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 has made conformity economically obsolete. Anything that can be standardized, systematized, replicated — AI can do it cheaper, faster, at scale. The universal has become worthless. What has value now is the singular.

This is where Rami Kaminski’s concept of otroversion becomes economically urgent.^¹

Part 1: Why outsiders are forced into individuation

What otroversion is not.

Kaminski spent forty years as a psychiatrist before coining the term. He kept seeing patients who were socially capable, often charming, deeply empathic — and who described a persistent sense of not belonging.

Introverts, in the Jungian sense, recharge through solitude and find sustained social interaction draining. They can be socially skilled, even warm in groups, but the calibration of social performance depletes them. Solitude is recovery.

Extroverts gain energy from external stimulation. Groups invigorate them. Solitude feels empty. They orient outward, seeking connection.

Both share something the otrovert does not. Both experience belonging as meaningful. The introvert may prefer smaller circles, but when they find their people, they feel at home. The extrovert thrives in collective energy. Both can say, "These are my people."

The otrovert cannot say this, no matter how much they might want to.

What otroversion is.

Otroversion is a constitutional disinterest in experiencing group belonging. An otrovert can be entirely social. They can form profound one-on-one connections. They can be witty, warm, and present. But collective identity — the sense that you belong to a group, that the group’s values are your values, that membership defines who you are — does not register.

It is closer to color blindness than to a personality preference. A colorblind eye does not process certain wavelengths; the otrovert’s psychological system does not process group cohesion the way others do. They can see the group. They can intellectually understand what belonging means, but they do not accept it as the only path to self-actualization.

This produces a particular paradox. The otrovert is often popular. They are not withdrawn or hostile. They participate, sometimes actively. But they participate from the outside — present physically while remaining mentally elsewhere. Because they cannot merge into collective thinking, they experience an isolation that intensifies precisely when they are surrounded.

Kaminski notes that all children are otroverts before school. They live in their own imaginative worlds, construct their own rules through play, and relate closely to parents but are not yet embedded in group identity. Then comes school. Group behavior becomes the measure. The child who cannot find the communal impulse that binds the others begins to feel fundamentally wrong.

That wrongness persists. The otrovert may learn to perform belonging. They may become skilled at it. But the performance never becomes reality. There is always a distance between the person they appear to be and the person they actually are.

Why otroverts are economically positioned for the AI age.

The otrovert is forced into individuation by structural necessity.

Because they cannot hide in the collective, they have to become themselves. This is not a choice. It is a requirement for psychological survival. You cannot borrow your identity from a group that will not claim you. You cannot defer your thinking to a consensus that feels like a foreign language. You have to develop your own authority early.

In Robert Kegan’s stages of consciousness, most people spend decades in the socialized mind — identity drawn from external approval, organized by what others think, consensus mistaken for truth.^² The otrovert gets pushed out of that stage young. They have to move toward the self-authoring mind, where you can hold your own perspective separate from what the group believes.

The movement is painful. It is lonely. But it generates something economically valuable. The otrovert develops what I think of as an inner gyroscope. They learn to articulate their own meaning. They become capable of economic articulation — taking what they have discovered about themselves, about how they see the world, and communicating it in a way that creates value for others, not because those others agree, but because the clarity itself has worth.

In the old economy, this was a liability. Individuation made you harder to manage, harder to systematize, harder to fit. The system rewarded subordination, and the otrovert’s inability to subordinate was treated as a problem to solve.

In the new economy, dominated by the universalization of AI, individuation becomes the differentiating asset. Everyone now has access to the same tools. Everyone can generate similar outputs. The only thing that cannot be replicated is your particular way of seeing and articulating the world. Your perspective, earned through active individuation, not borrowed from the group.

The outsider has been forced to develop this. Otroverts are structurally positioned for an economic moment they did not choose and may not have recognized.

Part 2: Solitude as creative practice

Individuation does not happen in a vacuum. It happens in solitude. And for most people, solitude is intolerable.

Anthony Storr made a quiet argument in Solitude: A Return to the Self.^³ He pushed back on what had become foundational in modern psychology: that humans are, above all, relational beings. That health and growth emerge from connection.

Storr was not rejecting relationship. He was observing variation. There is, he wrote, “considerable variation in the depth of relationships which individuals form with each other,” and some people — particularly those engaged in creative work — require solitude not as refuge but as primary medium.

Some of the most profound and healing psychological experiences which individuals encounter take place internally, and are only distantly related, if at all, to interaction with other human beings.

His evidence was historical. The solitary scholars. The artists working alone. Einstein, Newton, Maxwell — producing their greatest work almost entirely by themselves. Not because they were antisocial, but because their work required an architecture that groups actively prevent: deep focus, uninterrupted thought, the kind of concentration that depends on being unavailable to others for long stretches.

Adam Phillips works the same territory differently. In On Kissing, Tickling, and Being Bored, he treats boredom as a psychological state worth investigating.^⁴ When the external is removed — when you are alone with yourself with nothing to do — what happens?

Most people experience this as unbearable. They reach for distraction. But boredom, Phillips argues, is not emptiness. It is where you encounter yourself unmediated. It is where you have to become interesting to yourself rather than relying on external entertainment.

The otrovert is already comfortable here. They do not experience solitude as punishment or deprivation. They experience it as a natural habitat. They have been in this space since childhood, developing their thoughts without the permission or validation of the group.

Mihaly Csikszentmihalyi’s work on flow gives this its final architecture.^⁵ Flow is total absorption — ego dissolved, action moving from one moment to the next without self-consciousness. Csikszentmihalyi observed that many of the deepest flow experiences happen in solitude, in focused engagement with something that matches both challenge and skill.

The ultimate test for the ability to control the quality of experience is what a person does in solitude, with no external demands to give structure to attention.

Most people fail this test. Solitude feels empty without an external structure. But those who learn to inhabit it, who organize it around challenges that matter, “have passed the test for having achieved a creative life.”

The otrovert does not have to pass this test. They are already living it. The constitutional distance from groups means they are already in the space where individuation deepens. The question shifts from how do I learn to be alone? to what do I make while I am here?

This is where practice becomes essential. Not practice as repetition. Practice as disciplined engagement. Every day spent in real solitude — thinking your own thoughts, pursuing your own questions, articulating your own vision — is a day you are developing the particularity that cannot be replicated. You are not competing on efficiency. You are getting to know yourself.

In an age of AI universalization, this practice becomes economically central. The hours you spend in solitude developing your perspective are hours you are building your only non-replicable asset.

Part 3: Creative surplus as market differentiation

I have spent years working with the concept of creative surplus — in writing, Critical Business School, and most directly through coaching individuals and teams.^⁶ The idea has three movements.

Discovery. Understanding what you actually believe, not what you have been told to believe. This is the work of solitude. Asking yourself real questions. What do I actually think about this? What matters to me, and why? Most people never get here because the group is always ready with answers. The otrovert has no choice but to find their own.

Articulation. Taking what you have discovered and making it communicable. This is where most people stop. They have the depth — they have developed their perspective through years of solitude and individuation — but they do not know how to surface it. They cannot make their inner life legible to others.

Integration. Bringing that articulation into the world in a sustained way. Not a single essay or conversation. A practice. A body of work. A living idea. A way of operating that consistently communicates a developed perspective.

Economic articulation is the bridge between Articulation and Integration. The movement from private depth to public value. Saying, clearly and compellingly, what you actually see, in a way that creates value for others — not because they agree with you, but because your clarity invites their own.

For most people, this three-part movement is aspirational. It requires years of developmental work before it becomes available. For the otrovert, it is already underway, usually without language for it. Discovery happened because the group never gave them answers. Articulation began because isolation alone was not enough — they had to communicate something of what they had found. Integration is the work still ahead.

What changes now is the economic context.

In the twentieth century, creative surplus was a nice-to-have. Organizations paid for execution, not perspective. They rewarded people who could implement systems, follow protocols, and produce standardized outputs. The person with a developed inner life and a singular way of seeing the world was, at best, tolerated — at worst, called difficult.

AI has collapsed that economy. The execution layer — the standardized, replicable, protocol-driven work — is being automated at an accelerating rate. What remains economically valuable is everything that cannot be universalized. Judgment. Perspective. The particular way you see a problem and articulate a solution that no one else could articulate in quite that way.

The inner life you have been developing in solitude. The perspective you have been forced to articulate because the group would not give you a ready-made identity. The clarity you have earned through active individuation. All of it is now the primary differentiating asset in the market.

Critical Business School is built around this recognition. The curriculum is not about fitting people into existing systems more efficiently. It is about helping people see that their individuation — their outsiderness, their solitude, their hard-won clarity — is their most valuable professional asset, and giving them the tools to articulate that asset in ways that create economic value.

The practitioners who teach at CBS are not academics delivering theory. They are people who have done the work of becoming themselves and can help others do the same. The premise is simple: the most important things you know, you learned by living. Learning to articulate that knowledge — to surface it and communicate it with precision and authority — is the economic work of this moment.

For otroverts, much of this is recognition more than training. They have been doing the developmental work for years. What CBS offers is language, structure, and community — not the community of belonging, but the community of mutual recognition. A space where outsiderness is understood as a resource rather than a liability. Where solitude is honored as practice rather than pathology. Where creative surplus is named as the thing they have been building all along.

The new economic logic

The convergence forms a new economic logic for the future of work. AI universalizes everything it touches. Individuation is the only thing that resists universalization. Otroverts are forced into individuation early. Solitude is where individuation deepens. Economic articulation is how individuation becomes value. Creative surplus is the accumulated expression of a life spent becoming distinctly yourself.

The question the old economy asked was: how well do you fit? The question the new economy asks is: how distinctly are you yourself, and how clearly can you articulate what that means?

These are not soft questions. They are the economic questions of this moment. And the people who have been living outside the group, inhabiting their solitude, developing their perspective without the permission of consensus — they are, unexpectedly, the people most prepared to answer them.

Self-knowledge and business are the same. In the age of abundant AI-driven utility, all we have is art.

If this resonated, you might also like Brief, Prompt, Practices on the difference between an inner question and an outer task, and A Living Idea on why ideas need a life of their own to matter.

^¹ Rami Kaminski, MD, The Gift of Not Belonging: How Outsiders Thrive in a World of Joiners (Hachette, 2025). Kaminski’s term otrovert derives from the Spanish otro — “other” — describing a person facing in a direction different from that of both the introvert and the extrovert.

^² Robert Kegan, In Over Our Heads: The Mental Demands of Modern Life (Harvard University Press, 1994). Kegan maps adult development as a movement from the socialized mind through the self-authoring mind to the self-transforming mind — each stage a deeper capacity to hold one’s own perspective without collapsing into the group’s.

^³ Anthony Storr, Solitude: A Return to the Self (Free Press, 1988). A direct rebuttal to the assumption that mental health is primarily a function of close relationships.

^⁴ Adam Phillips, On Kissing, Tickling, and Being Bored: Psychoanalytic Essays on the Unexamined Life (Harvard University Press, 1993). Phillips treats boredom not as an absence of stimulation but as the precondition for desire — the empty space inside which one’s own appetites can become legible.

^⁵ Mihaly Csikszentmihalyi, Flow: The Psychology of Optimal Experience (Harper & Row, 1990). The original study mapped the conditions under which attention, challenge, and skill align into self-sustaining engagement.

^⁶ Critical Business School is a year-long program in Brooklyn for life-long learners pursuing creative leadership through individuation rather than credentialing.

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

This post is for paid subscribers.

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.

Read more

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…

Read more

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.

Read more

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

Read more

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 …

Read more

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.

Read more

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 …

Read more

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.

Read more

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.

Read more

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…

Read more

Read more

Series note: This is the first installment in a 10-week series drawn from Creative Surplus: Identify, Articulate, and Integrate Your Unclaimed Creativity (Revised Edition, 2026). Each week, we’ll walk through one chapter of the book. The first four posts are free. Starting in Week 5, the series will be available only to paid subscribers.

Read more

Most conversations about AI start with what it can do. This one started with what it actually is.

At the first AI Literacy Salon, hosted by In Process Coaching and joined by guests Noa Dolberg (Google’s Material Design), Cherae Robinson (Head of Platform, Flybridge), and (Founder, Deliberate Works), we spe…

Read more

There is a difference between designing a highway system and designing fewer accidents.

The highway system is designable. You can specify it, model it, hand it to engineers, and what emerges will closely resemble what you drew. You can point to the blueprint and say: that is what we are building. The materials are known, the steps are known, the o…

Read more

In a recent AI Literacy workshop, I asked the prompt: *What do you wish an algorithm could predict?* As the answers moved from the practical towards bigger, harder questions, I arrived at a realization I haven’t been able to shake since.

Algorithms cannot predict anything subjective.

That sounds obvious when you say it like that. But the implication…

Read more

I have been running Men in Progress for a few months now. As I reflect on the group and our conversations, I realize that most men who find their way to this kind of work are not starting from zero.

They’ve read widely, thought carefully, and had the conversations that men seldom get to have. They take the question of how to live seriously. And yet…

Read more

Deconstruction is the act of noticing what you’ve had to set aside about yourself to stay legible. Derrida developed it in the 1960s from a simple observation: language is alive. It moves. It generates meaning beyond what anyone intended, pointing in directions its speaker never planned. He called this différance — the idea that meaning is never f…

Read more

Most people think growth means knowing more. More frameworks, more skills, more certifications. But there’s a different kind — one that changes not what you know, but how you know. That distinction is everything.

Robert Kegan, the Harvard developmental psychologist, spent decades mapping how adults make meaning. Most of us, he found, operate from w…

Read more