Tag: Reflection

Categories
Business History

The Architecture of Unseen Influence

We build our monuments over the wrong graves. It’s a bad habit of ours, this craving for the lone genius—the larger-than-life figure who supposedly commands the tides of progress by sheer force of will. But look beneath the surface of how things actually get built. The reality is messier. And a hell of a lot more interesting.

Take Thomas Edison. Secular saint of American ingenuity. The wizard who single-handedly lit up the dark. Except he didn’t. Edison wasn’t a solitary creator; he was a brilliant, ruthless aggregator of other people’s breakthroughs and a master of public relations. He invented the bulb, sure, but his real masterpiece was the myth of himself. In the process, he eclipsed the collective sweat of his own labs and the far more elegant alternating-current systems of his rivals. He’s our most overrated figure—not because he lacked talent, but because his shadow blinded us to how progress actually happens.

Morgan Housel nailed this structural blind spot by tracing the tangled ancestry of major turning points:

“Every current event – big or small – has parents, grandparents, great grandparents, siblings, and cousins. Ignoring that family tree can muddy your understanding of events, giving a false impression of why things happened… Viewing events in isolation, without an appreciation for their long roots, helps explain everything from why forecasting is hard to why politics is nasty.”

Look past the blinding light of the celebrity inventors and you find the long roots that actually remade our world. Take FCC Part 15. It’s an event almost no history textbook bothers to mention. In the early 1980s, a lone staff engineer named Dr. Michael Marcus looked at three chunks of the radio spectrum—stuff discarded as “garbage bands” reserved for industrial microwave ovens—and saw an opening. The entire telecom establishment thought he was chasing a recipe for chaotic interference.

Marcus didn’t blink. He spent years pushing through a dry, technical ruling in 1985 to open those garbage bands for unlicensed public use. A total footnote. Yet that single, unheralded bureaucratic open door laid the invisible foundation for Wi-Fi, Bluetooth, and the entire wireless ecosystem running your life today. Marcus didn’t get a ticker-tape parade; he got political friction and a quiet transfer to a back-office enforcement role. No hero on horseback. Just a guy in a cubicle who rewired the world.

We do the same thing with politics. We rank presidents by the volume of their rhetoric or the body count of their wars. Meanwhile, men like Chester A. Arthur get left in the dusty margins of trivia. Arthur was the ultimate product of the spoils system—a New York machine politician who climbed to power on institutional corruption. Then James A. Garfield was assassinated, and Arthur was thrust into the big chair. Something clicked. Instead of feeding the machine that birthed him, he turned inward, defied his old patrons, and signed the Pendleton Civil Service Act. He dismantled the very patronage system he’d mastered. It was a stunning act of quiet integrity that killed his political future but saved the republic’s administrative soul.

Or take Frances Perkins. Ask the average student who gave them the weekend, the forty-hour work week, unemployment insurance, and the abolition of child labor, and you’ll get a blank stare. Perkins was FDR’s Secretary of Labor. She wasn’t a regular on the campaign posters. She just stood in the back of the room, turning abstract economic suffering into concrete human safety nets.

I’ve been sitting with this for a few days, thinking about my own career—and the times I mistook the loudest person in the room for the smartest. I chased the visionary founders with the spellbinding pitches. I ignored the quiet engineers and the mundane infrastructure choices that actually determine whether an idea scales or snaps. It takes a few painful, expensive missteps to realize that the real compounding interest of progress is almost always generated in the dark.

History isn’t a solo act. It’s an intricate, mostly anonymous collaboration between accidental reformers, stubborn bureaucrats, and regulatory footnotes. If you want to understand where we’re going, stop staring at the stage lights.

Start looking at the wiring.

Categories
Writing

Still Learning

I never thought about rhythm in my writing. Not once.

A lifetime of writing. More essays than I can count. One book. And the sonic quality of my sentences — the way they moved, or failed to move, through a reader’s mind — simply wasn’t something I considered. I was too busy trying to say something true. I thought that was enough.

What changed was reading differently. Not for pleasure anymore, or not only for pleasure. David Perell conducts long interviews with writers about how they actually work — not what they believe about writing, but what they do, physically, at the desk, in the dark, before anyone sees it. He asks the same structural questions of very different writers and the patterns emerge slowly, the way patterns always emerge: first you see it once and think nothing of it, then you see it again, then you can’t stop seeing it. Rhythm came up constantly. Always in different language. Pacing. Breath. Music. Momentum. Always pointing at the same thing.

Then I found this from Susan Orlean:

My new preoccupation was on the sonic quality of my writing — the rhythm and tone of the sentences. I began reading all my work out loud, listening for places that lagged and dragged, that didn’t sparkle. I knew it was unlikely that anyone else was reading my stories out loud, but I was convinced that you do “hear” writing in your head as you read, and this pushes you (or stalls you) through the piece. I wanted the music — that is, this subconscious tonal effect — to match the subject.

I stopped. Read it again.

Because she was describing something real — something I had been doing wrong for twenty-five years without knowing it was wrong. You don’t know what you can’t hear. That’s the whole problem. The silence where the knowledge should be is itself silent.

I don’t read my work out loud. There’s something strange about it, something that breaks the spell — you stop being a writer and become an actor, hearing your own sentences hanging in the air, too exposed. But I do read and read again, more carefully now, looking for the wobble. Orlean’s point holds regardless of method: you hear writing in your head as you read it, and that hearing either carries you forward or it doesn’t. The ear that matters is the one inside.

George Saunders has a practice he describes in A Swim in a Pond in the Rain: he reads from the beginning of a piece over and over, and the moment something feels off — a word, a rhythm, a single syllable landing wrong — he stops and fixes it before moving forward. Never skips the trouble spot. Never tells himself he’ll come back. His opening pages accumulate dozens of passes before he ever reaches the end. What he’s really doing, underneath the technique, is training himself to feel the exact microsecond when a reader’s attention would start to drift. To catch the loss before it happens.

That’s not craft instruction. That’s building a new sensitivity where there wasn’t one before.

John McPhee works from the other direction entirely. His famous boxes — index cards, sorted into piles, piles arranged into sequences, nothing drafted until the structure is known — are about architecture before a single word is written. He’s deciding which rooms exist, and in what order, before he furnishes any of them. Where Saunders builds outward from one true sentence, McPhee builds downward from a blueprint.

But they’re asking the same question. McPhee: is this section in the right place? Saunders: is this word in the right place? Both listening for the moment the piece loses its hold on the reader. Both doing triage on something most writers never even examine.

What I’m still learning — slowly, and late — is that rhythm isn’t decoration. It isn’t the thing you tend to after the real work is done. It’s structural. A sentence moving at the wrong speed for what it’s carrying fails the thought itself, not just the ear.

There’s something else I’ve been thinking about. If rhythm is the thing that’s hardest to hear in your own work — if the ear takes years to develop — then maybe the most useful writing tool isn’t a grammar checker. Those are solved. What isn’t solved is the rhythm problem. An editor who listens for the wobble, explains what’s failing and why, and works through the fix with you rather than just patching it. Not a red pen. A teacher.

I’ve been experimenting with exactly that. An AI editor I call Clark. His job isn’t correctness. It’s the sonic quality of prose — the rhythm — the same thing Orlean was describing, the same sensitivity Saunders spent years training. Clark finds what’s working as hard as what isn’t. And when something fails, he explains what the reader’s inner ear is hitting and why. Helpful.

I didn’t know much about rhythm in writing when I was fifty. Didn’t know it at sixty.

I’m not entirely sure I know it now. But I know it more than I did, which might be the only kind of knowing that’s real.

A lifetime of writing. Still learning how to listen.

Categories
Friends Gratitude Kindness Living

The One Thing Money Doesn’t Buy

Somewhere there is a couch that launched a hedge fund.

It belonged to a man named Carter, and for the better part of a year it was where Dan Loeb slept while he figured out what came next. No office. No fund. No Third Point. Just a friend’s apartment and the specific grace of someone who didn’t need you to have already become something before they let you in the door.

When Loeb finally landed at Jefferies, Carter gave him a few hundred thousand dollars to manage. That became a million. The million became seed capital. Third Point was built on top of it — thirty years of it, billions of dollars of it — and all of it traces back, in some straight unbroken line, to a couch and a person who said yes before the evidence was in.

Patrick O’Shaughnessy asked him about it near the end of a long conversation. The kindest thing anyone has ever done for you — it’s the question O’Shaughnessy always asks, and it always cuts through. Loeb had just finished making a case for kindness as a serious value, not a soft one. Something that belongs at the top of the hierarchy, he said, next to honesty and intelligence. The mechanism that unlocks empathy. He noted, almost reluctantly, that it also compounds in business — before adding that the moment you start treating it as an investment, you’ve already lost the thread.

Then he quoted Palmer Luckey.

The one thing money doesn’t buy you is friends that believed in you when you had nothing.

Luckey built Oculus in his parents’ garage. Sold it for two billion. Founded Anduril. He has spent his adult life proving that if you are relentless and strange and right, you can make almost anything happen with money. And what he noticed, somewhere in all of that, is where money stops. Not at luxury. Not at access. It stops at loyalty that predates your success. You cannot purchase the memory of Carter’s couch. You cannot acquire, at any price, the specific knowledge that someone held you when you were nothing yet.

I have been thinking about the people in my own life who did some version of this. Not always with money. A call made on your behalf before you knew you needed it. A door held open to a room you couldn’t see. These moments are nearly invisible when they happen. They only become legible later, once the room turns out to matter — once you can look back and trace the line.

The line is always shorter than you think. And it always ends at a person.

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 Living

The Threshold

There is a specific feeling. You are trying to understand something — a medical term in a lab report, a clause in a contract, how a particular piece of software actually works under the hood — and you hit the edge of what you know. The territory beyond is unfamiliar and the path is unclear, and something in you decides, quietly and almost without announcement: I don’t know how to figure this out.

And then you move on.

Marc Andreessen, talking to Joe Rogan recently, buried something important inside a longer riff about AI prompting tricks. Most of his list was the kind of thing you’d read in a productivity newsletter — ask it to steelman both sides, pretend it’s a panel of experts. Useful, not revelatory. But one observation was different: pay attention to the exact moment you think “I don’t know how to figure this out.” That’s the moment you should open the AI.

He said it almost offhandedly. I haven’t been able to stop thinking about it.

What he’s really describing isn’t a technique. It’s a behavioral pattern that most of us developed so gradually we don’t recognize it as a choice. The feeling of epistemic overreach — of arriving at the edge of one’s competence — became, over decades, a stopping condition. We learned to treat not-knowing as a wall rather than a door because, most of the time, it functionally was one. The library was closed. The expert was unavailable. The research was paywalled. You moved on.

The habit calcified. Now it persists even when the conditions that produced it no longer apply.

I notice it in myself, and I’m someone who is genuinely curious — who likes knowing how things work, who will follow a thread further than most people bother to. That’s not modesty; it’s relevant context. Because even with that disposition, I still hit the wall. I’ll be reading something and encounter a concept I only vaguely follow — some nuance in immunology, some historical episode I’ve only half absorbed — and I feel the familiar slight contraction, the small withdrawal. I read past it. The curiosity was there. The friction was higher.

Curiosity alone was never enough. What determined whether I pushed through wasn’t how much I wanted to understand — it was whether understanding felt retrievable at all. Most of the time, it didn’t. So I moved on, and the curiosity found something else to chase.

There’s a darker version of this worth sitting with. The people who never developed the quit reflex — who hit not-knowing and felt compelled rather than defeated — are, disproportionately, the ones who built things. The intellectual persistence wasn’t incidental to their contributions; it was probably constitutive of them. Curiosity as stubbornness. The refusal to accept the wall as final.

Elon Musk is the limit case. When he decided he wanted to go to Mars and found the rockets prohibitively expensive, he didn’t defer to the aerospace industry’s consensus about what was possible. He started reading propulsion manuals and cold-calling engineers. The quit signal either never fired or got overridden so fast it made no practical difference. The result was reusable orbital rockets, which the industry had largely decided weren’t worth pursuing. The dig reflex, taken to its extreme, rewrote what was considered feasible.

But the trait is undifferentiated. It doesn’t come with a calibration mechanism. The same refusal to accept expert consensus that produced SpaceX also produces a certain amount of confident wrongness — the Twitter decisions, the Covid takes, the occasional foray into geopolitics with the certainty of someone who has read a lot of Wikipedia. The dig reflex, unregulated, has no obvious stopping condition.

AI doesn’t change that underlying trait. What it changes is the access cost for everyone else.

For most of human history, the friction wasn’t random. It selected for people whose drive was strong enough to overcome it regardless of cost — the right connections, the right institution, the time to burn. Now that friction is lower for everyone, nearly to zero, for an enormous range of questions.

What I’m trying to build is the opposite of the quit reflex. Not the Musk version — boundless, uncalibrated, occasionally catastrophic. Something more modest: the habit of checking before giving up. Noticing the moment of not-knowing and treating it as a question rather than a verdict.

It requires noticing the moment. Which is harder than it sounds, because the reflex is fast and the moment is brief.

The contraction happens. You’ve already moved on. Somewhere behind you, the question is still there.

Categories
Living Serendipity Travel

The Conditions of the Unexpected

There is a flight I took in 2001 that I have never fully stopped thinking about. Not the flight itself — a forgettable three-hour hop in a middle seat — but the two-hour delay that preceded it. The gate agent’s apologetic crackling over the intercom. The way I surrendered to the terminal, found a bar stool, ordered something I didn’t need. The man next to me was reading a book I recognized. We talked for two hours. He told me about a job. I didn’t take it — but I spent three months considering it, which is its own kind of detour. I came out the other side different in ways I still can’t fully account for.

I have told this story before as a story about luck. I’m not sure that’s what it is.

Alexander Krauss spent years going through the records of science’s major discoveries — Nobel Prize winners, the landmark non-Nobel findings, more than 750 in all — looking for the mechanism behind what everyone had been calling serendipity. The telescope trained on an unexpected patch of sky. Fleming’s contaminated petri dish. The chance observation that shouldn’t have meant anything but did.

What he found upended the romance of the story. The discoveries that seemed most accidental, most shaped by the caprice of an unlucky sneeze or a mislabeled sample, turned out to follow a pattern. Nearly all of them happened shortly after a researcher gained access to a new tool. The accidental observation of cells under an improved microscope. X-rays discovered through a discharge tube nobody had pointed in that direction before. The first planet beyond our solar system, caught by a spectrograph that hadn’t existed a few years earlier. What looked like lightning striking the same improbable spot again and again was actually the same thing each time: a new instrument creating the conditions under which something unexpected could be seen.

Krauss calls this “engineering serendipity.” The phrase stops me every time I read it, because it sounds like a contradiction and turns out to be the most practical sentence in the philosophy of discovery. You can’t engineer the specific surprise. But you can engineer the conditions that make surprise likely. You can build the lens before you know what it will show you.

This distinction — between engineering an unexpected discovery and engineering the conditions for unexpected discovery — is one I’ve been carrying around like a stone in my pocket. Because I think it applies far outside the laboratory. I think it’s one of the central design problems of a life.

The book trend critics are calling “Digital Nostalgia” is, depending on how you read it, either the most sentimental or the most diagnostic thing happening in literary culture right now. The novels topping lists this spring are full of people losing their recordings, waking up in centuries without algorithms, mourning the weight of analog things. Ben Lerner’s new novel begins with a dropped phone in a hotel sink — the recording gone, the moment unrecoverable. Caro Claire Burke’s Yesteryear sends a social-media influencer back to an 1855 that is nothing like the one she curated for her followers: cold, filthy, unfiltered, and somehow more real.

What readers are reaching for in these books is not the past per se. It’s the texture of a life that wasn’t predicted in advance. The feeling of not knowing what came next because nothing had pre-sorted the possibilities. Nostalgia, in its root meaning, is pain at being far from home. What Digital Nostalgia seems to be mourning is something more specific: the disappearance of accident from everyday life.

I notice this in small ways. My phone knows where I’m going before I’ve decided to leave. The algorithm has predicted, with unsettling accuracy, what I will want to read next. The coffee shop I found by walking down an unfamiliar street now gets recommended to me, which is useful and also somehow diminishes the thing I found. The city I live in has become a more efficient version of itself. Less of it surprises me than used to.

This is not entirely bad. But something is lost in the smoothing. And the books people are buying tell you what.

The urbanist argument for cities has always included, at some level, an argument for density as a serendipity engine. You put people in proximity. You make them share transit and sidewalks and bars and parks. Intersections happen. Ideas cross. The great creative explosions of modern history — Florentine painting, Viennese psychoanalysis, the Bell Labs cafeteria — were products less of individual genius than of designed proximity. People who wouldn’t have met each other kept meeting each other.

What’s interesting about Krauss’s argument is that it generalizes this principle to the history of science in a way that makes it quantifiable. It’s not just that cities were generative because they were dense. It’s that they were generative because they were full of new tools — printing presses, coffeehouses, salons — that created new surfaces where minds could collide and refract in new ways. The tool doesn’t make the discovery. It makes the discovery possible, and likely, and reproducible by others.

Which brings me back to the airport bar.

The two-hour delay created an unstructured interval I hadn’t planned for. I didn’t know what to do with it, so I sat somewhere I wouldn’t normally have sat. The man next to me had a book that served as an opening. We were both temporarily outside our routines, which is another way of saying: we were both in a new instrument, looking at something we hadn’t known to look for.

What I’ve been slow to admit is that this kind of moment doesn’t just happen. It happens to people who are outside their routines. It happens in places where unlike people are forced into proximity. It happens when you sit down somewhere without your headphones, without a screen to retreat into, in the condition of being briefly unoptimized. The delay was the tool. The discovery followed.

So here is the tension I keep returning to: you can engineer the conditions for serendipity, but you cannot engineer serendipity itself, and the engineering has to be genuinely open-ended or it stops working. If you design a system that produces specific surprises, you haven’t built a serendipity engine. You’ve built a surprise dispenser, which is a different and lesser thing. Amazon’s “you might also like” feature is not serendipity. It is prediction wearing serendipity’s clothes.

The difference is whether the system preserves its capacity to show you something it didn’t know you needed to see. A new microscope could reveal anything. A recommendation algorithm reveals only a constrained neighborhood of the space of things you’ve already wanted. The former is a lens. The latter is a mirror.

I think this is what the Digital Nostalgia readers are grieving, without quite being able to name it: not the analog past itself, but the unoptimized interval. The moment between knowing what you wanted and finding it, when anything might happen. That space has been shrinking for twenty years, and the algorithm’s promise — to eliminate friction, to anticipate, to smooth — has turned out to be partly a promise to eliminate possibility.

The question I’m sitting with is whether it’s recoverable. Not globally — I’m not interested in the manifesto version of this argument, the call to smash the phones or return to the forest. But personally. Whether I can design my own life to include enough genuine aperture — enough unoptimized intervals, enough new tools, enough places where I am briefly outside my routine and available to be surprised — to keep the surprises coming.

I have some guesses about what this looks like. Reading outside my field. Saying yes to the conversation I don’t have time for. Choosing the longer route. Leaving earlier so the delay doesn’t feel like a crisis.

These are small things. They are also, if Krauss is right, approximately how all the important discoveries get made.

The flight eventually boarded. I didn’t take the job. But I thought about it for three months, which means I thought about my actual life for three months — what I wanted from it, what I was settling for, what I hadn’t been willing to name. The man at the bar didn’t change my path. He changed my angle of view, briefly, enough. I’ve been a little suspicious of smooth trips ever since.

Categories
Living Serendipity

Why Comfort Zones Block Serendipity and Growth

Barista preparing coffee with customers sitting and chatting in a cozy café
Customers enjoy coffee and pastries in a warm, inviting café

Serendipity used to be the default setting of my days, but recently I find myself having a quiet, losing negotiation with the front doorknob every time I try to step outside. There is a specific, invisible weight to the handle on a quiet evening—a subtle, undeniable gravitational pull that recommends I simply stay inside. My favorite reading chair feels less like comfort these days and more like an anchor.

I have been writing in this space since 2001. If you look back through the archives of my life—both the digital ones and the memories filed away in my head—you will find a younger version of myself who frequently and willingly threw himself into the unknown. Back then, I assumed serendipity would always just be there, waiting for me to stumble into it on a diverted commute or during a late, unplanned dinner.

Lately, I’ve noticed a subtle shift. As I’ve gotten older, my comfort zone has hardened from a permeable boundary into a brick wall. The things that once sparked a quiet thrill of spontaneity—a sudden change of travel plans, an unfamiliar route home, saying yes to an event where I know absolutely no one—now often trigger a low-grade exhaustion before they even begin. I find myself pre-calculating the energy cost of every deviation from the routine. I weigh the known comfort of my home against the unpredictable variables of the outside world, and the home usually wins.

But I have been sitting with a growing realization lately: when we meticulously optimize our lives for comfort, we inadvertently foreclose on serendipity.

Serendipity requires a loose grip. It demands a willingness to be occasionally inconvenienced. You cannot schedule a chance encounter, and you cannot algorithmically generate a moment of sudden, blinding clarity. Those things only happen in the messy, unmapped spaces between our planned destinations. They live in the friction of the unexpected.

I often think about the writers and thinkers who deliver sentences with such compression and weight. Their most profound insights didn’t arrive because they stayed perfectly insulated from the world. They arrived because they allowed themselves to be interrupted by it.

I am trying to learn how to open the door again. It doesn’t mean manufacturing chaos or pretending I have the boundless, restless energy of my thirties. Acknowledging my own changing capacity (especially physically) is necessary, but using it as an excuse to stop exploring is a mistake.

Overcoming this gravity means making a conscious, deliberate choice to leave the itinerary blank for an afternoon. It means taking the long way home, even when the usual route is faster. It means accepting that the discomfort of stepping outside the routine is the unlock to open a new experience.

The architecture of a well-lived life isn’t built out of safety. The most interesting rooms are the ones we never intended to enter but just happened into.

Categories
AI Blogs/Weblogs

How to Refresh Dated Blog Articles

Woman typing on laptop at wooden table in cafe with coffee and pastry
A woman working on her laptop at a sunny cafe table with coffee and pastry

This afternoon I used the following prompt to help me assess posts I’d written a few years ago for updating:

I have a personal blog at https://sjl.us
Please review my blog posts that are between two and five years old and give me a prioritized list of which ones you think I should update.

I was curious how well it would do at this task. Turns out I was pleasantly surprised. Here’s the result:

Here’s my prioritized list of your blog posts (published roughly April 2021–April 2024, i.e., 2–5 years old as of April 2026) that I recommend updating, ranked from highest to lowest priority.

I reviewed the site structure, monthly archives, and indexed posts via searches. Your blog has dozens of posts in this window (mostly personal essays, photography, history, productivity/PKM, and heavy AI experimentation from the 2022–early 2023 wave). I prioritized based on:

  • How much the topic has aged (AI/prompting/tech tools change fastest; photography, personal reflections, and history are more timeless).
  • Potential value of an update (adding 2026-era insights, new examples, current tool versions, or follow-up reflections makes the post fresher and more useful to readers).
  • Thematic clustering (your AI/PKM series from 2022–2023 forms a natural arc that would benefit from a cohesive refresh).

I focused on the highest-impact ones rather than every post. Many others (e.g., pure street photography, freeway essays, family stories like the Tracy obituary, or 2021 COVID-era reflections) are still strong as-is and don’t need updates unless you want to add new photos or minor notes.

Top Priority (Strongly recommend updating soon — these are the most dated but highest-potential)

  1. Multi-step prompting for Claude (August 11, 2023)
    https://sjl.us/2023/08/11/multi-step-prompting-for-claude/
    Why update? Early Claude-specific prompting techniques; the entire field (Claude 3/4 families, GPT-4o-class models, Grok, etc.) has advanced dramatically. Easy win: expand with 2026 best practices, new multi-step examples, and comparisons.
  2. My Current PKM Stack as of September 2023 (September 20, 2023)
    https://sjl.us/2023/09/20/my-current-pkm-stack/
    Why update? Details your Obsidian/Instapaper/Feedly/Drafts workflow at the time. Tools and plugins have evolved a lot; readers love current “state of my stack” posts. A 2026 version would be highly engaging.
  3. Using AI to Help Write (November 15, 2022)
    https://sjl.us/2022/11/15/using-ai-to-help-write/
    Why update? Pure GPT-3-era experimentation. Perfect opportunity to contrast 2022 capabilities with today’s multimodal models and show how your own AI-assisted writing process has matured.
  4. LLMs = Dream Machines (December 11, 2023)
    https://sjl.us/2023/12/11/llms-dream-machines/
    Why update? References to early hallucination discussions and Andrej Karpathy’s tweet feel historic now. Update with current “dream machine” examples and how you use LLMs in 2026.
  5. Crafting Effective Prompts for Your AI Assistant (Claude, ChatGPT, Bard, etc.) (September 9, 2023)
    https://sjl.us/2023/09/09/crafting-effective-prompts-for-your-ai-assistant-claude-chatgpt-bard-etc/
    Why update? Another core prompting/PKM-adjacent piece from the explosion period. Pair it with the multi-step post for a nice “2023 vs 2026 Prompting Guide” refresh.

High Priority (Worth updating — clear value-add)

  1. An AI Thanksgiving (November 22, 2022)
    https://sjl.us/2022/11/22/an-ai-thanksgiving/
    Why update? Fun GPT-3 + DALL·E experiment. Readers would love a 2026 “then and now” version with newer models/image generators.
  2. Hacking Creativity with AI (August 22, 2023)
    https://sjl.us/2023/08/22/hacking-creativity-with-ai/
    Why update? Early chatbot creativity techniques; the creative workflow space has exploded since then.
  3. On the Minimum Viable Environment (MVE) and Apple’s Vision Pro (July 1, 2023)
    https://sjl.us/2023/07/01/on-the-minimum-viable-environment-mve-and-apples-vision-pro/
    Why update? Pre-launch speculation. Vision Pro shipped in 2024 — you can now add real-world usage, ecosystem updates, and whether MVE thinking held up.
  4. Drafts – a tool for idea capture (April 16, 2022)
    https://sjl.us/2022/04/16/drafts-a-tool-for-idea-capture/
    Why update? The app was celebrating its 10th anniversary then; it’s now 14+ years old with major feature/UI changes. Your long-term usage makes this a great “then vs now” post.

Medium Priority (Nice-to-have updates if you have time)

  1. Reading Books in 2022 (May 11, 2022)
    https://sjl.us/2022/05/11/how-im-reading-books/
    Why consider? Kindle/app habits and highlighting workflows have evolved; easy to refresh with current tools and your 2026 reading volume.

Other notable 2023 AI-adjacent posts (e.g., NotebookLM deep-dive from Dec 2023, Explorations of PKM from Oct 2023) would slot in here if you want to do a broader “AI/PKM 2023 Retrospective” series.

Lower Priority / Probably Leave As-Is

  • Photography series (e.g., “Capturing the Art in Everyday Scenes,” Paris posts, “Redwood Circle,” etc.) → Timeless and visual; they hold up well.
  • History/personal essays (e.g., “Ode to a Queen,” “The World’s Most Beautiful Freeway,” “Remembering Blue Chip Stamps,” “Old Man Walking,” 2021 book recs, “Stuck in Neutral”) → Evergreen or emotionally resonant; updating could dilute their original voice unless you have new material.
  • Holiday/personal posts (e.g., Thanksgiving 2023, Merry Christmas 2021) → Fine as snapshots in time.

Quick recommendation on approach: Start with the top 5 (they form a nice cluster around AI prompting/PKM). Updating them together would create a strong “2023 AI Reflections – Revisited in 2026” section or category on the blog. Many of these posts already reference each other, so cross-linking updated versions would be powerful.

If you’d like me to pull full content from any specific post, draft sample update language, suggest new sections, or help with images/AI-assisted rewrites, just let me know! Your blog has a great reflective voice — these updates would keep it feeling current without losing that personal touch.

Categories
Living Space

Apollo’s Ghosts and the Artemis Return

I watched the Artemis mission splash down yesterday, a modern silver capsule returning from the silent void around the moon. It was a beautiful, flawless return, but watching it, I felt an unexpected tug of melancholy. It transported me back.

I remembered being a kid, mesmerized by the grainy, ghostly black-and-white television broadcasts of the early American space program. I remember the static, the deliberate countdowns, the collective held breath of a nation when the first man walked on the lunar surface. Space felt like the ultimate frontier—an endless trajectory of human ambition.

This morning, with those images still knocking around in my head, I listened to a podcast discussing the long, quiet gap in manned lunar exploration. And then, one commentator dropped a detail that stopped me in my tracks: the spacecraft for Apollo 18 and 19 had already been built. They were fully assembled. Ready to fly. And then, the program was simply killed.

I’ve been sitting with that quiet, heavy fact for a few hours now.

Think about the sheer human effort locked inside those unflown machines. The engineering, the late nights, the calculus, the welding of titanium, and the dreams of astronauts who trained for a lunar surface they would never touch. Those spacecraft became monuments to an aborted future. They are the physical embodiment of a decision to stop.

We do this in our own lives, don’t we?

We spend months, sometimes years, building the architecture of a new idea. We assemble the parts. We do the research, we write the drafts, we lay the groundwork for a career pivot, a new business, or a creative project. We build our own Apollo 18. We get it to the launchpad, fully fueled by our initial enthusiasm.

And then—we just stop. We pull the funding. We let the gravity of daily life, or the friction of doubt, kill the mission before the countdown even begins.

The tragedy of Apollo 18 wasn’t that it failed; it was that it was never given the chance to experience the friction of the atmosphere. It never left the safety of the assembly building.

We are taught that patience is a virtue, but sometimes patience is just stubbornness in disguise—an excuse for not hitting the ignition switch. We convince ourselves that the conditions aren’t quite right, that the budget isn’t there, or that the timing is off. We leave our greatest capabilities sitting in the hangar, slowly gathering dust.

The return of Artemis yesterday was a reminder that we can always go back. We can dust off the launchpad. But the compound interest of abandoned projects is a heavy debt to carry.

The chaos of launch isn’t an obstacle to the mission; it is the environment in which the mission earns its meaning.

If you have built something—if you have put in the time, the sweat, and the architecture—don’t leave it in the hangar. Let it fly. Even if it burns up, it is so much better to have launched than to remain perfectly intact and perfectly grounded.

Categories
Living Music Writing

The Tonic Chord of a Life

We spend a good portion of our lives surrounded by noise. Not just the literal kind—the hum of traffic or the ping of notifications—but the internal noise of unresolved tensions.

I was reminded of this while listening to a recent conversation between David Perell and the legendary journalist Tom Junod (https://youtu.be/JnHTUyZjwiY). Towards the end of their sprawling, beautiful discussion, Junod introduced a metaphor about writing that made me pause the audio and just sit with it for a moment. He talked about the “tonic chord.”

“Musicians, you know, back in the day, they were always looking for the tonic chord. And writing, I’m always looking for the tonic chord… where all the discordant harmonies are resolved in a single ba-boom, you know, at the end of Beethoven or whatever… looking for some sort of resolution to the stuff that gnaws at me.” [00:39:42]

It’s a striking image. In music theory, the tonic is the home base, the center of gravity. It is the chord that finally brings rest after a long sequence of tension and suspense. Without the preceding dissonance, the tonic chord has no power. The chaos isn’t an obstacle to the resolution; it is the very environment that makes the resolution meaningful.

This applies far beyond the blank page. We are all, in our own ways, searching for our tonic chords.

We carry around the stuff that gnaws at us—the contradictions in our relationships, the career choices that look good on paper but feel hollow in the chest, the quiet hypocrisies we tolerate in ourselves. These are the discordant notes. We spend so much of our lives trying to ignore them, turning up the volume on our daily routines to drown out the clash. Or we try to fix them with brute force, stubbornly demanding harmony before we’ve even listened to the melody.

But maybe the point isn’t to erase the tension. Junod’s genius—both in his essays and in this metaphor—is his willingness to sit with the discomfort. He looks directly at the friction. He places two opposing truths right next to each other, letting them rub like tectonic plates, waiting patiently for that final chord to finally release the pressure.

I think about the architecture of a well-lived life in much the same way. The most resonant moments I’ve experienced haven’t come from a smooth, unbroken string of successes. They usually arrive right after a period of intense confusion or struggle—a sudden moment of clarity on a foggy morning walk, a tough but honest conversation with a friend, or finally letting go of an idea that had lost its spark.

That sudden ba-boom of clarity. The release.

We are taught from childhood that a good life should be harmonious. But true harmony is earned. It requires us to listen closely to the discordant parts of our lives, to bear witness to our own messes and mysteries, and to patiently search for the truth that finally brings them all together.

Often, it is the ultimate act of self-awareness.

Seek serendipity.

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