I recently downloaded an app called Flighty. As Ben Cohen described it in the The Wall Street Journal, “Flighty was built by aviation geeks for aviation geeks.” It uses all kinds of data to predict whether your flight will be on time or late, and if so by how much. It often beats the airline apps with updates. As an app it’s beautifully designed. And it’s insightful, showing your most frequent airports, the number of miles you flew last year—and how many times around the Earth (or the Moon) that represents. I’m hooked.

While I expected to travel a lot when I took this job nearly six years ago, the first couple of years I didn’t go anywhere because of the pandemic. But now the world has largely returned to its pre-Covid pace, and Flighty tells me that my 47 flights so far this year (and there are still a couple to come in December) have taken me 47,012 miles, which is 1.9x around the Earth. I’ve also evidently spent 10 hours in flight delays (which frankly ain’t bad given those numbers)—and 48 percent of my flights have actually landed early!

So that’s fun and all. But for a perhaps unexpected question, I want to ask you: How do you feel reading all that? What, if any, sensations do you notice arising?

There could be some judgment (“That’s a big carbon footprint”). There could be some envy (“You must have airline status”). There could be some pity (“Oy, that must suck to travel so much”). It could be something else, or a combination of multiple thoughts or feelings.

The French sociologist Pierre Bordieu coined a term he called “habitus.” Here’s a fairly standard definition of the idea: “A set of attitudes and beliefs embodied in how people think, feel, speak, and gesture. The habitus conditions and shapes how individuals perceive the world around them, their sense of place, and life choices.” Where a “vibe” in our contemporary parlance is a superficial, momentary feeling about the atmosphere in a particular setting, “habitus” gets at deeper structural stuff: the ways we’re conditioned to act and speak, the things we’re conditioned to value, within cultural structures from families to communities to societies.

Applying habitus to an analysis of Flighty, one might start to think about the culture (or cultures) of frequent flierdom. One can start to ask questions like, “What are we really talking about when we talk about this culture of airports and flights and airline rewards programs?”

Perhaps because of Flighty, perhaps because last week I was in fact on four flights in four days, all of this was in the background when I encountered Anand Giridharadas’s essay about the Epstein emails in the New York Times. Giridharadas has been issuing some deep and blistering critiques of philanthropy and elite culture for years, and he analyzed the situation with that in mind. While not undermining the culture of rape and abuse at the heart of the story, Giridharadas also aimed to flesh out the habitus illustrated in the emails. Here’s his central point:

What [Epstein’s] correspondents tended to share was membership in a distinctly modern elite: a ruling class in which 40,000-foot nomadism, world citizenship and having just landed back from Dubai lend the glow that deep roots once provided; in which academic intellect is prized the way pedigree once was; in which ancient caste boundaries have melted to allow rotation among, or simultaneous pursuit of, governing, profiting, thinking and giving back.

I will be honest and say that I felt myself implicated in that, if not directly—I’m not jetting into and out of Davos or Aspen on a private jet; I fly commercial between O’Hare and LaGuardia; and I have told philanthropists directly when I thought they were misbehaving—then indirectly. I went to an elite private university (Yale) and received a Wexner Graduate Fellowship that paid my way through rabbinical school and had a large (and overwhelmingly positive) influence on my career. I’ve rubbed shoulders with people like the folks Giridharadas describes and, like many other nonprofit leaders, I have felt the gravitational pull of their philanthropy—again, if not directly, then indirectly.

But there is something about this depiction of flying around constantly, jetting in and out of cities and making that the basis of valuation, that is both a little familiar and a little icky. (“Many of the Epstein emails begin with a seemingly banal rite that, the more I read, took on greater meaning,” Giridharadas notes: “The whereabouts update and inquiry… ‘Just got to New York — love to meet, brainstorm,’ the banker Robert Kuhn wrote to Mr. Epstein.” And later: “Whereabouts are the pheromones of this elite.”) Again, I don’t generally text people when I land and ask if they’re free—that reflects a pretty phenomenal level of presumptuousness/entitlement—but I recognize the conversation that involves a sentence like this: “I was in Manhattan to do a talk, then I went up to Westchester for an event, then back to Riverdale for a meeting, then flew back to Chicago in time for bedtime, and was on a plane to DC the next day.” That, in fact, was my first half of last week.

Where does the ick factor come from in all this? At root, I think, it’s the sense of rootlessness—the constant moving about, never being truly being at home anywhere, and the sense that these very powerful people were trying to fill the related spiritual abyss in their soul with power and domination. And that, of course, butts up against an antisemitic trope, most powerfully deployed by Josef Stalin against Russian Jews, who the Soviets referred to as “rootless cosmopolitans.” So on top of the original ickiness, there are layers of additional complication.

Jacob, whose story we come to focus on centrally in Parashat Vayetzei, is notable for many reasons, one of which is that he is our ancestor who struggles the most to be at home—with himself, his family, and his geographic place. Even more than his grandfather Abraham, Jacob moves around—from his childhood home in Be’er Sheva to his uncle’s home in Padan-Aram, then back to the land of Canaan, then finally to Egypt. His name Yisrael, of course, connotes his constant struggle: to come to terms with his twin brother, with himself, with his wives and children, with the Holy One. He is never settled, never at ease.

All of that can sometimes make it feel like Jacob is a rootless character. Yet our tradition suggests that Jacob’s lesson is precisely the opposite: What Jacob figures out is that, wherever he is, he can in fact be deeply rooted. This is the reading that Rabbi Aharon of Karlin offers on the words vayifga bamakom, which the Torah uses to describe Jacob’s encounter with Mount Moriah when he first sets out on his journey: “Pegiah connotes prayer [as the Talmud posits], but it also connotes a genuine, sudden, deep encounter. Thus a person should pray that they find the ‘place’ that is particularly their own… Here, in this world, we should try to be at one in whatever place we find ourselves… Your heart should not be separate from the actual place you are standing or sitting.”

A few years ago historian James Loeffler published a book about the creation of human rights law, which was largely led by Jews. In a rejoinder to Stalin, he called it “Rooted Cosmopolitans.” It’s a great phrase to consider, particularly at a moment when our community, our people, is engaged in deep and often contentious reflection about particularism and universalism—or, more simply, where and when we feel at home.

Here in the United States, many of us, including me, are celebrating Thanksgiving this week. As it does like clockwork every year, the holiday causes me, and perhaps you as well, to reflect on some key questions: Where, when, why, and how do we feel at home here, if at all? Do we feel at home as Jews today? If so, why? If not, why not?

But the holiday also offers us an opportunity to experience some deeper at-homeness, perhaps: The spiritual rootedness that’s available to us when we can gather with family and friends, when we can take a walk among trees whose leaves are falling away, when we can, in moments of stillness, express gratitude for the blessings in our lives. If we allow it to do so, Thanksgiving might remind us that we can, in fact, be spiritually at home in whatever moment we find ourselves. And there is nothing more Jewish than that.

Before my recent weeklong retreat, I was worried about a few things. As I wrote recently, being off the grid for that long is a significant absence for all involved, a rehearsal of death. So I was worried about the effect that would have on my family. And I was a little worried about being away from work for a week. But those were ultimately not major sources of concern. What had me really worried was my mother.

As I have shared in this space before, my Mom has Alzheimer’s, and it is now at a more advanced stage. She’s still her cheerful self, but her world is pretty small and focused at this point. The conversations, like her day to day activities, don’t take her very far.

My worry came from the fact that I have become something of a tether for her. I recently downloaded her cell phone activity and analyzed it with the help of AI. I found that over half of her outgoing calls are to my number. While that tracks with my experience, it didn’t do anything to allay my concern: If the main person you talk to outside your living quarters isn’t there to answer the phone, and you can’t remember why they’re not there, how would you feel?

I contemplated some solutions. The most elaborate started with the reality that we really do have the same conversation multiple times a day. So I thought that perhaps there was an AI out there that could record my voice and impersonate me while I was away. I mean, on the one hand, it’s not so crazy: If it could help allay her anxiety, then there’s a case to make. On the other, ick: there is something gross about the inauthenticity.

The central drama of Parashat Toldot revolves around Jacob’s deception of his elderly father Isaac. As Avivah Zornberg observes in her classic study of Genesis 27, the axis of tension lies in the collective worry—Jacob’s, Rebecca’s, Isaac’s, and the worry of we the readers—that Jacob is dissembling, and/or that he’ll be found out. “If my father touches me, I shall appear to him as a trickster,” Jacob frets when Rebecca introduces her plan (v.12). Isaac, suspicious that something is afoot, tells Jacob (who is dressed as Esau), “Come closer that I may feel you, my son—whether you are really my son Esau or not” (v.21). And then, when Jacob comes in for inspection, his father exclaims, “The voice is the voice of Jacob, yet the hands are the hands of Esau” (v.22).

Zornberg quotes a midrash from Pirkei d’Rebbe Eliezer: “When Jacob left his father’s presence, he left adorned like a bridegroom and like a bride in her ornaments. And there descended on him reviving dew from heaven, and his bones were covered with fat; and he, too, became a champion fighter and athlete.” She comments: “The description suggests a radiant awareness of new possibilities that springs from deep within the self. The bones that are covered with fat evoke the text in Proverbs 15:30: ‘Good news puts fat on the bones.’ The ‘good news’ of the blessings — considered as an existential event, rather than merely as words spoken — gives Jacob a sense of health and power that affects his very bones. In Hebrew, the word for “bones” — atzamot— is closely related to the word for “self” — etzem. What is nourished — even created anew — in Jacob is the essence of his selfhood.” (Zornberg, 178) As she observes earlier on, Jacob “must enter the world of seeming, of enactment, of performance, in which authenticity can be defined only retroactively” (154).

For many people, the work of defining and understanding ourselves is the project of a lifetime. And as the story of Genesis 27 illustrates so profoundly, it is not work that belongs only to us: It is interpersonal, intergenerational, social, existential. That is, it isn’t only up to us. We do not want to understand ourselves to be tricksters, deceivers—and we don’t want to be seen that way by others. But the work of attuning our own voice to the voice of Divinity working within us is not easy, nor always necessarily pleasant. Much of life takes place within that tension. And as my colleague Rabbi Marc Margolius might say, “What an opportunity for practice!”

Ultimately, just before my retreat, I recorded a new voicemail message: “Hi, this is Josh. I’m away on a silent retreat and will be back on November 2. If this is my mother, this is to remind you that I’m away and to tell you I love you very much. If it’s anyone else, leave a message.” She was fine. And I felt better knowing that it was my voice she’d hear.

Questions for Reflection & Conversation:

• Is there a moment (or moments) in your life when you struggled to discern something about your etzem, the “true you?”

• What was difficult about that moment?

• Who or what, if anything, helped you navigate it?

• Is there anything you wish you had done differently?

A pretty cool moment occurred the other day while I was walking the dog. It was a sunny but cold day and I was listening to a talk by Gil Fronsdal about Metta practice (Pali for lovingkindess, or perhaps what we would call Hesed). All fairly normal—for me, at any rate.

Early on in the talk, Gil uttered a casual line that, probably without intending it, lit me up. He observed that it generally just feels better when our hearts are open. They don’t naturally want to be constricted.

As I said, this was a casual line in a 45-minute talk. But it literally stopped me in my tracks. Why? Because it took me back to a podcast interview I did with Rabbi Shai Held a few months ago. The topic of that conversation was the Rabbinic phrase rachmana liba ba’ei, which is usually translated from the Aramaic as, “The Merciful One desires the heart.” Shai and I had a long and rich conversation unpacking that phrase. But here on the sidewalk on a cold day in November, it was like a lightning bolt shot through me with a new understanding.

That’s because just the night before I had been reading French rabbi-philosopher Marc-Alain Ouaknin’s The Burnt Book. Now, a warning: This is not a simple read. At all. There’s a lot of 20th century French philosophy—thinkers like Emmanuel Levinas and Maurice Blanchot (I happen to love that stuff, but I admit it’s an acquired taste). And there’s a lot of amazing but fairly esoteric Torah. This is not a beach read.

For the last few months I’ve been in a wonderful havruta about the book with two soul-friends. And the night before this dog walk I read a passage in which Ouaknin discusses Rebbe Nachman of Bratslav’s understanding of tzimtzum, or Divine self-contraction, which in Lurianic Kabbalah is essential for the creation of the world. Ouaknin points out that Rebbe Nachman introduces some slightly different, but quite significant, terminology in his rendering of this idea.

Significantly, he teaches that the Infinite One performed tzimtzum and created the universe out of rachmanut, i.e. rachamim, which we often render as “compassion.” But, Ouaknin observes, “Rachmanut comes from the term Rechem, the ‘womb,’ ‘uterus.’ He goes on to quote the French-Jewish thinker Shmuel Trigano: “It describes the uterine nature of the womb, that is to say, the capacity of the uterus to be what it is: to conceive the fetus… It is the capacity of the rehem to open up, to make an empty space in the heart of fullness of the person and to make room for the embryo, for a being Other. Rachmanut is essentially the ability to conceive someone other than oneself.” (273)

In Lurianic Kabbalah, the result of the tzimtzum is an empty space, within which creation occurs. For Ouaknin, the fact that Rebbe Nachman adds the dimension of rachamim, this “uterine” capacity to expand and be the bearer of something wholly other is monumental. It sets up an entire way of seeing the world, and an ethics that honors and makes space for the Other in a profound way (a la Levinas).

So all that was going through my mind as I walked the dog and heard this line about the heart naturally wanting to be more expansive than constrictive. And it made me re-think the line that Shai had started with: rachmana liba ba’ei. Yes, the most basic understanding of those words is that rachmana is Harachaman, the Merciful One. But a good Hasid would also be open to playing with the meaning slightly, in which case you might get: the heart wants to embody this quality of rachamim, i.e. the heart itself wants to be expansive, rather than constricted. To me, anyway, that was a hiddush, a new insight. Cherry on top: I delightedly recorded a voice memo and texted it to Shai to tell him, and we had a lovely exchange about it.

Isaac, about whom we read in Parashat Chayei Sarah, is the first character in the Torah who directly expresses love. While God assumes that Abraham loves his son (“Take your son, your only, the one whom you love” in Gen. 22:2), the Torah tells us explicitly that Isaac loved Rebecca: “Isaac then brought her into the tent of his mother Sarah, and he took Rebecca as his wife. Isaac loved her, and thus found comfort after his mother’s death” (Gen. 22:67).

Rashi, quoting Bereshit Rabbah, offers some additional color: “While Sarah was living, a light had burned in the tent from one Sabbath eve to the next, there was always a blessing in the dough (a miraculous increase) and a cloud was always hanging over the tent (as a divine protection), but since her death all these had stopped. However, when Rebecca came, they reappeared.” The midrash paints a picture of the re-emergence of openness and growth after a period of narrowness and constriction, and we extrapolate that, perhaps, the characters and their hearts likewise opened and expanded.

Rachmana liba ba’ei: The heart wants to be expansive. As Sylvia Boorstein told me once, “I don’t like how I feel when I’m pissed.” Yet it is so easy for our hearts to enter the metzarim, a state of closed-offness, a place of anger and pain. Sadly, we see that in abundance in our world.

May our mindful practice of Torah help us cultivate more rachmanut, more compassion and more expansiveness in our hearts. May those who are hurting be comforted, and may all who are in narrow places emerge into greater freedom, joy, and love.

Questions for Reflection:

• In your own life, when do you notice your heart feeling more constricted? What contributes to it? How does it feel in the rest of your body? What about when your heart is more expansive? 
• What, if anything, helps you to move from a constricted heart to an expansive one? 

Last Shabbat fell on the tenth day of the Hebrew month of Marcheshvan, exactly a month after the tenth of Tishrei—which is better known as Yom Kippur. And while it was entirely a coincidence that last Shabbat was the culmination of a weeklong silent retreat I attended at the Insight Retreat Center in Santa Cruz, CA, the voice of Albert Einstein is chuckling inside my head, saying, “Coincidence is God’s way of remaining anonymous.”

At a certain point, it started to occur to me that this kind of retreat was a lot like an extended Yom Kippur. How so? The Mishnah lists five prohibitions we observe on Yom Kippur: 1) No eating and drinking. Okay, we do eat and drink on these kinds of retreats. But it’s a very different kind of consumption: Slow, mindful, intentional, and as a result a lot less than I normally eat at home. 2) No bathing. Again, yes there was bathing. But it was much less, and much less hurried or casual, than usual. Most folks showed up in the meditation hall in simple, baggy clothes—which reflected the general vibe that we don’t need to concern ourselves with appearance so much.

3) No anointing (wearing perfume). Like many retreat centers, this one stocked scent-free soaps and shampoos out of an inclusive sensibility, as there are folks who find those smells difficult to sit with. 4) No shoes. While most folks would wear shoes when going outside or working in the kitchen, one definitely does not wear shoes in the meditation hall or frankly in most of the retreat center. Just like on Yom Kippur, the idea here is to try to have direct contact with the ground. 5) No sexual activity. This is an explicit part of the expectations of the retreat—both for the safety and well-being of everyone participating, and as part of the practice. It’s an opportunity to notice, perhaps, when erotic or sexual impulses might arise—and then to let them fade away and not act on them.

Yom Kippur also includes the prohibitions of Shabbat, and in this case the parallel was most notable by way of refraining from technology use. We were off phones and screens for a week. We didn’t drive in cars or listen to music or podcasts or the radio. It was only on my long plane ride back to Chicago Sunday morning that I found out anything about the (truly epic!) World Series that had taken place that week—or any of the week’s other news. And while I’m used to doing that once a week from my own Shabbat practice, it’s quite a detox to do it seven days in a row.

Beyond all of this, the retreat evoked Yom Kippur most substantially in the fact that we spent virtually all of our waking hours in meditation of some kind. Each day there were nine or ten formal sits in the meditation hall, lasting 30 to 45 minutes. In between we did walking meditation indoors or on the beautiful grounds outside. For those of us who, like me, spend most of the day of Yom Kippur in shul, there can be a feeling of connection.

By Shabbat, the effect of all of this was that my sitting meditation had reached a really wonderful place. I was able to be very close and present with the breath, without a sense of mental noting (“I’m breathing in, I’m breathing out”) or intruding words or thoughts. I felt a deep sense of wholeness of body, mind, and spirit—perhaps what in Buddhism is termed samadhi, or what we might call yishuv hada’at (a settled mind) or meshivat nefesh (restoring the soul). During one of my sits on Shabbat afternoon, that closeness with the breath was such that I became aware that, when we get to the end of our lives, this is really all there is: just this breath, and then it will stop. It felt like I was rehearsing my own death—in the best possible way.

As Andrea Castillo, one of the retreat teachers, pointed out in a dharma talk that evening, that is exactly what we were all doing. Leaving everything and everyone behind for a week—loved ones, coworkers, pets—is a way of preparing them and us for the fact that eventually we will be gone. And getting to a point like that in meditation practice is a way of doing that for ourselves. If a retreat is about letting go, then this is the foundational letting go that all of us will eventually have to do.

Abraham is more associated with Rosh Hashanah than Yom Kippur, yet the word hineni, “I am here,” has become associated with both holidays. Hineni shows up three times in Genesis 22, the Binding of Isaac, which we read this week. Rashi, quoting Midrash Tanhuma (on Gen. 22:1), comments that Abraham’s hineni in response to the Divine call is a model for us: “Such is the answer of the pious,” he says. “It is an expression of humility and readiness.” Yes, hineni connotes fullness and even courage—but at its core, I think, Rashi is saying that hineni also evokes a kind of appropriate absence or emptiness too: We’ve let go of our clinging, of things that might delude us, and we’re able to see clearly that we are simply here. And then, just on the other side of hineni, will be einini: I am not here. The line is preciously thin.

This prompts me to pose two questions for all of us to consider:

1. When you are able to get quiet enough to really sense it, what, if anything, do you find yourself clinging to? What might you need or wish to let go of in order to live more simply and fully?

2. Does your practice of Torah and Judaism support you in that process of letting go? If so, how? If not, why not? And is there perhaps one practice that could help you do so a little more?