Building creative culture at work and in the classroom

I’ve been working in distributed, self-organizing teams for a couple of decades and change. I’ve worked in startups, big corporations, and distributed open source teams. For the past twelve years, I have been at Automattic. Over the years, we have iterated fully distributed work and creative culture into a 500 person company that has managed to survive over a decade, have low turnover, and rate well among freelancers.

The Top Companies WNW Creatives Would Kill to Work for Full-Time — Free Range

One of my driving motivations for helping build one of the first distributed companies was accessibility. I wanted a place to work compatible with my autistic operating system and my anxiety. Distributed work where I can work from the comfort of home and communicate mostly via text suits me well. It suits other neurodivergent and disabled folks too. Distributed work is a good base for building a culture compatible with neurodiversity and the social model of disability.

I’d like to share a peek at our culture using the writing of my co-workers and of journalists. The practices of distributed companies have lessons for classrooms, particularly regarding accessibility and inclusive communication. Bring your own comfort, backchannels, and psychological safety are important notions that benefit teams of adult creatives as well as teams of creative kids. We parents and teachers must recognize that kids need digital skills if they’re going to thrive in a digital world. We can develop those skills in an inclusive way that uses technology not for remediation and assessment, but for collaboration. Communicate, collaborate, iterate, and launch. The best of

How we communicate

How we hire

How we organize

How we include

And how we flow

The business world is changing. It seems I’m riding the wave. High.

DSISD Commons #1: On passwords, interaction badges, differentiated instruction, recess, checklist manifesto, agile manifesto, cultural agility


Use a password manager, and never reuse passwords.

Interaction badges

Chapter 11 of NeuroTribes, In Autistic Space mentions interaction badges (also called color communication badges). These are used at autistic conferences and are becoming popular at tech conferences and company meetups.

Differentiated Instruction

Articles on differentiated instruction with a focus on neurodiversity, assistive tech, and structural ideology.


Recess is necessary. Provide students with Space, Trust, Time, and Loose Parts.

Checklist Manifesto

Checklists manage anxiety and provide cognitive net during journeys of cognitive control. We use checklists at home in the Checklist Manifesto style.

Agile Manifesto and Cultural Agility

Agile teams, distributed collaboration, and the hacker ethos of flexible improvisation and rapid iteration are important cultural literacy for project-based learning.

The best architectures, requirements, and designs emerge from self-organizing teams.

DSISD Mentorship and the Future of Work


Promethean > Pastoralist

One way to understand the shift from credentialist to hacker modes of social organization, via young people acquiring technological leverage, is through the mythological tale of Prometheus stealing fire from the heavens for human use.

The legend of Prometheus has been used as a metaphor for technological progress at least since Mary Shelley’s Frankenstein: A Modern Prometheus. Technologies capable of eating the world typically have a Promethean character: they emerge within a mature social order (a metaphoric “heaven” that is the preserve of older elites), but their true potential is unleashed by an emerging one (a metaphoric “earth” comprising creative marginal cultures, in particular youth cultures), which gains relative power as a result. Software as a Promethean technology emerged in the heart of the industrial social order, at companies such as AT&T, IBM and Xerox, universities such as MIT and Stanford, and government agencies such as DARPA and CERN. But its Promethean character was unleashed, starting with the early hacker movement, on the open Internet and through Silicon-Valley style startups.

As a result of a Promethean technology being unleashed, younger and older face a similar dilemma: should I abandon some of my investments in the industrial social order and join the dynamic new social order, or hold on to the status quo as long as possible?

Source: Breaking Smart: Getting Reoriented

A basic divide in the world of technology is between those who believe humans are capable of significant change, and those who believe they are not. Prometheanism is the philosophy of technology that follows from the idea that humans can, do and should change. Pastoralism, on the other hand is the philosophy that change is profane. The tension between these two philosophies leads to a technology diffusion process characterized by a colloquial phrase popular in the startup world: first they ignore you, then they laugh at you, then they fight you, then you win.

A thriving frontier of constant tinkering and diverse value systems must exist somewhere in the world.

The result is a virtuous cycle of increasing serendipity, driven by widespread lifestyle adaptation and cascades of self-improving innovation. Surplus and spillover creating more surplus and spillover. Brad deLong’s slouching towards utopia for consumers and Edmund Phelps’ mass flourishing for producers. And when the virtuous cycle is powered by a soft, world-eating technology, the steady, cumulative impact is immense.

Like purist software visions, pastoralist visions too are marked by an obsessive desire to permanently win a specific, zero-sum finite game rather than to keep playing the non-zero-sum infinite game.

When the allure of pastoralist visions is resisted, and the virtuous cycle is allowed to work, we get Promethean progress. This is unpredictable evolution in the direction of maximal societal impact, unencumbered by limiting deterministic visions. Just as the principle of rough consensus and running code creates great software, consumer surplus and spillover effects create great societies.  Just as pragmatic and purist development models lead to serendipity and zemblanity in engineering respectively, Promethean and pastoral models lead to serendipity and zemblanity at the level of entire societies.

Source: Breaking Smart: Prometheans and Pastoralists

At the center of any pastoral we find essentialized notions of what it means to be human, like Adam and Eve or William Whyte’s Organization Man, arranged in a particular social order (patriarchal in this case). From these archetypes we get to pure and virtuous idealized lifestyles. Lifestyles that deviate from these understandings seem corrupt and vice-driven. The belief that “people don’t change” is at once an approximation and a prescription: people should not change except to better conform to the ideal they are assumed to already approximate. The belief justifies building technology to serve the predictable and changeless ideal and labeling unexpected uses of technology degenerate.

We get attached to pastorals because they offer a present condition of certainty and stability and a utopian future promise of absolutely perfected certainty and stability. Arrival at the utopia seems like a well-deserved reward for hard-won Promethean victories. Pastoral utopias are where the victors of particular historical finite games hope to secure their gains and rest indefinitely on their laurels. The dark side, of course, is that pastorals also represent fantasies of absolute and eternal power over the fate of society: absolute utopias for believers that necessarily represent dystopias for disbelievers. Totalitarian ideologies of the twentieth century, such as communism and fascism, are the product of pastoral mindsets in their most toxic forms. The Jeffersonian pastoral was a nightmare for black Americans.

When pastoral fantasies start to collapse under the weight of their own internal contradictions, long-repressed energies are unleashed. The result is a societal condition marked by widespread lifestyle experimentation based on previously repressed values. To those faced with a collapse of the World Fairs pastoral project today, this seems like an irreversible slide towards corruption and moral decay.

Source: Breaking Smart: The Allure of Pastoralism