Some follow-up thoughts from the discussion at the second AI Literacy salon that took place at Index Chinatown on May 13th1.

What is actually evolving, and what is only being assembled?

When we put minds and machines on the same track, pointed at the same horizon, is that a real comparison? Is what you call growth the same thing a model is doing when a better one ships and replaces it? Is anything in that room growing, or is most of it just being built?

Everything starts and ends in language. Most days, it feels limiting. The shape other people press you into, the experience, an old clarity that blocks what’s next. But with vertical development, we can start to identify doors where the walls are, waiting to be opened. Tired language opens up for deconstruction, and meaning is waiting to be found and shared. Language is where value lives. Economics and communication are the same act. Your consciousness is not action-dependent. You are not the sum of last week’s shipment; your value is your utility plus your aesthetics: your way of seeing the world, your way of being you, and intuiting decisions (design and decision making are the same).

A culture of productivity sells the opposite. A reductive person and a reductive algorithm (all algorithms are reductive) speak the same statistical language.

Answering what you know but can’t explain is how you get closer to your aesthetics2.

Machines do not evolve. They get built, and when the next one arrives, the last one goes in a drawer. Saying a machine evolves is like saying your iPhone grew from your telephone. That the rotary handset on your grandmother’s kitchen wall slowly stretched, brightened, and learned to be a camera. It did not. Someone designed each step. Someone threw the previous one out. That is not evolution. It is a replacement for a flattering verb.

Evolution is the slow transformation of something that remains itself through change. There is something that is you that remains as you change and become. The phone does not. A model does not. You do.3

Use language as a lockpick, because it is how you find yourself underneath the consensus. Trust the part of you that was creating before it could name what it was doing. That part is not borrowed. Stop letting output (job titles are output, too) decide who you are. The source is upstream and quieter. And take the word evolution back from the things that are only being rebuilt.

You and the machines were never in the same race. You were never in a race at all. The only thing in that room with a past, a future, and the same interior connecting them was you. The machines will be replaced. You are the one who actually grows.

To stretch the line between machines and nature, consider if this project from Jonathon Keats (Ep 9) is generative art.

AI Literacy is the ability to know when to go from the general to the specific, to learn the way we think, so as to be able to discern when others around us (machines or people) are doing the same.

Integration is not monetization. It is alignment.

Integration is the third movement: folding what you have discovered and articulated back into your life and work. It is the most difficult of the three, because it asks you to change. Not just what you think, but how you show up.

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Self-leadership begins when we learn to draw a frame without drawing a picture. Every other mode of communication is, in effect, telling people what to do rather than enabling them to be themselves.

Frame and picture

All mental frames are constellations of ideas, interpretive tools that create a way to see the world. A picture is a snapshot, disembodied and transacted.

It is the picture of a living forest, rather than the forest itself.

They are both forms of communication; both can be done in earnest, but they are materially different.

When we draw the picture, we create an artifact. We hand someone a finished thing. We say: here is the answer, here is the model, here is what good looks like. It feels generous because it is concrete and transferable. It feels like leadership, because we are pointing them to a specific destination.

But when we draw the frame, we hand someone a place to stand. We say: here is the question, here is the distinction, here is what to attend to. It feels less generous because nothing is finished. We aren’t delivering a destination; we are giving them the orientation from which they can find their own.

Picture-drawing is the default form for almost everyone who is trying to help. Instructions, examples, templates, best practices, “here’s how I did it,” with real generosity. The dependence it creates is also real. The picture works while we are in the room. When we leave, the picture goes with us, and the person who receives it is left holding the memory of its value rather than the value itself.

Generative value

The test for whether a thought is a picture or a frame is simple. Does it stay once we leave the room? A generative frame is what people remember when they have already forgotten what we said. This is the reason “enabling people” and “telling people what to do” feel close but are not close at all.

Telling people what to do produces motion in the room. Enabling people produces motion after the room is empty.

Recreational and transformational value

Value can be recreational or transformational. The most obvious example is information — in a book, a talk, an email.

If a communication signal is no longer helpful when the speaker leaves the room, we can think of it as a limited experience. It is recreational. Whereas if a piece of communication opens space in our thinking, through high-context confusion1, through deconstruction, through a frame that does not immediately resolve, our intuition uses that space, that slack, to travel and integrate into our ways of being. That is transformational.

When communication is transformational, we take it for its frame rather than a picture. It leaves us with a new way of seeing the world and being ourselves. We can feel the choreography of recreational communication, like the expected rhythm of a non-fiction book or the satisfying click of a well-told story. Transformational communication has no choreography; it is embodied and travels differently for everyone in the room.

Storytelling is recreational, not transformational.

This is where storytelling reveals its limit.

Storytelling is one of the most powerful tools in recreational communication. A good story is a closed picture: beginning, middle, end, all of it pre-drawn. It moves you, but it moves you across an arc the storyteller has already finished. When the story ends, you have the picture. You do not have the frame.

A story describes an experience, but not its meaning. For the meaning to land, either the storyteller has to reveal it, or the receiver has to decipher it on their own. Both seldom happen, which is why most stories end as entertainment2, no matter how serious they were meant to be.

You can love it, quote it, recommend it, even live by it for a while. But you cannot reproduce the internal change it made on your own, because the change came packaged inside someone else’s world. The frame was held by the storyteller, not given to you.

This is why storytelling, for all its beauty, is closer to entertainment than to change. It is excellent for recreational value. It is rarely sufficient for transformational value. The arc that makes a story satisfying is the same arc that prevents it from becoming yours.

Editorial, pedagogical, transformational

Three forms of communication name three stations on that gradient.

Editorial communication is answers. Facts, claims, conclusions. Its job is to convince — to move someone to agree, to buy, to act. Its value is efficiency: the shortest path from the question someone is holding to the answer we already have. The reader leaves with information, and the information is useful for as long as it remains accurate.

Pedagogical communication is questions and answers. It teaches a skill. It promises a steady future: if you adopt this method, under these conditions, this will reliably happen. Its value is expertise — “I have walked this terrain, here is the map and how to read it”. The reader leaves with a capacity, but a capacity that is still organized by my map (pre-packaged).

Transformational communication is a form of mind, questions, and answers. It does not just teach a skill; it changes the shape of the mind that holds the skill. Its value is individuated meaning. It does not enroll the reader into my way of seeing; it enrolls them into their own. The reader leaves as a self-author.

The three forms differ in how much they leave behind once the speaker is gone. Editorial leaves the answer, and only while the answer remains relevant. Pedagogy leaves the method, and the method depends on the conditions the expert observed, still holding. Transformational leaves a form of mind, which keeps producing answers and methods of its own, in conditions the original author never saw.

Editorial is the clearest and easiest to understand, and travel; it is necessary. Pedagogical is what we might call the processing layer, the university course, the HR mandated offsite: useful, and easy to mistake for the growth. Transformational is where people become and integrate their creative surplus. It creates motion and establishes practices that far outlive any minutes in a room or off-site. It shifts and grows, as ideas come and go. It is the only one that draws a frame and lets the picture become the reader’s.

This is why the frame matters more than the picture, why the nutgraf matters more than the lede, and why a story, however well-told, cannot be transformative.

Invitation

This week, I invite you to seek and cherish transformational communication. Notice which signals stop working when the sender disappears, and which ones keep producing inside you long after the conversation ends. Those second ones are the frames. Those are the ones worth keeping.

Integration is not monetization. It is the act grounded in one’s creativity.

Integration is the third movement: folding what you have discovered and articulated back into your life and work. It is the most difficult of the three, because it asks you to change. Not just what you think, but how you show up.

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CBS is opening an AI Literacy school in Brooklyn. Learn more →

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I recently met myself. Or something that was supposed to be me. Delphi had been trained on my content. ElevenLabs had been trained on my voice. By any reasonable technical standard, the result was impressive. The cadence was right. The vocabulary was plausible. And yet the moment I heard it, I knew something was off. Not broken. Off. The simulatio…

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Week 6 of 10 – Creative Surplus: A Chapter a Week

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The act of writing and rewriting is creativity. Total clarity is production.

Articulation is the second movement: putting language on what you have discovered. If discovery is about paying attention, articulation is about giving form. It is the bridge between the internal and the external, between the intuition and the conversation, between the surplus and the world.

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In the early 2000s, researchers studying epilepsy patients identified a single neuron in one patient’s brain that fired only when she encountered Jennifer Aniston. Her photograph, her name in text, even a stylized cartoon drawing — the same cell, every time. That is how human cognition organizes meaning: symbolically.

Large language models work dif…

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AI has inverted the economic logic of the twentieth century. For a hundred years, the market rewarded conformity. Standardization. The ability to fit into systems, follow protocols, and produce consistent output that matched specifications. The person who could subordinate their particularity to organizational demands thrived.

That era is ending.

AI…

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Week 5 of 10 – Creative Surplus: A Chapter a Week

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In abundance, all we have is philosophy.

Discovery is the first movement of creative surplus: paying attention to what is already present but unacknowledged. It sounds simple. It is not.

We are trained to look outward – at the market, at competitors, at trends, at data. The entire apparatus of professional life is oriented toward external signals. What does the customer want? What is the industry doing? Where is the opportunity? These are important questions. But they are not the questions that lead to creative surplus. They are the questions that lead to optimization.

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Not literally. Metaphorically. A project that's quietly over. A role you've outgrown. A relationship that's already changed but hasn't been named. A version of yourself that's still hanging around, taking up space. A belief you stopped believing months ago but haven't gotten around to burying.

Endings are everywhere. We're just avoiding meeting them. We treat them as failures instead of thresholds. We rush past them, or pretend they aren't happening, or quietly grieve them alone in the middle of a Tuesday. We almost never give them the attention they're actually asking for.

That cost is an opportunity. Unfinished endings have a way of crowding out whatever wants to come next. You can't make room for a new thing while you're still secretly hosting the old one.

That’s the premise of A Little Death, a new elective at Critical Business School, hosted by The voice notes above are from an exchange Danya and I had while building this.

Over four Thursdays in May, we'll move through pleasure, avoidance, ritual, and action. We'll tell stories. We'll make things. We'll sit with what's unfinished.

What if an ending were a climax rather than a collapse?

Why don't we prepare for the end — personally, institutionally, at all?

What's dying in or around you right now, and what might that be making room for?

Some of it will be uncomfortable. A lot of it will feel surprisingly alive. You won't be doing it alone, which turns out to matter more than you'd think.

Electives seek movement. You won't leave fixed. You'll leave a little more open — and a little more ready for whatever's been waiting on the other side of the thing you haven't let go of yet.

Four sessions. May 1, 8, 15, 22. 1 pm ET. 60 minutes. On Zoom. $200 for the whole arc.

If something in you just nodded, that's the part to listen to.

Sign up: https://luma.com/a-little-death

You can listen to Danya and Alma in conversation on episode 7 of the podcast.

There is a particular kind of overwhelm that doesn’t feel like being stuck. It feels like the opposite. You’re flooded with energy, with ideas, with urgency. You want to move, you feel like you should move, and everything around you seems to be asking you to. The pressure builds. So you move.

And then you move again. And then again.

And somehow, thr…

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A note before we begin. Next week's post opens Part II of this series—the transition from ideas to practice. It begins with the first of three movements: discovery, the art of paying attention to what is already present in your work but unacknowledged.

Paid subscribers will receive the full chapter – subscribe here.

Aesthetics is what does not fit in your job description.

That is the whole argument. But let me unfold it, because this simple idea has consequences that reach into how we think about creativity, identity, and professional life.

Subject and Object

Consider two dimensions. The first is the subject: the person—designer, accountant, gardener, teacher, engineer, nurse. The question is whether they can use whatever does not fit their professional role. That is the measure of their creativity. Not their skill within the role, but their capacity to exceed it.

The second is the object: the things they make. Do those things carry a quality that exceeds their function? Do they have aesthetics? A report that is not just clear but beautiful. A garden that is not just productive but strange. A lesson that is not just effective but memorable in a way that has nothing to do with the curriculum.

Your job description is your “cutout” in the world: the shape the market gives you, the professional archetype you occupy. Periodically, you peek out behind it. Aesthetics is the pun a barista writes on a coffee cup. It is the quirky hat a professor wears on the first day of fall. It is the hand-drawn diagram that the engineer leaves on the whiteboard. It is the human leaking through the professional.

These moments are not trivial. They are the visible evidence of a person’s creative surplus finding its way into the world. They are the places where someone is more than their role, and where their work is more than its function.

Ambiguity as Aesthetic

When we confuse people, something interesting happens. We ask them to restructure their values and ways of being in the world. We force them to reach for a new frame, a new category, a new way of understanding what they are encountering. This is uncomfortable. It is also one of the most powerful things a creative person can do.

Confusion–or more precisely, constructive miscommunication–is a prompt for creativity. Not the confusion of incompetence, but the confusion of encountering something that does not fit. The more we can place ourselves in a safe and generous space of misunderstanding, the more we discover what we actually believe. Constructive miscommunications ask you to understand your own values by forcing you to articulate them in response to something unexpected.

This interest in exploration can become a habit: a cycle of questioning, articulation, and integration. The act of writing and rewriting is creativity. Total clarity is production, and production is never creative. Creativity always carries some ambiguity – some residue of the unknown that survives the articulation.

I am not arguing for obscurity. Obscurity is a failure of communication. I am arguing for high-context confusion—the kind that creates space for the other person to bring their own meaning, interpretation, and surplus to the encounter. When both people in a conversation are working at the edge of what they know how to say, something new can emerge that neither of them brought into the room.

That something is thirdness. We will return to it in Week 9.

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PSA: There is a new place for this community to connect

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There is a version of your life that is working exactly as designed. Your attention flows toward the same kinds of problems. Your professional network reinforces the same assumptions about what’s valuable, what’s possible, and what counts as smart. Your habits of thinking—the shortcuts, the heuristics, the fast reads on situations—have been tuned …

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Everything is design, and not all professional design is creative.

Design differs from production. This sounds obvious, but the confusion between them has shaped entire industries, educational systems, and careers. Understanding the difference is essential to understanding creative surplus, because the surplus lives precisely in the gap between the two.

Production is the execution of known solutions for known problems. It is skilled, it is valuable, and it is necessary. But it operates within a frame that is already established. The brief is written, the requirements are defined, the success criteria are clear. Production moves from A to B along a path that someone has already mapped.

Design, at its root, is something else entirely. It is an epistemic operator — a way of knowing, not a way of making. It is the act of putting language and shape on what we do not yet understand. It is not about arriving at the right answer. It is about discovering the right question.

The Problem with Frameworks

Many unifying frameworks — Design Thinking, Human-Centered Design, Double Diamond, Sprint methodology — conflate the epistemic and the industrial. They take the genuine cognitive act of design and package it as a production process: five steps, three phases, a workshop with post-it notes and a deliverable at the end.

These frameworks are not useless. They generate group consensus, which is valuable in organizational contexts. They create a shared language for talking about ambiguity, which is genuinely difficult. They give permission for exploration within structures that would otherwise default to pure execution.

But what they produce is often consensus about average versions of the past. They ask a room full of people to converge on a shared understanding, which by definition excludes anything that only one person in the room can see. The most interesting thought — the one that does not fit any category, that resists the post-it note, that cannot be voted on — is the first casualty of the framework.

There is a genuine chasm between group work and design as I am defining it here. If design is genuinely about operating in the unknown — if it draws on wisdom rather than accumulated knowledge — then the challenge of creating shared language for truly unstructured ideas becomes immense. Intersubjective spaces — the cognitive territory between people — are extraordinarily difficult to navigate when the ideas being discussed do not yet have names.

This does not mean groups cannot design. It means that the standard approach — gathering people, running exercises, producing deliverables — often produces something more like well-organized memory than genuine discovery. The output looks new but is made of old parts, rearranged.

Separating Creativity from Production

One way through this is to separate the act of creativity from the act of production. They are different operations, requiring different orientations, different conditions, and often different people — or the same people in different modes.

The creative insight is one thing; its execution is another. If the creative idea is systemic rather than artifact-based — if it describes a way of seeing rather than a thing to make — then it can survive the production process without being reduced.

Think of it this way: the creative person is not the one who makes the best thing. The creative person is the one who sees what has not been made yet. The producer, who may be extraordinarily skilled, is the one who brings that vision into material form. Both roles are essential. But they operate with different orientations to time — the creative looks forward into the unresolved; the producer looks back to the pattern, the template, the proven method.

A designer might build their own system for navigating the unknown, or they might use existing frameworks. A non-designer might do the same. What matters is not the professional title but the orientation. Are you working from what you know, or toward what you do not? The first is production. The second is design.

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If your entire professional identity is organized around serving clients, you’ve collapsed yourself into a role. You’ve become the helpful expert. The reliable partner. The one who always delivers. But that’s a persona, not a person. And when you only show up as a persona, the work might look great …

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This essay began at a Men in Progress session, after the prompt “what do you love.” Sitting with the answers in the room, I noticed: before we love multiple things, we love one thing. The rest of this is an attempt to understand why that might be true of more than love.

There is a stage before belief becomes a position. Before you can hold an idea, you have to be held by it.

This is not a metaphor. It is an ontological claim.

When a person first encounters a genuinely new idea — not a variation on something they already think, but something that re-describes reality — they do not evaluate it. They are inside it, provisionally. The idea is not a proposition to assess. It is an experience to inhabit.

Piaget called this assimilation: the new thing gets absorbed into the existing structure. But there is a moment before that, before the organism has decided whether to incorporate or reject, where the new thing simply lands. Lands as a felt disturbance. A kind of cognitive weather.

This is where ontology lives. Not in the conclusion — not in “I now believe X” — but in the initial condition: the world, for a moment, is differently shaped.

Most people use the word “ontology” to mean something academic: a theory of what exists, a philosophical position about the nature of being. But lived ontology is something more immediate. It is the background of givens that a person moves through without noticing, the implicit shape of the world they inhabit.

You do not choose your ontology the way you choose a belief. It is more like choosing a language — except that you do not choose it at all. It arrives first through the body, through early experience, through what was made visible and what was made invisible, through the culture’s unspoken metaphysics. By the time you have enough self-awareness to examine it, you have already been shaped by it for years.

This is what Bourdieu meant by habitus: the system of durable dispositions that shape perception, judgment, and action — formed through accumulated experience, mostly before reflection was possible. The habitus is not a belief you hold. It is the structure through which beliefs become thinkable at all. To speak of “choosing beliefs” in this context is to mistake the surface of a very deep structure.

What this means practically is that whenever you encounter an idea that will genuinely change you — not inform you but change you — you first encounter a specific, embodied version of it. Not the abstract principle. The instance.

You do not first encounter “grief is love with nowhere to go.” You encounter your grandmother’s kitchen after she has died, and something in you reorganizes, and only later, maybe years later, does the sentence arrive to name what happened.

You do not first encounter “power operates through discourse.” You encounter a teacher who told you that your instinct was wrong, and the way everyone in the room nodded, and the slow collapse of your certainty — and then maybe you read Foucault, and you feel the retroactive recognition. The idea was already in your body. The theory gave it a name.

This is the epistemological version of “the map is not the territory.” But it is more than that. The map, in this case, only becomes legible to you because you have already, at least partially, walked the ground.

The Living Idea and the Dead Concept

There is a difference between knowing an idea and being inside it.

You can know that “systems are more than the sum of their parts” as a sentence. You can define emergence, cite Donella Meadows, pass a test on it. And yet the idea may remain inert — a concept you carry the way you carry a fact about a country you have never visited.

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PSA: I'm excited to announce the first online elective at Critical Business School — A Little Death, with Danya Shults, on endings and what they make room for. If you've been curious about CBS but aren't in New York, this is your way in. Four Fridays in May, 1 pm EST. $200, open to the public. Register here.

We are living through a moment when machines can do an extraordinary amount of what used to pass for creative work: write ad copy, generate images, draft strategies, produce code, compose music, and optimize campaigns. Everything that can be reduced to a pattern – everything that operates within known categories – is increasingly automated. By the time you read this, the capabilities will have expanded further.

It is the end of the confusion between creativity and production.

For decades, we conflated the two. Being “creative” meant producing things—ads, designs, strategies, content. The creative industries were production industries with better aesthetics. But production is the execution of known patterns, however skillfully done. Creativity is the act of stepping outside the pattern – introducing something that does not yet have a category, a name, or a market.

Machines can produce. They cannot be creative, because creativity requires the faculty of not knowing – of sitting with uncertainty, of feeling drawn toward something that has no name yet. Machines are architectures of correlation. They find patterns in existing data and generate variations within those patterns. They are extraordinarily good at this. But they cannot step outside their training data. They cannot ask a question they were not prompted to ask. They cannot feel the restlessness that signals something unknown is trying to emerge.

In a world where production is abundant and cheap, creative surplus is the only thing that cannot be replicated. It is the irreducibly human contribution – the thinking that no algorithm anticipated, the question no one thought to ask, the connection between domains that no training data contains.

This is why identifying your creative surplus is no longer a nice-to-have. It is the central question. Development is the only work.

When All Matter Is Available

When all material needs are met – when technology provides, when tools are plentiful, when information is free – our innate tendency toward interestingness and meaning finds its way through new channels. An abundance of utility asks for introspection. A plenty of technology asks for navigation. When everything is available, the question is no longer what can I get but what do I want – and the deeper question: what do I want that I do not yet know I want?

We are living in a moment of extraordinary abundance. Information, connectivity, tools, platforms, AI assistants - all available, all accessible, all overwhelming. The scarcity is not of resources but of attention, meaning, and direction. In such a world, the philosophical question – what matters? what is worth my attention? where is my creative surplus pointing? -- becomes the practical question. It is not a luxury to ask what you practice. It is a necessity because without that question, you will lose time and attention to someone else’s priorities.

This is not abstract. Every coaching session I have conducted eventually arrives at this point. The person has the skills, the network, the track record. What they lack is clarity about their own direction, a direction that their surplus and the ability to keep the world at bay as they listen to it.

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The Block essay that Jack Dorsey and Roelof Botha published last week is worth engaging with. The historical arc and the argument that AI can now perform the information-routing function that hierarchy has always performed are real.

There’s a word that appears nowhere in the essay: development. As in human development. As in, the question of whethe…

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