Two Steps Forward, One Step Back: What Prison Taught Me About Teshuvah

For many years, I visited people in prison.

Some were serving time for relatively minor offenses. Others had done some of the worst things imaginable. Their stories were different, but over time I began to notice a pattern in how many of them experienced their sentences.

The first stage was anger.

They were angry at themselves, at the system, at the people around them, and sometimes at the entire world.

The second stage was two steps forward, one step back.

I would watch someone make real progress. They would take responsibility, work on themselves, and begin rebuilding from within. Then, suddenly, something would happen. A disappointment. A rejection. A reminder of the past.

Boom.

The progress seemed to disappear. The optimism drained out of them, replaced by anger, despair, or self-pity.

Then, for some, came a third stage: peace.

Not peace with what they had done, and not freedom from consequences. It was the peace that came from no longer running from the truth. They accepted responsibility for why they were there and began asking how they could grow through it.

I have been thinking about those stages during Elul.

Without getting into every detail, I have made my share of mistakes. I have hurt people. I have fallen short of the person I want to be. As Rosh Hashanah approaches, I am taking the work of teshuvah seriously.

Last week, I found myself squarely in that second stage.

It had been an extraordinary week. I felt that real inner work was happening. I was beginning to find my place in Jerusalem and to feel hopeful about what might come next.

Then, boom.

Something knocked me backward. By Wednesday, I was still working through it.

Teshuvah is rarely a straight ascent. Feeling inspired does not mean the work is finished, and being knocked down does not mean the progress was false.

Right now, the lessons seem to be humility, patience, and a more honest understanding of myself. None of that work is especially pleasant. All of it is necessary.

I do not know when I will reach that third stage, or whether teshuvah ever allows us to remain there permanently. Perhaps peace is not a destination, but the ability to keep returning to the work without anger, excuses, or despair.

For now, that is my task this Elul: to take responsibility, to keep growing, and to understand that one step backward does not erase the two steps forward.