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I’ve been a CEO, a founder (twice). I led resilient, diverse, remote-first teams across the tech and media industries.
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Ways of moving

2026-04-15 01:35:00

I HEAR SOME VERSION of this about once a week: “I’ve been doing this thing for 15, or 20, or 25 years, and I don’t think I can do it anymore. But when I think about what else I could do, I draw a blank.” One of the questions I am wont to ask when I hear this is, what would you do if money was no object? And often—not always, but often enough to be a pattern—the floodgates open up. I would teach high school math. I would make ceramics. I would paint or write or play music all day long. I would work at the library, coach youth soccer, open a café. I would bake the best bread, make the best arepas, open a noodle shop. I would be with my kids. I would take care of my elders. I would teach poetry or history or art to anyone who wanted to learn. I would grow vegetables in that abandoned lot. I would be a farmer, a journalist, a park ranger. And so on. Which of course frames up the blank wall that appeared in the first statement: the difficulty isn’t in naming something we would like to spend our time or energy on. It’s in finding the match between how we would like to be and what capitalism will permit us to do while still keeping a roof over our head, and food in our bellies.

I think this is important to remember: we aren’t faced with an absence of imagination. We’re faced with the constraints of a system that does not have our best interests at heart.

The bad news is there is no manual for making this kind of transition. There is no rule book, no 7-step process, no orderly path you can follow. Changing your work is tough, and it takes time and (usually) money as well as spirit and fortitude and the support of the people around you. The good news is you aren’t the only one who’s ever hit this particular point in your work (we all get there, one way or another) and there are broadly some patterns you can use to think with your own situation, and from where you can begin to experiment and explore where this moment might take you. These patterns aren’t exhaustive, and they aren’t exclusive of each other; take them as a starting point for thinking about your own journey, not solutions to adopt but prompts to play with.

Bend toward the light

Imagine a tree, happily growing in a nice sunny spot for many years. Its got deep roots and long, leafy branches, and a bunch of shade-loving bushes and vines prosper beneath it. Then a great big building goes up nearby, and all the gorgeous afternoon sun that it depended on is blotted out. It can’t uproot itself and walk a ways, but it can lean those long branches over to where the sun still shines and so continue to thrive.

Moving into the light means taking small step from where you are to someplace close by that just might be a little more fruitful. The laid-off federal worker finds a job in city government, bringing their skills to a work at a different scale. The university professor shifts into administration, taking what they know of their students to improve the application process. The nurse at a big city hospital takes a traveling gig and learns what it’s like to work and live in a small town for a little while. And so on. You’re not uprooting your work so much as reorienting it a few degrees.

Note that what counts as nearby isn’t always near to your industry but near to your network—that is, the people around you. The bank manager who coaches an adult hockey league meets the director of a company that sells sports equipment and happens to be looking for someone to join their finance team—and boom, the sun is shining. So when you think about your network here, think about your colleagues and comrades in your field, but also your friends, neighbors, all your kith and kin in all the communities you belong to. This is also a good excuse for making more connections within those communities: your future work is just as likely to emerge from a job application as from a book club, school bake off, or weekly game night.

Plant a tree

Maybe you’ve reached your branches as far as they can go and you’re still not getting enough light. Then you might have to plant a new tree where the conditions are better. This looks like taking the skills and experience you’ve gathered over all those years and building something new: the product engineer leaves the day job and starts a consultancy. The high school teacher starts a service connecting students to internship opportunities at local small businesses. The designer teams up with a friend who’s a chef to concept and open a new diner, in a neighborhood that’s been long neglected by restauranteurs. A group of journalists team up to launch a worker-owned magazine, covering the topics the big media companies have abandoned.

These last few examples are instructive: like so many things in life, planting a tree is best done with friends. You’re going to have to prospect different locations and you may have to plant and nurture a few trees before you know which one is most likely to thrive. By teaming up with one or a couple of people, you can bring more skills and energy to making it work. You can also create the kind of support system you need to be patient during the early days, when the tree is but a sapling and isn’t ready to bear fruit.

Walk a ways

Sometimes a long drought leaves the earth so famished, nothing will grow for a while. Sometimes the forest becomes a lake, the snow-capped mountain once covered with conifers is overtaken by grass. There are times when you can’t see any fertile land as far as the eye will take you, and then you have to get up and walk.

The civic tech worker goes back to school for a degree in urban development. The journalist signs up for a training program to become an emergency medical technician. The designer gets an internship at their local brewery. In each of these cases, someone is starting over in a new field, one in which they need some training or schooling to get up to speed. Obviously, this takes time, and some investment of money, as you may either need to pay for that schooling, or work for lower pay to start out, or both. But if the alternative is to stay in parched soil, the cost of moving may still outweigh the cost of staying put.

These moves rarely happen all at once. The designer started home brewing some years ago, and chatted with folks at various breweries, before deciding to explore it further. The civic tech worker had been reading about urban development for a while, and attending community engagement sessions. The journalist was on the healthcare beat and got to know folks in the local nurses union, and so on. The point here is you don’t make a decision to go back to school, or start in a whole new field, all at once. You explore the things you’re interested in, get to know some people, and then look for ways to experiment in a new direction.

However you move, this is not a moment to go it alone. You are not the only one who has arrived here, with the awareness that the work you used to do—perhaps the work you once loved—is no longer recognizable. Odds are someone standing very nearby you is asking the same questions, and wondering the same things. Ask how they are doing, what they’re thinking, what’s coming up for them as they contemplate their own moves. Maybe you can keep each other company for a while as you get underway. Maybe you can stay in touch when the time comes for you to each venture in different directions. Maybe your paths will cross again someday, under blue skies and amid green, fertile fields.


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Summer sf work/shop

2026-04-14 00:52:00

In Yevgeny Zamyatin’s We, the totalitarian One State has invented a surgery that can remove a person’s imagination. Just cut it right out, so that it never bothers them again. For it is the imagination—the ability to imagine a different world, to envision that things could be other than they are—that represents the greatest threat to the totalitarian state. It brings to mind the quote from Martín Espada that I’ve had tattooed at the top of the work/shop page for some time now:

No change for the good ever happens without being imagined first, even if, at the moment we imagine this great change, it seems absolutely impossible. History teaches us, too, that we are the agents of this great change. It doesn’t come from the White House; it comes from our house.

The White House part hits harder every day. No vision of a future that is life-giving will ever come from that demolished house! It is our own homes, our own neighborhoods and walkways and watering holes, our own workplaces—whether that be where we do our waged work or our art work or our care work—where we can exercise our imagination toward different, and brighter, futures.

Espada was writing in 1996, but he was also writing many years before that and many years since; he was, and is, writing for us. Writing breaches the space-time continuum, reaches forward and back and across; writing is a magic of time-travel, of invention and creation, of abolition and reconstruction, of change. What Espada’s assertion here always reminds me of is how critical it is to maintain a vast horizon of imagination, to practice imagining different ways of being and living and making change with each other, to counter the narratives of inevitability and austerity that try to worm their way into our hearts and minds, foreclosing those always-possible futures. Who wants you to believe that only one future is possible, the one they declare? The fascists and tyrants, the wannabe dictators, all the emperors prancing around with no clothes.

You know better, but it can be hard to keep that knowing top of mind, to hold that tiny flame in your hands while the wind batters at you and the rain pours down and the dawn seems so far away. That’s what this work/shop is for: to give you space to bring this knowing into the day, to fortify it against the investor brain worms and chickenhawk executives, the credulous tech media and the institutional scaremongering, the incessant banging of the drums of war. Your imagination needs a protected cove to recuperate and gather strength, to practice and build muscle, to learn the ways to defend itself when it ventures back out to sea, among the storms and thrashing waves.

Here is what we will do: we will write, letting that imagination loose, giving it room to wander and explore and open up as we so rarely do in our day-to-day. We will notice that writing, for ourselves and our comrades, notice what it is bringing up, what it surfaces and exposes, what fears, desires, longings, and more have been lurking out of sight. We will think together about what these noticings tell us, and how we can work with them, how we can wrap our hands around them and shape them and make things of them. We will draw from many liberatory practices and philosophies—abolitionist thinking and feminist economies, utopian demands and anti-work imaginaries, transformative justice, narrative strategies, and of course, speculative fiction modes and movements. You will learn strategies for expanding your attention, for relinquishing habits that keep your imagination bound and small, for bringing all those wanted and imagined futures closer to hand.

You can read all about the work/shop here. The next cohort will take place Wednesdays, 12pm-1:15pm EDT (UTC-4) from May 27–July 1, 2026. Applications are open now. The application is short, and is designed to provide just enough information for me to design a balanced cohort. As always, you must agree to abide by the code of conduct to be considered. Applications are due before noon EDT (UTC-4) on Wednesday, April 22. Everyone who applies will hear from me the following week.

I will leave you now with one final thought: the tyrants and despots, the bare-assed emperors, they fear one thing from you above all else—your own vision and clear sight, your ability to see them for what they are, to see the future for the open, undiscovered potential it always is. You keep your chin up not for pride but because it lets you see further afield, beyond their boots and brags, to the clear, open sky.


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Don’t be an ass

2026-04-09 00:16:00

This is a handy set of guidelines for using AI at work, acknowledging that if you toss unexamined AI-output onto your colleagues for review, they will not thank you for it. The principles here are to be responsible for whatever you are sharing—whether you used AI or not—and to be transparent about when you did use AI. I would use these guidelines not as-is but as starting point for a discussion with your own teams about how you are working together, and how that work is changing. Already I am seeing examples of the gendered and racial dynamics of how AI-generated code and docs are being shared: cishet white men are much more likely to share workslop without first doing any reading, while women and people of color are more likely to be on the receiving end of a request to review that slop. If you recognize yourself in the first part of that dynamic—well, here’s your invitation to stop being an asshole; if you recognize yourself in the latter, you can use these guidelines to get a discussion going, but at some point, you’re going to have to refuse.


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Mouthwords

2026-04-02 01:13:00

BRIAN MERCHANT writes about the abrupt Sora shutdown and notes one important component of that whole fiasco: the most common response to slop is revulsion. I think we need to acknowledge that this is also the case for most workslop: the documents, pull requests, emails, Slack messages, and so on that have been made with so-called AI and heedlessly tossed at colleagues without review are generating sentiments that range from, at best, exhaustion and boredom, to, at worst, disgust and intense despair.

You have to wonder why workslop like this even exists. Documents and whatnot are all mechanisms for communicating between humans—a communication that is always lossy, because creating a shared understanding between people is, and always will be, one of the hardest things we’ll ever do. Workslop dramatically increases that lossiness, with what we mean to say drifting further and further away from us, mediated through machines that smooth out the tone and blur the intent until we are saying nothing at all. This is perhaps the point: the less we are able to communicate with each other, the less power we have to negotiate the conditions of our work.

We need to see the advent of workslop in the context of the technological aims of the last several decades, one of which has been to obfuscate the human labor involved in everything from driving to cooking to gathering (which I will note is one of our oldest human activities). Tap a few buttons and a meal appears at your door, or a car arrives to whisk you away, or a bag of supplies manifests itself. All the people who worked to make that happen—the cooks, the farmers, the designers, the engineers, the factory workers, the ship’s crews, the longshoremen, the mods, the pilots, the janitors, the bankers, the diplomats and council members the world over, and so on—are hidden away, made invisible. It’s not that that labor doesn’t matter any more—there are good reasons that a port strike is taken very seriously—it’s that we are invited, even required, to avert our eyes.

Likewise, we don’t see the trillions of lines of code that fed the slop machines so that it could pump out a bloated, confusing, and ultimately brittle new feature for us. We don’t see the uncountable number of thoughtfully-written documents behind the one our colleague just sent us, the one that proposes a change in policy that is almost certainly illegal. And we definitely do not see the beleaguered worker tasked with reviewing and responding to this slop, who slouches ever deeper in her chair with each new message, until she wonders whether or not she will ever be able to get up. The tools and experiences imposed upon other workers have, as they inevitably would, come home to roost.

Two decades ago, David Graeber warned that having a bullshit job—a job with no obvious utility or purpose—was one of the most debilitating experiences any worker could have. Workslop is bullshit work at scale. This will get framed as a morale problem, which is true enough. But I promise you the technocrats pushing the slop machines do not give the slightest of fucks about your morale. This isn’t their problem; it’s yours.

So—what to do about it? I’ve seen a number of patterns emerging so far: teams discussing and defining new norms for how to pass around AI-generated documents, mostly coming down to the requirement to review and edit what you share before sharing it. Likewise: rules about the size of pull requests, or the number of PRs you can open at once, or good faith requests to limit the number of new wiki posts each week. But for these norms to stick they have to have some teeth. And that means you have to at some point refuse.

You have to refuse to review the 10,000 line PR which was submitted with a six-hour deadline. You have to refuse the sloppily bot-generated contributions to your open source project. You have to refuse to edit the slide deck that gets half a dozen things wrong about the business model, and the blog post that is so generically written you lose the will to live in the first paragraph. You have to refuse to read the proposal from the person who also hasn’t read it. You have to refuse to respond to the automated Slack message that seems entirely devoid of meaning whatsoever.

And you have to talk to the people around you—and when I say talk here, I mean with your mouths, the way humans have spoken to each other for millennia—about what the fuck is going on. Because like it or not, that’s the only way through this mess. Only by talking to each other can we counter the massive gaslighting and propaganda about how all this is inevitable (it isn’t) or about how you have no power whatsoever to change it (you do). Only by talking to each other can we enter that genuinely creative and generative space—not in the machine sense of sloppily recapitulating what’s come before, but in the profoundly human sense of sparking something new into existence—a space that only ever occurs in the encounters between people, in relationship to other humans and the more-than-human world. Only by talking to other people can we recall that we are humans, with human needs, one of which is not to be programmed like machines.

There is, as I am wont to point out, risk here. There is always risk! So long as you are a body, you are at risk of harm. There is risk in everything that you do and do not do. Your choice isn’t between risk and safety but different kinds of risk: choose well.


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Come back

2026-01-20 20:42:00

FAR BE IT for me to add to the habit discourse, a field so overgrown with weeds that we must wade in with machete in hand, but I’m going to chance it. We are in the first month of the year, in the late middle of that month, a time when habits looked upon with novelty and eager commitment begin to look a little dull or heavy, a moment when a “streak” is likely to come to an abrupt and regretful end. The problem I want to draw your attention to isn’t the interruption of the habit—which was inevitable—but the fact that the streak mentality transforms an interruption, a pause, into a failure, a score set back to zero. Now you must start over again, as if you hadn’t done something for eighteen or twenty or one hundred days, but were doing it for the first time, only now with a deficit, because you must catch up to your old score. The longer the streak, the harder the restart, the more punishing the interlude.

The theory behind a streak is that by making that break into a penalty, you will be less likely to take it. Fair enough. But you will take a break someday, because a body needs breaks. A habit isn’t built on successive days or weeks, enumerated and enumerable. A habit is built on the movement of return. It’s coming back to something, again and again, in precise rhythms or otherwise, that transforms an effort into a habit, an act of will into an act of way.

In meditation, you learn quickly that even while your body is still, your mind moves and scatters, drifts and wanders. The point in meditation isn’t to stop thinking—that’s impossible. It’s to notice that you’ve wandered off the path, and come back, again and again and again. To come back to the breath, the only habit we only ever break once.

It can seem frivolous in times like these to think of making new habits. What’s a habit against an occupation, against a genocide, against a dictatorship? What matters about journaling, or doing our art, or moving our bodies, or taking a walk in the midst of a dying empire? But if we do not make our own habits, they will be made for us, by forces who want us isolated, anesthetized, consumed, harried in our work lives and sloven in our spirits. What we do is who we are, and we remake ourselves each time we come back to the work that matters, the work of becoming free. If you’ve wandered off—when you wander off—you have only to return.


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Walking

2025-11-18 19:35:00

THERE’S A MOMENT in most work lives where we find ourselves in a place that no longer fits. Maybe we worked really hard to get here, climbing up ravines, hacking our way through thick forests, a clear idea of where we would arrive once we made it through this difficult passage. But when we got here it wasn’t at all what we thought it would be. Or maybe we wandered this way, not quite knowing where we were going, always taking the most welcoming path, following that stream or those people. But now that we’re here, it doesn’t seem like a good place to linger. Then we may feel surprise or confusion, or perhaps shame at not having made better choices. Maybe we were pushed this way, and we seethe in resentment. Always there is fear.

However we got here, we’re here, on the edge of this cliff, a rock face behind us, looking out over a valley we cannot reach. It’s a long way down, and we don’t have a rope or a net. And we can’t know what’s down there anyway. From up here, it looks like green pastures and shady forests. But we know, now, that the world is full of mirages, that light and shadow can trick the eye and heart. That what looks like a welcoming grove can just as easily turn out to be haunted.

These are moments when we begin to realize that we may have to make a big change—leave an industry, change careers, turn back or turn off the path we’ve been on. And what I’ve noticed is that those moments always seem, in retrospect, to have been foreshadowed. Somewhere back on the path that got us here we started to see the signs—the people we were walking with turned out to be competitors instead of comrades, or the weather seemed always to be beating us back, or we couldn’t stop thinking about that spur we passed by, wondering where it might have taken us. The realization arrives as something we already know, a stone that’s been in our shoe for a while and which we’re only now plucking out and taking a good long look at.

So: take a look. Sit down and really look at this place where you find yourself. Look at it as if you just got here, because in some way you have—you are seeing it anew, as someone who now realizes they cannot stay. Take stock of the local flora and fauna, the topography, the residents. Notice the other visitors, the folks who carry their bags on their shoulders, as if ready to leave; some of them might turn out to be good traveling companions. Nose around the different camps, see what’s happening, what’s changing, what people are preparing for. Ask a lot of questions of the people you encounter, and listen closely to what they have to say.

When you become someone who is contemplating moving on, the place you’re in changes. You become a pebble in its shoe, a sign that some change is underway, a portent of more to come. Alone, you may be nothing more than an irritant, but an irritant in a vulnerable place can play both havoc and peace. Join with others, and the pebble becomes a rock slide, a boulder, a cairn that shows the way to another path, a trail that leads you-know-not-where, but certainly away from here.

Even the steepest cliff has a hidden footpath or two; even the sharpest rock face contains crevices, caves, handholds. You might have to hunt around for them; you might have to venture down a few dead ends to find them. You may have to unburden yourself before you can fit through. But they’re there, ready and waiting. And the fear is there, too, of course, a messenger urging you to be careful where you place your feet, to keep a grip on your walking stick. Fear, too, is a good traveling companion on journeys such as these; it keeps you sharp and attentive, aware of all the opportunities and pitfalls that surround you. But don’t let it keep you from walking.


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