Most outreach advice focuses on finding companies: make a list of targets, research them, pitch them. It rarely works because companies don’t hire you; people do. And people don’t respond to pitches; they respond to signals. If your outreach isn’t producing anything, the problem usually isn’t volume. It’s that you’re broadcasting what you think the market wants to hear into networks that already know what to expect from you.

Here’s a different way to think about it.

Confuse your networks

All networks calcify over time; patterns cement. You already exist between several networks, but your communication habits flatten that position into a single, predictable channel — a false sense of limited optionality. Your network has categorized you: they know what you do, what you’d say, what to send your way. Which means they’ve stopped paying attention.

Confusing your own habits is the first step to reopening the pathways of meaning; show up somewhere unexpected, share a living idea which is still forming, break the pattern. What moves through those reopened pathways is creativity, not utility: energy traveling from where you actually think–the back of the house–out to others. This isn’t about finding new people so much as energizing the connections you already have. Most of them are dormant, waiting to be woken up.

Confusion, in this sense, is not noise. It’s the signal that something is becoming. People respond to movement.

Find people before companies

Companies, as collections of people, necessarily lean into efficiency, of communication, of doing. It’s an overlooked fact that the more people there are in a room, the more mechanistic and clear things need to be, and the less creative things get. Coordination has a cost, and it’s paid in exactly the ambiguity, opinion, and strangeness that make your signal worth receiving.

Which is why outreach aimed at companies fails: you’re broadcasting creativity into a machine built to filter it out. A person, though, can still be confused in the productive sense: surprised, moved, made curious. So look for the person, whose work you hold an actual opinion about, someone already moving through the same contexts you are. If they left the company tomorrow, would you still want the conversation? If the answer is no, you were never looking for a person.

Lean into your opinions

Be more yourself, rather than what the market expects of you. Sanding your edges down to fit a job description makes you interchangeable, and interchangeable people compete on price and availability. Your opinions are the only part of your signal that nobody else can broadcast.

Lean into the ways you think, rather than the things you make. Deliverables are comparable; a way of thinking isn’t. Broadcast the specificity of your aesthetics, not the general utility anyone else can produce. Specificity compounds. It yields results over time and sometimes converts to short-term gains too. Generality does neither.

Why this works

You are a system of information, broadcasting into and receiving signals from the world. All systems do what they’re designed to do, so if you keep sending the same signals to the same networks, you’ll keep getting the same results. Introducing confusion invites change, and once we open communication channels, we create optionality.

It is only from optionality that new work comes, not the other way around. You don’t get a larger set of possibilities by landing work; you simply unearthed one in the same menu you’re holding, so you will inevitably be in the same spot once this project is done.

To-do

• Break one habit your network has you filed under. Don’t be beholden to platforms; if something resonates in one place, move it to a better channel. This alone will wake up dormant connections

• Lean into an opinion that feels exciting rather than immediately commercial

• Pick three people (not companies) who inspire you, and get in touch directly

• Never share something you made without the way you think about it

• Measure outreach not by responses (objective) but by energy and optionality (subjective)

• When you’re done, begin again.

The systems we care about- organizations, markets, cultures, the people in the room you’re sitting in- were not designed. They emerge, becoming and responding to the openness of the world they’re connected to.

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Movement is not something you can hand to another person. You can only transmit a motion you already carry.

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Machines are architectures of correlation. We are architectures of care.

This is the final installment. We have spent nine weeks moving through the foundations, the three steps, and the forces that shape creative life. This week, I want to close with two things: a clear-eyed look at AI and creativity, and then the full collection of prompts developed over five years of weekly practice in circles and the Critical Business School.

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Aesthetics can’t be general, because then it would be a utility1.

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Week 9 of 10. Creative Surplus: A Chapter a Week.

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No technology makes a meaningful exchange any better than it already is.

This week covers the most ground in the book. Three chapters on communication, marketing, and the tools we think with. They belong together because they share one question: what happens to creative surplus when it meets mediation, optimization, and scale?

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Thought leadership is a media business. It runs on the economics of attention: a post, a talk, a byline, a quote in someone else’s deck. The currency is reach, the unit of exchange is the impression, and the relationship with the audience is transactional by design — you publish, they consume, the loop closes. At its best, it’s editorial work. It …

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Week 8 of 10. Creative Surplus: A Chapter a Week

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A circle is a band practice for solo artists.

In 2019, I set out to build an intentional co-creation space: a place where people could show up with their creative surplus and use it. Not a networking group or a community in the LinkedIn sense. Not a mastermind or an accountability circle, but a space where communication and discourse come before roles and transactions, where people arrive as persons rather than personas.

I called it Circles, distinctly not a community.

That space has been running continuously since 2019, through a pandemic, through the rise of remote work, through the arrival of generative AI, through the slow disillusionment with online community that has defined the last half-decade of the internet. What we learned in that time changed how I think about gathering, belonging, and creative collaboration.

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

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Integration is not monetization. It is alignment.

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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.

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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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