This summer, I have been going back and forth to Philadelphia to help my parents with their big move to Crown Heights. I am inspired by their courageous choice to begin anew in their senior stage of life. The decision to make this seismic shift came gradually, after much soul-searching, prompting some soul-searching of my own along the way.

Teshuva, the central High Holiday concept of repentance, serves as a central motif for a distinctly Jewish take on personal development. Just as in the overall desire for betterment of one’s general life circumstances, the degree of actions one undertakes to that end varies on the nature of what requires improvement. So too, in the realm of emotions and spirituality.

There are times when circumstances call for slight tweaking: one gets a bit older and recognizes the need to slow down and craft a more holistic life/work balance. There are other times however when the situation requires a major paradigm shift, whether it means retiring or more dramatic action, such as moving to a different city better suited to current needs.

Changing work habits in that situation is akin to changing the lightbulbs in the boardroom of a troubled company when what’s needed is fresh thinking from a new or retooled board.

Teshuva (repentance) is the same way. There is a basic version that addresses unhealthy behavior patterns. In those instances, the Teshuva is more about learning how to pull back from actions that throw off the soul’s body balance, and disrupt the circular flow of good energy. In these instances what is required is often a mixture of regret, willpower, restraint, and a more focused mindfulness wisdom to steer clear of circumstances that expose that particular vulnerability. There is a different level of Teshuva, however, that is less about breaking free from whatever brings us down and more about moving toward that which makes us feel free.

I guess you could call that the difference between “moving out” and “moving in.”

If Elul is about wrestling with whatever is off, then it requires a “moving out” mindset that is symbolized by the well-known adage associated with this month, where the King (as a metaphor for G-d) encounters his subjects in the field, in the act of making the necessary adjustments to the psyche. In that mode, implementing the necessary adjustment(s) is a suitable response. The following month beginning with Rosh Hashanah is more about saying to oneself, “OK, I left where I couldn’t be anymore and moved away from the darkness, but now I need to ‘move in’ and discover new means of connecting and being in the light. Moving out is how we play defense in order to avoid losing. Moving in is us feeling frisky enough to play offense and try our hand at winning.

The continuation of the Elul metaphor is again helpful. On Rosh Hashanah, the King as G-d is back in his palace in his full splendid radiance. When we are meeting the king in his palace we are signaling that “moving out” away from the places that scare us is not enough anymore.

May the Almighty G-d, King of our restraint, who graces our dance in the fields with the demons that haunt us, as we endeavor to break free of despair, grace us as well with his presence of Chesed, his infinite love, acceptance, and understanding, and manifest as the King of our journey back inward/upwards, who welcomes us back into the palace of light, hope, and renewed connectedness.

Much Love,

Rabbi Yossi

Rabbi Yossi Lipsker is the founder and director of Chabad of the North Shore in Swampscott.