For the last couple of years, it has felt at times that our youngest child, who turns 14 in a few weeks, has needed his own social secretary. Between school and camp, he has attended a veritable parade of coming-of-age celebrations (bar mitzvahs, bat mitzvahs, b-mitzvahs—or as the van of a local non-kosher caterer that nevertheless does a lot of Jewish events puts it a little ironically, “mitzvahs”). There have been stretches of many weeks where he has spent Shabbat at someone else’s home, only to go that evening to a party for another friend in a different community. It’s frankly quite a wonderful problem to have.

These affairs have been a real study in contrast and diversity. Some are pretty modest, with food that’s often homemade and a synagogue social hall that has been decorated by the family. Others have been galas at swanky hotels or event venues, with live bands and fancy hors d’oeuvres. Some are strictly kosher, others make accommodations for kosher-keepers. Some involve mitzvah projects as part of the event, others talk about a project the child-now-adult (sort of) has done on their own time. If the four species of Sukkot (palm, myrtle, willow, and citron) represent diversity, then Toby has had a tour of it over the last two years.

I don’t think it’s just the rabbi in me, nor the career nonprofit professional in me, that finds myself most drawn to those celebrations where the essence is strongest: Where, no matter how stylish and numerous the giveaways may be or how famous the entertainment is or how many people the family was able to employ in putting on the event, what comes through is a sense that this child and this family are living a meaningful, thick, and sacred Jewish life. I hope that Toby and his friends—and, let’s be honest, their parents and grandparents—feel that way too. That, as our friends down the proverbial religion street might say, is the reason for the season.

I wrote recently about Dolly Parton, and her reminder to us that, no matter how much we may acquire materially in life, we can’t take it with us. After what has hopefully been a process of healthily right-sizing ourselves during Elul, Rosh Hashanah, and Yom Kippur, Sukkot provides us with a physical opportunity to explore and metabolize this lesson further.

Hillel Zeitlin, the great Warsaw teacher of neo-Hasidism, shares the following teaching:

The Sukkah contains many symbols and secrets enumerated in the midrashim and books of kabbalah. But the simplest allusion of all is that we have nothing to rejoice over in our world when we are in a good state, nor is there any reason to be grieved when we derive no pleasure from it. In either case, we are nothing but sojourners here.

So far, so Buddhist. The sukkah, with its nature as a temporary dwelling, invites us to experience and embody impermanence—which can help us liberate ourselves from whatever emotional state we might be in. As the Torah itself states, “You are but strangers and sojourners with Me” (Lev. 25:23).

But Zeitlin continues with something more than impermanence:

There is no sense or purpose to our lives if we have not acquired something good here. To what is this comparable? To a merchant traveling to a fair whose primary concern is not to find a good inn, but rather the merchandise he will purchase there. And if one finds a good inn there, but returns from the fair empty-handed, what does he have to show for the whole fair?

So the goal is not simply to let go, it’s also to acquire—which seems like a paradox. How can you let go of things if you’re trying to acquire things at the same time? The answer, it would seem, is that we want to be acquiring the right goods: not those things that might seem to have greatest material value, but those that are of the greatest spiritual worth—the things, perhaps, that money can’t buy.

Zeitlin concludes the teaching with a story often told about Rabbi Yisrael Meir Kagan, also known as the Chofetz Chaim, the name of his work on mindful speech:

They tell of a certain rabbi, a genius and a tzaddik, whom a passing guest entered to visit in his home, and found no furniture in his house.

The guest asked him: “Rabbi, where is your furniture?” “And where is your furniture?” the Rabbi answered him with a question. “Why, I am merely a guest passing through!” “And I, too, am merely a guest here,” the Rabbi answered him.

Sukkot is an exercise in recalibrating our sense of at-homeness. “All seven days of Sukkot,” says the Mishnah, “one should make one’s sukkah their permanent dwelling, and make their house their temporary dwelling” (Sukkah 2:9). If home is a place in which we feel powerful, into which we can invite guests, then Zeitlin’s teaching about the Chofetz Chaim invites us to ask, What is it to be at home in a world in which we are already fundamentally guests to begin with?

That, of course, is not only a question for Sukkot. But the holiday is a time when we are invited and challenged to enter it deeply. So, this Sukkot, what illusions about our permanence are we holding onto that it’s time to let go? What truths about our own impermanence do we ignore that it’s time to take up? And how can we live as guests in this world while helping all to feel welcome and at home?