Jonathan Roth was a man in despair. For as long as he could remember, things hadn’t worked out for him. For starters, he was born into poverty, and not long after his twelfth birthday, his father succumbed to illness. After that, he fell in with the wrong crowd in an attempt to ease the financial burden at home.

But then came the big blow. He was caught selling drugs, and was sentenced to ten years in prison.

Life behind bars was difficult, to say the least. He couldn’t bear not being able to make life’s simple choices. Worst of all, he was weighed down by feelings of blame and resentment towards himself over his errors. Not a day went by without him mentally replaying his previous mistakes. He was nearing his wits’ end, when he was unexpectedly given a new lease on life.

One weekend, an organization that services the needs of Jewish inmates organized an extended Torah study retreat in Crown Heights for Jews in federal prisons. The program included participation in the Lubavitcher Rebbe’s farbrengen (public gathering) on a Shabbat afternoon.

Something about the Rebbe’s manner intrigued him, and he listened carefully to the talk being given on the Torah portion of the week.

“There is something unfair about the punishment meted out to the supporters of the biblical spies sent by Moses to scout out the land of Canaan,” the Rebbe was saying.

“Granted, they had sinned by expressing disinterest in ascending to Canaan, and consequently were destined to die without setting foot there. But why weren’t they brought to the border of the desert to live out the rest of their lives in one location? Why were they made to travel for forty years, and live a taxing life of transience and upheaval?”

The Rebbe continued by quoting the Midrash that teaches that wherever the Israelites traveled, they converted the physical ground upon which they trod. Greenery and vegetation replaced the barren and arid Sinai terrain. Wherever they went, they made inroads of civilization in an otherwise uninhabitable wilderness.

“So, theirs was a trek of positive transformation, not just meaningless and unnecessary travel from one place to the next. Hence their extended journey wasn’t only a punishment, but was also a privilege.”

The Rebbe’s next words grabbed him.

“How is this ancient story relevant today? A person can find himself stuck in a virtual desert, a place on the map or in his psyche that doesn’t seem civilized, where he feels unable to be true to himself or to express himself freely. Why is he there—just because of bad luck or foolish errors?

“Take, for example, the situation of a prisoner. Why is he behind bars? It can’t be just because he committed a crime. After all, many free people commit the same crime! They weren’t caught, you say? So why was he caught? Not only because he is a shlemazel . . .

“You see, if there is one place on earth that is most unG‑dly, it is prison. In prison a person is stripped of that which makes him uniquely human: his freedom. For this reason, there is no punishment of jail in Jewish law.

“But there are certain souls which, becuse of their potency, were handpicked by Providence to enter the spiritual wilderness that is incarceration, and transform it through meaning and spiritual creativity. Few people can achieve the inner freedom necessary to survive, and even thrive, in a prison environment.

“And it is these elevated souls that end up ‘doing time.’

“Now, it’s true that these people have committed crimes, and must be held accountable for their actions. But like the ancient spies, their mistakes only superficially account for their predicament. Besides, we have the right to wonder why certain people and not others are born into dire circumstances, or with immoral tendencies which lead them down destructive paths.

“But the idea here is that, ironically, immoral impulses allude to unique spiritual powers. In the words of the Talmud: ‘The greater one is, the stronger is his evil inclination.’ Another relevant Talmudic statement: ‘G‑d doesn’t give his creations challenges they cannot overcome.’

“As it turns out, then, the people in jail are not the dregs of society, but have the potential to be its most far-reaching members!”

Needless to say, Jonathan’s life turned around. For the first time in his life, rather than seeing himself as a victim, he began to see himself as someone who possessed a unique destiny few are chosen for. A fate which others naturally curse, he came to view as a source of blessing.

What’s in it for me?

In the counterintuitive worldview of Judaism, moral and religious crises are an indicator not of weakness, but of strength.

And the script of life and history is a coauthorship between the divine and man, between the laser-precision of Providence and the folly of human mistakes.

We are all on a journey through our personal deserts, each of us equipped with the tailor-made gear—circumstances, impulses, and talents—that enables us to make flowers out of sand, establish life where death once reigned, and bring meaning to the random and mundane.

Based on Likkutei Sichot, vol. 13, pp. 16–19, and a talk of the Rebbe in 5745.1