or deficient, how do we go about identifying these before they become major liabilities and cause severe adverse consequences? Most approaches for cheshbon hanefesh advocate for some kind of daily or weekly “goal setting”, e.g., “This day I will work on setting an intention to do [x], or practice being [x] and then doing an end of day or week-end review of how we did.” You may want to start keeping a gratitude list – regularly keeping track of the things you are thankful for in your life.

The key is small steps at some regular cadence. The results over time are transformative. After a while, this process becomes automatic and gets easier to do. As a matter of fact, many practitioners report that they almost have to continue the practice. It is not only cathartic, but also when they don’t do inventory and deal with the items that are making them feel stuck, resentful, angry, or afraid, they may feel severe and emotional and even physical discomfort. After all, fear, resentment, anger, and anxiety all have physiological manifestations. The catharsis that ensues from disciplined regular cheshbon hanefesh can be truly healing and a powerful enabler for positive change.

With the Jewish New Year ahead of us, it’s a great opportunity to get a jump on this work and enter 5784, a better, improved you.

P.S. If anyone is interested in learning more or practicing together, the author would welcome that very much.

Get to know the author

Alex Rayter (WHP San Francisco 18) is a Soviet-born Russian-speaking Jew who immigrated to the states with his family in '87 when he was 10 years old. As a young man who did not have a sense of identity, he attended hebrew school, had a Bar Mitzvah, but was then disconnected from community involvement through his teens and twenties until a life-transforming trip to Israel in 2009.

Alex heeded the call to service in the community from the organizations which sponsored the trip and is now one of the more committed and visible young leaders in the community, being recognized with the Dinkelspiel Award by his Federation and a Distinguished Borrower Award by HFLA for outstanding service to the community. In his personal life, Alex is a partner in a successful IT consulting firm and a married father with three children, ages 25, 21, and 7 years old. One of Alex's proudest moments was the opening of a Donor Advised Fund and making a gift from that fund in the name of his late grandfather, who was the family patriarch and his Jewish mentor, to Rambam hospital in Israel, something his grandfather gave to for many years. Continuing that legacy is very important to Alex. He hopes to continue a life of service to the community.