Maybe it’s because I come from a family of three boys. Or maybe it’s because I’m the father of three boys. Or perhaps it’s because I spent so much time in the Boy Scouts as a kid, or that I went to an Orthodox rabbinical school whose students were all young men. Whatever the reasons, I’ve long cared about masculinity and the experience of men.

I can remember already as a college student noticing that feminism seemed to have given many women I knew a more robust vocabulary for articulating what it meant to be a woman—and that a lot of men seemed to struggle in comparison. And though gender conversations have only gotten richer and more complex in the ensuing decades, the situation when it comes to masculinity doesn’t feel like it has gotten much better. If anything, it may have gotten worse.

From the Access Hollywood tape to “Quiet, Piggy,” the most powerful man in the world (one of them, anyway) has subjected the culture to a decade of shallow, toxic and violent masculinity. And the culture has followed suit: Humility and open hearts have been out, arrogance and closed fists have been in. As a father, I have worried about raising young men in such a culture.

This week I felt some more jolts. First I read about the latest outrageous attack on Palestinians by about 100 young Jewish men in the West Bank, which included the torching of homes. Then I read about violent, abusive hazing of pledges by the AEPi chapter at the University of Wisconsin-Madison. (AEPi is a Jewish fraternity; my son is a member of the University of Illinois chapter.) And both of those stories came in the same week as the lawsuit of Jane Doe against Cornell University for a vile case of sexual assault.

There are undoubtedly other elements to all of these stories, but I can’t help but wonder about how the young men involved in them imagine what it is to be a man—and whether a different conception might have a healthy effect. Because all of these stories have come to light during Sukkot, I’ve been thinking about them in the context of the sukkah and home.

We can trace the origins of a good chunk of our ideas—and even our laws—about home to ancient Rome. Central to the Roman concept of the domus was the notion of the paterfamilias, the male head of household—who could exercise virtually unchecked power within his property. Hence the phrase: “A man’s home is his castle”—emphasis on man. All of which is to say that gender roles and ideas of home are deeply interwoven.

Sukkot, of course, comes to upend our idea of home: Our home is not, in fact, our castle. It is not a place to be closed off and seemingly protected from the rest of the world. Farkert, just the opposite: Home is a place, a state of being, in which we are existentially, spiritually secure enough to open up—to guests, to the precariousness of nature, to the unknown, to the stranger. A man who is animated by deep fear of protecting his home from threats is, more often than not, a man who isn’t at home with himself. As Rabbi Jonathan Sacks wrote in his classic, The Dignity of Difference: “Those who are confident in their faith are not threatened but enlarged by the different faith of others. In the midst of our multiple insecurities, we need that confidence now.”

This Shabbat marks Shemini Atzeret, the final holiday in our fall cycle. Outside of Israel, it is also the Shabbat on which we traditionally read Kohelet (Ecclesiastes). So, two teachings.

The first is a commentary on a midrash about a verse from Kohelet: “Better is a poor and wise child than an old and foolish king…” (4:13) The Midrash offers: “‘A poor and wise child’—this is the Good Inclination (Yetzer Hatov); ‘an old and foolish king’—this is the Evil Inclination (Yetzer Hara).” Rabbi Simcha Bunim of Peshischa adds: “The Evil Inclination is called an ‘old king’ because it ages and renders everything stale. The Good Inclination is called a ‘child’ (yeled) because it continuously renews and refreshes everything; and it is called ‘poor’ (misken) because it is humble. Since it is humble, it is always happy, for the source of joy is found in humility (hachna’ah).”

I don’t think the humility Reb Simcha Bunim is talking about is meekness. I think it’s self-awareness, which is the foundation of being able to make space for others in the world. Such humility is the touchstone of a kind of at-homeness—and masculinity—that is not about shutting out or dominating others, but the spacious generosity that gives rise to genuine joy.

Thus the second teaching, which comes from Rabbi Menachem Mendel of Vitebsk (1730–1788). Like many others, he notes that Shemini Atzeret is unusual: “It has no matzah, no shofar, no Four Species.” There is no symbol on this holiday. Why? “On Shemini Atzeret, we reach the level of supreme joy, which does not require any external symbol—this is the joy within one’s essential self. One is full of sadness and worry only when one is far from oneself. However, when one becomes close to oneself, joy overflows. Shemini Atzeret is a holiday unto itself (b’atzmo): a holiday of the joy of full selfhood (atzmiut).”

This, of course, does not only apply to men, it applies to all human beings of all genders. All of us are on our own version of the collective journey towards what we hope can be healthy, secure, open and generous human lives. Having dwelled in the spiritual safety of the sukkah, may we step back into our homes with a renewed faith in ourselves, in our Torah, in the Divine, and in one another—and may we live with the courage to make our homes and the world a sukkat shalom.

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?