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Desirable Difficulties

People are always surprised when they find out I speak Spanish. I don’t speak perfectly, but well enough to hold a real conversation, and well enough that occasionally someone asks ¿De qué país son tus padres? Which is the real compliment.

But the more common question is ¿Cómo aprendiste el español? and I find that question itself telling. In the US, while we all take language classes in school, virtually no one ends up even passably proficient…so much so that there’s not even an expectation. The richest country in the world, and we seem to have made our peace with monolingualism, conveniently blaming geography and the global dominance of English.

My path was accidental, and it started with my seventh-grade teacher, Sr. David Donch.

El Señor Donch

He was an American from New Jersey who’d joined the Peace Corps in his youth, wound up in Venezuela, and didn’t come back until he brought a beautiful Venezolana with him. He was unconventional in the best sense: he threw out the textbook—which I’m sure cost him countless hours of curriculum development—and replaced it with vocab bingo cards and audio cassettes. (To this day I associate la sal and el azúcar together because they shared a bingo square.)

When I moved to a different school the following year, my new Spanish teacher was a gringa with a flat accent and a standard-issue textbook (“turn to page 78 for today’s lesson”). So my parents retained Sr. Donch as a tutor, and he’d make the trek across St. Paul to our house. Then one day he mentioned he needed to repair the roof of his casita in the Venezuelan Andes, and suggested I come along to really learn the language. And do some fly fishing.

I was fourteen. My parents (amazingly) said yes. But it changed everything.

My Month in Venezuela at Age 14

We landed in Maracaibo with duffel bags, my very first passport, and an English-Spanish dictionary. The first night we stayed with friends of Sr. Donch’s, and I sat there absorbing the language—or trying my best to—while missing the vast majority of it. Total sensory overload.

The moment I remember most vividly: I walked into a shop and asked for la coca (or something approximating cocaine) instead of una Coca-Cola. The place erupted. The heat rose in my cheeks as I laughed at myself, but embarrassment is an extraordinarily effective teacher.

But no one tells you that you have to be willing to look like an idiot. That there’s really no other path forward. Shane Parrish puts it well: “we’re often unwilling to look foolish in the short term to succeed in the long term.” But with language, that trade-off isn’t optional: you either make the mistakes or you don’t learn; full stop.

The other aspect of this was the fullness of the immersion. We spent the majority of the trip in the beautiful mountainous region of Trujillo, where very few people spoke English—and Mr. Donch was deliberate about not bailing me out. It was a full commit, which was hard at first. But I wasn’t placed with a host family where English crept back in at the dinner table, nor was I surrounded by fellow English speakers the way so many study abroad programs inadvertently arrange things…where your native tongue becomes a constant refuge and the whole point is quietly defeated.

The Mechanics of It

Looking back, a few things stand out that I think generalize beyond Spanish:

You have to let language wash over you rather than chase every word. If you try to translate everything in real time, you’ll fall behind and miss what comes next. But here’s the thing: we already do this in our native language without realizing it. Have you ever been half-listening to someone and suddenly gotten caught off guard by an unexpected turn of phrase (because you’d already mentally finished their sentence for them)? That’s collocation at work: the phenomenon where certain words reliably travel together, and a fluent brain learns to anticipate the pairing. Salt pulls pepper; trial pulls error. In corpus linguistics it’s defined as words that co-occur more often than chance would predict, but experientially it’s just what fluency feels like from the inside. When you’re learning a new language, you don’t have those grooves yet — every phrase is a surprise, which is why the immersion strategy works: you’re forcing those associations at speed. At some point you stop translating and just start anticipating, and that’s when things unlock.

Accent matters more than you’d think, and for an unexpected reason. I ended up sounding reasonably native—partly, I think, because of an ear trained by music and years of mimicking sounds—while having vocabulary gaps that a six-year-old wouldn’t have. But the effect was that native speakers engaged with me as if I knew what I was doing. They didn’t switch to English out of pity but rather kept going. Compare this to others among my friends and family who have impeccable grammar (correct tenses and conjugation, etc.), but comically American accents: native speakers jump to accommodate them out of sympathy, which is nice but hinders improvement. The friction I got from sounding like I belonged was itself a form of instruction.

Memory works through collision and surprise. Sal and azúcar are fused in my brain because they bumped into each other on a bingo card. The cocaína incident is seared in because it was a learning moment. These are what cognitive science researchers call desirable difficulties, the counterintuitive finding that harder, less comfortable learning conditions produce better long-term retention than easy, smooth ones. Fluency isn’t built through frictionless repetition, but instead through the moments that make you wince.

The AI Question

Which brings me to the thing I keep thinking about.

AI is close to making real-time translation seamless. In the very near-term—I don’t want to be in the game of AI prediction—you’ll be able to speak to anyone in any language and be understood, without ever having learned a word. Which raises the obvious question: does learning a language even matter anymore?

But the better question is what AI does to the process of learning itself.”

Done right, an AI tutor could be extraordinary: infinitely patient, available at 01:00, able to accommodate your precise needs relative to where you are. Conversational AI built specifically to teach could replicate the immersive pressure I felt in Trujillo without requiring a plane ticket.

Some learners will use it this way, but the temptation runs the other direction: why struggle to produce a sentence when the AI will just produce it for you? Why tolerate the embarrassment of the wrong word when you can simply not speak and let the tool speak for you? The risk is that AI removes friction entirely for everyone, regardless of style, if we let it.

And here’s what I keep coming back to: even if tinkerers and systematizers learn differently, even if some people need structure and others need to poke at things until they yield, I suspect there’s a floor of friction below which nobody actually learns. The form of difficulty may vary. But difficulty itself doesn’t.

Sr. Donch intuitively understood this, which is why he deliberately didn’t make things easy. He made things interesting, and then he made things hard in the right ways: bingo cards as a mnemonic device, a total-immersion trip with no English escape hatch.

The question for anyone building AI tools is whether we’re designing for that same principle, or whether we’re quietly engineering away the very resistance that produces learning.

¿Me entendés?

— ᴘ. ᴍ. ʙ.

First published: 2026-02-27 | tweet | cast | subscribe

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