Categories
Living New York City Serendipity

The Grammar of Looking Up

The apartment was across from Penn Station, which meant that for one stretch of months in the mid-1970s, the architecture of my days was decided by trains I never took. I walked east instead, every morning, toward the United Nations, where a man named Frank Smith ran a personal development course that IBM SRI had decided its young people should sit through. I don’t remember most of what Frank said in that room. I remember one thing he said about the street outside it.

He told us we should start looking up. Literally — on our walks back and forth across midtown, Penn Station to the East Side and back, twice a day, rain or not. Not all the way, usually. Mostly it was a floor or three: the window line just above the awnings, the cornice on a building you’d never once registered had a second story, let alone a sixth. The full climb to the rooflines — gargoyles, setbacks, terra cotta lions — was the occasional reward. Almost no one looks up in New York, he said, not even a little. The city trains you out of it. Too much at eye level demands your attention — the cabs, the steam, the man asking for change, the woman walking too slowly in front of you — so everything above your own eyeline disappears by consensus, not just the tops. Habits can be replaced. Look up enough times, even just a floor or three, and you’ll see a different city than the one everyone else is seeing.

I tried it. Walking up past the Pierpont Morgan stretch, or wherever the route took me, chin lifted some small number of degrees, feeling slightly foolish. Most days that was the whole of it — a window line, a row of air conditioners, a sign painted directly onto brick decades before anyone called that vintage. Every so often the chin would tip back further, and there’d be something up there worth the extra degrees. A gargoyle with its mouth open mid-roar, forty years before air conditioning made gargoyles decorative rather than necessary. But that was the rare find. The habit was the floor or three. Nobody else on the sidewalk was seeing any of it, because nobody else on the sidewalk was looking at all.

The chin came back down on its own a couple of times a week, somewhere around a street corner with a slice joint on it, because New York seems to put one on every corner whether you need it or not. You smelled it before you saw it — that specific combination of tomato, oregano, and hot grease that has no name I’ve ever found. Looking up was Frank’s discipline.

The pizza smell required none. It just reached out and took your head by the chin and turned it level again, toward the window with the steam on the glass and the guy folding a slice in half before he handed it over.

It is a small thing Frank Smith said in a room near the UN fifty years ago, and I have carried it around since the way you carry around a key to a house you no longer own. I don’t know what happened to the course, or to IBM SRI’s faith in such courses, or to Frank himself. I know what happened to the habit. It outlived the year, outlived the apartment across from Penn Station, outlived several cities I’ve lived in since that didn’t have the same vertical drama to reward the looking. I still do it. I did it last week on a walk that had nothing to do with midtown at all, tilting my head back on a street in California to find whatever was up there worth finding, and catching myself mid-gesture, thinking: that’s Frank’s, that one, still running fifty years later on the program he installed.

Most of what we’re taught to notice, we’re taught by people who wanted something from us — a sale, a vote, a grade. Frank wanted nothing, as far as I could tell, except that we see more of the city than we’d been seeing. It’s such a small ambition for a teacher to have. Look up. That’s the whole curriculum. And it’s the only thing from that course, the only thing from that whole strange year of being instructed in personal development by a man whose face I can no longer quite reconstruct, that I still do, unbidden, on every street I’ve walked since.

Categories
AI

The Shape of the Question

Marc Andreessen made two claims recently that don’t quite fit together, and I haven’t been able to stop pulling at the seam.

The first: for almost any topic, the top AI systems now give him better answers than the world-class experts he could call on the phone. And he can call basically anyone. This isn’t a casual observation from someone without access — it’s a meaningful data point about what AI is actually doing to the value of expertise.

The second: the only real skill left in using AI is knowing what to ask. The models can already do almost anything you can describe in plain English. The bottleneck lives in your own head.

Hold those two claims next to each other. If the AI beats the experts, then the quality of your question only has to clear a low bar — good enough to unlock what the system already knows. You don’t need to ask like a cardiologist to get a cardiologist-quality answer. You just need to ask.

Except that’s not how it works in practice. And the gap between the two claims is where something important lives.

The better the question, the better the answer — even from a system that already knows more than any human alive. Expert-level interrogation of a superhuman system produces something qualitatively different from naive interrogation of the same system. The gap between a good question and a bad one doesn’t shrink because the underlying capability grows. It may widen. A sharper instrument in an unskilled hand doesn’t close the distance — it just makes the skilled hand more lethal.

What the AI has done is commoditize answers. What it has not done — cannot do — is commoditize the ability to know which question to ask.

There is a concept from epistemology that keeps surfacing here: the unknown unknown. Donald Rumsfeld made the phrase famous and then spent years living down the mockery, which was unfair, because the underlying idea is genuinely important. There are things you know you don’t know — the gaps you can name, the questions you can form. And there are things you don’t know you don’t know — the territory you can’t even see the edge of. The naive user of AI operates almost entirely in the second category. They ask what they already suspect. They get answers that confirm the shape of what they already believe. The system is brilliant and they are using it as a mirror.

The sophisticated user has learned to ask the AI to challenge their assumptions. To find the holes. To steelman the opposing view. To identify what’s missing from the framing. That second posture requires a kind of intellectual self-awareness — an ability to stand outside your own thinking and interrogate it — that is neither common nor easily taught.

Here is the uncomfortable implication: that self-awareness is not randomly distributed. It correlates with education, with reading, with having thought carefully about hard things for a long time. The people best positioned to ask good questions are, largely, the people who already had access to good answers through the old system. The gate moved. It didn’t disappear.

There’s a democratic story told about AI and I believe parts of it. The kid in rural South Dakota with a good question now gets an answer that rivals what the partner at McKinsey gets.

But access to information was never really the binding constraint. The binding constraint was always the ability to know what information you need — to feel the shape of your own ignorance precisely enough to ask for what fills it. That skill wasn’t distributed by the old system and it won’t be distributed by the new one. It has to be built, slowly, through years of reading and thinking and being wrong and trying again.

What AI may actually be doing is widening the gap between people who ask well and people who don’t — making the former dramatically more capable while leaving the latter approximately where they were, just with a faster way to get answers to questions they already knew to ask.

Somewhere right now, someone is sitting with the most capable thinking tool in human history, asking it to write a cover letter. The tool will do it beautifully. And the gap will quietly widen.

Categories
AI Thinking Tools

Outsourcing Thinking but not Understanding

There’s a line mentioned in a recent discussion by Andrej Karpathy that I keep turning over: You can outsource your thinking but you can’t outsource your understanding.

It sounds like a warning. Maybe it is. But the more I sit with it, the more it feels like something older — a distinction philosophers have been trying to draw for centuries, suddenly made urgent by the fact that we now have a tool that makes outsourcing thinking almost frictionless.

Here’s what I notice when I use AI well: I get the answer, and I feel satisfied. There’s a small dopamine tick. Task closed. But if someone asks me an hour later to explain the reasoning, I often can’t. The thinking happened — somewhere — but not in me. I was a conduit. A confident one, too, which is the dangerous part.

This is different from looking something up. When I Google a fact and paste it into a document, I know I’m borrowing. The seam is visible. But when I ask an AI to reason through a problem with me, the output arrives in first person, in fluent prose that matches my own register, and something in my brain says I worked this out. The seam disappears. That’s new. That’s the thing we don’t yet have good instincts for.

Karpathy’s deeper point is about construction. He’s a builder by temperament — his mantra, which he traces to Feynman, is that if you can’t build it, you don’t understand it. What you can’t yet construct, you merely think you understand. There are always micro-gaps in your knowledge, invisible until you try to arrange the pieces yourself and find they don’t quite fit. The AI doesn’t change that equation. It just makes it easier to mistake the map for the territory — and to feel strangely proud of a map you didn’t draw.

Hesse understood this, in a different century and a different idiom. In Siddhartha, the young seeker travels to meet the Buddha himself — the most perfectly articulated wisdom in the world, delivered by the man who actually found it. Siddhartha listens, acknowledges that the teaching is flawless, internally consistent, the most complete account of liberation ever assembled. And then walks away. Not from arrogance, but from recognition: even the Illustrious One cannot hand you his liberation. The path was his. He walked it. That walking is not transferable, no matter how perfect the description of the destination. Received knowledge, however exquisite, is not the same as earned knowledge. The gap between them is exactly the size of your own unlived experience.

That’s the same argument, made across two and a half millennia. Feynman says you have to build it. Hesse says you have to live it. Karpathy says the AI can do neither for you.

He’s also made a related observation about educational video — that a lot of content on YouTube gives the appearance of learning but is really just entertainment, convenient for everyone involved. Nobody has to do the hard part. AI-assisted thinking has the same shape, just more intimate. You’re not passively watching — you’re actively typing, prompting, engaging. It feels like cognition. But engagement isn’t understanding. Typing a question is not the same as wrestling with it.

I don’t think the answer is to use AI less. That’s not Karpathy’s argument either — he’s spent the last year building a school premised on AI tutors expanding what people can learn. The lesson is about custody. When I hand a problem to an AI, I need to stay in the loop as a learner, not just as a reviewer. There’s a real difference between asking give me an answer and asking help me build the reasoning. The first outsources thinking. The second — if you insist on it, if you refuse to be a passenger — can still leave the understanding in you, where it belongs.

But insisting is the work. And the work is now easier to skip than it has ever been.

Understanding isn’t a product you receive. It’s a residue — what settles in you after genuine struggle, after the confusion and the dead ends and the small hard-won moments of clarity. Siddhartha couldn’t get it from the Buddha. You can’t get it from the AI. Karpathy’s line is a custody argument: the thinking can travel, but the understanding has to stay home.

What unsettles me is that we’re building tools that make the borrowing invisible — that dress outsourced reasoning in the first person, that let us feel like we’ve understood something we’ve only processed. Siddhartha at least knew he was walking away from the teaching. He felt the gap. We might not even notice ours.

Categories
Living Writing

The Loop and the Pixel

There is a distinct muscle memory associated with the 1950s classroom. It smells of chalk dust and floor wax, but mostly, it feels like the cramping of a small hand wrapped around a pencil. We didn’t just learn to write; we were initiated into the discipline of the loop. The Palmer Method or Zaner-Bloser weren’t suggestions—they were rigorous architectures of communication. We made endless rows of O’s and l’s, tilting the paper just so, learning that language required flow, connectivity, and a certain deliberate grace.

Then, the world sped up.

By the 1990s, the loops began to unravel. As keyboards clattered their way into dominance, the efficiency of the printed letter—and eventually the typed pixel—took precedence over the artistry of the connected script. By 2010, the erasure was formalized; cursive was dropped from federal education standards (Common Core) to make room for “electronic literacy.” We traded the unique signature for the standardized font. We gained speed, certainly, but I often wonder what we lost in the translation.

“New Jersey this week joined a list of more than 20 states slanting in favor of bringing cursive instruction back to classrooms. Lessons on the looping letters were dropped from federal education standards in 2010, part of a shift toward focusing on electronic literacy.” — The New York Times

It seems the pendulum is swinging back. Proponents argue for its utility—the ability to read historical texts or a grandmother’s birthday card—but I believe the resurgence touches on something deeper.

In an increasingly digital world, cursive is an act of resistance. Typing is percussion; it is staccato and disconnected. Cursive is string; it is continuous and fluid. When we write in cursive, we are physically connecting thoughts, linking one letter to the next without lifting the pen. It forces the brain to slow down and the hand to dance.

As we stare into screens that demand our instant reaction, perhaps we are realizing that we crave the friction of pen on paper. We are bringing the loops back not because they are faster, but because they are human.

Categories
Creativity Educated

Software for your brain…

Categories
Apple

When “Today at Apple” Lost Its Spark: A Fan’s Disappointment

Sketch Walk at an Apple Store

I used to be one of those people who’d eagerly check the “Today at Apple” schedule at my local Apple Store. There was something magical about walking into that sleek, glass-walled space and knowing I was about to learn something new—something creative. Whether it was a deep dive into photo editing on the iPad, a music production workshop with GarageBand, or even a coding session with Swift Playgrounds, these courses felt like a gateway to unlocking the full potential of Apple’s tools. They weren’t just tutorials; they were experiences that left you inspired, with skills you could actually use.

That was before Covid hit. Like so many things, “Today at Apple” had to adapt, and I get it—health and safety first. But what started as a necessary pivot to online sessions has, over time, turned into something else entirely. The program I once loved has been stripped down to the basics, and honestly, it’s disappointing.

The Golden Days of “Today at Apple”

Let me take you back. Picture this: It’s 2019, and I’m sitting in an Apple Store, surrounded by other curious minds, as an instructor walks us through advanced storytelling techniques using Final Cut Pro. We’re not just learning how to trim clips; we’re learning how to craft a narrative, how to use pacing and sound to evoke emotion. By the end of the session, I felt like I’d leveled up—not just in software proficiency, but in creativity. That was the beauty of “Today at Apple” back then. It wasn’t about teaching you the bare minimum; it was about pushing you to explore what was possible.

And it wasn’t just me. I’d see people of all ages—kids, professionals, retirees—engaging with these courses, each walking away with something valuable. The program had depth. It had variety. It had soul.

The Post-Covid Shift

Then came 2020. The world shut down, and so did the in-store “Today at Apple” program. When the program finally returned in person, it wasn’t the same. Gone were the advanced courses that challenged you to think differently. Instead, the curriculum now feels like a series of “Intro to [Insert Apple Product Here]” sessions.

Take the photography workshops, for example. Pre-Covid, you could attend a course on mastering manual camera settings or creating a photo essay. Now? It’s “How to Take a Great Photo with Your iPhone”—a session that, while useful for beginners, barely scratches the surface for anyone who’s spent more than five minutes with the Camera app. It’s like going from a masterclass to a quick-start guide.

Why This Matters

I know what you’re thinking: “It’s just a free course at an Apple Store. What did you expect?” Fair point. But here’s the thing—Apple has always positioned itself as a company that champions creativity. Their entire brand is built on the idea that their tools can help you “think different” and create something extraordinary. “Today at Apple” was a tangible extension of that ethos. It was a way for Apple to say, “Hey, we’re not just selling you a device; we’re giving you the skills to make something amazing with it.”

Now, it feels like they’re just checking a box. The courses are still there, but the heart is gone. It’s as if Apple has decided that most users only need the basics, and that’s a shame. Because the people who showed up to those advanced sessions? They were the ones pushing the boundaries, the ones who saw Apple’s tools as more than just gadgets—they saw them as instruments of creation.

A Plea to Apple

So, Apple, here’s my plea: Bring back the depth. Bring back the courses that challenge us, that inspire us to go beyond the basics. You’ve got the resources, the talent, and the audience. Don’t let “Today at Apple” remain a relic of what it once was.

In the meantime, I’ll keep my old course notes and screenshots from those pre-Covid sessions. They’re a reminder of a time when walking into an Apple Store meant more than just buying the latest iPhone—it meant learning how to make something beautiful with it at the intersection of technology and liberal arts.

Note: this post was crafted by me with writing help from Grok by xAI.