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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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2026-10-28 22:20:00

A project manager is excited to finally have a job offer after months of looking; but when she reviews the benefits package she discovers there’s no employer coverage for dependents’ premiums. After talking to a benefits manager, she finds herself steered towards a high-deductible, health-savings style plan.

The people officer at a two hundred-person tech company shares the news that their health provider is raising the rates by twenty percent. Unwilling to bear the costs, they are switching back to their previous provider, one employees reported was near impossible to use because the network was too small and every claim was preemptively denied.

A coffee shop has made a point of providing health benefits to their staff, retaining many of the same people for years. But rates are now so high they must either cut benefits or lay some people off. Collectively, the staff decides to preserve everyone’s job and accept a stipend they can either use towards buying a plan on the state marketplace, or else pocket and do with as they please. Several members of the staff, looking at the cost of premiums, decide to go without.

A seasoned engineer teams up with a few long-time colleagues to start a cooperative consultancy. They have the network and the skills and as soon as they start quietly telling people they’ll be available, they have a short list of prospective clients. But when they sit down to do the math on how they will structure the business, one cost looms large and menacing: health insurance.

None of this is new, but the trends have been accelerating and the train, running downhill for years now, is picking up speed and rattling in its tracks. What before was a rumble or quiet worry is now a panic-inducing up-all-night nightmare. And it’s the whole system, not merely some small neglected corner: egregious cuts to Medicaid, slashed subsidies for ACA plans, hospitals gobbled up by private equity when they aren’t being summarily closed, huge cost increases for the elderly on Medicare, increasingly automated and capricious claims denials, public plans for teachers on the brink of collapse, pharmacies closing right and left, a horrific deportation campaign contributing to a nursing shortage, and on it goes, all the while health insurers rake in record profits. And there’s no refuge for people with purportedly good jobs, the kind that once seemed like a solid bet for decent healthcare, with the biggest rate increase in decades hitting employers, who are either passing those costs on or simply giving up.

Perhaps a few people will slip through the barricade and end up at the vanishing number of very large companies that still provide halfway decent healthcare—for a while, at least. But no healthcare system can survive as the covered population gets smaller and older. And even if you manage to be one of the lucky few, how many of your friends and kin will not be? Their health matters to you, too.

This is not a problem with an individual solution. You cannot manifest your way to good health insurance or keep hospitals open with pluck. There is no strategy that you can execute that will guarantee that you get health insurance even as the rest of the system crumbles. No amount of the right training or hard work or connections are going to get you to a place where you don’t have to worry about health insurance any more. You need to gather up everyone else in the same camp—which is just about all of us at this point—and fight.

The only way through this mess is politics. The only way through is Medicare for All.

We’re approaching the eve of that most frightening of American holidays, open enrollment. This whole experience is designed to make you think that the only choice you have is between the very expensive plan and the even more expensive one, both of which will be miserly with care should you need it. It’s designed to make you feel stuck in your job, unable to leave even though you desperately want to, because the work you really want to do doesn’t cover benefits. This, of course, was the whole point of employer-sponsored health insurance in the first place: to make you dependent on your employer, when they should be dependent on you. That was never a good bargain for workers, and it’s an untenable one now.

So: use the horror of open enrollment to talk about rising healthcare costs at your workplace and recruit your coworkers to the cause. Don’t let your employer dump higher costs on you without a fight. Find the people in your neighborhood who are already organizing for M4A and pitch in. Canvas this weekend for the candidate most amenable to supporting universal healthcare, and whoever wins next week, don’t let them off the hook. This will not be easy—getting what you deserve in a system that prefers your desperation never is. But we’re out of other options.

And if we get this right? Imagine what else we can do.


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Break what should be broken

2026-07-22 00:09:00

A COUPLE OF WEEKS ago, I wrote on A Working Library about James C. Scott’s concept of anarchist calisthenics, and I want to expand on it a bit here, because I think it is a very useful—even existentially necessary—skill to be practicing in our workplaces these days. Scott describes living in Germany in 1990 and noticing that the locals seem scandalized by his casual jaywalking—even when crossing a road where there obviously aren’t any cars for miles. Perplexed by this response, he writes:

As a way of justifying my conduct to myself, I began to rehearse a little discourse that I imagined delivering in perfect German. It went something like this. “You know, you and especially your grandparents could have used more of a spirit of lawbreaking. One day you will be called on to break a big law in the name of justice and rationality. Everything will depend on it. You have to be ready. How are you going to prepare for that day when it really matters? You have to stay ‘in shape’ so that when the big day comes you will be ready. What you need is ‘anarchist calisthenics.’ Every day or so break some trivial law that makes no sense, even if it’s only jaywalking. Use your own head to judge whether a law is just or reasonable. That way, you’ll keep trim; and when the big day comes, you’ll be ready.”

I think there are two kinds of skills being practiced here: the first is the skill of judging whether a law (or rule, norm, edict, order, etc.) is just or reasonable. This requires considering why it exists; whether that reasoning makes sense under current, or indeed any, circumstances; and what the risks are of breaking it. There’s a kind of reflexive questioning or consideration here, not accepting any rule at face value, but upon encountering a rule, taking a moment to look at it critically. To practice this way is to break the habit of passively receiving things as they have been given you, to become adept at noticing where rules are wrong-headed or worse.

The second skill is the actual breaking of that law when you deem it right to do so, whether because it is of no consequence (as with jaywalking across an empty road) or because the consequence of compliance is too great. This is the key thing here: we practice breaking rules not for the sake of rule-breaking but because a great many rules do harm, and often our only defense against that harm is to refuse to comply.

Scott points out that people of subordinate rank or class often cannot afford to openly revolt against rules or leaders they disagree with. But a quiet but collective non-compliance can be just as effective, and with far less danger to the individual rule-breakers. Witness reports of engineers cheating to get to the top of inane token leaderboards, an act that required no coordination and no outright objection—but which still managed to torch those leaderboards into the ground.

Cheating about AI usage is on the order of Scott moonwalking across a street without a car in sight; that is, it’s not all that risky, and—on its own—likely not all that impactful either. But we’re not interested only in what any individual act of rule-breaking does to the world; we’re interested in how each act prepares you to break much bigger rules when the times require it. And, my friends, the times are here. Tech companies are falling over themselves to collaborate with the Department of War. Hospitals are continuing to abandon their trans patients while nurses are being replaced with AI-powered software; disabled employees have been targeted for layoffs; surveillance tech is being deployed across our cities with predictably dangerous consequences; and systems developed to help people buy groceries are at risk of being recruited in the Trump administration’s ongoing assault on immigrant communities. If your work doesn’t already touch one of these or similarly thorny issues, it likely will soon. What will you do if you’re ordered to refuse care to someone in need? If you’re told to approve a PR that shares sensitive data with a federal agency? If you’re tasked with making a list of disabled employees? How will you be ready?

Some months ago a group of scientists with more than fifty years of collective service left the National Institutes of Health after concluding that the storied scientific organization had been so perverted by the administration that they could no longer uphold their oath of office. They left us with a word of caution: “Please decide where your red line is so you can choose to act before the line is already behind you.” I will add: please practice stepping back from that line before you get too close. Break a rule, refuse a request, drag your feet, cheat or sabotage or leak to the press—look around and you’ll see endless opportunities to engage those muscles, to build up the skill and strength you will need, and soon.


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Fall sf work/shop

2026-07-20 20:04:00

IN URSULA LE GUIN’s Always Coming Home, which takes place in what might be far future California, the people of the Valley tell stories about the “backward-heads.” These are people who literally have their heads on backward, and are said to lurk in the poisoned lands where human people can no longer live. Stories of backward-heads are among the most frightening and ghoulish ghost stories told in the Valley: a child would run screaming if they imagined seeing one, and an actor merely turning to look over their shoulder in a play would send a shiver through the crowd.

The unnamed editor of the book calls the backward-heads “the literalization of a metaphor” and connects them to the people who lived generations before—people who had caused vast desolation to the land and sea, whose waste continued to litter the world, causing sickness and death.

The people of the Valley did not conceive that such acts as they saw and felt much evidence of in their world…had not been deliberate. In their view, human beings did not do things accidentally. Accidents happened to people, but what people did they were responsible for. So these things human beings had done to the world must have been deliberate and conscious acts of evil, serving the purposes of wrong understanding, fear, and greed. The people who had done these things had done wrong mindfully. They had had their heads on wrong.

We seem to be surrounded by backward-heads: executives abandoning commitments to the climate and diversity, gleefully inking deals with the Department of War, sucking up to would-be emperors, eliminating jobs right and left and telling those that remain they have to work themselves to the bone. Those of us with our heads on straight can sometimes wonder if we’re the only ones left, if our only chance of survival is to twist our heads around and join them. But what kind of survival would that be?

We must look forward, even on the days when that future seems hazy and the horizon unclear, even when it seems like we cannot imagine next week let alone next year. That’s what this work/shop is for: to give you space to pause and look around, to fortify your imagination against the wrong-headedness and fear and greed, the incessant banging of the drums for war. To imagine a different future is to practice a different way of being in the present, to build muscle for seeing things as they really are (not as the backward-heads want them to be), to see where the seeds of that future are already planted, and to commit yourself to helping them grow.

Here is what we will do: we will write, using the practice of speculative fiction to shift our thinking out of the day-to-day, to give our imagination room to wander and explore. We will notice that writing, for ourselves and our comrades, notice what it is bringing up, what it surfaces and exposes, what fears, longings, and wisdom have been lurking out of sight. We will think together about these noticings, learning methods for working with them, understanding where we can shape them and where they shape us, how stories can be written and rewritten. 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.

The backward-heads walk backwards into the future, but we practice our imagination by walking straight ahead, into a future that isn’t determined and isn’t inevitable, but is made step by step by—careful, curious, deliberate—step.

Applications are open

You can read all about the work/shop here. The next cohort will take place Wednesdays, 12:00 PM-1:15 PM EDT (UTC-4) from Sep 16–Oct 21, 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 Thursday, July 30. Everyone who applies will hear from me the following week. If you have any questions at all, don’t hesitate to reach out.


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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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