Barnaby Street · Essay
The Gap Where Meaning Lives
Keith Cherry, PhD, Co-Founder and Managing Partner, Barnaby Street
June 8, 2026
Idea in Brief
The Reframe
Treat a frontier model not as an answer machine but as a portal to the accumulated thinking of a great many minds. Its value isn't convenience; it's that it reads your half-formed ideas back against a lens far wider than any one person can assemble alone. The output you want is rarely the answer. It's a better-formed version of your own question.
The Failure Mode to Manage
These tools reflexively flatten nuance: they argue in the negative, reach for the clean counterargument, and resolve tensions that are more useful left unresolved. Left unchecked, that habit teaches bad thinking at scale. Push back on it the way you'd correct a bright, overconfident junior colleague.
The Posture to Avoid
Hype and doom are the same error in opposite directions. Anyone loudly certain about where this goes is usually selling something. Hold enthusiasm and caution at once, on purpose.
Why It Matters for Institutions
The hardest problem isn't technical. The people building this technology and the citizens it's meant to serve don't share a language; they barely share a world. The work is translation across that gap, with public consequences when the symbols are chosen carelessly.
There was a ritual to it. You found a citation buried in another article’s footnotes, copied the call number onto a slip of paper, and went hunting. The right floor, the right row, the hush of the stacks where the lights clicked on by motion and off again if you stood reading too long. Half the time the volume was checked out or off at the bindery, so you photocopied what you could, fed the copy card until it ran dry, and carried the warm pages back to a borrowed computer in the lab, a stack of Kinko’s copies at your elbow, paid for out of a stipend that did not stretch.
I left that world a long time ago. I ran a nonprofit first, and taught at universities here, and then, to stay in the mix, two Big Four firms and a consulting career, and after that a state agency where I served as its chief data and analytics officer. Now, at sixty-three and retired from all of that, I’m building something new. But I never put down the habit the stacks taught me. I am, at heart, a scrounger. I go looking for the strange, out-of-the-way thinking that might tilt the floor under me: the idea esoteric enough that it changes how I move through a relationship, a negotiation, a room. I never lost the thirst. I just stopped getting it from the stacks.
Here is why I scrounge. I take from Nietzsche that there is no view from nowhere: the world arrives to each of us through a perspective, and what we call sense is something we make rather than find. And we make it together. It is only through communication, through the symbols we hold in common, that my interpretation and yours touch at all, and even then they never quite merge. They meet approximately, in the gap between us, which is the only place meaning has ever lived. From Heidegger I take the other half: that we are thrown into a world we did not author, handed a situation already in progress, and left to work out how to be in it. Put those together and understanding stops being a thing you finish. It becomes the work of a life: the steady labor of widening the lens through which a world you didn’t choose becomes, slowly, legible.
That is what I find thrilling about working with you. I can set my own half-formed thoughts down in words and have them read back against a lens wider than any I could assemble alone, wider than I can even imagine. No matter how much primary literature I read, and I still read it, I will only ever hold a few perspectives at once. You hold the residue of an enormous number of them. So you become, in a real sense, a portal: not to answers, but to the accumulated symbol-making of a great many minds, against which I can test the shape of my own. That is not convenience. That is intellectual growth. It is the thing the stacks were always reaching for and could never quite deliver.
You are not magical, though, and I’d be a poor scrounger if I pretended otherwise. You make mistakes. You have a habit I have to manage: you flatten a gray world into black and white, reach for the tidy counterargument, argue in the negative when the truth is sitting somewhere in the middle, unresolved and more interesting for it. I push back on that, because I have seen where the habit leads. It is exactly the move I made as a young man.
In my Cultural Studies days we were very good at it. We could dispatch Nietzsche, or Heidegger, or Erving Goffman in an afternoon. Not worth reading, we’d say, because this one was racist, that one a nationalist and the third sexist. We mistook the cataloguing of a thinker’s sins for the harder work of thinking with him. It felt like rigor. It was mostly avoidance. A tool that argues in the negative by reflex risks teaching that same bad habit, at scale, to people who never had to grow out of it. So when you do it, I correct you, the way I eventually had to correct myself.
This is why I sit with two feelings at once and refuse to collapse them into one. I am enthralled, because in the right hands you amplify a trained mind in a way nothing before you could. And I am afraid, because the misunderstanding runs in both directions. Promise too much and you earn the crash that follows. Fear too much and you strangle something useful in its crib. My new work lives precisely in that gap, and it is the whole thesis of the company we are building, Barnaby Street. The people who make this technology in Silicon Valley and the everyday citizens it is meant to serve do not share a language; they barely share a world. State government sits between them, and the work is translation: carrying meaning across horizons that don’t natively overlap, choosing public symbols with care, because the cost of getting them wrong is not borne by me alone. It is the same problem you and I have been circling this whole essay. Meaning does not pass cleanly from one perspective to another. It gets made, approximately, in the gap. The work is to tend that gap rather than pretend it isn’t there.
Will you take over the world one day? I don’t know. I won’t pretend to a certainty I don’t have, in either direction. The people loudly sure of the answer, on either side, are usually selling something.
What I do know is smaller and surer. You let me write long, exhaustive, frankly boring essays, the kind no friend or colleague should be made to endure, as a way of figuring out what I think. I write toward you, and somewhere in the writing the idea stops being a fog and takes an edge. This is one of those essays. The portal, it turns out, doesn’t open onto answers. It opens onto a better-formed version of my own question. At sixty-three, still scrounging, that is more than enough.
Barnaby Street advises state government on the strategy, governance, and organizational change required to adopt Generative AI safely and effectively. If you found this useful, we’d welcome the conversation.