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Don't let them tell you what to think

A protest

Last year I wrote a little about how I hope AI will be used, using the GPS navigation in my car as an analogy:

I like my GPS. I use it pretty much every time I drive. But it’s not going to make the final decision about which way I go.

Perhaps it seems obvious, but I’d like to extend that analogy to news, media, and influencers.

We all need journalism — and particularly investigative journalism — to inform us and help us make better decisions. We need to take in sources, form opinions based on them, and vote accordingly as a baseline. But democratic participation doesn’t start and end with voting: we also need to know how to use our voices, spend our money, organize our communities, and, in areas we feel particularly strongly about, protest.

I do think we all need to use our voices. I’m wary when people are silent: whether this is their intention or not, silence is acquiescence to the status quo. If our government is doing something harmful on our behalf and we don’t speak out about it, or an atrocity is taking place somewhere and we choose not to speak up, our lack of action is an endorsement. Change only happens when people speak up.

But this only makes sense when we make up our own mind. If our opinions that copy what’s popular, or what a particular news outlet has to say, then we’re not exercising our democratic rights at all. We’re handing over that power to someone else. When we let someone make our mind up for us, using our voice is just amplifying their voice.

When people complain that we’re not all watching the same newscasts anymore, that’s the world they want to create: one where we’re all getting the same narrow band of information and forming opinions in the same way. That’s not democracy; that’s homogeny. It’s worth considering whose voices could be heard in that world. How diverse was it? Who was really represented?

Similarly, while there is certainly disinformation put out in the world that’s designed to coerce people to exercise their democratic rights in a particular direction (often towards fascism), some people have also used the words “misinformation” and “disinformation” (or “fake news”) to describe reporting that they simply don’t like.

This is the playbook of Trumpworld. When all of journalism is painted as biased and “fake news” — as Trump has taken pains to do — supporters are left with the officially-endorsed channels like Fox News, OANN, and Newsmax. They receive a narrow band of information that becomes the basis of their opinion-making. For example, during Trump’s presidency and beyond, these channels frequently pushed narratives that undermined trust in mainstream media, labeled critical reports as conspiracies, and even presented alternative facts about significant events like the COVID-19 pandemic and the 2020 election results. This systematic discrediting of journalism fosters an echo chamber that isolates its audience from opposing viewpoints and critical analysis.

But there’s a streak of this in Democrat-land, too: a subset of the community that’s sometimes been described as “blue MAGA” for its use of similar rhetoric. Here, any voice that criticizes Biden is also described as fake news, or even a Putin plot. For instance, when progressive commentators or journalists critique Biden’s policies on immigration or healthcare, they are sometimes met with accusations of undermining the Democratic agenda or aiding Republican narratives. This phenomenon isn't as pervasive as Trumpworld’s approach, but it highlights a discomfort with internal criticism within certain Democratic circles. While I’d clearly prefer a Democratic America to one run by Trump, this dismissal of uncomfortable sources as being fake because we don’t like them is no less undemocratic.

And, of course, the same goes for people who learn how to vote and what to think from their places of worship. In some religious communities, congregants are encouraged to vote in line with specific doctrinal beliefs, which can limit their exposure to broader societal issues and alternative viewpoints. It’s a hell of a waste of a free mind and a democratic bill of rights.

We need to consume information from a variety of sources, be critically aware of the biases and origins of those sources so that we can properly evaluate and contextualize them, and then make up our own minds, regardless of whether our conclusions are popular or not.

Making up our own minds has gotten a bad name lately through people who “do their own research” and end up promoting ivermectin for covid, believing that vaccines cause autism, or that climate change isn’t real. I’m not arguing for abandoning critical reasoning or scientific fact here; quite the opposite. The antidote to this kind of quackery is stronger critical thinking and source evaluation, not — as some have argued — restricting our information diet to a few approved sources.

New voices and sources matter. The world changes. Lots of things that were wildly unpopular and sneered at in the past are now part of ordinary life. For example:

  • Abolition
  • Women’s suffrage
  • Access to birth control
  • Interracial marriage
  • Marriage equality
  • The 40 hour work-week

Each of these things were hard-won by people who were very much outside the mainstream until they weren’t. Consider what it would have meant to be silent while each of those struggles for basic rights were underway, or what it might say about a person if they stayed silent because doing otherwise would affect their job prospects or earnings potential. These ideas weren’t popular to begin with, but they were right.

Even the internet was dismissed as a weird fad in the nineties. The mainstream press didn’t think it would catch on; people inside newsrooms had to fight to establish the first news websites. Memorably, one British magazine called it “the new name for ham radio” — just a few years before it took over the world.

What matters is not adherence to the values of a tribe. We aren’t better people if we demonstrate that our values are the same as an accepted set. The world isn’t like supporting a sports team, where you put on a red or a blue jersey and sing the same songs in the stands. It’s nuanced, and each of us can and should have our own nuanced perspectives that are informed by our lived experiences and those of the people around us, and a set of diverse, freely-reported information sources.

For the avoidance of doubt, my values are vehemently anti-war, pro-immigration, and fiercely on the side of diversity, equity, and inclusion. I believe in the right to choose. I believe that trans women are women and trans men are men. I believe that too-small government leads to big corporate power, and too-big government leads to authoritarianism, so a continual balance must be found. I believe that universal healthcare is a fundamental human right. I believe guns must be controlled. I roll my eyes when people complain about socialism in America, because usually what they mean when they use that word is what I’d consider to be basic infrastructure. I think there needs to be a ceasefire in Gaza and in Ukraine. I dislike patriotism because I think it encourages people to care more about people who are geographically close to them. I believe Ayn Rand’s “morality of self-interest” is an excuse to act without compassion. I like startups and believe in the right to start and run a business — and that they can be the vehicle for great change. I think climate change is not just real and behind many of the geopolitical decisions we’re seeing playing out today. I believe that the civil rights marches and movements of the 2020s are the signs of really exciting progressive change. I believe Trump must not become President. I believe a progressive world is a better world.

And I believe in talking about those things and why I believe them. Loudly. Even when it’s uncomfortable. There is no media outlet I’m aware of that publishes based on that exact set of values. You might nod your head in agreement with some of them and be angered by others.

The news I read and the information I gather is my GPS. I appreciate the signal, and it will certainly inform my actions and beliefs. I’m still going to find my own way.

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Escaping the 9-5

The silhouette of a man holding his arms out, representing freedom

Imagine a life where you dictate your own schedule, free from the confines of a traditional job.

That’s a thought experiment I’ve been playing with lately: what would it look like if this was my last ever job? How might I optimize my lifestyle for freedom?

By that I don’t mean that it would be the last time I needed to earn money. I work in non-profit news; nobody does this because they want to become rich beyond their wildest dreams. Even tech salaries feel distant from this vantage point. To be clear, I’m doing this work because it’s important, and I have no plans to leave.

Regardless, I think it’s an important thought experiment. What if this was the last time I worked a job with regular hours and a boss and a hierarchy? What would it look like to have a lifestyle that was less bound to working norms, so that I could choose how to spend my day, or my week, or my year?

This desire to seek a lifestyle less bound by traditional working norms is shaped by two big influences:

  • My working life in startups, which was very much self-driven
  • My own parents, who had their own publishing startup for a key part of my childhood.

My parents’ ability to dictate their schedules and norms meant that I was able to have childhood experiences — in particular, trips to mainland Europe and the US — that would have been much harder otherwise. (These things didn’t need all that much money; they needed time.) That lifestyle did something else important, too: it showed me that it was attainable, and that a person doesn’t need a 9-5 to live. That perspective, in turn, allowed me to become a founder and build new things.

I would like to do the same for our son. Honestly, selfishly, I would also like to do it for me.

What are the roads to more independence when you aren’t independently wealthy?

Here are some options I’ve considered:


The first potential path to independence is through entrepreneurship.

I’ve founded two startups in my life. The first one was bootstrapped for the first couple of years before raising a round from British investors; the second was kicked off with a small amount ($50K) of accelerator seed money.

My life has changed since then. In particular, my capital needs have shot up. There’s a child and daycare and a mortgage in the picture, which is radically different from my life as a twenty-something prepared to live on Pot Noodles and scrape by with little money. A working life of open source, mission-driven startups, and non-profit news means that my savings are meager and wouldn’t support a new venture. A friends and family round is out of the question for me, as it is for anyone who doesn’t come from wealth.

Building a startup means working hard on it while holding down my day job, until it reaches the point where it has enough traction to raise a seed round. The barrier for that traction is rising steadily; it probably needs to be making tens of thousands of dollars a month for a seed investor to find it interesting. Still, that isn’t insurmountable — particularly with a co-founder. I have more product, engineering, and organizational growth skills than ever before, and I believe that I could do it.

But also: at the point where it’s making tens of thousands of dollars a month, assuming a low running cost, that’s more than enough to sustain me! It doesn’t need to be a high-growth startup. It could be a small business that is content to do quite well. A Zebra, perhaps. The disadvantage is that the upside is limited: it’s unlikely to make me wealthy beyond my wildest dreams. But what if that isn’t the goal? If the goal is freedom, a modest income is wonderful.

Consulting or Coaching

I have coaching training, and I’ve previously coached founders across a portfolio of mission-driven startups. In many ways, my roles as a CTO / Head of Engineering / Director of Technology have been largely coaching-based too: effective 1:1s and frameworks for feedback are the lifeblood of building a team.

I’ve also got strong product design and design thinking training, and have run workshops and design sprints with many teams. I understand product fundamentals, how to instill product thinking in a team, and can shepherd a product (and product team) from insight to launch.

And I’m technical. I can architect software and write code; I can advise teams about how to think about new technologies like AI, or how to build their own software. I’ve done this in many different contexts, many, many times.

So I think I can offer a lot. The challenge with consulting of any kind, though, is that it’s essentially a freelance job: you’re working from contract to contract, or from session to session, which means that you’re constantly having to sell yourself for the next thing, at least until your reputation has reached the point where people are asking for you.

Perhaps a retainer model would work: enough people subscribing to receive your attention and you have a steady income. Too many, though, and you can’t support them all. Too few, and you need to be in sales mode all the time. Still, it seems attractive from the provider end; the question, of course, is whether any customers would actually go for that. My guess is probably not — at least until you have enough glowing referrals.

Selling Products

In a way, this seems like the most attractive option: sell a finite product that doesn’t require your direct involvement, so that you can spend your time building the next product to sell, until you have a portfolio of products that sell without you and generate a reasonable income.

There are plenty of influencers who peddle “passive income”. My strong belief is that they’re all scammers, and that the dream of financial independence is what they’re all actually selling. Still, there are clearly people who sell things on the internet, and some of them do quite well.

These include:

  • Books: Yay for books! Of course, the idea that you’ll make an income from books alone is a pipe dream. Even bestselling published authors often don’t leave their jobs until they’ve had a few successes in a row. There are more books being published and it’s harder to break out. Full disclosure: I am writing a book! But I don’t expect it to cover my costs. I’m doing it because there’s a story I want to tell. (And then I’ll do it again, because there are more stories to tell.)
  • Courses: Do people really make a lot of money from these? I mean, maybe. It feels like courses mostly fall into the same category as books: something you do because you want to share some knowledge or potentially demonstrate some expertise, but not something you do as a money-making venture in its own right.
  • Apps: Hmm. This was a great idea in 2008. Some software really does support independent developers, though — but my suspicion is that the software that does the best are actually services, which fit better into my “startup / small business” description above.

A Portfolio

I think this is the real answer: it isn’t just one thing. Likely, a repeatable income is cobbled together from threads of at least some of the above elements: building a service, offering coaching or consulting, and selling individual products.

One danger here is that attention is spread too thinly: because multiple threads are required, you necessarily have less time to spend on each. Consequently, the quality of each element may suffer.

This approach no longer puts all eggs in one basket, which means there’s (in theory) more tolerance for one thread to fail. But it also means that you’re spinning plates in order to try and keep them all working. Because there’s less time for each, and attention is split, there’s a real chance of all of them failing.

Still, overall, it feels like the most resilient approach, with the most room for experimentation. It’s by no means the least work, but minimizing work isn’t the goal: that would be maximizing freedom, which isn’t the same thing.

What do you think? Have you made this leap? Did it work for you? I’d love to learn more.

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Innovation depends on inclusion

The word

A few weeks ago I wrote about how solving the challenges facing the news industry requires fundamentally changing newsroom culture. While newsrooms have depended on referrals from social media and search engines to find audiences and make an impact, both of those segments are in flux, and audiences are therefore declining. The only way to succeed is to experiment and try new things — and, therefore, to have a culture where experimentation and trying new things are supported.

While the article was focused on journalism, the same changes are required for any organization to succeed in the face of rapid technological change. Building an open culture of experimentation is just as important for technology and manufacturing companies as it is for news: every organization experiences challenges in the face of major change.

Okay, but how?

Building a great culture is non-negotiable. The question, of course, is how you build it.

There are a few versions of this question to consider. For me, the most interesting are:

  1. How do you build a great culture from scratch in a new organization?
  2. How do you build a great culture in an established organization that has not yet invested in building one?
  3. How do you build a great culture in an established organization that has an entrenched bad culture?

Of course, to consider this, you have to have a firm opinion of what constitutes a good or bad culture. I strongly believe it relates to building an open, nurturing culture of experimentation, which I have previously written about in depth:

The best teams have a robust, intentional culture that champions openness, inclusivity, and continuous learning — which requires a lot of relationship-building both internally and with the organization in which it sits. These teams can make progress on meaningful work, and make their members valued, heard, and empowered to contribute.

One indicator

I believe the litmus test of such cultures is inclusivity.

Consider this hypothetical scenario: the individual contributors in an organization complain to management that underrepresented members of the team are not able to be heard in meetings and that their ideas are always overlooked.

The managers could react in a few different ways:

  1. Dismiss the complaints outright.
  2. Try to make the complaints go away as quickly as possible so everyone can get back to work.
  3. Listen deeply to the complaints and to the people affected, then work with the whole organization to get real training and build better processes in order to ensure everyone can participate and is heard.

Only the third option represents an open, inclusive organization. The first is obviously dismissive; the second is arguably even worse, as it allows managers to delude themselves that they’re doing something while actively trying to do the bare minimum. (They might privately roll their eyes at having to do it to begin with.) In the third scenario, managers stop and listen to the people affected and work with them in order to effect real change.

Now consider: what happens if nobody brings that complaint to begin with?

In a truly inclusive organization, nobody has to bring that complaint, because managers are constantly assessing the well-being of their teams, and likely receiving continuous, honest feedback. This doesn’t happen by default: the culture of the organization has to be well-considered to ensure that a focus on inclusivity is a cherished value, and that everyone feels emotionally safe to contribute without needing to put on a work persona or mask away aspects of their identities.

This has certain prerequisites. In particular, it’s impossible for an organization with a top-down leadership style to be inclusive, by definition. Even if upper management is truly representative of the demographics and backgrounds of the wider organization and its customers (which is never true), top-down leadership misses the perspectives and ideas of people lower down the hierarchy. Gestures like “ideas boxes” are performative at best. If they wouldn’t be out of place in your organization, its culture is probably top-down.

Organizations can foster inclusivity by implementing regular feedback mechanisms, providing training on both inclusivity and management, promoting transparent communication, and establishing clear systems and boundaries which allow managers to say “yes” more often.

The received wisdom is that rules are barriers to innovation. But it turns out that establishing the right kind of structure helps innovation thrive.

The tyranny of structurelessness

News often does have a top-down culture, inherited from the editorial cultures of old-school newspapers. It’s not alone: finance, law, and many other legacy industries also suffer from this problem. This is a giant headwind for any kind of real innovation, because every new idea essentially has to achieve royal assent. There’s no leeway for experimentation, trying stuff, or getting things wrong — and managers are more likely to take credit for any successes. If something doesn’t fit into the manager’s worldview, the “no”s come freely. But, of course, that worldview is derived from their own experiences, backgrounds, and contexts, rather than the lived experiences of other people.

Structureless organizations, where culture has been under-invested in, tend to have these characteristics. If it’s not the managers dictating what happens, it’s the loudest people in the room, who tend to be the people who come from relative privilege. Without structure to ensure inclusivity, inevitably you’ll lose out on valuable perspectives and ideas.

It just so happens that the structures that establish inclusive practices also form the backbone of intentional cultures for everyone. It’s not just people from vulnerable communities who aren’t necessarily heard; by creating structures that intentionally lift those voices up, we lift up everybody and ensure everyone gets an equitable say.

Ensuring that all voices collaborate on the strategy of the organization and are able to define the work makes for better work, because a wider set of ideas and perspectives are considered — particularly those that managers might otherwise be blind to.

Inclusivity should never be considered a nice-to-have: in addition to being the morally correct path, it’s the key to unlocking an innovative culture that has the power to save existing industries and establish new ones. The people who roll their eyes at it are doomed to live out the status quo. Ultimately, inevitably, they will be left behind.

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Community survey 2024

I consider myself really lucky that people stop by and read my posts. Thank you!

Every year I like to pause and ask folks a little bit more about themselves, what they’re worried about, and what they’re interested in. It’s a really short, anonymous survey that helps me out on many levels. Feedback is always a gift.

This year, there’s another reason for this survey, too: I’m considering offering services to organizations that want to tackle specific technology challenges — particularly educational institutions, newsrooms, and technology companies for whom engineering is not their primary activity.

I’ve led product design and innovation sprints for many different companies and have been directly involved in multiple innovation accelerators. I have a well-tested process that really works, and this is one way I might be able to add value.

This survey will help me figure out which problems and ideas people are thinking about, which will help me figure out how helpful I can be.

But I’d also just love to know what you’re thinking about.

To fill in the survey, click here. Thank you for your feedback!

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Protecting artists on the fediverse


Over the weekend, I started to notice a bunch of artists moving to Cara, a social network for artists founded by Jingna Zhang, herself an accomplished photographer.

The fediverse is a decentralized cooperative of social networks that can interact with each other: a user on one network can follow, reply, like, and re-share content from a user on another network. The whole thing depends on an open standard called ActivityPub, shared community norms, and a cooperative culture.

Of course, my first reaction was that Cara should be compatible with the fediverse so that its content could be more easily discoverable by users on social networks like Threads, Flipboard, and Mastodon. Cara is explicitly set up to be a network for human artists, with no AI-generated content, which will be increasingly valuable as the web becomes flooded with machine-made art. The fediverse would allow them to publish on sites like Cara that are set up to support their needs, while finding a broad audience across the entire web.

From its About page:

With the widespread use of generative AI, we decided to build a place that filters out generative AI images so that people who want to find authentic creatives and artwork can do so easily.

[…] We do not agree with generative AI tools in their current unethical form, and we won’t host AI-generated portfolios unless the rampant ethical and data privacy issues around datasets are resolved via regulation.

I’d love to follow artists on Cara from my Mastodon or Threads accounts. But how does Cara’s AI stance square with the fediverse? How might artists on Cara find a broad audience for their work across the web without risking that art being used as training data without permission?

The first thing a site can do to prevent its content from being used as training data is to add exclusion rules to its robots.txt file. These theoretically prevent crawlers owned by model vendors like OpenAI from directly accessing art from the site. There is nothing that legally binds crawlers from obeying robots.txt; it’s less enforceable than a handshake agreement. Still, most claim that they voluntarily do.

But even if robots.txt was an ironclad agreement, content published to the fediverse doesn’t solely live on its originating server. If Cara was connected to the fediverse, images posted there could still be found on its servers, but they would also be syndicated to the home servers of anyone who followed its users. If a user on Threads followed a Cara user, the Cara user’s images would be copied to Threads; if a user on a Mastodon instance followed that user, the images would be copied to that Mastodon instance. The images are copied across the web as soon as they are published; even if Cara protects its servers from being accessed by AI crawlers, these other downstream fediverse servers are not guaranteed to be protected.

By connecting to the fediverse, one might argue that servers implicitly license their content to be reused across different services. This is markedly different from RSS, where this is explicitly not the case: there is legal precedent that says my RSS feed cannot be used to republish my content elsewhere without my permission (although you can, of course, access its content in a private feed reader; that’s the point). But on the fediverse, the ability to reshare across platforms is core functionality.

The following things are all true:

  • Content published to the fediverse may be both re-copied to and served from other peoples’ servers
  • Those servers may have different policies regarding content use
  • In the absence of a robots.txt directive, AI crawlers will scrape a website’s data, even if they don’t have the legal right to
  • Some servers may themselves be owned by AI vendors and may use federated content to train generative models even without the use of a scraper

As a result, there is no way an author can protect it from being used in an AI training set. The owners of a fediverse site wouldn’t have the right to make a deal with an AI vendor to sell the content it hosted because they wouldn’t have the copyright to all of that content in the first place. But because AI crawlers greedily scrape content without asking for permission, unless the site explicitly opts out with robots.txt, it doesn’t matter.

This leads me to a few conclusions:

  • It is a moral obligation for every fediverse site to prevent crawling of federated content by robustly setting robots.txt directives at a minimum
  • Discussions about adding content licensing support to the fediverse are even more important than they appear
  • Someone needs to legally prevent AI vendors from using all available data as training fodder

A fediverse (and a web!) where Cara can safely join while adhering to its principles is a more functional, safer network. To build it we’ll need to support explicit licensing on the fediverse, create a stronger standard for user protections across fediverse sites, and seek more robust legal protections against AI crawler activity. While these are ambitious goals, I believe they’re achievable — and necessary to support the artists and content creators who make the web their home.

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Unoffice Hours


I’m enamored with Matt Webb’s unoffice hours: a way to chat with him about anything, without needing to email him first, for 30 minutes.

As Matt says:

I loved those open conversations over coffee in the Before Times. There’s an ostensible reason to connect, so you talk about work, or compare notes about an idea, or whatever. But then the unexpected emerges. (Sometimes you have to hunt for it.) There are things in your head that you only know are there when you say them. And there are encounters with new ideas and new perspectives.

Exactly. So let’s do it.

Introducing my own Unoffice Hours: I’ve set aside a little time on Fridays to connect about anything.

Here are some topics that might be interesting to chat about:

  • Feedback on a project you’re working on (startups, software, a writing project)
  • Following up on something I’ve written in this space
  • Product and technology strategy in the public interest (news, education, libraries, other mission-driven organizations)
  • The indie web
  • Fostering a collaborative organizational culture
  • Saying hello

Matt calls the effect “manufactured serendipity”; I call it “intentional serendipity,” but the intent is the same. It’s good to chat and meet people, and you never know where it will lead.

To book a 30-minute chat, click here.

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Dispatches from the media apocalypse

A man holding a burning newspaper

Without serious intervention, newsrooms are going to disappear. Changes to social media and the advent of generative AI threaten their businesses and the impact of their work. They need to own their online presences outright and build direct relationships with their communities—and they need to do it now.

Social media audiences are plummeting. Less than 35% of internet searches lead users to click on a website. The views and engagement that newsrooms depend upon to survive are disappearing.

It’s happening quickly. Semafor’s Max Tani reported recently:

Washington Post CEO Will Lewis is introing the paper’s new “Build It” plan today. In a meeting with staff, he noted that the paper lost $77 million over the past year, and saw a 50% drop off in audience since 2020: “To be direct, we are in a hole, and we have been for some time."

Addressing this challenge will require radical changes to how newsrooms invest in and build technology.

In this post, I’ll attempt to describe the challenges in more detail and then discuss how they can be more adequately addressed.

Some context: my move into news

I’ve recently gained a new perspective on these challenges. For over a decade, I’ve worked adjacent to news and journalism. I’ve seen the industry as an engineer, startup founder, product lead, investor, and advisor. More recently, I decided I could be more useful in directly leading technology efforts inside newsrooms. It’s been eye-opening, rewarding work.

My experience alongside news was diverse. I built product for newsrooms, founded a startup used by public media, invested in early stage media startups, and have taught human-centered product design to teams at organizations like the New York Times and the Associated Press, as well as at institutions like the Newmark School of Journalism and the Harvard Kennedy School of Government. I’ve built software, founded, grown, and supported startups, and taught product design to some of the biggest names in journalism.

My immersion inside newsrooms has been much more recent. ProPublica investigates abuses of the public trust by government, businesses, and other institutions. I’ve worked on technology strategy for the last year, first as a contractor, and now as its Senior Director of Technology. Before that, I was the first CTO at The 19th, which reports on the intersection of gender, politics, and power.

I made this career shift at a pivotal moment for journalism—though it seems every moment for journalism over the last fifteen years has felt pivotal. The industry has struggled to weather the seismic shifts brought about by the internet, which have impacted its business, the state of our politics, and public discourse. It’s been a struggle for decades.

The audience threat

It’s getting harder and harder for newsrooms to reach their audiences — and for them to sustain themselves.

I’ve often remarked that journalism treats the internet as something that happened to it rather than something it can actively shape and build, but it at least had some time to adjust to its new normal. The internet landscape has been largely static for well over a decade — roughly from the introduction of the iPhone 3G to Twitter’s acquisition by Elon Musk. People used more or less the same services; they accessed the internet more or less the same way. Publications and online services came and went, but the laws of physics of the web were essentially constants.

Over the last year in particular, that’s all changed. Shifts in the social media landscape and the growing popularity and prevalence of generative AI have meant that the rules that newsrooms began to rely on no longer hold.

At their heart, online newsrooms have a reasonably simple funnel. They publish journalism, which finds an audience, some of which either decide to pay for it or view ads that theoretically cover the cost of the work. Hopefully, they will make enough money to publish more journalism.

This description is a little reductive: there are lots of different revenue models in play, for one thing. I’m particularly enamored with patronage models that allow those with the means to support open-access journalism for anyone to read freely. Still, some are entirely ad-supported, some are sponsored, and others are protected behind a paywall (or some combination of the above). For another, journalism isn’t always the sole driver of subscriptions. The New York Times receives tens of millions of subscribers from its games like Wordle and Connections, as well as its Cooking app.

Still, there are two pivotal facts for every newsroom: their work must reach an audience, and someone must pay for it. The first is a prerequisite of the second: if nobody discovers the journalism, nobody will pay for it. So, reaching and growing an audience is crucial.

For the last decade and a half, newsrooms have used social media and search engines as the primary way to reach people. People share stories across social media—particularly Facebook and Twitter—and search for topics they’re interested in. It’s generally worked.

Over the last year, social media has radically fragmented. Twitter transformed into X under its new management; users began to flee the platform in the face of more toxic discourse, and active use plummeted. Facebook is slowly declining and referrals to news sites have fallen by 50% over the last year. Instagram is not in decline. Still, it’s harder to post links to external sites there, which means that while newsrooms can reach users, they have more difficulty converting them to subscribers.

On top of these changes, we’ve also seen the rise of Threads, Mastodon, and Bluesky, as well as a long tail of other social apps, platforms, and forums on which to reach people. Audiences on social media used to be found in a very small number of places and are now spread out across very different platforms. The fediverse and AT Protocol also yield different problems: which instance should a newsroom choose to make its home? How can it measure engagement in what it posts in a decentralized system so that it knows what’s working and where it should continue to invest its meager resources?

Much has been written about newsrooms’ inability to move away from X even as it has become a hotbed of white supremacy and far-right rhetoric. The honest truth is that it still drives significant traffic to their websites, and in an environment where traffic referrals are dropping overall, intentionally further deepening the traffic shortfall is understandably not a career risk newsroom leaders are willing to make.

Social media isn’t the only way newsrooms are finding it harder to find an audience. Even search engines, long the stalwarts of the web, are moving away from referring traffic.

As search engines move to make AI-driven answers more prominent than links to external websites, they threaten to reduce newsroom audiences, too. More than 65% of Google searches already ended without a click to an external site. Now, it’s planning to roll out AI-driven answers to over a billion people. It’s not that other links are going away entirely. Still, because AI answers are the most prominent information on the page, clickthroughs to the external websites where the answers were found initially will be significantly reduced.

A similar dynamic is at play with the rise of AI services like ChatGPT, emerging as stiff competition for search engines like Google. These services answer questions definitively (although not always correctly), usually with no external links on the page. ChatGPT could learn from a newsroom’s articles and display information gleaned from an expensive investigative story while never revealing its source or allowing readers to support the journalism.

Generative AI models seem like magic: they answer questions succinctly, in natural language, based on prompts that look a lot like talking to a real human being. They work by training a neural network on a vast corpus of information, often obtained by crawling the web. Based on these enormous piles of data, AI engines answer questions by predicting which word should come next: a magic trick of statistics empowered by something close to the sum total of human knowledge.

That’s not hyperbole. It’s not a stretch to say that OpenAI’s ChatGPT and Google’s Gemini were trained on most of the internet, including websites, published books, videos, articles, art, science, and research. They couldn’t function without this data — but, ironically, they rarely credit their sources for any of it. Users see the benefit of fast answers; the sources of that information are starved of oxygen.

We’re at the foothills of both changes: social media is likely to fragment further, and generative AI will become even more prevalent as it becomes more powerful. Newsrooms can no longer rely on their old tactics to reach their audiences, and they will need to build new tactics that take these trends into account if they hope to survive.

Some models are more resilient than others

The 19th’s Alexandra Smith recently wrote about the state of play in Columbia Journalism Review:

In our current reality, journalism exists in various formats splintered across platforms and products. People are just as likely to get their news on Instagram as from a news website. It no longer makes sense to rely primarily on measuring readership by traditional website metrics.

This is a depressing fact if you rely on paywalled subscriptions or ad impressions. Nobody’s looking at your ads if they’re consuming your journalism off-platform, and how can you possibly get someone to subscribe if they never touch your app or website? Instagram and TikTok don’t have built-in subscriptions.

Over the years, many people have suggested micropayments — tiny payments you make every time you read a news article anywhere — but this depends on everyone on the web having some kind of micropayment account that is on and funded by default and the platforms all participating. It’s a reasonable idea if the conditions are right, but the conditions will never be right — and, like subscription models, it shuts out people who can’t pay, who are often the people most in need of public service journalism to begin with.

For newsrooms like The 19th, the picture is much rosier: like most non-profit newsrooms, it depends on donors who support it based on its journalistic impact. (The same is true of ProPublica, my employer.) That impact could occur anywhere, on any platform; the trick is to measure it so donors can be informed. Alexandra developed a new metric, Total Journalism Reach, that captures precisely this:

Right now, it includes website views; views of our stories that are republished on other news sites and aggregation apps, like Apple News; views of our newsletters based on how many emails we send and their average open rates, reduced for inflation since Apple implemented a new privacy feature; event attendees; video views; podcast listens; and Instagram post views.

This is clearly valuable work that will help newsrooms like The 19th prove their impact to current and potential donors. The quote above doubles as a useful example of the places The 19th is reaching its audience.

It’s worth considering how these might change over time. Some of the media Alexandra describes are inside The 19th’s control, and some are less so.

Supplier power

In his classic piece How Competitive Forces Shape Strategy, Michael Porter described five forces that shape competitive strategy. One of them is supplier power: the ability of providers of essential inputs to a business to exert influence over the organization. If suppliers to the industry have too much power — because there are few alternatives, for example — they can effectively force the company’s strategy by raising costs or enforcing adverse policies.

Newsrooms’ platforms for reaching their audiences, such as social media and Apple News, currently have outsized supplier power over the journalism industry. As a result, the industry is disproportionately vulnerable to the effects of business decisions made by the owners of those platforms.

In April, Instagram introduced a new automatic filter, switched on by default, to remove political content, which affected many newsrooms, and illustrates the kind of changes service providers can make on a whim.

Newsrooms on Apple News tend to see a multiple of the number of reads they see on their websites, but Apple could pull the product tomorrow. Even today, the number of views you get highly depends on which stories the Apple News team chooses to highlight. Ads in publications on Apple News need to use Apple’s ad network. It’s a closed shop. Apple News is only successful because it comes installed by default on Apple devices; hundreds of similar news aggregators have all failed to survive in their own right. It’s a precarious place to hang your hat.

We’ve already discussed the impact of search engine design decisions like prioritizing AI over click-through rates. Only one search engine is prominent enough to have disproportionate supplier power: a position Google has bought by spending over $21 billion a year to be the default search engine in every web browser.

However, not all conduits to readers have this outsized supplier power as a feature. Social media platforms, search engines, and news aggregators are all run by wealthy individual companies like X, Meta, Google, and Apple, who have the potential to exert their power. If you choose to leave them for any reason, you’re also leaving behind the relationships you’ve built up with your audience there: there’s no audience portability.

In contrast, email, podcasts (real podcasts, not the single-platform kind where you ink an exclusive deal with Spotify or Audible), and the web are well-used methods to reach audiences that aren’t owned by any platform. There are certainly market leaders for each communication type. Still, each is based on an open protocol that no single company controls — which means, for those methods, no supplier can exert adverse supplier power. If one service provider misbehaves, you can simply switch to another without losing functionality. You can bring your audience with you. They’re safer methods, as long as enough readers want to be reached in those ways.

That’s why so many publications have focused their strategies on their email newsletters. Everyone already has an email address, and (barring technical difficulties) if a publisher sends a subscriber a message, they’re guaranteed to receive it. Moreover, people engaged enough to hit the “subscribe” button are far more likely to convert to donors or upgrade to a paid subscription.

Newsletters, unfortunately, are also in decline. Open rates have fallen over the last decade; Gmail’s dominant position and aggressive filtering have made it harder for newsletters to be noticed; there’s more competition for attention. There aren’t any great ways for new readers to discover newsletters — those subscription pages are subject to the same internet traffic dynamics as articles. It’s getting harder and harder to direct new visitors to subscribe, which is why we see more overt “please subscribe” popup overlays on news sites. The focus has needfully shifted to converting more existing subscribers into donors or customers rather than widening the funnel and finding more newcomers.

Newsrooms need alternative media that allow them to make direct connections with their audiences. These media must be free from undue supplier power and have a large base of existing users that can be tapped into.

So what else is out there?

The answer is not much. Yet.

The innovation squeeze

Most non-profit newsrooms have tiny technology teams. The 19th, when I was CTO, had two engineers in addition to me; ProPublica has four. (Other interactive developers work on standalone stories but don’t address platform needs.) In contrast, I led a team of twenty-two engineers at the last startup I worked at, and we had over a hundred at Medium.

To bridge that gap, there is a small community of digital agencies that make supporting newsroom platform needs a core part of their business. Probably the most famous are Alley and Upstatement, but there are around a dozen more that are actively used by newsrooms.

They do beautiful work and are an excellent way for a newsroom to start strong with a modern brand and a well-functioning web platform. I strongly recommend that a new newsroom consults with them.

There is an emerging dynamic, though, where the technology vision for a newsroom is outsourced to the agencies. As we’ve discussed, a newsroom’s success and impact depend highly on core internet technologies like the web and email. Newsrooms quite reasonably spec and build a platform based on what will work well today. However, because the vision and expertise for harnessing the internet lie with the agencies, they don’t have any meaningful technology capability for innovating around what will work well tomorrow.

Newsrooms absolutely need to focus on today. That’s an obvious prerequisite: they must meet their audiences, subscribers, and donors where they’re at right now. However, they also need to be aware of what is coming down the road and prepared to experiment with, engage with, and potentially help shape new technologies that could impact their businesses in the future. If the internet changes, they need to be ready for it. To reference an overused Wayne Gretzky quote: you need to skate to where the puck will be, not where it is right now.

Nobody knows for certain where the puck will be. That means newsrooms need to make bets about the future of technology — which, in turn, means they must have the capacity to make bets about the future of technology.

Most newsrooms already have technical staff who maintain their websites, fix broken platform stacks, and build tools for the newsroom. These staff must also highlight future business risks and allow them to experiment with new platform opportunities. In a world where newsrooms rely on the internet as a publishing mechanism, technology expertise must be integral to their strategy discussions. And because technology changes so quickly and unpredictably, maintaining the time, space, and intellectual curiosity for experimentation is critical.

Nothing will work, but anything might

Experimentation doesn’t need to be resource-intensive or time-consuming. Alongside in-house expertise, the most important prerequisite is the willingness of a newsroom to test: to say “yes” to trying something out, but being clear about the parameters for success, and always rooting success or failure in a concrete understanding of their communities.

I’ve written before about how, if the fediverse is successful, it will be a powerful asset to media organizations that combines the direct relationship properties of email with the conversational and viral properties of social media. At the same time, there’s no doubt that the network is relatively small today, that the experience of using Mastodon falls short of corporate social networks like the Twitter everyone remembers, and that features like blocking referrer data makes life much harder for audience teams. There are lots of good reasons for a resource-strapped management team to say “no” to joining it.

At the same time, because it has the potential to be interesting, some newsrooms (including my employer) are experimenting with a presence. The ones who make the leap are often pleasantly surprised: engagement per capita is dramatically higher, particularly around social justice topics. Anecdotally, I discovered that posting a fundraising call to action to the network yielded more donations than from every other social network — combined.

It’s worth looking at Rest of World’s “More Ways to Read” page — a massive spread of platforms that runs the gamut from every social network to news apps, messaging platforms, audio, newsletters, and RSS feeds. The clear intention, taken seriously, is to meet audiences where they’re at, even if some of those networks have not yet emerged as a clear winner. All this from a tiny team.

However, experimenting isn’t just about social media. It’s worth experimenting with anything and everything, from push notifications to website redesigns that humanize journalists to new ways for communities to support the newsroom itself.

On the last point, I’m particularly enamored with how The 19th allows members to donate their time instead of money. Understanding that not everyone who cares about their mission has discretionary spending ability, they’re harnessing their community to create street teams of people who can help promote, develop, and share the work in other ways. It’s brilliant — and very clearly something that was arrived at through an experimental process.

I learned a formal process for human-centered experimentation as a founder at Matter, the accelerator for early-stage media startups, which changed the way I think about building products forever. A similarly powerful program is now taught as Columbia Journalism School’s Sulzberger Fellowship. If you can join a program like this, it’s well worth it, but consultants like Tiny Collaborative’s Tran Ha and Matter’s Corey Ford are also available to engage in other ways. And again, the most important prerequisites are in-house expertise and the willingness to say “yes”.

To achieve this, they must shift their cultures. The principles of experimentation, curiosity, and empathy that are the hallmarks of great journalism must also be applied to the platforms that power their publishing and fundraising activities. They must foster great ideas, wherever they come from, and be willing to try stuff. That inherently also implies building a culture of transparency and open communication in organizations that have, on average, underinvested in these areas. As Bo Hee Kim, then a Director of Newsroom Strategy at the New York Times, wrote back in 2020:

Companies will need to address broader issues with communication, access, and equity within the workplace. Leaders will need to believe that newsroom culture has a bigger impact on the journalism than they understood in previous years — that a strong team dynamic is as important as their sharp and shiny stars. Managers are key to this transition and will need to reset with a new definition of success, followed by support and training to change.

Gary P. Pisano in Harvard Business Review:

Too many leaders think that by breaking the organization into smaller units or creating autonomous “skunk works” they can emulate an innovative start-up culture. This approach rarely works. It confuses scale with culture. Simply breaking a big bureaucratic organization into smaller units does not magically endow them with entrepreneurial spirit. Without strong management efforts to shape values, norms, and behaviors, these offspring units tend to inherit the culture of the parent organization that spawned them.

Creating an innovative culture is complex, intentional work. But it is work that must be done if news organizations are to innovate and, therefore, survive.


The internet is changing more rapidly than it has in years, creating headwinds for newsrooms and jeopardizing independent journalism’s viability. We need those organizations to exist: they reduce corruption, inform the voting public, and allow us to connect with and understand our communities in vital ways.

These organizations must own their digital presence outright to shield themselves from risks created by third parties that wield outsized supplier power over their business models. They must build direct relationships with their communities, prioritizing open protocols over proprietary systems. They need to invest in technology expertise that can help them weather these changes and make that expertise a first-class part of their senior leadership teams.

To get there, they must build an open culture of experimentation, where transparency and openness are core values cemented through excellent, intentional communication. They must be empathetic, un-hierarchical workplaces where a great idea can be fostered from anywhere. They must build a mutual culture of respect and collaboration between editorial and non-editorial staff and ensure that the expertise to advise on and predict technology challenges is present and well-supported in-house.

Experimentation and innovation are key. Newsrooms can discover practical ways to navigate these challenges by testing new strategies, technologies and mindsets. The road ahead is challenging, but with strategic investments and a forward-looking approach, newsrooms can continue to fulfill their vital role in a well-functioning democratic society. The best time for action was ten years ago; the second best time is now.

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Think twice before exercising your stock options

Number go up

I recently wrote a short aside about stock options:

But in general, for regular employees, I think options are rarely worth it. They typically require an up-front investment that many employees simply can’t make, so it’s a bit of a fake benefit to begin with, and their future value is little more certain than a lottery ticket.

Hunter Walk kindly reshared it on a few networks with some of his own thoughts; a conversation with Tony Stubblebine arose in the comments that Hunter wrote up as its own post. In particular, he says it helped him articulate the ups and downs of private stock to the average person:

For much of a startup’s life new FUNDING VALUATIONS are LEADING indications of POTENTIAL. They are what someone is willing to pay for shares today based on what they believe the company CAN DO in the FUTURE.

DOWN ROUNDS and RECAPS are LAGGING indications of PERFORMANCE. They are what someone is willing to pay for shares today based upon what the company HAS DONE in the PAST.

It’s a great post, and the comments from Tony were thoughtful. Which led me to feeling a bit bad about how flippant and imprecise my original post had been.

So, on that note, I’d love to define options, make some corrections, and dive a little deeper into my core argument.

The ins and outs of options

First, let’s define options and explain why they’re so common as a factor of startup compensation.

An option is the right to buy a specified number of shares in a company at a specific price. That price is typically defined by an external auditor. It’s good practice for this to happen once a year, but it’ll also be triggered when the company raises a round of equity funding (i.e., when it sells shares to outside investors in order to raise significant capital).

If a startup were simply to grant stock directly to employees, it would be taxable as compensation. Options are almost always non-taxable at the point where they are issued, so they’re a favorite way to give employees the ability to see some of the potential upside in a venture.

Typically in a startup you’ll receive an option grant as part of your compensation package. So, for example, you might receive the right to buy (“exercise”) 40,000 shares at 50 cents a share (the “strike price”). This is almost always on what’s called a vesting schedule: you won’t be able to buy any shares in the first year, but then when you cross that threshold (the “cliff”), you’ll be able to buy 25% of your allocation (the first 10,000 shares in my example). Over the next three years, the amount of your allocation that you can exercise will increase proportionally, until you can buy them all at the end of four years.

If you leave the company, you usually only have 90 days to exercise whichever options have vested. Some particularly progressive companies extend that exercise window — sometimes to a couple of years. But for 80-90% of startups, it’s 90 days.

If the startup is excited about keeping you, you may find that they’ll grant you more options periodically, each with their own vesting schedules. This, they hope, will keep you at the company.

In my example above, you might have done the math to realize: 40,000 shares at 50 cents a share is $20,000. You would need to lay out that amount of money to acquire the shares — and you need to hope that the company’s shares increase in value in order to see any upside.

If the company’s share price has increased in the time between the options were granted and when the employee exercises them, the difference is taxable. In the above example, recall that my options are for 40,000 shares at 50 cents a share. Let’s say I choose to exercise them all at the end of my four year vesting period: as we’ve discussed, I pay $20,000. But let’s say that the real fair market value has risen to 75 cents a share. The difference between 40,000 shares at 50 cents and 40,000 shares at the market value of 75 cents is $10,000 is usually taxed as income. So I’m actually paying $20K + income tax on another $10K. (This isn’t by any means the full extent of potential tax implications; I’m not going to touch ISOs and AMT in this post, for example.)

Early employees, who join before most funding rounds have taken place, will receive options with a very low exercise price. Later employees will usually receive options with a higher price, because more growth and fundraising has taken place in the interim. (Down rounds and recaps are certainly possible, though: many startups go through tough times where their valuation decreases. Not every graph always goes up and to the right.)

In both cases, any stock they buy is largely illiquid. Because the startup is likely a private company rather than a publicly traded one, their shares are not liquid. They will need to wait for the company to go public or hope that management will allow them to trade their stock on the secondary market.

Some corrections

So the first thing to say is: no, options are not really like a lottery ticket. They are a sort of gamble, but it’s one where (depending on your position, seniority, and what size the company was when you joined) you have a say in the outcome.

The second, which I’ve already corrected in the original post is: as Hunter pointed out in his post, a recap is not the thing that actually lowers the stock price. It’s a trailing signal of what the company has already done. A change in stock price is an effect of what has already happened.

And a clarification: options don’t require an up-front investment at the time that they’re granted. You invest at the time when you exercise them, which may still be as a lump sum.

Why I think exercising options isn’t worth it for many employees

If you’re on a rocket ship startup, exercising your options is almost certainly worth it (depending on the strike price of your particular options grant). The problem is: how do you know you’re on a rocket ship? Or, given that most startup employees won’t be part of a startup with hockey-stick growth, how can you be reasonably sure that your company will grow in such a way that exercising your options is worth it?

90% of startups fail. That doesn’t mean that every startup has an equal 1 in 10 chance of success: a lot depends on a range of factors that include internal culture, management expertise, execution quality, and market conditions. Still, there is not a small amount of luck involved. Most startups won’t make it.

You should never make an investment that you can’t afford to lose. As Hunter says in his post:

Don’t behave as if they’re worth anything until they actually are

Don’t over-extend yourself to exercise [options] in scenarios which put your financial well-being at risk.

If you’re obviously, unquestionably on a rocket ship: by all means, buy the options. (Yes, sometimes it really is obvious.)

If it’s not clear that you’re on a rocket ship, but you’re feeling good about the startup, and you can definitely afford to spend the money it would take to exercise your options: knock yourself out. Honestly, I don’t really care what people with wealth do in this scenario. My worries do not relate to you.

If it’s not clear that you’re on a rocket ship and spending the money to exercise your options would be a stretch: I would suggest you think twice before doing so. I also would warn you to never take out debt (which many startup employees do!) in order to exercise your options.

And that’s really the crux of my argument.

Startup employees without significant independent spending power who work for a venture with an uncertain future and who did not join their ventures at a very early stage — which I would argue describes most startup employees — should think long and hard before exercising their options.

It’s more than a little bit unfair that the people who can most easily realize upside from the startups they work for are people who already have wealth. Granting the ability for employees to buy shares directly at their fair market value is limited, too: this would make them investors, who the SEC says mostly need to be accredited. The definition of accreditation is either being a licensed investor, earning over $200,000 a year for the last two years, or having a net worth of over a million dollars excluding the value of their home. So the door is effectively closed to people from regular backgrounds.

I wish more equitable systems were commonly in use. Some different tactics are in use, which include:

  • Restricted Stock Units. Here, stock is granted directly as part of an employee’s compensation. Upside: the employee has the shares. Downside: they’re taxed on them as soon as they vest, and selling them is restricted. So the employee effectively receives an additional tax bill with no way of recouping the lost funds until much later (if they’re lucky). RSUs are common in later-stage companies but very uncommon in riskier, early-stage companies for this reason.
  • Phantom stock. Really this is a bonus plan tied to stock performance, income tax and all.
  • Profit sharing. Which is only useful if the startup makes a profit (most don’t).

While some have value in their own right in particular contexts, I see them as compensation strategies that might sit alongside stock options, rather than replacing them.

I would love it to be less risky for the employees who are actually doing the work of making a startup valuable to see more of the upside of that work. But, at least for now, my advice remains to take those inflated Silicon Valley salaries and bank them in more traditional investments.

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Some ShareOpenly updates

ShareOpenlyIt’s been a little over a month since I launched ShareOpenly, my simple tool that lets you add a “share to social media” button to your website which is compatible with the fediverse, Bluesky, Threads, and all of today’s crop of social media sites.

You might recall that I built it in order to help people move away from their “share to Twitter” buttons that they’ve been hosting for years. Those buttons made sense from 2006-2022 — but not so much in a world where engagement on Twitter/X is falling, and a new world of social media is emerging.

People have been using it, and I’ve had lots of great feedback.

So, today, I’m pleased to announce releases for two of the biggest requests people have made for the tool.

A share icon

A share button needs an icon. That was clear from the very beginning. It needs to be something distinctive — this is a different kind of social media share tool — but also immediately recognizable as a share icon.

I reached out to one of the best designers in the field: Jon Hicks, whose excellent work includes the new Thunderbird logo, Disney’s SpellStruck, Spotify’s icon set, and Truck, an excellent record store in my hometown. I was delighted when he agreed to create a share icon for ShareOpenly.

This icon works really well at small and large sizes: in sidebars, in footers, and wherever you need to help people share. Click the version embedded here to share this very post:


A WordPress plugin

Lots of people have asked me for an easy way to embed a ShareOpenly link into WordPress.

David Artiss, a support lead at Automattic’s excellent WordPress VIP service, has written a WordPress plugin that is now available in the official WordPress plugin directory. He writes more about it in an announcement blog post on his site:

Simply download the plugin, activate it and you’ll find a link added to the bottom of every WordPress post or page. A simple settings page allows you to change the sharing text, as well as whether it appears on posts and/or page content.

Boom! It couldn’t be easier.

I really hope that the new icon and the WordPress plugin make it easier to include more open sharing to your website. ShareOpenly is suitable for everything from small blogs to large publishers.

Manually creating a share link

Of course, you don’t need to use the WordPress plugin. You can embed a share icon onto any web page using this code:

<a href="#" id="shareopenly"><img src="" alt="Share to social media"></a>
  document.querySelector('#shareopenly').addEventListener('click', (e) => {
    let href = 'https://' + 'shareopenly' + '.org/share/?url=';
    href += `${encodeURIComponent(window.location.href)}&text=${encodeURIComponent(document.title)}`;
    window.location.href = href;

Or you can construct the URL yourself by following the instructions on this page.

Have fun, and please keep the feedback coming! You can always email me at

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The baby stack at 20 months

Silhouette of a toddler at the beach (stock photo).

When our son reached nine months old, I published this UsesThis-style list of products and services we were using; I had previously published one before he was born.

He’s twenty months old now: walking around and using words. He straddles the worlds between being a baby and a little boy, but becomes more like the latter every day.

I thought this was a good time to update the list.


Stroller: Our Uppababy Cruz V2 is still holding strong, although we use it less and less. We’re in the lucky position of being able to walk to daycare, and he quite often just wants to walk alongside us. (The stroller comes in most handy when we’re late.)

Travel Stroller: New to our mix is the Joolz Aer (now superseded in their lineup by the Aer+). It’s light as hell and folds up to easily fit in an airplane’s overhead bin, which has been useful for both short and long-haul trips. When we’re not on the move, it permanently lives in the trunk of my car.

Car Seat: We still use the Clek Foonf, which is like the tank of car seats. It’s solid and he seems to find it comfortable, although it’s beginning to be an effort to get him in and out of it. That’s more of a function of my tiny car than the seat itself; it’s more likely that I’ll upgrade the latter than the former.

Travel Car Seat: We’ve added a Cosco Scenera car seat to our mix. It’s light and cheap, and is really straightforward to install into a new car (for example a rental) or into an airplane seat. The thing we haven’t cracked yet is traveling on a plane without this kind of car seat: it’s bulky enough that it would make one-parent flights with him next to impossible. (If you’ve made this transition, please tell me how. I’m considering a CARES airplane safety harness, but how safe is, it, really?)

Bed: We’re in the final months or weeks of the Ikea Sundvik crib and Naturepedic Classic Organic Cotton Crib Mattress, which have served us incredibly well. If he wasn’t using a sleep sack, he would have easily scaled its walls and climbed out bed already. It’s time for a Real Bed (and therefore time for a Real Bedroom). Model TBC.

White Noise: We’re still using the Hatch Rest, although I’m not fully sure why. Habit at this point? He does love boffing the top of it to get it to change color and sound.

Baby Monitor: We’re still on the Nanit Pro. It’s been fairly good for us, but it definitely has shortcomings. The humidity sensor almost never works, and the device itself will fairly often disconnect from the wifi. He’s also been known to shake it like a wizard’s staff. We’re not measuring how long he’s been awake, etc, anymore, so we don’t use the recordings as much as we used to. But it’s nice to be able to get a notification when he’s stirring.

Changing Mat: Any surface will do at this point. Towels, standing up in a chair with a rubber mat to protect it — whatever. About one out of twenty times he’ll end up on the Peanut, but it was much more useful when he was a little potato.

Kitchen Stool: The Cosco Kitchen Stepper has become a mainstay: he can stand on a protected tower while watching us cook, or helping out himself.

High Chair: The Stokke Tripp Trapp has grown with us. We’ve stopped using the built-in tray, which has made it a little easier to clean: instead, we push him in to the table, and he eats alongside us. Having everyone be first-class participants around the dinner table has been lovely.

Travel Booster: We’ve been known to bring the Fisher-Price booster seat with us (it’s in the back of my car right now), although it’s happened less and less lately. Most restaurants we go to — when we eat out, which is rarely — have high chairs, and I suspect future friends and family visits will be marked by him eating on one of our laps.

Food: He’s eating what we eat more often than not. We keep Annie’s Mac and Cheese stocked just in case, and Trader Joe cottage cheese and apple sauce have become staples. But we’re mostly off the food pouches, powders, and specialized food products.


This gets its own section at this point. There are a few real standouts:

Uppstå toddler walker: I can’t overstate how much he loves this thing. It took him a little while to get used to it, but it’s grown with him. He’ll put his favorite things in it and walk them around the house, sometimes at speed. Just incredible value for money based on how often he plays with it.

Fisher-Price Little People Airplane and School Bus: I’m almost certain these didn’t play songs and noises when I was a kid. They certainly do now, but it’s easy to switch off the sounds if you don’t want them. He plays with both continuously. It’s sort of weird to see how Fisher-Price toys have evolved — I kind of miss the peg-like figures they used to come with — but he’ll have the same nostalgic feelings for these that I have for mine. Just, um, look out underfoot.

Plantoys Wonky Fruits & Vegetables and Assorted Vegetables: These are simple enough — wooden fruits and vegetables joined with little velcro pads — but he loves taking them apart and putting them back together again. They come with a little wooden “knife” that makes it easier to split them.

Melissa & Doug Pull-Back Vehicles: He thought they were cool when he was much younger (they were a much-appreciated first birthday present), but these days he knows how to pull them back and make them go. We find them all over the house.

Busy Bee: Apparently the best-selling toddler toy in Aotearoa New Zealand. He loves pulling it along behind him, to the extent that it can usually be used as a distraction from just about anything else.


Many, many times a day, he’ll demand to be read to. Seems like a good thing to me. Our collection of books is always rotating, but I thought it would be fun to list our stalwarts.

Hooray for Birds!, by Lucy Cousins: I could recite this verbatim. At this point, so can he, so I’ll often stop to let him fill in the blanks with the various bird noises. It’s lyrical, offers lots of opportunities to the reader to make silly voices, and is lots of fun.

Little Blue Truck, by Alice Schertle and Jill McElmurry: Rhythmic and perfectly wordsmithed; almost a song. You’ll find that you quickly get your engine noises, animal sounds, and “beep beep beep!”s to a professional level. Like Hooray for Birds!, he’ll often now come in with the right noises at the right time.

Each Peach Pear Plum, by Janet and Allan Ahlberg: I loved this book as a kid, and now he does, too. He calls it “Each Peach” and asks for it by name. (“Each Peach! Each Peach!”)

Guess How Much I Love You, by Sam McBratney and Anita Jeram: I like, half-jokingly, to call this the classic tale of toxic one-upmanship. But it’s sweet, and easy to give heart and voice to. I love him to the moon and back, too.

Jamberry, by Bruce Degen: This book makes no sense! It’s like a commercial for berries! But that doesn’t matter - he loves it.

I’m looking forward to introducing him to books for slightly older children that we have waiting in the wings; in particular, The Story of Ferdinand, Make Way for Ducklings, and Dogger, which are my top-three favorite picture books of all time.

Screen Time

Yes, we’re a Ms Rachel household. Lately, he’s been asking for my old pal Grover by name. And there’s a channel on YouTube called Helper Cars — origin unknown — that seems to be designed to appeal to his psyche.

We’re not completely comfortable with screen time, but it’s definitely become a thing. I figure it’s fine in moderation, and all of the above have some educational content to them.


I’m retiring this portion of the baby list: we don’t use any software to track or help parent him anymore, save for the ubiquitous MyChart from the pediatrician and the Procare daycare-management app that lets us know when he’s eaten and sends us photos of his day from time to time. We just, you know, listen to him, and try to figure out what he needs. We’ll look up recipes and activities from time to time, but there’s nothing special about that; we do it for ourselves, too, and you all know how Google works.


Photo by Daiga Ellaby on Unsplash

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Where I'm coming from

The silhouette of a man walking downhill

I’m paralyzed by the world. We seem to be at a kind of crossroads.

There’s so much to be appalled by, so much to be worried about, and I worry that not saying something might be considered to be acquiescence or approval.

So, in this moment, I thought I’d actually take a step back and explain what my worldview actually is. It’s perhaps overly ambitious, but I want to declare I think is important, and what drives me to say the sorts of things I do. And, yes, these same factors also drive the decisions I make about where I work and how I build software.

As always, I would like to read yours.

My view on the world — as is true of yours, and of everybody’s — is a function of my lived experiences, and the lived experiences of the people I care about.

It’s not about leading the world; it’s about living in a peaceful one

I was born in the Netherlands, grew up in England, spent time in Austria, went to school in Scotland, and have been in the United States since my early thirties. My dad is Swiss-Dutch-Indonesian; my mother was American on one side and Ukrainian on the other. They met in Berkeley in the early seventies and were heavily active in various progressive causes as activists. My dad in particular, who was drafted into the US Army after his family moved to America as a teenager, organized Vietnam War protests in the Bay Area, and was often harassed by the police.

My parents intentionally left the US to raise me. The closest thing I have to a hometown is Oxford, famous for its universities, where academic families are constantly coming through. My peers at school came from all over the world — including from behind the iron curtain — and experiencing the different smells and tastes of peoples’ homes was completely normal.

At the same time, I was a third culture kid for almost all of my childhood and early adulthood, and identified with no national identity. I never felt any real ties to any particular geographic place for its own sake. I was raised an atheist and have never felt religious ties (even though, as a child in England, I went to a Church of England school where we were made to pray every day). What I did identify with, very strongly, was family.

My dad is one of the youngest concentration camp survivors: he spent his early years in a Japanese-run camp in Indonesia, which still colors the way he sees the world. His mother had nightmares every single night for the rest of her life; I will remember hearing her screams though the walls forever. His father, who I never got to meet, was a resistance leader who was forced to dig his own grave multiple times. I’ve heard stories about the camps and what happened afterwards for my entire life. Even when they returned to the Netherlands, Indo people like my dad’s family were an ethnic minority and treated poorly. They eventually moved to California, thanks to a local sponsor, where they ran a gas station on highway 12 in Sebastopol. My uncle was severely beaten up for daring to serve Black people. The gas station itself was routinely shot at — once killing the family dog — simply because it was run by immigrants.

My great grandfather escaped Ukraine twice. His village was destroyed by the White Army as part of vicious Pogroms. When he emigrated to the US, he secularized, changing his name in the process in order to sound less Jewish. Eventually he became the General Manager of the Pennsylvania Joint Board of the Amalgamated Shirt Workers. I’ve previously posted excerpts from my grandfather’s obituary that discuss that experience as well as my grandfather’s experience as a Jewish POW in Germany during WWII.

My grandfather, by the way, ended up translating Crime and Punishment into English, and taught in the Slavic and Eurasian Studies and History departments at the University of Texas at Austin for forty years. He met Albert Einstein, had coffee with Sylvia Plath, discussed philosophy with Hannah Arendt, and never quite realized his dream of being a poet. In the end, he married into an institutional American family: my great grandfather was a WWI test pilot and eventually became a diplomat who negotiated the US withdrawal from Haiti. (This fact of my family history is, I want to be clear, not an endorsement of the US’s behavior overseas, including in Haiti.)

So, all of this is to say: I have no interest in patriotism, let alone nationalism. It’s not a value I hold, and I’m not excited by any country having a leadership position in the world. I find flag-waving to be petty. What I care about are values: the democracy, inclusion, and co-operation that can lead to a lasting peace. I’m repelled by military strength, because I’ve seen what various militaries did to my family. I’m repelled by anti-immigrant sentiment, because I come from refugees and immigrants. I don’t like the idea of assimilation, because I’ve seen the richness inherent in lots of cultures. Forced assimilation — which is usually into a conquering culture — is tantamount to subjugation.

National exceptionalism — American exceptionalism, or European exceptionalism, come to that — is ridiculous on its face. Cold wars and imperialist foreign policies are things to avoid, not things to perpetuate. No country is the “best”, and even the idea of “a best country” is narrow-minded. No religion is the “best”; please enjoy practicing yours, but please don’t impose it on anyone else. There are definitely people who think McCarthy’s witch hunt against communism was right in spirit, even if they condemn the historical event itself — let’s just say they and I harbor some very different ideas about what an open, democratic society should look like.

Nations aren’t what’s important. Principles are. Specifically, the principles of openness, inclusion, fairness, peace, equity, and democracy.

What matters is that everyone can live a good life, wherever they are, whoever they are, and however they identify, free from threat of violence or exploitation. Ideological or national superiority aren’t useful values. What matters is the experience of being a human, everywhere. What matters is avoiding the killing and horror of war. What matters is honoring the beautiful diversity of the world.

A strong operating system for all

I was only half-joking when I compared governments to operating systems. While they certainly don’t map perfectly to actual software operating systems, I do think they provide a very similar purpose: to create a bedrock of services and infrastructure in order to ensure society runs smoothly.

What does “society runs smoothly” really mean? I’ll return to my definition above. What matters is that everyone can live a good life, wherever they are, whoever they are, and however they identify, free from threat of violence or exploitation. Freedom of expression, association, and to pursue one’s best interests are important here: what John Locke called the pursuit of happiness. To ensure the safety of that pursuit, I think John Locke’s version of a social contract — the idea that we surrender a little personal liberty in order to make evolving common agreements in the best interests of everyone — is important.

I can’t be a libertarian because I see the importance of the trade-offs here. One role of the operating system is to prevent the vulnerable from exploitation: public goods like universal healthcare, public education, and integrated public transit ensure that people who are not wealthy have the opportunity to build a great life. One of the most visceral reactions I’ve ever had in my life was discovering Ayn Rand, and then, to my horror, discovering that beyond just getting into her novels, some people actually believed in her ideology of everyone for themselves.

Healthy communities are an important part of all of our well-being. Once again: every person deserves to live a good life. We all live in a complex, interconnected network of people, and what happens to someone else also affects us. Caring for the whole network is also in our own best interests. It can’t be everyone for themselves.

It’s hopefully obvious from my definition, but I don’t think GDP (or money at all) is a great way to measure a society, either. It doesn’t say much about what an ordinary person’s experience actually is. It doesn’t measure human well-being, and that’s how we should be thinking about how well we’re doing. I’m less interested in is the stock market going up? than is being poor a death sentence? as a question — and I don’t think the first necessarily leads to a reduction in the second. More and more people agree.

One important function of the social operating system is welfare, which ensures that people don’t fall though the cracks. There are others, some of which I’ve already mentioned: education, transit, and healthcare.

I couldn’t have founded my first startup if I hadn’t had the benefit of the excellent National Health Service. Millions of PR dollars have been spent in the US to paint social infrastructure as being a bad thing, but I never once had to worry about going to the doctor under universal healthcare. I didn’t have to worry about losing health insurance when I quit my job. I could just do it. Say what you want about free markets, but I think that freedom of optionality — having broad choices regardless of income or personal net worth — comes closer to real personal freedom than a world without that kind of social infrastructure.

Here in the United States, it doesn’t come automatically: you need people to fight for you. I’ve lost five members of my family to an incurable genetic disease. One of them was my mother, who I helped care for over the course of a decade — which was, in fact, the reason I moved to the US to begin with. She was a teacher, and the great medical care she received was only possible because of the incredible negotiating power of her teacher’s union. While there should have simply been universal healthcare to look after her, their incredible negotiating power literally lengthened her life by eight years. Unions can be amazing institutions; while not every union is great, the concept of them is. And in a world without the social infrastructure to care for the vulnerable, they are vital.

This should be the purpose of the law, too: to prevent harm and exploitation, particularly of the vulnerable, in service of maintaining the ability to have a good quality of life. But the law itself, alongside tradition and the twin ideas of unity and stability, often does the opposite. It has often used as a way to maintain a status quo where vulnerable people are exploited for other peoples’ benefit.

This runs deep: some of the earliest police forces in America were slave patrols. A law that only benefits the powerful or upholds an unjust status quo is, in itself, unjust. Unity that depends on adherence to the values of the powerful (and on the silence or silencing of the vulnerable) is a sham. Stability based on prioritizing the needs of an in-group to the exclusion of others is definitionally fascism. A claim that moderate values are more reasonable only makes sense to people who don’t need more radical change in order to achieve equity.

Being awake to those injustices is not a binary: it’s not something you either are or not. It’s an ongoing, uncomfortable process of education and coming to terms. There are lots of ways to deal with and redress them, the comparative merits of which are up for discussion. What’s clear to me, though, is that dismissing their existence outright, and painting them with a reductionist brush in order to rob them of importance, is in itself a perpetuation of those injustices.

When people started talking about being “woke” and taking to the streets to demand restorative justice, I was relieved and excited. This is what moving forward looks like. In contrast, I see people harping on about the harms of “woke-ism” as being part of the dying gasps of the twentieth century: that adherence to tradition and unity and stability in service of the same old inequalities. Change is good; particularly here.

Change can also be easy. Using a preferred pronoun costs you nothing except for letting go of a tradition. The tradition, in other words, gets in the way of someone’s chosen identity being recognized. Same-sex marriage costs you nothing except for letting go of a tradition. The tradition once again gets in the way of someone being able to realize their needs. Your religious beliefs might forbid same-sex marriage; then simply don’t get same-sex married. Practice your own religion to your heart’s content, but don’t enforce your traditions on anyone else. Refer to someone as they would like to be referred; treat everybody with respect. It seems foundational. A fear of change or adherence to a tradition should not be a barrier to making the world more just or treating our fellow humans with respect.

Let’s return again to the core idea: every person deserves to live a good life. Of course, who we consider to be a “person” is important. Thomas Jefferson incorporated Locke’s version of a social contract into the Declaration of Independence, even going so far as to say that “all men are created equal,” but he famously kept slaves. These days, we might ask about our spheres of concern: do we care about people in our families? Our neighborhoods? Our towns and cities? Our churches? Our ethnicities? Our value structures? Our states? Our countries? Our regions? The world? How do we relate to people outside of those spheres?

For reasons I’ve tried to explain above, I’d love it if we considered the world to be what we care about; the welfare of a person in Gaza is just as important as the welfare of a person next door, even if we might not share a religion or care for the regime they live under. In fact, depending on their context, their welfare might be more important, because they need more help to bring them to that reasonable standard of living, free from violence and exploitation.

Because our definitions of what a good life is vary, and because no government can possibly claim to represent or understand the complete set of needs and lived experiences in its populace, participative democracy is the only equitable model for government. What’s important here: everyone can vote without hindrance, votes are fair, anyone can become a representative, decisions are actually made at the ballot box rather than in court, and there is real choice. (If there’s a candidate whose values you hate, do what you can to persuade your fellow voters to vote for someone else. That’s what democracy is.)

Those principles are core. It might surprise you to learn that I’m not inherently against the idea of billionaires, and certainly not against the idea of starting businesses and finding success in doing so. But it must be done without exploiting other people and preventing them from being able to live a good life. It must be done without perpetuating injustices, for example by eroding workers’ rights, forcing a minimum wage that is too low to live well on, lobbying for unequal laws, or fighting against their ability to negotiate for better working conditions. Can it be done without those things? I don’t know. But if it can’t, then it shouldn’t happen.

So what does this have to do with the internet?

I see the web as a platform as being rooted in the kind of internationalism I believe in. The internet itself is a physical manifestation of the idea that we are all connected.

Anyone can publish, anywhere, and be read by anyone, anywhere. That’s amazing! Anyone can start a business and find users all over the world. That’s also amazing! It’s the most borderless, open platform we’ve ever created. The potential to learn about the lives of people we would never otherwise meet, in places we would never otherwise visit, is colossal. We can share ideas and, even more importantly, build empathy globally. I couldn’t be more excited about that. That’s what keeps me building.

It’s easier to dehumanize someone you don’t know. The internet has the potential to allow everybody to become knowable. I see that as a route to peace, and to a better world where exploitation can no longer happen in the shadows.

What I’m not enthused by is the idea that the internet is here as an exercise in furthering any one country’s interests: that one nation’s worldview should trump another’s. At its best, it’s an international commons: an overtly progressive space by design.

I support the indieweb and the fediverse because those technologies harness for the benefit of the public, rather than for the profit and entrenched power of a tiny few. I see silos and centralized services as being anti-democracy, because the whims of a monarch-like figure can have a profound impact on which information we’re allowed to see. We’ve seen that most obviously recently with Elon Musk’s acquisition of Twitter, but it was previously also true of Facebook, and of every large service that aimed to intermediate peoples’ connections with each other. If one entity controls what we see and can learn about, they will abuse it, always.

I’m imperfect. Of course I am. I’ve made terrible mistakes and, from time to time, I’ve hurt people. But that doesn’t mean I can’t try.

I’ve built open source platforms for organizing educational institutions and non-profits; I’ve supported newsrooms that help to create a more informed voting population; I’ve worked in newsrooms that help speak truth to power. It’s not because I love social networking in itself, or because I want to get rich by building software.

It’s because I remember the sound of my Oma having nightmares through the walls. I see the nationalists and isolationists as trying to divide people into in-groups and out-groups. I see hoarding wealth as akin to building walls. I see conservatism as being a way to preserve the kind of bigotry that can grow and explode into the kinds of hatred that swallow whole families. Quixotic as it might be, I see connecting people as a way to help prevent it all from ever happening again.

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The xenophobic, un-American TikTok ban

A phone showing TikTok with the Chinese flag in the background

The requirement for TikTok to relinquish Chinese ownership or face a nationwide ban was signed into law today, as an add-on to a foreign aid bill:

But even as ridiculous as it is to tack on a TikTok ban to foreign spending support, Biden had made it clear he supported the TikTok ban anyway. Still, it does seem notable that, when signing the bill, Biden didn’t even mention the TikTok ban in his remarks.

This is a couple of years after Meta, clearly threatened by the app’s enormous growth, started employing a PR firm to kick off an anti-TikTok campaign.

There are a few worries at play:

  • TikTok will irresponsibly collect enormous amounts of data about hundreds of millions of Americans, something no other social network would ever do
  • There’s a possibility that TikTok will be used to spread propaganda, unlike every other social network
  • TikTok is Chinese, not American

The third is most pertinent. These are clearly things — gathering data, spreading propaganda — that only American companies should do to Americans (or to the rest of the world).

Ironically, banning a service from the open internet nationwide is exactly the kind of thing that China has done again and again through its Great Firewall. Rather than protect American users through the kinds of far-reaching privacy legislation that we need, government chose to address TikTok alone on the basis of what amounts to xenophobic protectionism.

It’s the kind of xenophobia we saw at a Senate hearing on child safety earlier in the year:

“You often say that you live in Singapore,” Cotton said before demanding to know where Chew’s passport was from (Singapore, obviously) and whether he’d applied for citizenship in China or the US (no, said Chew). “Have you ever been a member of the Chinese Communist Party?” he then asked abruptly, as if hoping to catch Chew by surprise. Chew’s response wasn’t shocked so much as fed up. “Senator! I’m Singaporean!” he reiterated. “No.” (Singapore is not part of China.)

The Verge further made this point:

It’s not even necessary to make the case that China might have undue influence over TikTok. Apple, for instance, has weathered years of critiques about its relationship to the Chinese government; no reasonable person has ever suggested this hinges on Tim Cook being a secret communist. Instead, it’s a line of questioning that seems simply designed to play on Chew’s foreignness — even when it’s got nothing to do with the topic at hand.

It’s not that TikTok is particularly harmful compared to other similar apps: it’s that we’re deathly afraid of China.

I find it unsettling that a global platform - the internet, that is - which seeks to connect everyone in the world is being undermined for Americans in this way. Should this precedent spiral, it’s not unreasonable to think that more foreign services that threaten American incumbents will be banned or forced to divest. The result would be a National Internet, culturally and economically cut off from the rest of the world: something so dystopian that I’ve written it into science fiction stories.

Beyond nationalism, the propaganda argument may ironically cover for the fact that viewers are likely to encounter a wider range of international viewpoints:

Anti-China hysteria may be completely grounded in xenophobia, but some legislators clearly also don’t care for the content of TikTok. Raja Krishnamoorthi, an Illinois Democrat supportive of the anti-TikTok legislation, recently raised concerns over TikTok’s content recommendations. TikTok has been criticized for presenting its users with “pro-Palestinian” content. It has been a major source of videos of the unfolding atrocities in Gaza, and a ban of TikTok could, as the Independent’s Io Dodds reports, “clobber the pro-Palestine movement,” supporters of which have used the platform effectively for communication.

Current Affairs concludes:

The disconnect between the American people’s interests and the priorities of national politicians has never been more stark. We need to resist their attempt to get us to be afraid of Chinese people, and to control platforms where viewpoints unfavorable to U.S. imperialism are given a public airing.

This in itself feels un-American: a violation of the democratic rights enshrined in the First Amendment and the principle of free speech. We have the right to learn about those viewpoints, and to receive media created elsewhere in the world. Just as on the web itself, which allows us to learn about the world from a variety of perspectives, we’re richer for it.

I imagine there will be a battery of lawsuits from the international investors who actually own TikTok on the back of this legislation. It’ll be interesting to see what happens, and what the response from other nations will be.

Personally, I just think it’s stupid.

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It’s my mother’s birthday. She would be 72 today.

The week we lost her, I wrote this piece, which I re-read today.

In it, our friend Anita Hurrell remembered her like this:

One time you drove us in the van to the seaside and we ate sandwiches with cucumber in them and I thought they tasted delicious and I felt this strong sense of deep content sitting with Hannah in the back listening to her singing and humming for the whole journey. I have no idea where we went, and in my head it was nowhere in England, but rather part of the big-hearted, loving, funny, relaxed, non-conformist world of your family in my childhood - full of your laughter and your enormous kindness.

[…] I look back and see […] what a true feminist you were, how much of parenting you seemed to do much better than we do these days, how generous and homemade and fun and kind the world you and Oscar [my dad] made was.

I feel so privileged to have had that childhood. To have had a mother like her.

In the piece I read at her memorial, I said:

Before I was born, both my parents were involved in struggles to support affirmative action and tenants’ rights. She described herself as having been radicalized early on, but it’s not particularly that she was radical: she could just see past the social templates that everyone is expected to adhere to, and which perpetuate systemic injustices, and could see how everything should operate to be fairer.

That was true on every level. She wanted she and [her siblings] to all be treated equally, and would make it known if she thought the others were getting a raw deal. She tried her best to treat Hannah and I equally. If someone made a sexist or a homophobic remark around her, she would call it out. If someone was xenophobic, or unthinkingly imperialist, she would bring it up. She was outspoken - always with good humor, but always adamant about what really mattered.

When our son was born, I wrote:

The last time I saw you, just over a year ago, you were in a bed in the same institution, your donated lungs breathing fainter and fainter. I kissed you on the forehead and told you I loved you. You’d told me that what you wanted to hear was us talking amongst ourselves; to know that we’d continue without you. In the end, that’s what happened. But I miss you terribly: I feel the grief of losing you every day, and never more than when my child was born.

[…] In this worse universe that doesn’t have you in it, I’ve been intentionally trying to channel you. I’ve been trying to imagine how you would have shown up with them, and what your advice for me would have been. I’ve been trying to convey that good-humored warmth I always felt. You made me feel safe: physically, yes, but more than that, emotionally. I want to make them feel safe, too: to be who they really are.

That first piece from three days after we lost her:

I want to honor her by furthering what she put into the world. The loving, non-conformist, irreverent, equity-minded spirit that she embodied.

Her values are the right ones, I’m sure of it — her non-conformity, her progressivism, her intellectual curiosity, her fearlessness and silliness (and fearless silliness), her gameness for adventure, her internationalism, her inclusive care and love for everybody and absolute disregard for the expectations other people had for her, or for nonsense tradition, for institutions, or for money.

She is the best person I’ve ever met and could ever hope to meet. I’ve been so, deeply sad, every day, but grief isn’t enough to honor her, and I wish I’d been better at doing that.

I miss you, Ma. I love you. I’m so, so sorry.

Ma, long before I was born

Ma with me as a young boy

Ma making her way down to the beach

Ma in Scotland, making the grimace emoji face

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Share Openly

You know all those “share to Facebook” / “share to Twitter” links you see all over peoples’ websites? They’re all out of date.

Social media has evolved over the last year, yet nobody has “share to” links for Mastodon, Bluesky, Threads, etc. There have been a few attempts to create “share to Mastodon” buttons, but they haven’t taken the larger breadth of the new social media landscape into account.

So I’ve built a prototype, which I’ve called ShareOpenly.

At the bottom of every article on my site, you’ll see a “share to social media” button. Here’s the button for this article.

If you click it, you’ll be taken to a page that looks like this one:

Share Openly share screen

You can select one of the pre-set sites in the list, and you’ll be taken to share a post there. For example, if I click on Threads, it will take me to share there:

But if you, for example, have a Mastodon instance, or a Known site, or an indieweb site at a different domain, you can enter that domain in the box, and ShareOpenly will try and find a way to let you share the page with that site.

ShareOpenly will do a few things first:

  1. If it’s on a “well-known” domain — eg, — it’ll send you to the share page there.
  2. It checks to see if it can figure out if the site is on a known platform (currently Mastodon, Known, hosted WordPress,, and a few others). If so — hooray! — it knows the share URL, and off you go.
  3. It looks for a <link rel=“share-url”> header tag on the page. The href attribute should be set to the share URL for the site, with template variables {text} and (optionally) {url} present where the share text and URL should go. (If {url} is not present, the URL to share will be appended at the end of the text.) If it’s there — yay! — we forward there, replacing {text} and {url} as appropriate.

Once you’ve shared to a site, the next time you visit ShareOpenly, it will be in the quick links. For example, I shared to my site at in the example above, and now here it is in the links:

It’s early days yet — this is just a prototype — but I thought I’d share what I’ve built so far.

If you want to add ShareOpenly to your own site, please do! Just replace the URL and test in this link - - with your own. You can also just visit the ShareOpenly homepage to share a site directly.


Syndicated to Indienews

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Building engineering

Software developers

I’ve spent most of my career — now well over two decades of it — building things on the web. I’ve worked as a software developer, I’ve founded a couple of my own companies, and I’ve often found myself leading teams of engineers. Right now I’m the director for both engineering and IT (although there are teams of people who write code who aren’t under my wing — newsrooms are complicated).

Over time, a lot of my work seems to have become less about “what shall we build?” or “how shall we build it?”. Those questions are always vitally important, but there are prerequisites that sometimes need to take center stage: things like “what are we here to do?”, “how should we work together?”, and “how do we think about what matters?”

I’ve been sharpening my thinking about the necessary conditions to do good work, and how to achieve them. Here’s a window into how I’m thinking about these ideas across three dimensions: Organizational Context, Team Leadership, and Technology Trends.

Words painted on the street: passion led us here

Organizational Context

There’s an unattributed but often-quoted management strategy cliché that says: culture eats strategy for breakfast. I’m a believer. Culture contains the fundamental building blocks of how an organization acts as a community: its values, beliefs, attitudes, norms, processes, and rules. Without a strong one, you cannot succeed — regardless of what your strategy looks like. Conversely, a great strategy, by definition, is one that incorporates building a great, intentional culture. Without one, your team is more likely to burn out and leave, you’re much less likely to build something high-quality, and you’re unlikely to foster new ideas.

Software engineering, at least in the places I’ve practiced it, is all about innovation. The focus is rarely on maintaining the present, although some degree of maintenance is always necessary. Instead, it’s about building the future: figuring out what we’ll need our platform to look like in two to five years and finding ways to get there. It’s a creative pursuit as much as it is about rigor and craft, and it’s about values and taste as much as it is about business necessity.

This dynamic is well-served by some organizational cultures and actively undermined by others. The trick is figuring out which you’re in, and finding ways to either embrace the former or build a buffer zone for the latter.

One popular way of looking at organizational culture is the Competing Values Framework, which defines four distinct overall culture types — all four of which are usually present to different degrees inside an organization.

  • Adhocracy: an organic, unbureaucratic way of organizing work that challenges the status quo, formal titles, and hierarchy in favor of a focus on risk-taking and innovating at speed.
  • Clan: a family-like culture that, again, is relatively unbureaucratic, without much structure, where rules tend to manifest as social norms rather than edicts or rigid process.
  • Hierarchy: where an emphasis is placed on top-down control from upper management in order to create predictability and lower risk. Roles are clearly defined, rules are codified, and even internal communication tends to be stratified.
  • Market: a culture optimized around competition, both with competitors and internally. Measurable results are central, but the workplace can easily become toxic because everyone is trying to better themselves vs their peers.

Like many frameworks, the reality is not actually as cut and dry as this. Instead, I think these categories are best thought of as facets of an organizational culture. In some organizations, hierarchy and market focus may have a heavier emphasis; in others, innovation and collaboration.

I vastly prefer working within organizations that look like the first two environments — adhocracies and clans — and I’d hazard to say that almost every single engineer, designer, and product manager I’ve ever worked with feels the same way. Hierarchical systems are inherently creatively stifling: innovation can’t take place in an environment with predominantly top-down control. The same goes for hyper-competitive environments: while the competition might be motivating for some in the short term, it’s really hard to collaborate effectively and build on each others’ ideas if everyone is trying to get ahead of each other.

Hierarchies in particular definitionally strip your authority in favor of top-down direction, forcing you to negotiate through layers of politics to make any kind of change. Most good engineers are collaborators, not cogs, with ideas, expertise, and creativity that should be embraced. But hierarchy demands cog-like behavior, and creates institutional fiefdoms that tend towards bureaucracy, inhibiting any really new work from being done if it hasn’t been rubber-stamped. These aren’t great places for a creative person to work.

As Robin Rendle put it recently:

This is the most obvious thing to say in the world, but: the hard work should never be the bureaucracy, it should be designing things and solving technical problems. If the hard work ain’t the hard work, ya gotta bounce. Don’t kill yourself trying to tell people that.

That isn’t to say that every team in an organization should work the same way or strive for the same culture. It might be that a legal, compliance, or safety team needs to work in a more rigid way as a system of control, or that a sales team needs to be intensely market-oriented. Or those things might not be true at all! My point is that it’s a mistake for engineers to assume that because they work best in a particular kind of environment, everyone should work that way. Every organization is comprised of a mix of culture types, and every team needs to work in a way that allows them to do their best work.

This may seem obvious, but we often talk about a single team’s working style setting the cultural norms for a whole organization. For example, it’s common for an organization to be described as engineering-led or sales-led. To be clear, this is a false choice: there should simply be people-led organizations that are inclusive of different interdisciplinary needs and styles of working.

For that to be a reality, top-level leadership in particular needs to acknowledge that not every team works the same way. For my purposes, this means acknowledging that engineering needs a particular kind of culture in order to thrive (and is important enough to have its own culture and be deserving of autonomy).

A prerequisite to this is understanding the potential for a technology team (or any team) in the first place. That’s less likely to happen in organizations where it’s treated as back-office, paint-by-numbers work. If an organization can’t see the importance of a team’s work, and if it inherently does not respect the effort and expertise inherent in those roles, it’s going to be very difficult for them to do good work.

My bias is to lean heavily on storytelling and listening as tools for fostering understanding: finding ways to explain why the work of product and engineering is important in the context of the whole organization, and how that expertise can be leveraged in order to benefit everybody. It’s okay to not understand what an engineering team has the potential to do from the outset, but if organizational leaders continue to not understand, that’s on me. The way to get there is through being transparent about what we’re doing, how we’re thinking, and which challenges we expect to encounter.

It really matters. Mutual understanding begets mutual respect.

There needs to be an explicit understanding between teams, mutual respect between parties that encompasses their expertise and different ways of working, and loose protocols for how everyone is going to communicate with each other that is compatible with their different styles of working.

I shouldn’t presume to tell a team from another discipline what they need to do their job, just as they shouldn’t presume to tell me. I should treat another team as the expert in its discipline, and they should treat my team as the expert in mine.

Throughout all this and despite our differences, we’re all in the same boat. We need to all be pulling in the same direction, motivated around a single, motivating mission (why we’re all here), vision (what is the world we’re here to try to create), and strategy (what are we going to try and do next to make it a reality).

The role of upper management is to set the direction, foster a culture that supports everyone, and help to build those protocols (all while not running out of money). One role of team leaders is to navigate those protocols and act as a buffer where there is friction.

Silhouettes of people walking down a hill. One is in front

Team Leadership

Vulnerable, open leaders make it safe for everyone to take risks and show up to work as they are.

So far I’ve written a lot about how engineering teams need organizational support that starts with a compatible culture that is founded on respect. But even in an environment that is un-hierarchical, transparent, informal, respectful, and open, with clear organizational goals and a defining mission, there’s more work to be done in order to create an environment where engineers can do their best work.

As I wrote last year:

The truth is that while some of the tools of the trade are drawn from math and discrete logic, software is fundamentally a people business, and the only way to succeed is to build teams based on great, collaborative communication, human empathy, true support, and mutual respect.

Leaders need to be stewards of those values. I believe — strongly — that this is best achieved through servant leadership:

[Servant leadership] aims to foster an inclusive environment that enables everyone in the organization to thrive as their authentic self. Whereas traditional leadership focuses on the success of the company or organization, servant leadership puts employees first to grow the organization through their commitment and engagement. When implemented correctly, servant leadership can help foster trust, accountability, growth, and inclusion in the workplace.

Each of these are important; I would also add safety. A blame-free environment where everyone can speak openly, be themselves, make mistakes, and not feel like they have to put on a mask to work is one where people can take risks and therefore innovate more effectively.

When you’re facilitating a brainstorming exercise, you might intentionally throw in a few out-there suggestions to make participants feel comfortable to take risks with their own contributions. Similarly, one of the roles of a leader is to push the envelope, and maybe risk looking a bit silly, in order to allow other people to feel more comfortable taking risks with their work — and when they do, to cheerlead them, support them, and help them feel comfortable even if their ideas don’t work out.

In a hierarchical team, the leader might ask if team members are adhering to their standards. In a supportive team, the leader might primarily ask how they are doing at supporting their team. It’s not that you don’t ever ask if someone isn’t performing; it’s more to do with the center of gravity of assessment. Supportive teams put the employees first.

Fostering that sort of team culture heavily depends on how a manager shows up day to day. A manager who isn’t vulnerable, doesn’t reveal much of themselves, and requires homogeneity is — probably unintentionally — fostering a hierarchical culture where masking is the norm rather than a supportive one where people are free to to be themselves.

The same sorts of fractal dynamics that affect inter-team collaboration apply to inter-personal collaboration, too. Everyone is different and has different working and communication styles, and homogeneity should never be the goal.

You can tell a lot by a team’s approach to feedback. If it is given in one direction — from managers down — then you likely have a hierarchical culture where team members may be less able to speak up and share their ideas. (The same is true if feedback is sometimes given to managers but rarely acted on.) I’ve observed that the most successful teams have clear, open, 360-degree feedback loops, where everyone’s feedback is directly sought out and incorporated — from team members to managers, between team members, and from manager to manager.

Another observable difference in team cultures can be seen through the kinds of norms that are enforced. To the extent that there are hard and fast rules on a team, they should be grounded in a purpose that supports forward motion, rather than to provide comfort to leadership or simply to enforce sameness.

As illustration, here are two contrasting examples of norms I’ve often seen enforced on teams:

  • Source code is written to adhere to common style guidelines, and is peer reviewed.
  • Cameras should be turned on during video calls.

Common coding style rules are a social contract that lower the cognitive load of working with code that someone else on the team has written, removing important roadblocks to everyone’s work; peer review is a really great channel for feedback, learning, and preventing bugs. Meanwhile, enforcing that cameras should always be on during video calls only serves to make some people less comfortable on the call.

Ultimately, success here is measured in what you ship, how happy your team is, whether they recommend working at your organization to their friends, and how long people stick around for.

A robot and a person holding hands

Technology Trends

It’s important for an engineering team to not just have a competence in working with technology but to have strong opinions about it, its implications, and how it intersects with the lives of the people it touches. They should strive to be experts in those issues, learning as much as they can from relevant publications, scholars, and practitioners.

It would be ludicrous to examine the use of AI but not study its ethical issues. Not only is there a moral hazard in not understanding the subject holistically, but by leaving out topics like bias, intellectual property violations, and hallucinations as you investigate bringing AI into your work, you actually create liability for your organization. It’s both an ethical duty and good due diligence.

Similarly, imagine studying blockchain a few years ago but not covering its environmental impact or its potential for use in money laundering. Leadership might have been excited by the potential for financial growth, but by not examining the human impacts of the technology, you would have missed substantial risks that might have created real business headwinds later on.

Or imagine relying on developing code as a core function of your organization and not staying on top of new techniques, approaches, exploits, and technologies to build with. Your team would effectively be stuck in time without any real way to progress and stay relevant, creating a risk that your product would suffer over time.

Or, come to that, imagine working in a fast-moving field like technology and not forming a strong, informed opinion about how it will change that is rooted in learning, experimentation, and active collaboration with experts and other organizations.

This is another area where an open, collaborative, inclusive culture can be helpful. Giving space to team members who want to share their knowledge and ideas about a subject, and entrusting them to cover it from their perspective, helps allow for topics to be covered through the lens of a variety of diverse lived experiences. But by practicing and championing the idea of inclusion as a core team value, you encourage team members to actively go and speak to diverse experts and gather a variety of viewpoints. The gene pool of ideas is widened as you investigate a subject and your own ideas and resulting products and strategies will be stronger as a result.

In a hierarchical culture where strategy is set from the top down, this kind of broad, inclusive learning might not be as effective, or it might not be present at all. Servant leadership helps ensure that everyone has the space to learn and grow with respect to topics they may not have mastered yet, or that their perspectives are championed. You simply have access to fewer ideas from fewer perspectives, and you’re wildly limited as a result.

Those same open feedback channels that create well-functioning, communicative teams can also serve as a way for team members to learn from each other. The principles of openness, inclusion, respect, openness to risk, and collaboration can serve as guiding lights as teams navigate new technologies and help their respective organizations get to grips with these topics. Leaders have a role in fostering learning and knowledge-sharing on a team, and ensuring that it is a first-class activity alongside writing and architecting code.

Stenciled letters on a wall: Live, Work, Create.


A lot of the things that are important to get right with engineering aren’t really about engineering at all. The best teams have a robust, intentional culture that champions openness, inclusivity, and continuous learning — which requires a lot of relationship-building both internally and with the organization in which it sits. These teams can make progress on meaningful work, and make their members valued, heard, and empowered to contribute.

At a team leadership level, servant leadership is a vital part of fostering a culture of innovation and adaptability. By prioritizing the well-being and development of the people on their teams, leaders are making an investment that leads to higher performance, more nuanced strategy, more resilience, and lower churn.

At an organizational leadership level, a clear strategic direction and a focus on inclusivity help to provide the leeway to get this work done. I don’t know if you can succeed without those things; I certainly know that you can’t create a satisfying place for engineers and other creative people to work.

The most interesting and successful organizations have an externally-focused human mission and an internal focus on treating their humans well. That’s the only way to build technology well: to empower the people who are doing it, with a focus on empathy and inclusion, and a mission that galvanizes its community to work together. And, perhaps most importantly to me, that’s the only way to build a team that I want to work on.

That’s how I’ve been thinking about it. I’d love to read your reflections and to learn from you.

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Exploring AI, safely

I’ve been thinking about the risks and ethical issues around AI in the following buckets:

  • Source impacts: the ecosystem impact of generative models on the people who created the information they were trained on.
  • Truth and bias: the tendency of generative models to give the appearance of objectivity and truthfulness despite their well-documented biases and tendency to hallucinate.
  • Privacy and vendor trust: because the most-used AI models are provided as cloud services, users can end up sending copious amounts of sensitive information to service providers with unknown chain of custody or security stances.
  • Legal fallout: if an organization adopts an AI service today, what are the implications for it if some of the suits in progress against OpenAI et al succeed?

At the same time, I’m hearing an increasing number of reports of AI being useful for various tasks, and I’ve been following Simon Willison’s exploratory work with interest.

My personal conclusions for the above buckets, such as they are, break down like this:

  • Source impacts: AI will, undoubtedly, make it harder for lots of people across disciplines and industries to make a living. This is already in progress, and continues a trend that was started by the internet itself (ask a professional photographer).
  • Truth and bias: There is no way to force an LLM to tell the truth or declare its bias, and attempts to build less-biased AI models have been controversial at best. Our best hope is probably well-curated source materials and, most of all, really great training and awareness for end-users. I also would never let generative AI produce content that saw the light of day outside of an organization (eg to write articles or to act as a support agent); it feels a bit safer as an internal tool that helps humans do their jobs.
  • Privacy and vendor trust: I’m inclined to try and use models on local machines and cloud services that follow a well-documented and controllable trust model, particularly in an organizational context. There’s a whole set of trade-offs here, of course, and self-hosted servers are not necessarily safer. But I think the future of AI in sensitive contexts (which is most contexts) needs to be on-device or on home servers. That doesn’t mean it will be, but I do think that’s a safer approach.
  • Legal fallout: I’m not a lawyer and I don’t know. Some but not all vendors have promised users legal indemnity. I assume that the cases will impact vendors more than downstream users — and maybe (hopefully?) change the way training material is obtained and structured to be more beneficial to authors — but I also don’t know that for sure. The answer feels like “wait and see”.

My biggest personal conclusion is, I don’t know! I’m trying not to be a blanket naysayer: I’ve been a natural early adopter my whole life, and I don’t plan to stop now. I recently wrote about how I’m using ChatGPT as a motivational writing partner. The older I get, the more problems I see with just about every technology, and I’d like to hold onto the excitement I felt about new tech when I was younger. On the other hand, the problems I see are really big problems, and ignoring those outright doesn’t feel useful either.

So it’s about taking a nimble but nuanced approach: pay attention to both the use cases and the issues around AI, keep looking at organizational needs, the kinds of organic “shadow IT” uses that are popping up as people need them, and figure out where a comfortable line is between ethics, privacy / legal needs, and utility.

At work, I’m going to need to determine an organizational stance on AI, jointly with various other stakeholders. That’s something that I’d like to share in public once we’re ready to roll it out. This post is very much not that — this space is always personal. But, as always, I wanted to share how I’m thinking about exploring.

I’d be curious to hear your thoughts.

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Startup pitch: Fediverse VIP

An illustrative sketch of a new service

Here’s my pitch for a fediverse product for organizations.

Think of it as WordPress VIP for the fediverse: a way for organizations to safely build a presence on the fediverse while preserving their brand, keeping their employees safe, and measuring their engagement.

We’ve established that the fediverse is large and growing: Threads has around 130M monthly users, Flipboard has 100M, Mastodon has a couple of million, and there’s a very long tail. And the network is growing, with more existing services and new entrants joining all the time. It is the future of the social web.

But the options for organizations to join are not fully aligned with organizations’ needs:

  • Flipboard is a good solution for publications to share articles directly, but not individuals to interact as first-class fediverse citizens.
  • Threads allows anyone to have an independent profile, but there’s no good organizational way to keep track of them all.
  • Mastodon allows you to establish communities, but you need to work with a hosting provider or install it yourself.
  • There’s no really great way to know that a profile really does belong to an organization. For example, on Threads, verification is at the ID level, and costs an individual $11.99 a month.
  • There’s no way to style profiles to match your brand, or to enforce brand guidelines.
  • There’s no analytics.
  • There are no brand or individual safety features like allowing safety teams to co-pilot an account if it’s suffering abuse.
  • There’s no shared inbox to manage support requests or other enquiries that come in via social media.

Fediverse VIP is a managed service that allows any brand to create individual fediverse profiles for its employees and shared ones for its publications, on its own domain, using its own brand styles, with abuse prevention and individual safety features, and with full analytics reporting.

For example, if the New York Times hypothetically signs up for Fediverse VIP, each of its reporters could have an account, letting everyone know that this is a real New York Times account. If you click through to a profile, it will look like the New York Times, with custom links that click through directly to NYT content. On the back end, multiple users can contribute, edit, and schedule posts for shared accounts.

Each Fediverse VIP instance has its own analytics, so you can learn more about the content you’ve published and how it performed — and build reports that instance administrators can share with their managers. And in the unfortunate event that an account suffers abuse, a member of their staff can copilot an account and field incoming messages, or a third-party service can be brought in to help ensure everybody is safe. There are full, shared blocklists on both an individual and domain level, of course. And highly-available support and training is included.

Finally, components, libraries, and APIs are made available so that social features — including “share to fediverse” — can be deeply integrated with a brand’s existing site.

Fediverse VIP is an annual subscription, tiered according to the number of followers an instance receives. Its first market would be media companies that are having trouble figuring out how to maintain a presence and maintain both trust and audience attention in the midst of rapid change in the social media landscape.

The venture would be structured as a Delaware Public Benefit Corporation, and would raise traditional venture funding in order to become the way organizations maintain an institutional presence on the open social web. As part of its mission, it would seek to devote resources to make the open social web as big and as successful as possible.

This isn’t a deck; it’s more of a first-draft sketch. But I think there might be something here?

Obvious disclaimers: this is a sketch / idea, not a solicitation. Also, the New York Times is just an example and had nothing to do with this idea.

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Some personal updates

I write a lot about the intersection of technology and society here, and lately a lot about AI, but over the last year I’ve written a little less about what I’ve been up to. So, this post is an update about some of that. This isn’t everything, by any means — 2023 was, frankly, a hard year for lots of reasons, which included not a small amount of personal loss and trauma — but I wanted to share some broad strokes.

We’re now based in the Greater Philadelphia area, rather than San Francisco. There have been all kinds of life changes: it’s the ‘burbs, which is weird, but I’m writing this on a train to New York City, which is now easily within reach. I grew up in Oxford and could easily go to London for a day trip; now I have the same relationship with NYC. We haven’t yet brought the baby to the city, but that’s coming. (He’s not a baby anymore: we have a delightful toddler whose favorite things, somehow, are reading books and brushing his teeth.)

I joined ProPublica as Senior Director of Technology after working with the team as an advisor on contract for a while. ProPublica publishes vital American journalism: you might remember the story about Supreme Court Justices with billionaire friends that broke last year, or the story about Peter Thiel’s $5 Billion tax-free IRA. You might also have come across Nonprofit Explorer and other “news apps”. Our technology philosophy is very compatible, and it’s a lovely team. I’m hoping we can revive The Nerd Blog.

I work mostly remotely and spend a lot of my time at my desk looking like this:

The author, alone, in a Google Meet room

(Guess the books! Yes, that’s also an issue of .net — specifically, one from decades ago that showcased Elgg.)

My website is still powered by Known, and I still intend to invest time and resources into that platform. I’ve also finally accepted — between having a toddler, a demanding job, an ongoing project (more on that in a second), and other commitments — that I’m not going to be making a ton of contributions to the codebase myself anytime soon. But there’s a pot of money in the Open Collective, and I’m eager to support open source developers in adding functionality to the platform. The first stop has been adding ActivityPub support to make Known compatible with the fediverse. The next stop will be improving the import / export functionality so that it (1) functions as expected (2) is in line with other platforms.

I’ve been struggling with writing a book. I’ve had the benefit of really great 1:1 coaching through The Novelry, and was making great progress until I realized I needed to revise a major element. It’s been a slog since then: I have printouts of my first draft covered in Sharpie all over my office. My fear of being terrible at this increases with every sideways glance at the unfinished manuscript (which seems, somehow, to be staring back at me). I’m certain that as soon as I send it out into the world I’ll be ridiculed. But I’m determined to get it to the finish line, revise it, send it out, and do it again.

As painful as writing the draft has been, I also love the act of it. Writing has always been my first love, far before computers. Don’t get me wrong: I don’t claim any sort of literary excellence, in the same way that I enjoy making dinner for everyone but would never call myself a chef. I’ve got huge respect for anyone who’s gone down this road and actually succeeded (hi, Sarah, you are radically inspiring to me). It’s a craft that deserves care, attention, and practice, and stretching these muscles is as desperately uncomfortable as it is liberating. I find the whole process of it meditative and freeing, and also simultaneously like pulling every fingernail from my body.

So, uh, we’ll see if the end result is any good.

I’ve been helping a few different organizations with their work (pro bono): two non-profits that are getting off the ground, a startup, and a venture fund. Each of them is doing something really good, and I’m excited to see them emerge into the world.

Also, my universe has been rocked by this recipe for scrambled eggs. So there’s that, too.

What’s up with you?

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Platforms are selling your work to AI vendors with impunity. They need to stop.

Some WordPress source code

404 Media reports that Automattic is planning to sell its data to Midjourney and OpenAI for training generative models:

The exact types of data from each platform going to each company are not spelled out in documentation we’ve reviewed, but internal communications reviewed by 404 Media make clear that deals between Automattic, the platforms’ parent company, and OpenAI and Midjourney are imminent.

Various arms of Automattic made subsequent clarifications. Specifically, it seems like premium versions of WordPress’s online platform, like the WordPress VIP service that powers sites for major newsrooms, will not sell user data to AI platforms.

This feels like a direct example of my point about how the relationship between platforms and users has been redefined. It appears that free versions of hosted Automattic platforms will sell user data by default, while premium versions will not.

Reddit announced a similar deal last week, and in total has made deals worth $203M for its content. WordPress powers over 40% of the web, which, given these numbers, could lead to a significant payday for the company. Much of that is on the self-hosted open source project rather than sites powered by Automattic, but that number gets fuzzier once you consider the Jetpack and Akismet plugins.

From a platform’s perspective it seems like AI companies might look like a godsend. They have an open license to tens or hundreds of millions of users’ content, often going back years — and suddenly, thanks to AI vendors’ need for legal, structured content to train on — the real market value of that content has shot up. It wouldn’t surprise me to see new social platforms emerge that have underlying data models designed specifically in order to sell to AI vendors. Finally, “selling data” is the business model it was always purported to be.

It’s probably no surprise that publishers are a little less keen, although there have been well-publicized deals with Axel Springer and the Associated Press. The deals OpenAI is offering to news companies for their content tend to top out at $5M each, for one thing. But social platforms don’t trade on the content themselves: they’re scalable businesses because they’re building conduits for other peoples’ posts. Their core value is the software and an enormous, engaged user-base. In contrast, publishers’ core value really is the articles, art, audio, images, and video they produce; the hard-reported journalism, the unscalable art, and the slow-burning communities that emerge around those things. Publishing doesn’t scale. The rights to that work should not be given away easily. The incentives between platforms and AI vendors are more or less aligned; the incentives between publishers and AI vendors are not.

I don’t think bloggers and social video producers should give those rights away easily either. They might not be publishing companies with large bodies of work, but the integrity of what they produce still matters.

For WordPress users, it’s kind of a bait and switch.

While writers may be using the free, hosted version of a publishing platform like WordPress, they retain the moral right of authorship:

As defined by the Berne Convention for the Protection of Literary and Artistic Works, an international agreement governing copyright law, moral rights are the rights “to claim authorship of the work and to object to any distortion, mutilation or other modification of, or other derogatory action in relation to, the said work, which would be prejudicial to his honor or reputation.”

The hosted version of WordPress contains this sentence about ownership in its TOS:

We don’t own your content, and you retain all ownership rights you have in the content you post to your website.

A reasonable person could therefore infer that their content would not be licensed for an AI vendor. And yet, that seems to be on the cards.

So now what?

If every platform is more and more likely to sell user data to AI platforms over time, the only way to object is to start to use self-hosted indieweb platforms.

But every public website can also be scraped directly by AI vendors, in some cases even if they use the Robots Exclusion Protocol that has been used for decades to prevent search engine bots from indexing unauthorized content. A large platform can sue for violation of content licenses, but individual publishers are unlikely to have the means — unless they gather together and form a collective organization that can fight on their behalf.

If every public website is more and more likely to be scraped by AI vendors over time, the only way to object is to thwart the scrapers. That can be done electronically, but that’s an arms race between open source platforms and well-funded AI vendors. Joining together and organizing collectively is perhaps more effective; organizing for regulations that can actually hold vendors to account would be more effective still.

It’s time for publishers, writers, artists, musicians, and everyone who publishes cultural work for a living (or for themselves) to start working together and pushing back. The rights of the indie website are every bit as important as the rights of organizations like the New York Times that do have the funds to sue. And really, truly, it’s time for legislators to take notice of the untrustworthy, exploitative actions of these vendors and their platform accomplices.

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A musician playing an electric organ

Hunter Walk writes:

The checks being cut to ‘owners’ of training data are creating a huge barrier to entry for challengers. If Google, OpenAI, and other large tech companies can establish a high enough cost, they implicitly prevent future competition. Not very Open.

It’s fair to say that I’ve been very critical of AI vendors and how training data has been gathered without much regard to the well-being of individual creators. But I also agree with Hunter in that establishing mandatory payments for training content creates a barrier to entry that benefits the incumbents. If you need to pay millions of dollars to create an AI model, you won’t disincentivize generative AI models overall, but you will create a situation where only people with millions of dollars can create an AI model. In this situation, the winners are likely Google and Microsoft (in the latter case, via OpenAI), with newcomers unable to break in.

To counteract this anticompetitive situation, Hunter previously suggested a safe harbor scheme:

AI Safe Harbor would also exempt all startups and researchers who have not released public base models yet and/or have fewer than, for example, 100,000 queries/prompts per day. Those folks are just plain ‘safe’ so long as they are acting in good faith.

I would add that they cannot be making revenue above a certain safe threshold, and that they cannot be operating a hosted service (or provide models that are used for a hosted service) with over 100,000 registered users. This way early-stage startups and researchers alike are protected while they experiment with their data.

After that cliff, I think AI model vendors could pay a fee to an ASCAP-like copyright organization that distributes revenue to organizations that have made their content available for training.

If you’re not familiar with ASCAP and BMI, here’s broadly how they work: when a musician joins as a member, the organization tracks when their music is used. That might be in live performances, on the radio, on television, and so on. Those users of the music — production companies, radio stations, etc — pay license fees to the organization, and the organization pays the musicians. The music users get the legal right to use the music, and the musicians get paid.

The model could apply rather directly to AI. Here, rather than one-off deals with the likes of the New York Times, vendors would pay the licensing organization, and all content creators would be compensated based on which material actually made it into a training corpus. The organization would provide tools to make it easy for AI vendors and content creators alike to provide content, report its use in AI models, and audit the composition of existing models.

I’d suggest that model owners could pay on a sliding scale that is dependent on both usage and total revenue. One component increases proportionally with the number of queries performed along a sliding scale at the model level; the other in pricing tiers associated with a vendor’s total gross revenue at the end-user level. So for example, if Microsoft used OpenAI to provide a feature in Bing, OpenAI would pay a fee based on the queries people actually made in Bing, and Microsoft would pay a fee based on its total corporate revenue. Research use would always be free for non-profits and accredited institutions, as long as it was for research or internal use only.

This model runs the risk of becoming a significant revenue stream for online community platforms, which tend to assert rights over the content that people publish to them. In this case, for example, rather than Facebook users receiving royalties for content published to Facebook that was used in an AI model, Facebook itself could take the funds. So there would need to be one more rule: even if a platform like Facebook asserts rights over the content that is published to it, it would need to demonstrate a best effort to return at least 60% of royalties to users whose work was used in AI training data.

Net result:

  • Incumbents don’t enjoy a barrier to entry from copyright payments: new entrants can build with impunity.
  • AI vendors and their users are indemnified from copyright claims against their models.
  • AI vendors don’t have to make individual deals with publishers and content creators.
  • Independent creators are financially incentivized to produce great creative and informational work — including individual creatives like artists and writers who might not otherwise have found a way to financially support their work.
  • The model shifts from one where AI vendors scrape content with no regard to the rights of the creator to one where creators give explicit consent to be included.

The AI horse has left the stable. I don’t think shutting it all down is an option, however vocal critics like myself and others might be. What we’re left with, then, is questions about how to create a healthy ecosystem, how to properly compensate creators, and how to ensure that the rights of an author are respected. This, I think, is one way forward.

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Stop what you're doing and watch Breaking the News

Stills from the documentary, Breaking the News

Breaking the News, the documentary about The 19th, aired on PBS last night and is available to watch for free on YouTube for the next 90 days.

It’s both a film about the news industry and about startups: a team’s journey to show that journalism can and should be published with a more representative lens. It’s also not a puff piece: real, genuine struggles are covered here, which speak to larger conversations about race and gender that everyone needs to be having.

I worked with The 19th for a period that mostly sits directly after this film. My chin — yes, just my chin — shows up for a fraction of a second, but otherwise I’m not in it. My association with it is not why I’m recommending that you watch it.

The 19th is not a perfect workplace, in part because no such workplace exists. It has struggles like any other organization. But there was a thoughtfulness about culture and how work gets done that I’ve rarely seen elsewhere. Some of those policies were developed in direct response to workplace cultures that are prevalent in newsrooms, including narrow leadership demographics, hierarchical communication, a focus on work product rather than work process, and lack of goal-setting.

My experience was privileged, in part because of my position in the senior leadership team, but for me it was a breath of fresh air. There aren’t many places where I’ve felt calmer at work. Some of that is because of the early conversations and hard work that were captured on film here.

From the synopsis:

Who decides which stories get told? A scrappy group of women and LGBTQ+ journalists buck the white male-dominated status quo, banding together to launch The 19th*, a digital news startup aiming to combat misinformation. A story of an America in flux, and the voices often left out of the narrative, the documentary Breaking the News shows change doesn’t come easy.

You can watch the whole documentary for free here. And if you haven’t yet, go subscribe to The 19th over on its website.

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Social, I love you, but you’re bringing me down

A big thumbs-down made of people

This weekend I realized that I’m kind of burned out: agitated, stressed about nothing in particular, and peculiarly sleepless. It took a little introspection to figure out what was really going on.

Here’s what I finally decided: I really need to pull back from using social media in particular as much as I do.

A few things brought me here:

  1. The sheer volume of social media sites is intense
  2. Our relationship with social media has been redefined
  3. I want to re-focus on my actual goals

I’d like to talk about them in turn. Some of you might be feeling something similar.

The sheer volume of social media sites is intense

It used to be that I posted and read on Twitter. That’s where my community was; that’s where I kept up to date with what was happening.

Well, we all know what happened there.

In its place, I find myself spending more time on:

  1. Mastodon
  2. Threads
  3. Bluesky
  4. LinkedIn (really!)
  5. Facebook (I know)
  6. Instagram

The backchannel that Twitter offered has become rather more diffuse. Mastodon, Threads, and Bluesky offer pretty much the same thing as each other, with a different set of people. LinkedIn is more professional; I’m unlikely to post anything political there, and I’m a bit more mindful of polluting the feed. My Facebook community is mostly people I miss hanging out with, so I’ll usually post sillier or less professionally relevant stuff there. And Instagram, until recently, was mostly photos of our toddler.

I haven’t been spending a ton of time interacting on any of them; it’s common for almost a full day to go between posts. Regardless, there’s something about moving from app to app to app that feels exhausting. I realized I was experiencing a kind of FOMO — am I missing something important?! — that became an addiction.

Each dopamine hit, each context switch, each draw on my attention pushes me further to the right on the stress curve. Everyone’s different, but this kind of intense data-flood — of the information equivalent of empty calories, no less — makes me feel awful.

Ugh. First step: remove every app from my phone. Second step: drastically restrict how I can access them on the web.

Our relationship with social media has been redefined

At this point we’re all familiar with the adage that if you’re not the customer, you’re the product being sold.

It never quite captured the true dynamic, but it was a pithy way to emphasize that we were being profiled in order to optimize ad sales in our direction. Of course, there was never anything to say that we weren’t being profiled or that our data wasn’t being traded even if we were the ostensible customer, but it seemed obvious that data mining for ad sales was more likely to happen on an ad-supported site.

With the advent of generative AI, or more precisely the generative AI bubble, this dynamic can be drawn more starkly. Everything we post can be ingested by a social media platform as training data for its AI engines. Prediction engines are trained on our words, our actions, our images, our audio, and then re-sold. We really are the product now.

I can accept that for posts where I share links to other resources, or a rapid-fire, off-the-cuff remark. Where I absolutely draw the line is allowing an engine to be trained on my child. Just as I’m not inclined to allow him to be fingerprinted or added to a DNA database, I’m not interested in having him be tracked or modeled. I know that this is likely an inevitability, but if it happens, it will happen despite me. I will not be the person who willingly uploads him as training data.

So, when I’m uploading images, you might see a picture of a snowy day, or a funny sign somewhere. You won’t see anything important, or anything representative of what life actually looks like. It’s time to establish an arms-length distance.

There’s something else here, too: while the platforms are certainly profiling and learning from us, they’re still giving us more of what we pause and spend our attention on. In an election year, with two major, ongoing wars, I’m finding that to be particularly stressful.

It’s not that I don’t want to know what’s going on. I read the news; I follow in-depth journalism; I read blogs and opinion pieces on these subjects. Those things aren’t harmful. What is harmful is the endless push for us to align into propaganda broadcasters ourselves, and to accept broad strokes over nuanced discussion and real reflection. This was a problem with Twitter, and it’s a problem with all of today’s platforms.

The short form of microblogging encourages us to be reductive about impossibly important topics that real people are losing their lives over right now. It’s like sports fans yelling about who their preferred team is. In contrast, long-form content — blogging, newsletters, platforms like Medium — leaves space to explore and truly debate. Whereas short-form is too low-resolution to capture the fidelity of the truth, long-form at least has the potential to be more representative of reality.

It’s great for jokes. Less so for war.

I want to re-focus on my actual goals

What do I actually want to achieve?

Well, I’ve got a family that I would like to support and show up for well.

I’ve got a demanding job doing something really important, that I want to make sure I show up well for.

I’ve also got a first draft of a majority of a novel printed out and sitting on my coffee table with pen edits all over it. I’d really like to finish it. It’s taken far longer than I intended or hoped for.

And I want to spend time organizing my thoughts for both my job and my creative work, which also means writing in this space and getting feedback from all of you.

Social media has the weird effect of making you feel like you’ve achieved something — made a post, perhaps received some feedback — without actually having done anything at all. It sits somewhere between marketing and procrastination: a way to lose time into a black hole without anything to really show for it.

So I want to move my center of gravity all the way back to writing for myself. I’ll write here; I’ll continue to write my longer work on paper; I’ll share it when it’s appropriate.

Posting in a space I control isn’t just about the principle anymore. It’s a kind of self-preservation. I want to preserve my attention and my autonomy. I accept that I’m addicted, and I would like to curb that addiction. We all only have so much time to spend; we only have one face to maintain ownership of. Independence is the most productive, least invasive way forward.



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A creative process

The silhouette of someone walking above the cloudline.

Over on Threads, Amanda Zamora asks:

I'm plotting away on Agencia Media and some personal writing/reporting this weekend (over a glass of 🍷 and many open tabs). One of the things I love most about building something new is the chance to design for intended outcomes — how to structure time and energy? What helps quiet chaos? Bring focus and creativity? Inspired by Ben Werdmuller’s recent callout about new Mac setups, I want to know about the ways you've built (or rebuilt) your way of working! Apps, workflows, rituals, name 'em 👇

A thing I’ve had to re-learn about building and creating is the importance of boredom in the way I think. I know that some people thrive when moving from thing to thing to thing at high speed, but I need time to reflect and toss ideas around in my head without an imposing deadline: the freedom to be creative without consequence.

The best way I’ve found to do that is to walk.

The work I’m proudest of was done in a context where I could walk for hours on end. When I was building Elgg, I would set off around Oxford, sometimes literally walking from one end of the city to the other and back again. When I was building Known and working for Matter, I roamed the east bay, sometimes walking from Berkeley to the tip of Oakland, or up through Tilden Park. I generally didn’t listen to music or audiobooks; I was alone with my thoughts and the sounds of the city. It helped me to figure out my priorities and consider what I was going to do next. When I came up with something new, it was more often than not in the midst of one of those walks.

When you’re deep into building something that’s your own, and that’s the entirety of what you’re doing (i.e., you don’t have another day job), you have the ability to structure your time however you’d like. Aside from the possible guilt of not working a traditional office day, there’s no reason to do that. Particularly at the beginning stages, I found that using the morning as unstructured reflective time led to better, more creative decision-making.

Again, this is me: everyone is different, and your mileage may vary. I do best when I have a lot of unstructured time; for some people, more structure is necessary. I think the key is to figure out what makes you happy and less stressed, and to get out from behind a screen. But also, walking really does boost creativity, so there’s that.

I recognize there’s a certain privilege inherent here: not everyone lives somewhere walkable, and not everyone feels safe when they’re walking out in the world. The (somewhat) good news is that indoor walking works just as well, if you can afford a low-end treadmill.

So what happens when you get back from a walk with a head full of ideas?

It’s probably no surprise that my other creativity hack is to journal: I want to get those unstructured thoughts, particularly the “what ifs” and “I wishes”, out on the page, together with the most important question, which is “why”. Writing long-form in this way puts me into a more contemplative state, much the same way that writing a blog post like this one helps me refine how I think about a topic. Putting a narrative arc to the thought gives it context and helps me refine what’s actually useful.

The through line here is an embrace of structurelessness; in part that’s just part of my personality, but in part it’s an avoidance of adhering to someone else’s template. If I’m writing items on a to-do list straight away, I’m subject to the design decisions of the to-do list software’s author. If I’m filling in a business model canvas, I’m thinking about the world in the way the canvas authors want me to. I can, and should, do all those things, but I always want to start with a blank page first. A template is someone else’s; a blank page is mine.

Nobody gets to see those thoughts until I’ve gone over them again and turned them into a written prototype. In the same way that authors should never show someone else their first draft, letting someone into an idea too early can deflate it with early criticism. That isn’t to say that understanding your hypotheses and doing research to validate them isn’t important — but I’ve found that I need to keep up the emotional momentum behind an idea if I’m going to see it through, and to do that, I need to keep the illusion that it’s a really good idea just long enough to give it shape.

Of course, when it has shape, I try to get all the expert feedback I can. Everyone needs an editor, and asking the right questions early and learning fast is an obvious accelerant.

So I guess my creative process boils down to:

  • Embrace boredom and unstructured, open space to think creatively
  • Capture those creative thoughts in an untemplated way, through narrative writing
  • Identify my hypotheses and figure out what needs to be researched to back up the idea
  • Ask experts and do that research as needed in order to create a second, more validated draft
  • Get holistic feedback from trusted collaborators on that second draft
  • Iterate 1-2 times
  • Build the smallest, fastest thing I can based on the idea

There are no particular apps involved and no special frameworks. Really, it’s just about giving myself some space to be creative. And maybe that’s the only advice I can give to anyone building something new: give yourself space.

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Three variations on Omelas

The Ones Who Walk Away From Omelas, by Ursula K. LeGuin:

They all know it is there, all the people of Omelas. Some of them have come to see it, others are content merely to know it is there. They all know that it has to be there. Some of them understand why, and some do not, but they all understand that their happiness, the beauty of their city, the tenderness of their friendships, the health of their children, the wisdom of their scholars, the skill of their makers, even the abundance of their harvest and the kindly weathers of their skies, depend wholly on this child’s abominable misery.

The Ones Who Stay and Fight, by N.K. Jemisin:

But this is no awkward dystopia, where all are forced to conform. Adults who refuse to give up their childhood joys wear wings, too, though theirs tend to be more abstractly constructed. (Some are invisible.) And those who follow faiths which forbid the emulation of beasts, or those who simply do not want wings, need not wear them. They are all honored for this choice, as much as the soarers and flutterers themselves—for without contrasts, how does one appreciate the different forms that joy can take?

Why Don’t We Just Kill the Kid in the Omelas Hole, by Isabel J. Kim:

So they broke into the hole in the ground, and they killed the kid, and all the lights went out in Omelas: click, click, click. And the pipes burst and there was a sewage leak and the newscasters said there was a typhoon on the way, so they (a different “they,” these were the “they” in charge, the “they” who lived in the nice houses in Omelas [okay, every house in Omelas was a nice house, but these were Nice Houses]) got another kid and put it in the hole.

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The four phases

A fictional mainframe

This post is part of February’s IndieWeb Carnival, in which Manuel Moreale prompts us to think about the various facets of digital relationships.

Our relationship to digital technology has been through a few different phases.

One: the census

In the first, computers were the realm of government and big business: vast databases that might be about us, but that we could never own or interrogate ourselves. Companies like IBM manufactured room-sized (and then cabinet-sized) machines that took a team of specialized technicians to operate. They were rare and a symbol of top-down power.

Punch cards were invented in the 1880s, and were machine-sortable even then, although not by anything we would recognize as a computer today. In the 1930s, a company called Dehomag, which was a 90%-owned subsidiary of IBM, used its punch card census technology to help the German Nazi party ethnically identify and sort the population. (Thomas Watson, IBM’s CEO at the time, even came to Germany to oversee the operation.)

The first general-purpose digital computer, ENIAC, was first put to use to determine the feasibility of the H bomb. Other mainframe computers were used by the US Navy for codebreaking, and by the US census bureau. By the sixties and seventies, though, they were commonplace in larger corporate offices and in universities for non-military, non-governmental applications.

Two: the desk

Personal computers decentralized computing power and put it in everybody’s hands. There was no overarching, always-on communications network for them to connect to, so every computer had its own copy of software that ran locally on it. There was no phoning home; no surveillance of our data; there were no ad-supported models. If you were lucky enough to have the not-insignificant sum of money needed to buy a computer, you could have one in your home. If you were lucky enough to have money left over for software, you could even do things with it.

The government and large institutions didn’t have a monopoly on computing power; theoretically, anyone could have it. Anyone could write a program, too, and (if you had yet more money to buy a modem) distribute it on bulletin board systems and online services. Your hardware was yours; your software was yours; once you’d paid your money, your relationship with the vendor was over.

For a while, you had a few options to connect with other people:

  • Prodigy, an online service operated as a joint venture between CBS, IBM, and Sears
  • CompuServe, which was owned and run by H&R Block
  • America Online, which was originally a way for Atari 2600 owners to download new games and store high scores
  • Independent bulletin boards, which were usually a single computer connected to a handful of direct phone lines for modems to connect to, run by an enthusiast

(My first after-school job was as a BBS system operator for Daily Information, a local information and classifieds sheet in my hometown.)

In 1992, in addition to bulletin board systems and online services, the internet was made commercially available. Whereas BBSes, AOL, etc were distinct walled gardens, any service that was connected to the internet could reach any other service. It changed everything. (In 1995, my BBS job expanded to running what became one of the first classifieds websites.)

But for a while, the decentralized, private nature of personal computing remained. For most private individuals, connecting to the internet was like visiting a PO box: you’d dial in, would upload and download any email you had pending, browse any websites you needed to, and then log off again. There was no way to constantly monitor people because internet users spent 23 hours of the day disconnected from the network.

Three: the cloud

Broadband, the iPhone, and wifi changed everything. Before the advent of broadband, most people needed to dial in to go online using their phone line. Before the iPhone, cell connections weren’t metered for data, and there was very little bandwidth to go around. Before wifi, a computer needed to physically be connected with a cable to go online.

With broadband and wifi, computers could be connected to the internet 24/7. With the iPhone, everyone had a computer in their pocket, that was permanently connected and could be constantly sending data back to online services — including your location and who was in your address book.

It was incredibly convenient and changed the world in hundreds of ways. The web in particular is a modern marvel; the iPhone is a feat of design and engineering. But what we lost was the decentralized self-ownership of our digital worlds. More than that, we lost an ability to be private that we’d had since the beginning of human civilization. It used to be that nobody needed to know where you were or what you were thinking about; that fundamental truth has gone the way of the dinosaur.

Almost immediately, our relationship to software changed in a few key ways:

  • We could access all of our data from anywhere, on any device.
  • Instead of buying a software package once, we were asked to subscribe to it.
  • Instead of downloading or installing software, the main bulk of it could be run in a server farm somewhere.
  • Every facet of our data was stored in one of these server farms.
  • More data was produced about us as we used our devices — or even as we walked through our cities, shopped at stores, and met with other people — than we created intentionally ourselves.

While computing became infinitely easier to use and the internet became a force that changed global society in ways that I still believe are a net positive, surveilling us also became infinitely easier. Companies wanted to know exactly what we were likely to buy; politicians wanted to know how we might vote; law enforcement wanted to know if we were dangerous. All paid online services to build profiles about us that could be used to sell advertising, could be mined by the right buyer, and could even be used to influence elections.

Four: the farm

Our relationship is now changing again.

Whereas in the cloud era we were surveilled in order to profile us, our data is now being gathered for another set of reasons. We’re used to online services ingesting our words and actions in order to predict our behaviors and influence us in certain directions. We’re used to Target, for example, wanting to know if we’re pregnant so they can be the first to sell us baby gear. We’re not used to those services ingesting our words and actions in order to learn how to be us.

In our new relationship, software isn’t just set up to surveil us to report on us; it’s also set up to be able to do our work. GitHub Copilot learns from software we write so that it can write software automatically. Midjourney builds stunning illustrations and near-photorealistic images. Facebook is learning from the text and photos we upload so it can create its own text and realistic imagery (unlike many models, from data it actually has the license to). Far more than us being profiled, our modes of human expression are now being farmed for the benefit of people who hope to no longer have to hire us for our unique skills.

In the first era, technology was here to catalogue us.

In the second, it was here to empower us.

In the third, it was here to observe us.

In the fourth, it is here to replace us.

We had a very brief window, somewhere between the inception of the homebrew computer club and the introduction of the iPhone, where digital technology heralded distributed empowerment. Even then, empowerment was hardly evenly distributed, and any return to decentralization must be far more equitable than it ever was. But we find ourselves in a world where our true relationship is with power.

Of course, it’s a matter of degrees, and everything is a spectrum: there are plenty of services that don’tuse your data to train generative AI models, and there are plenty that don’t surveil you at all. There are also lots of applications and organizations that are actively designed to protect us from being watched and subjugated. New regulations are being proposed all the time that would guarantee our right to privacy and our right to not be included in training data.

Those might seem like technical decisions, but they’re really about preserving our ownership and autonomy, and returning those things to us when they’ve already been lost. They’re human, democratic decisions that seek to enforce a relationship where we’re in charge. They’re becoming more and more important every day.

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