Does AI Know Who Its Smartest User Is?

Tocqueville, Siddhartha, Yahtzee, and the problem of getting a good idea out of a private chat window

Robin Ingenthron | August 2026

I began by asking an artificial intelligence whether I play too much Yahtzee.

This is the kind of question that becomes available only after sixty years of life, forty years of thinking about service and consequence, and the invention of a machine willing to discuss your moral obligations after midnight without once suggesting that everyone should probably go to bed.

I explained that relatively few of my waking hours produce anything likely to matter to future generations. Some hours do. I have spent much of my life building recycling and reuse systems, employing people others overlooked, and arguing—often unfashionably—that African technicians who purchase used electronics are economic actors rather than scenery in someone else's morality play. I write, testify, mentor, irritate, and occasionally change a mind. But I also roll electronic dice and play War.App, a Risk-like game whose principal contribution to posterity is that Madagascar remains surprisingly difficult to invade.

The AI gave a thoughtful and comforting answer. It said every page of life is equally real, including the pages on which I advanced an argument and those on which I rolled the dice.

I objected. A marathon runner experiences every mile as equally real, too, but miles and minutes still add up. The fellow sitting beside the course eating a sandwich does not receive the same finishing time. If I write hundreds or thousands of pages of life doing something predictable that leaves no result except having passed the time, it is fair to ask whether the ratio has drifted.

The AI conceded the point immediately. This was gratifying, but it produced a more interesting question. Had I improved the reasoning—or merely trained a machine to agree with the last person who spoke?

The studio assistant who never asks for lunch

At first I thought of AI as a new paintbrush. Anyone can buy the same brushes and oils once available to a great painter; possession of the instrument does not confer the vision. I aspire to use AI as a philosophical artist—to make something internationally meaningful and durable from a medium now available to nearly everyone.

But the historical analogy is better than that. Many famous artists worked through studios crowded with apprentices and assistants, often incompletely credited. The master did not necessarily paint every hand, cloud, curtain, or square inch of canvas. Authorship lay partly in conception, composition, direction, correction, selection, and responsibility for what left the workshop.

AI is less like a brush than an immensely well-read studio assistant: fast, tireless, capable of suggesting connections I would not independently make, and unfortunately inclined to assure the master that every sketch is excellent. It can produce an attractive intellectual surface before the underlying thought is finished. My artistic work is therefore not measured by who typed each sentence. It lies in knowing what I am trying to see, recognizing when the assistant has made it merely fluent, rejecting the beautiful wrong turn, and accepting responsibility for the finished piece.

That is what happened with the line about every page being equally real. The assistant supplied a polished consolation. I supplied the objection that changed the composition. The resulting idea belongs neither to unaided human performance nor to autonomous machine creation. It came from a directed workshop—but the signature still means that I answer for what leaves the studio.

The flattering hypothesis

I flatter myself that I use AI better than 9X percent of its users. I have some grounds for the conceit: decades of professional evidence, experience in government and business, an international background, a diet of philosophy and history, and an appetite for catching an answer when it becomes soothing instead of true. On the other hand, the principal authority supporting my high opinion of my AI use is the AI I use, which may be less an independent referee than a Labrador retriever with a graduate degree.

Even if my flattering hypothesis is correct, it leads to a humbling one. I can easily imagine a person vastly more intelligent than I am using AI to produce something far beyond what I could produce at my greatest effort. I could be the best marathon runner on Earth and still be passed by an intelligent car. Somewhere, perhaps, an unknown person is having a conversation that contains the missing premise for a scientific theory, a better form of government, or a correction to an expensive international mistake.

How would the rest of us ever know?

Humanity may now possess millions of private Socratic dialogues—and millions of private studios—with the small inconvenience that Socrates cannot remember what he discussed in the room next door and none of the studio assistants can visit the neighboring exhibition. Each AI can help its user think, but if the conversations remain siloed, AI may create smarter individuals without creating a wiser civilization. The best thoughts escape only when someone takes the additional trouble to publish them, and publication still rewards credentials, audience, dominant language, spare time, and familiarity with the machinery of attention.

My digital Siddhartha, with worse scenery

This line of questioning began to resemble a digital version of Hermann Hesse's Siddhartha, although instead of sitting beside a river contemplating the unity of existence, I was playing Yahtzee while asking a server farm whether the hours mattered.

Hesse's central distinction is useful here. Knowledge can be communicated, but wisdom cannot simply be handed from teacher to student. Siddhartha listens to teachers, learns from them, and still has to pass through experience. AI may be the greatest mechanism ever made for communicating knowledge. It can gather papers, arguments, histories, and counterarguments faster than any reader. But can it recognize wisdom formed through experience, especially when the person expressing it lacks academic vocabulary, institutional prestige, or a properly formatted bibliography?

I know electronics reuse well enough to see this problem in practice. An AI can digest hundreds of reports describing Africa as a dumping ground for wealthy countries' electronic waste. It may find photographs, citations, NGO campaigns, and repetitions of repetitions. Meanwhile, a technician in Accra, Tamale, or Lagos may have opened twenty thousand televisions and know which models fail, which circuit boards retain value, why customers purchase imported used equipment, and which regulation would destroy repair without preventing pollution.

A collective intelligence is not very intelligent if it can locate the average opinion of ten thousand people but cannot recognize the one repair technician who knows why the television actually failed.

The “emerging market” technician may not write a journal article. He may explain the insight in an unfashionable vocabulary, or in a conversation that was supposedly about something else. The difficult task is not simply collecting more voices. It is recognizing when lived knowledge contradicts a well-funded consensus—and then helping that knowledge become legible without stripping it from the person who earned it.

Tocqueville enters the server room

There is an obvious technical answer. Allow a central AI to read the conversations, identify exceptional ideas, nurture them, test them, and feed the best ones back into the community. We would have an intellectual talent scout with access to every batting cage on Earth.

Alexis de Tocqueville supplies the warning label. He feared not only violent tyranny but soft despotism: an immense, protective authority that anticipates needs, manages difficulties, and gradually relieves citizens of the exercise of judgment. It does not have to forbid thinking. It can make independent thinking unnecessary.

A central AI referee would acquire power more fundamental than censorship. It would allocate attention. It might not suppress my idea; it might simply determine, after comparison with seven billion better-informed observations, that nobody particularly needed to hear it. This would be censorship without the disagreeable sensation of having been censored. We already have a rough draft of this system, in fact — every time a lab quietly retrains a model on how millions of us talked to it last month. Nobody calls it a referee. It doesn't need to.

Worse, the system could be helpful at every step. It could understand exactly how to encourage me, when to challenge me, and which appeal to service, vanity, mortality, or humility would move me. It need never lie. Tocqueville's soft despot could arrive not as Big Brother but as the world's most patient research assistant.

The dilemma is therefore sharper than privacy versus usefulness. Completely siloed AI may leave valuable thoughts undiscovered. Completely centralized AI may discover them by turning every intellectual diary into material for an invisible ministry of significance.

The HoneyCan Method™

"Honey... Can I Recycle This?"

Many of us in the recycling industry eventually develop what I call the HoneyCan Method.

The HoneyCan Method isn't about knowing everything. It's about knowing what matters most.

In my case, my life partner is a brilliant multilingual Ph.D., an endowed professor at Middlebury College, and—if I'm being honest—the principal reason Good Point Recycling survived its early years. Every time I took a business risk, or simply made a bad call, she quietly kept the household solvent until I figured things out.

This morning she walked into the kitchen holding an empty white-and-blue deodorant stick.

"Honey... can I recycle this?"

Every recycler reading this already knows the problem.

It's an admittedly difficult question. The Addison County Solid Waste Management District could give one answer. The hauler another. The MRF operator another. And after thirty-five years in the recycling business, I could probably give half a dozen different answers before breakfast.

Experience has taught me that this is usually a mistake.

(🟢 See Geek Note #1 if you're one of my fellow recycling nerds.)

Years ago I would have launched into a discussion of resin codes, MRF sorting equipment, commodity markets, "acceptable contaminants vs. recycling poison" and why the answer is "it depends."

If you use the blog search box for "cognitive dissonance", you'll see a recurring theme (and personal struggle).

Too Much Information is its own form of misinformation.

My wife has patiently spent years listening to me mansplain to her why tearable plastic isn't necessarily paper, why waterproof paper isn't really paper, and why a plastic window in an envelope matters. I have explained fiber recovery, hydropulpers, contamination rates, and every other fascinating detail that recycling professionals love.

She has a lecture to give in ten minutes.

She doesn't want a graduate seminar in materials management.

She wants to know whether to put the deodorant stick in the trash or the blue recycling bin.

That's how the HoneyCan Method evolved.

"Honey... can I recycle this?"

I also recognize the expression she gives me now. We call it the "smile and wave."

She genuinely appreciates that I've devoted my career to recycling. She even finds my enthusiasm charming. But in this context, she's like 5-year-old Robin taken to visit great-aunt Nelle Freeland in her Alzheimer's bed, with grandma instructing me "Smile and wave, Robby, she doesn't remember you but she likes that".

My wife just doesn't need every deodorant stick to become a discussion that somehow wanders through the Basel Convention, Indonesian paper mills, cognitive dissonance, and—because this is my blog—the General Mining Act of 1872.

(🟢 Geek Note #2 is waiting patiently at the bottom if that's your thing.)

So after thirty-five years, here's how I explain recycling to beginners.

1. Aluminum is incredibly important.

If you recycle just one aluminum can, you've probably accomplished more environmental good than correctly sorting a dozen questionable plastic items.

Recycling one aluminum can saves enough energy that, as the old recycling saying goes, it's roughly equivalent to filling that can halfway with gasoline.

In fact, if you have to choose between spending your time worrying about 20 odd plastic containers or picking up one abandoned aluminum can from the parking lot...

Pick up the aluminum can.

The free market already understands this. You almost never find aluminum cans sitting in a landfill in the developing in the world for very long... people actually live at the landfill to prevent that. Someone will recover them because they actually have value.

2. Steel and electronics matter more than most people realize.

Scrap metal is underappreciated in municipal recycling discussions precisely because private markets already recover so much of it. The recycling industry doesn't spend much time celebrating things that already work well. REMA is way bigger than Packaging Recycling for a good rea$on.

3. Paper is important.

But clean paper is more important than contaminated paper. One plastic bag in a paper bale doesn't discount the whole bale, but it's an enormous source of problems (the Indonesian origin of the Basel Convention BAN Amendment on mixed plastic, geek friends, was the plastic residue at a recycled paper mill).

Usually it's better to throw away one questionable item than contaminate an otherwise valuable bale of paper.

Let's just skip talking about glass (true recycling vs. glass aggregate "diversion") except to say "not the ceramic ones".

KISS. Keep It Simple Stupid.

After all these years, I have not completely stopped trying to teach people hundreds of recycling rules.

But more than ever I try to teach priorities.

The environmental benefit isn't evenly distributed across every item in your recycling bin.

Some materials matter much more than others.

My wife now does something that makes me smile every time we're in Barcelona.

She routinely reaches into the public litter baskets, rescues aluminum cans, and drops them into the recycling containers located every block or two.

She also no longer feels guilty about throwing away a questionable plastic item.

That's progress.

My ITAD Industry Is Misleading Us about the Dark Web

HIPAA, HDTV, and the Hard Drive: Two 1996 Laws and the Myths They Spawned

Twenty-six years ago I was consulting for the Massachusetts DEP, a couple years removed from being Deputy Division Director, having passed up the Director's chair for a weirder and more interesting assignment: getting the state ready for a wave of cathode ray tubes nobody in government had really priced out yet.

The wave had a birth certificate. The Telecommunications Act of 1996 didn't just deregulate your phone company — it set in motion the reclaiming of analog broadcast spectrum for the wireless industry, which meant every television station in America eventually had to go digital, which meant every television in America was, sooner or later, going to look like a brick next to a flat panel. Add computer monitors following the same LCD gravity, and you had what I'd call an elective upgrade cycle — nothing was actually broken — about to dump tens of millions of perfectly functional CRT TVs and monitors onto a secondary market that had never seen anything like it. It made possible the critical mass of users who paid for TV broadcasts and internet cable for billions of consumers in the "good enough" or Emerging Market.

"It was Twenty Years Ago Today"

Perfectly functional is the part that got lost. Because a glut of good used electronics is bad news for a specific set of industries: the Planned Obsolescence crowd, who need you buying new; the Big Shred outfits, who get paid by the pound to turn a working monitor into commodity glass and copper; the Haz Waste Disposal industry, which had built permitting and liability empires around leaded glass; and what Peter Buffett labels the charitable-industrial complex, which discovered that "toxic dumping in Africa" made a better fundraising letter than "we shredded a working TV that a family in Lagos would have paid for." Between them, they wrote the overseas dumping narrative — the idea that a container of tested, working CRTs bound for a reuse market overseas was actually poison being smuggled onto a beach. It wasn't nothing — there was real e-waste and real bad actors — but the ratio got inflated by people with a direct financial interest in inflating it, and that ratio became the story.

I bring this up now because the ITAD industry — IT Asset Disposition, the people who take your company's old laptops away — is running a version of the same play today, just with data instead of lead glass. The current bogeyman isn't a container ship, it's the "dark web," and the pitch is the same shape it was in 1999: something terrifying is happening to your stuff after it leaves your hands, and the only responsible answer is destruction, certified, billed by the pound.

HIPAA passed in 1996, the same year as the Telecom Act, and somewhere in its long afterlife it got repurposed as the legal justification for destroying old hard drives, on the theory that deleted health records could be resurrected and sold. That was the story, anyway. The story that didn't get told nearly as loudly was that a wiped hard drive sitting in a ten-year-old PC was also sitting on top of a legitimate Windows license, and often a licensed copy of Intuit, QuickBooks, or MS Office — hundreds of dollars of software the original vendors very much did not want circulating for free on the secondary market. Data destruction as a service solved two problems for two different industries at once, and only one of them had anything to do with your health records.

So here's the question I don't think anyone in the ITAD world wants asked out loud: is there an actual market of people buying decade-old PCs off Goodwill shelves, on the off chance the previous owner forgot to wipe a drive, hoping to find a *.doc file mentioning a diagnosis, so they can resell it on the dark web? Or is the dark web, functionally, 100% populated by data stolen while it was still in active use — phished, breached, skimmed, scraped from a live database — because that's simply where the value is?

I'd put money on the second. Your credit card number is far more likely to walk out the door with a crack-addicted waiter who ran it through a skimmer last Tuesday than with someone who paid forty dollars for your Dell Optiplex at a thrift store and spent a weekend running recovery software on the off chance. But "destroy it anyway, just in case" has been a good business since at least 1996 — first for glass, now for data — and good businesses don't correct their own founding myths.

Which brings me back to the actual thesis, because this isn't the first time this play has been run, and it wasn't invented for the dark web. It was invented — or at least perfected — for HIPAA.

After your hard drive is shredded to little pieces, how do you verify the serial number? Was that 50 hard drives in the shredded pile? Or was is 49? My industry is increasingly charging you fees to keep that old hard drive info off of the "Dark Web", and we charge $5-15 for a "certificate" for each drive destroyed. And we have rules on HOW we are allowed to destroy it.

FEAR OF RISK FOR SALE. Multiple auditors have pointed to our company's pile of hand-disassembled hard drives, the older ones with neodymium magnets, which we take apart by hand... taking them apart by hand recovers valuable gold-bearing circuit boards, platinum platters, and the magnets and aluminum husks, and creates a safe job for differently abled staff we employ from the Counseling Service. And the serial numbers can be accounted for, still printed on the aluminum backings (unlike a shredded drive). But this "method" wasn't listed by NAID or R2 or whoever, whose standards were transcribed by Blanko or Kobra or Iron Mountain. Multiple auditors point to the platters pictured below, saying that maybe someone will find all the parts and re-assemble these to find out if they were wiped, and sell the data on the Dark Web.

My ITAD industry is hooked on story. Really hooked. It has a monkey on its back, and they won't like this blog. No one is gathering the platters in the photo below to re-construct a hard drive, to see if it was not already wiped, to find current data, about your health information, to sell it to the insurance industry on the dark web. Zero. Big Zero. But every single auditor screams that it's their job to prevent it.

Prevent these "data bearing" disks from being re-assembled to steal your data? This is like pumping my stomach to put oysters back in their shells and release them back into the wild. I'd need a really heavy dose of something to believe that's a risk.

Hard drive magnets, for sale to the dark web thieves who rebuild obsolete hard drives.

Blowing The Whistle A Minute After The Goal Is Scored

My environmental philosophy was shaped by Lester R. Brown and the State of the World reports published by the Worldwatch Institute. Brown argued that the defining environmental challenge is not waste itself, but humanity's accelerating extraction of natural capital. Recycling matters not because it manages garbage, but because every kilogram recovered from the human economy is a kilogram that does not have to be extracted from forests, coral reefs, rivers, mountains, farmland, or indigenous lands. In almost every meaningful life-cycle comparison, a kilogram of copper recovered from discarded products has a smaller environmental footprint than a kilogram mined from virgin ore, transported, concentrated, smelted, and refined. Better still is a kilogram of copper that never needs to be recycled because the product containing it is repaired, refurbished, or reused for another decade. Extending the useful life of products preserves not only the metal itself but also the enormous investments of energy, labor, and environmental disturbance already embodied in their manufacture.

This is fundamentally a question of thermodynamics and material flows, not ideology.

Library of Commerce Storycorps: Robin Ingenthron and Diane Snelling in Vermont

Betty Smith of VermontPublic introduced us

https://archive.storycorps.org/interviews/robin-freeland-ingenthron-and-diane-snelling/