Sukkot and Baalei Teshuvah: The Challenge and Opportunity of Raising the Next Generation

The Vilna Gaon writes that the festival of Sukkot is set on the 15th of Tishrei because that is when the Clouds of Glory returned after the sin. These are, in essence, the clouds of those who return, and the sukkah commemorates those very clouds. Sukkot, in a deep sense, is the festival of baalei teshuvah (returnees to Judaism). During the Simchat Beit HaShoeva celebrations, they were given a unique place of honor. Even more so, the Sfat Emet explains (Sukkot 5636) that “those who return have no place—and the Holy One, blessed be He, gives them a place, and that is the sukkah… where they sit in the shadow of the Divine. And about this it is said: ‘In the place where those who return stand, even the completely righteous cannot stand.’”

I don’t think the Sfat Emet was referring to baalei teshuvah in the modern social sense — but almost every baal teshuvah can relate to this idea: “they have no place.”

A Life Between Worlds

On a deeper level, when God told Abraham, “Your descendants will be strangers,” the simple meaning is that the Jewish people would descend to Egypt. But on a more internal level, these descendants are also those who hear the call of “Go forth from your land, from your birthplace, and from your father’s house.” They remain, in a sense, “strangers” — without a fully defined place, often experiencing loneliness and partial belonging.

But this is only external.

Internally, it brings them closer to God than ever. It places them directly under the wings of the Divine Presence — within the shade of faith, surrounded by elevated spiritual light.

The Challenge of the Next Generation

However, these high spiritual lights come with a side effect: they are difficult to pass on to the next generation.

The second generation — the children, are not baalei teshuvah. They don’t have the same intensity of spiritual awakening. Often, their parents struggle to teach them how to serve God without that same emotional “light.”

The second generation can therefore be left without the “lights” and without the “tools.”

On one hand, they see parents who are spiritually inspired. On the other hand, those parents may not always be available to fully contain and guide the inner journey their children are going through. This can make the second generation somewhat of a “risk group.”

A Generation of Opportunity

The children of baalei teshuvah inherit something powerful from their parents: a deep sense of truth, and a refusal to settle for superficiality. This can push them to embark on their own journey, to seek deeper, more authentic connection.

Judaism did not end with Abraham. Even Isaac, a righteous son of a righteous father, needed to rediscover and reopen the wells that his father had dug. It wasn’t easy, but precisely because of that effort, his prayers were even more powerful.

Yes, there is more risk, but there is also greater potential.

The Role of Parents

To help children on their journey, it is essential to constantly invest in maintaining a warm, positive relationship of less criticism, less judgment, and more connection.

This is not easy. We naturally want the very best for our children, and it’s only human to hold high expectations. But if children feel they can never truly meet those expectations, they may quickly drift into dangerous emotional and spiritual places.

The Gift of Sukkot

The festival of Sukkot, by its nature, takes us out of our regular, familiar environment. It creates an opportunity for more shared experiences and deeper connection.

It is a time to increase moments of joy together, because shared joy is one of the greatest gifts we can give our children. It strengthens their sense of belonging and gives them the foundation they need to make healthy, meaningful choices in their lives.