Most of the questions people ask about AI are asked at the scale of the zeitgeist. Will it replace what I do? What is the future of my field? Which tools should I be using? They are reasonable questions, and they rarely lead anywhere, because the answers arrive in the same general register as the questions. Someone else’s forecast about marketing, design, or education tells you very little about your Tuesday.

AI Literacy, the way I teach it, lives on the line between the zeitgeist and self-authorship. The work is learning how you work, so that new tools have somewhere to land. You can’t integrate a tool into work you haven’t described.

Sort your work into general and specific

The first question is usually some version of whether AI will replace what you do. A more useful one is which parts of what you do are general, and which parts are yours.

List a week of tasks. Mark each one general if it is repeatable and could be handed to someone with a template. Mark it specific if it depends on your judgment, your relationships, or your taste. Most people are surprised by how long the general column gets, and relieved by it.

The general column is a shopping list of things to be built: automations, templates, and small digital products you make for yourself. The specific column is harder.

Describe your human skills with more specificity

Instead of asking about the future of your general field, I would rather ask about your personal, specific future of work.

Look at how people describe their human skills. Empathy, creativity, communication, strategic thinking. These words are the easiest thing for a model to reproduce, because they are general and reductive. A skill described generally has been automated in language, whether or not anyone has built the tool.

Early in a career, you get paid for discrete (general) utility. As you become more senior, you are asked to be economically articulate, specific in your ideas, and explain the meaning behind your decisions, enough that someone will pay for it.

Write prompts for yourself first

Some people are in a race for the shiniest tools, using the best prompts. But a prompt can’t be useful if it comes from a general place. The most useful prompts are grounded in the specificity of your thinking in order to produce a thing worth paying for, in attention and money.

As an exercise, pick a prompt from Creative Surplus, have your favorite LLM write an essay from your answer, and reflect on the process. Or send it over and comment below.

Map how you already work

Finally, which tools should you be using? That depends on how you already take in information, make decisions, and dispatch action.

I have never seen anyone disorganized become more organized by AI.
All systems are designed to do what they are already doing, and you, we all are, systems of information. As a system of attention, of moments of deep work, you hope to pay those moments to the right things, and that those moments will yield enough value. It is okay to want to be industrious and efficient, as long as you don’t relinquish your specific aesthetic.

Remember that value, hard economic value, that moves and invites people, is the combination of utility, the general kind that everyone provides and needs, and aesthetics, the specific form that utility is delivered in.

If you’re curious about this line of thinking, get in touch ot learn more about AI literacy, or follow along on Luma.

Everyone wants to do good work, with good people, for good money.

But not all money is good, and not everyone wants or believes they can bring their full selves to work.

Most accept the status quo, using phrases like "the nature of the beast." As a project, a configuration of work, people, and money is much more actionable than most people think.

The previous two pieces in this series covered the first two parts.
People come before companies, and work emerges from a generative system. Money arrives last because it is the most delayed: a trailing signal of value already created. If you make it your primary goal, you will inevitably grow bored with what you do, and your income will suffer.

Don’t make money being an expert

Expertise is a contract with your past.

It is your network telling you who you are and what you’re interested in, limiting the space you have to notice and the value you can bring to the people you care about.

An expert cannot change. Every new curiosity threatens the niche the market assigned it, so living ideas suffer. Experts–of the kind that get paid to give talks–will inevitably find creative surplus once they allow themselves to look.

Be believable

Believability is conviction without ego. The ability to say what you see, the value you can envision, plainly, and without convincing.

Most sales rely on drawing a risk and promising a remedy, normally with branded language (/crafted sales script). When we enroll people, we can use living language because our ideas are alive, and we are not beholden to scripted language imposed by bosses or industry.

Self-Author

In Berger’s taxonomy of adult development, the socialized mind takes its shape from the expectations around it. It is a stage everyone passes through and, economically, a ceiling.

A socialized mind prices itself by looking sideways: what do people like me charge, what do people like me do? It can only sell what has already been named.

A self-authoring mind writes its own economics. It holds multiple timelines, and meets with actions, large and small. The value around the corner, or the thing everyone is already asking for.

Retain your capacity to change

Clarity is a pricing decision. Total clarity–a fixed offer/niche/persona–is the easiest thing to buy and the most expensive thing to own. If the health of your practice is driven by current commitments, every new idea you want to share with others will have a material cost. The more innovative these ideas are, the higher the cost.

So choose how clear you want to be. Be precise enough to be trusted with present commitments, and open enough to have somewhere to grow.

That openness is the affordance through which future curiosities and the journey of getting to know yourself happen.

Lower the cost of change

The best, most sustainable way to make a living from the ideas you’re excited about is to configure an ongoing, sustainable balance between sameness and growth.

Dramatic reinvention every few years is expensive and daunting. Ongoing change is built of small actions compounding into a living, healthy practice. It is a yes-and operating system all the way down.

It is continuously helping people while tending to your ideas. It is a double bind between putting your language on your intuition in the back of the house and economic articulation in the front of the house.

Movement begets movement. Ideas that are alive and developing communicate excitement, which invites new conversations that inevitably lead to opportunities to do good work with good people. Stale, scripted language always brings with it sameness and transactional, circumstantial opportunities. Living ideas always find other living ideas, and thoughtful practitioners always find others who see more for themselves and for the world.

To-do

• Print your LinkedIn bio or job description. Use a pen to circle the loudest words and strike out the stale ones.

• Draft your economic articulation in your own words: what do you do for a living, and how is it different from everyone else who does the same? You can use this tool from AI Literacy.

• Write all of the lanes you’re active in; if you can’t name more than one, answer what you’re interested in.

• When you’re done, begin again.

This is the third post in a series.

Read the other ones below

AI is not new, and it’s not going away. What’s left to figure out is when it helps, when it just looks like it’s helping, and where your judgment actually starts. This twelve-week elective is built around that distinction. Three modules, of four sessions, built for the creative who wants to stop reacting and start discerning.

The second cohort of AI Lite…

Read more

This post is a follow-up to How To Find People.

Waking up your network only when you’re out of a job is all the proof you need that you’re transactional with people.

Most advice about finding work is advice about visibility: portfolio refresh, case studies language, and methodical outreach. It works occasionally, because what you’re broadcasting is general utility. If a client happens to have an open need the morning your email lands, you’re in luck. If not, you go back to hoping to be in the right place at the right time.

Timing only matters when the signal is generic. I’m available, and I do good work is useful only to someone already looking. A specific signal–this is how I think–doesn’t have to arrive during an open need, because it isn’t answering a need. It’s producing interest. And interest has its own energy.

Good work doesn’t come from talking about how you do what everyone else does.

You Are Your Own First Client

Being able to tend to and nurture the ways you think outlives any transactional engagement. If you are not curious about yourself, no one else would. Every work you get is downstream from that.

What you’re maintaining is a generative mindspace: a place of thinking that is in conversation with the world but protected from it. Somewhere you can articulate your intuition, the same intuition already driving all of your decisions, whether or not you’ve given it language.

Publish Opinions, Not Evidence

Most people publish proof of professionalism as a way to convince others of their utility. The alternative is to demonstrate bright, energized, independent thinking, and enroll people in it.

That shift matters more than it sounds. Convincing is what you do inside a transactional system, where you view yourself and others around you as products. Enrolling is what happens in a mutual worldview, where you are a living practice someone wants to be near. That means that you will have people in your orbit who can follow along when you move from graphic design to system thinking and computational linguistics.

Follow Value, Not Money

Pursue signals of value, and don’t confuse them with signals of money. Value is perceived and subjective; it exists in someone’s head. Money is a lagging, lossy readout of it, always arriving after value and never asking for innovation. Money keeps coming until it stops. It is up for the thoughtful person to sense what is coming and integrate it into their economic activity.

Keep a Consistent Routine

Be steady, rigorous, consistent, slightly dull. A practice needs a steady hand and the ability to negotiate with externalities. The ability to calibrate how expansive you can be at any given moment, based on life commitments, is the core of a long-term, living and growing practice that can nurture work-life balance and lead to doing good work with good people for good money.

The failure mode is neurotic effort: a spasm of visibility that stops the instant you get booked. Four months vanish into the project, it ends, and you resurface at zero.

That’s the cycle of forgetting yourself, and it repeats because the effort was never a practice. It was an emergency response, and emergencies end. A practice has no emergency mode.

Small actions compound, and they create ripples much further out than you can see.

You are a system that generates and broadcasts. Work is an output of that system, not an input to it. So the thing to maintain is the generative state itself.

A project doesn’t expand your possibilities. It connects to the optionality you already created. Good work comes from movement and energy.

Suggested to-dos

1. Make something meaningful nobody asked for

2. Publish an opinion, without convincing.

3. Keep a list of small actions.

4. When you’re done, begin again.

This post is a follow-up to:

The Enlightenment gave us light as an external thing. Reason was a lamp held up to a world laid out before us, a mechanism to be observed, decoded, and steered. The knower stood apart from the known. Kant’s motto for the whole age was Sapere aude, dare to know, and his definition of Enlightenment was “the …

Read more

​Every job consists of tasks. No matter how much we would like to avoid it, habits form over time, and those habits can be structured and eventually automated.

​Taylor’s scientific management (1911) invited systematic, standardized thinking to all aspects of work, essentially making…

Read more

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.

Read the next post in this series:

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.

Emergence is the opposite of design, but it is not a problem to be solved; it is an opportunity to learn and sense subjectivity rather than ignore…

Read more

An introduction limits what can happen next. A prompt expands it.

We treat introductions as neutral, even kind — a way of easing an encounter. But an introduction actually does pre-mediate. It creates furniture for conversation, an obstruction to people being themselves. Before you meet the person, you meet the description. Before you read the work, you…

Read more

Most people treat aesthetics as a personal touch. But without literacy, aesthetics is general and never yours. Aesthetics and literacy are the same cognitive act, operating in different planes but always connected.

Literacy is not what you produce. It’s how you move through knowledge. A literate person doesn’t just decode words; they individuate me…

Read more

It’s possible to be curious about someone’s work without being curious about them. To study the output, craft, the thing, and never reach the person who built it; how they think, their intuition, and who they are when they do what they do.

Most personal development treats people the same way. The weekend workshop, the offsite, and the annual intens…

Read more

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

We talk about leaders who “move” people, about ideas that are “moving,” about being “moved” by a piece of work — and we treat it as a metaphor. It isn’t, quite. Look at the words we reach for — emotion, motivation. Both are built around the s…

Read more

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.

Read more

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

Useful things are, by their nature, swappable. A hammer is a hammer for whoever picks it up. A kilowatt does the same work in any wire. A dollar is a dollar in any hand. That’s the whole point of a tool. It doesn’t care who’s holding it, and you ca…

Read more

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

This post is for paid subscribers.

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?

Read more

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 …

Read more

Creative surplus isn’t something you build toward or earn through years of grinding in a job you dislike. It’s the baseline condition of being a thinking, feeling, sense-making creature. The only question is whether you’re curious enough about yourself to recognize it and articulate it into the world.

Most economic thinking about creative work star…

Read more

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

This post is for paid subscribers.

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.

Read more

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

Read more

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.

Read more