Jonathan Pail
Lawyer and Lifelong Learner

Learning Humility

Illustration by Sivan Pail

When my daughter was born, I realized I had to change jobs. I was a “BigLaw” mergers and acquisitions lawyer, the kind of role that hijacks your life and devours all your time – every hour of every day, every day and every night, every weekday, every weekend, and every holiday. Forget about having dinner with your family or putting your child to bed; those are luxuries you can rarely afford. I enjoyed the challenge and was considered good at my job, but I wanted to be a good father too, and that meant I needed more time.

My plan was to become an in-house lawyer, a role that would be just as interesting but would have fewer side effects. The catch was that the positions I was looking for – those with challenging work, competitive pay, and the opportunity to grow – were very hard to come by. There are droves of talented attorneys scrambling for a very limited number of in-house opportunities at any given time. I had to find a way to stand out… but how?

My wife and I were living in a tree-lined neighborhood in Brooklyn where, on warmer days, the bustle of kids playing in the streets and in the park nearby drifted up through the windows of our second-floor walkup like a gentle breeze. Right around the corner from our home, in a nondescript house sandwiched between a martial arts studio and a day care center, was the local Chabad. A young couple ran the place: the Rabbi was responsible for the shul on the top floor, and his wife, the Rebbetzin, headed up the preschool on the bottom floor. We were not an observant family and would not ordinarily mingle with the Orthodox crowd, but we did get to know the Rabbi and Rebbetzin when my wife decided to send our daughter to preschool there.[1]

They had us over one evening for Shabbat dinner when it occurred to me that the Rabbi, as a spiritual leader, would naturally be acquainted with people from all walks of life. Perhaps he knew someone who could help me find a job? This was a theory worth exploring, and so as the evening was winding down, I drew my chair up by the Rabbi and gave him my spiel over cake and tea. It turned out he did have a good contact for me: the general counsel of a large company in the city. “I learn with him on a weekly basis,” the Rabbi said. “After Shabbos, why don’t you email me your resume and I’ll connect the two of you.”

When I got home that night, I found myself thinking about this person. Anyone who could be the Rabbi’s havruta, or Torah learning partner – which is what the Rabbi seemed to imply about the nature of their relationship – must have command of the Tanakh, Mishna, Gemara and the Commentaries. After all, the Rabbi was at the top of his game in this field. I imagined this person as a Yeshivish type, perhaps even a rabbi himself. There are not many general counsels out there with a background like that – if nothing else, he’d surely have an interesting story to tell.

Within a few days I had him on the phone, and I wasted no time breaking the ice. “So,” I said, “I heard you and the Rabbi learn together. Is that right?”

There was silence on the other end.

Bad cell service, I thought. I gave it another shot, this time raising my voice and drawing out the words in an attempt to break through to the other side. “How is it like to learn with the Rabbi?”

“Well, actually… I go to a Torah class that the Rabbi teaches,” he said, perplexed.

Wait. What?

I was dumbfounded – and quite embarrassed. Clearly, this guy was not who I expected him to be. But what really threw me off was that he had a completely different account of the story I’d heard from the Rabbi. Two people can have different subjective experiences of the same event – that would not be unusual – but here the disagreement was over a basic factual question: was the Rabbi learning or teaching? He was either sitting down taking notes or up by the chalkboard lecturing the class – it couldn’t go both ways!

To help me make sense of it, I reached out to a friend who was my authority for all things frum.

“Yup, that’s about right,” he said.

What is right?” I said, exasperated.

“The Rabbi was just being humble,” he said.

This friend would become my havruta, and years later, when I sat down with him to learn Mishna Eduyot, I finally understood what happened on a deeper level. Chapter 1 Mishna 3 tells the story of a debate between Hillel and Shamai – two of the preeminent sages of their generation – about the minimal quantity of drawn water that would render a mikveh (a ritual bath) unfit for use.[2] Hillel says a full hin (an ancient unit of measurement) of drawn water disqualifies the mikveh. Shamai disagrees, claiming that any amount short of nine kabs (three times more than a hin) poses no issue. Along come two weavers from the Dung Gate of Jerusalem and attest that Shemaya and Avtaliyon – two of the preeminent sages of the previous generation – said that the right answer was three logs (a quarter of a hin). All the sages, including Hillel and Shamai, then accept the weavers’ position as the law. In his commentary to this Mishna, Rashi writes: “This shows that no one should refrain from going to the house of study. There is no lower occupation than weaving… and there is no lower gate in Jerusalem than the Dung Gate, and yet all the sages of Israel settled the matter according to [the weavers’] testimony” (Kehati, M. Eduyot 1:3; author’s translation).

Fascinating. Hillel and Shamai, grand masters of Jewish law, had the humility to admit that they were wrong about Jewish law, and what’s more – they were humble enough to accept the truth from the lowest of the low. Humility, according to CS Lewis, is not thinking less of yourself but thinking of yourself less. Hillel and Shamai were not thinking about themselves at all. They were single-mindedly concerned with getting to the truth, and they did not let their egos or stature or anything else interfere with that objective.

I think this explains why the Rabbi said he was learning when he was actually teaching, at least by conventional standards. Here was someone who had spent his life from a very early age learning Torah, someone with a high degree of knowledge and competence in the subject matter. And here, on the other hand, was a mere greenhorn by comparison. But that made no difference to the Rabbi. Be prepared to learn from anyone, he seemed to be saying. God’s word is not something you can teach; it’s something you can only learn. What a beautiful idea.

You’re reading too much into it, some people tell me. That’s just the way they talk at Chabad. In other words, if “learning” is merely a code name for “teaching” in the Rabbi’s circle, maybe what came across as humility was really just a language barrier, a failure on my part to understand the Chabad vernacular. I am convinced that what I witnessed was in fact humility, but two things can be true at the same time: if the Rabbi’s choice of words was a habit of speech he picked up from his community, I think those words tell a remarkable story – they speak volumes about the values and ideals that the people of that community strive to live by.

This ties in to an interesting etymological twist. In Hebrew, the words for “to learn” and “to teach” are spelled the same way: lamed, lamed, mem, dalet. They are vowelized differently – lilmod  and lelamed – and belong to different verb families with distinct conjugation patterns – one is a pa’al verb and the other is a pi’el verb – a quirky feature of Hebrew grammar signifying that these are not different kinds of actions, but different degrees of the same action: teaching is a stronger form of learning.[3] Native Hebrew speakers would not typically use the verb this way, but in essence “teaching is nothing but ‘studying intensively,’” according to Rabbi David Fohrman. “When someone is so passionate about what he is studying that he can’t help but overflow and share his learning with others – well, that’s teaching” (Fohrman 163). When my son was three years old, he used to come home from preschool and say, “Ima, Aba, I want to show you what my teacher learned me today.” My wife and I would correct him – “You mean what your teacher taught you” – but on a very basic level he was right. He intuited that both concepts were fundamentally one and the same – an intuition that is borne out by the structure of the Hebrew language.

There is something similar going on in English. When Hamlet succeeds in outmaneuvering King Claudius despite acting in a way that might have frustrated this very objective, he says, “… that should learn us / There’s a divinity that shapes our ends, rough-hew them how we will” (Shakespeare 5.2.9-12; emphasis added).  When Becky Thatcher tells Tom Sawyer she wishes she could draw, Tom says, “It’s easy… I’ll learn you” (Twain 47; emphasis added). “Learn” clearly means “teach” in both cases. I think it’s safe to say that Shakespeare and Twain are reflecting how English was spoken in Elizabethan England and in Missouri of the 1840’s – it would not have been unusual to use the two words synonymously. Over the years, “teaching” has fallen away as one of the meanings of “learning,” so much so that in our day and age it is considered plain wrong to conflate the two. But the “learning” of old is making a comeback – and my Shabbat dinner with the Rabbi is a case in point.

Nothing came of my conversation with the general counsel, but I did eventually find a job that was everything I had hoped for and more. My wife and I moved out of Brooklyn and moved on with life, but there is something about that time that remains with me to this day, something more than just fond memories. With an effortless authenticity and grace, the Rabbi opened up for me another way of looking at the world, another way of acting in the world. Was he really learning? You be the judge. But before you decide, reflect on this: if you want to learn something – if you want to learn it really well – teach it!

 

Notes:

[1] My wife searched near and far for the right preschool, and ultimately decided that Chabad was the best choice because it was the most academic program available. When she told me about her decision, I wondered: What does “academic” mean when you’re talking about two-year olds? But I didn’t argue; my wife is a preschool teacher herself, and these things are completely within her purview.

[2] A mikveh needs to contain at least 40 se’ah (an ancient unit of measurement) of undrawn water to be fit for use. If drawn water falls into the mikveh before it is filled to 40 se’ah, it becomes unfit for use. The question being debated is what amount of drawn water is needed to render it unfit for use.

[3] Pi’el verbs often play off their pa’al counterparts this way. Other examples include: lishmor (to save) and leshamer (to preserve or conserve), livkot (to cry) and levakot (to cry out, bewail), and lishbor (to break) and leshaber (to smash).

Works cited:

  1. Kehati, Pinchas.  Kehati. Developed by Zeev Weinstadt, version 2.3, Kehati, 20 June 2025. Apple App Store.
  2. Fohrman, David. The Beast That Crouches at the Door: Adam & Eve, Cain & Abel, and Beyond. 2nd ed., Aleph Beta Press, 2011.
  3. Shakespeare, William. Hamlet. Edited by Barbara A. Mowat and Paul Werstine, Simon & Schuster, 2012.
  4. Twain, Mark. The Adventures of Tom Sawyer. Children’s Classics, 1989.
About the Author
Jonathan holds a Master of Laws (LLM) from Stanford Law School and a Bachelor of Laws (LLB) from Tel Aviv University, and is licensed to practice law in New York and Israel.
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