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A tech entrepreneur and writer trying to make the technology world more thoughtful, creative and humane. 
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How to know if that job will crush your soul

2026-01-12 08:00:00

Last week, we talked about one huge question, “How the hell are you supposed to have a career in tech in 2026?” That’s pretty specific to this current moment, but there are some timeless, more perennial questions I've been sharing with friends for years that I wanted to give to all of you. They're a short list of questions that help you judge whether a job that you’re considering is going to crush your soul or not.

Obviously, not everyone is going to get to work in an environment that has perfect answers to all of these questions; a lot of the time, we’re lucky just to get a place to work at all. But these questions are framed in this way to encourage us all to aspire towards roles that enable us to do our best work, to have the biggest impact, and to live according to our values.

The Seven Questions

  • If what you do succeeds, will the world be better?

This question originally started for me when I would talk to people about new startups, where people were judging the basic idea of the product or the company itself, but it actually applies to any institution, at any size. If the organization that you’re considering working for, or the team you’re considering joining, is able to achieve their stated goals, is it ultimately going to have a positive effect? Will you be proud of what it means? Will the people you love and care about respect you for making that choice, and will those with the least to gain feel like you’re the kind of person who cares about their impact on the world?

  • Whose money do they have to take to stay in business?

Where does the money in the organization really come from? You need to know this for a lot of reasons. First of all, you need to be sure that they know the answer. (You’d be surprised how often that’s not the case!) Even if they do know the answer, it may make you realize that those customers are not the people whose needs or wants you’d like to spend most of your waking hours catering to. This goes beyond the simple basics of the business model — it can be about whether they're profitable or not, and what the corporate ownership structure is like.

It’s also increasingly common for companies to mistake those who are investing in a company with those who are their customers. But there’s a world of difference between those who are paying you, and those who you have to pay back tenfold. Or thousandfold.

The same goes for nonprofits — do you know who has to stay happy and smiling in order for the institution to stay stable and successful? If you know those answers, you'll be far more confident about the motivations and incentives that will drive key decisions within the organization.

  • What do you have to believe to think that they’re going to succeed? In what way does the world have to change or not change?

Now we’re getting a little bit deeper into thinking about the systems that surround the organization that you’re evaluating. Every company, every institution, even every small team, is built around a set of invisible assumptions. Many times, they’re completely reasonable assumptions that are unlikely to change in the future. But sometimes, the world you’re working in is about to shift in a big way, or things are built on a foundation that’s speculative or even unrealistic.

Maybe they're assuming there aren't going to be any big new competitors. Perhaps they think they'll always remain the most popular product in their category. Or their assumptions could be about the stability of the rule of law, or a lack of corruption — more fundamental assumptions that they've never seen challenged in their lifetime or in their culture, but that turn out to be far more fragile than they'd imagined.

Thinking through the context that everyone is sharing, and reflecting on whether they’re really planning for any potential disruptions, is an essential part of judging the psychological health of an organization. It’s the equivalent of a person having self-awareness, and it’s just as much of a red flag if it’s missing.

  • What’s the lived experience of the workers there whom you trust? Do you have evidence of leaders in the organization making hard choices to do the right thing?

Here is how we can tell the culture and character of an organization. If you’ve got connections into the company, or a backchannel to workers there, finding out as much information as you can about the real story of its working conditions is often one of the best ways of understanding whether it’s a fit for your needs. Now, people can always have a bad day, but overall, workers are usually very good at providing helpful perspectives about their context.

And more broadly, if people can provide examples of those in power within an organization using that power to take care of their workers or customers, or to fight for the company to be more responsible, then you’ve got an extremely positive sign about the health of the place even before you’ve joined. It’s vital that these be stories you are able to find and discover on your own, not the ones amplified by the institution itself for PR purposes.

  • What were you wrong about?

And here we have perhaps one of the easiest and most obvious ways to judge the culture of an organization. This is even a question you can ask people while you’re in an interview process, and you can judge their responses to help form your opinion. A company, and leadership culture, that can change its mind when faced with new information and new circumstances is much more likely to adapt to challenges in a healthy way. (If you want to be nice, phrase it as "What is a way in which the company has evolved or changed?")

  • Does your actual compensation take care of what you need for all of your current goals and needs — from day one?

This is where we go from the abstract and psychological goals to the practical and everyday concerns: can you pay your bills? The phrasing and framing here is very intentional: are they really going to pay you enough? I ask this question very specifically because you’d be surprised how often companies actually dance around this question, or how often we trick ourselves into hearing what we want to hear as the answer to this question when we’re in the exciting (or stressful) process of considering a new job, instead of looking at the facts of what’s actually written in black-and-white on an offer letter.

It's also important not to get distracted with potential, even if you're optimistic about the future. Don’t listen to promises about what might happen, or descriptions of what’s possible if you advance in your role. Think about what your real life will be like, after taxes, if you take the job that they’ve described.

  • Is the role you’re being hired into one where you can credibly advance, and where there’s sufficient resources for success?

This is where you can apply your optimism in a practical way: can the organization accurately describe how your career will proceed within the company? Does it have a specific and defined trajectory, or does it involve ambiguous processes or changes in teams or departments? Would you have to lobby for the support of leaders from other parts of the organization? Would making progress require acquiring new skills or knowledge? Have they committed to providing you with the investment and resources required to learn those skills?

These questions are essential to understand, because lacking these answers can lead to an ugly later realization that even an initially-exciting position may turn out to be a dead-end job over time.

Towards better working worlds

Sometimes it can really feel like the deck is stacked against you when you're trying to find a new job. It can feel even worse to be faced with an opportunity and have a nagging sense that something is not quite right. Much of the time, that feeling comes from the vague worry that we're taking a job that is going to make us miserable.

Even in a tough job market, there are some places that are trying to do their best to treat people decently. In larger organizations, there are often pockets of relative sanity, led by good leaders, who are trying to do the right thing. It can be a massive improvement in quality of life if you can find these places and use them as foundations for the next stage of your career.

The best way to navigate towards these better opportunities is to be systematic when evaluating all of your options, and to hold out for as high standards as possible when you're out there looking. These seven questions give you the tools to do exactly that.

How Markdown took over the world

2026-01-09 08:00:00

Nearly every bit of the high-tech world, from the most cutting-edge AI systems at the biggest companies, to the casual scraps of code cobbled together by college students, is annotated and described by the same, simple plain text format. Whether you’re trying to give complex instructions to ChatGPT, or you want to be able to exchange a grocery list in Apple Notes or copy someone’s homework in Google Docs, that same format will do the trick. The wild part is, the format wasn’t created by a conglomerate of tech tycoons, it was created by a curmudgeonly guy with a kind heart who right this minute is probably rewatching a Kubrick film while cheering for an absolutely indefensible sports team.

But it’s worth understanding how these simple little text files were born, not just because I get to brag about how generous and clever my friends are, but also because it reminds us of how the Internet really works: smart people think of good things that are crazy enough that they just might work, and then they give them away, over and over, until they slowly take over the world and make things better for everyone.

Making Their Mark

Though it’s now a building block of the contemporary Internet, like so many great things, Markdown just started out trying to solve a personal problem. In 2002, John Gruber made the unconventional decision to bet his online career on two completely irrational foundations: Apple, and blogs.

It’s hard to remember now, but in 2002, Apple was just a few years past having been on death’s door. As difficult as it may be to picture in today’s world where Apple keynotes are treated like major events, back then, almost nobody was covering Apple regularly, let alone writing exclusively about the company. There was barely even an “tech news” scene online at all, and virtually no one was blogging. So John’s decision to go all-in on Apple for his pioneering blog Daring Fireball was, well, a daring one. At the time, Apple had only just launched its first iPod that worked with Windows computers, and the iPhone was still a full five years in the future. But that single-minded focus, not just on Apple, but on obsessive detail in everything he covered, eventually helped inspire much of the technology media landscape that we see today. John’s timing was also perfect — from the doldrums of that era, Apple’s stock price would rise by about 120,000% in the years after Daring Fireball started, and its cultural relevance probably increased by even more than that.

By 2004, it wasn’t just Apple that had begun to take off: blogs and social media themselves had moved from obscurity to the very center of culture, and a new era of web technology had begun. At the beginning of that year, few people in the world even knew what a “blog” was, but by the end of 2004, blogs had become not just ubiquitous, but downright cool. As unlikely as it seems now, that year’s largely uninspiring slate of U.S. presidential candidates like Wesley Clark, Gary Hart and, yes, Howard Dean helped propel blogs into mainstream awareness during the Democratic primaries, alongside online pundits who had begun weighing in on politics and the issues and cultural moments at a pace that newspapers and TV couldn’t keep up with. A lot has been written about the transformation of media during those years, but less has been written about how the media and tech of the time transformed each other.

A photo from 2004 of a TV screen showing CNN, with a ticker saying "Gary Hart Cyber Campaign Starts blog for possible 2004 presidential bid"

That era of early blogging was interesting in that nearly everyone who was writing the first popular sites was also busy helping create the tools for publishing them. Just like Lucille Ball and Desi Arnaz had to pioneer combining studio-style flat lighting with 35mm filming in order to define the look of the modern sitcom, or Jimi Hendrix had to work with Roger Mayer to invent the signature guitar distortion pedals that defined the sound of rock and roll, the pioneers who defined the technical format and structures of blogging were often building the very tools of creation as they went along.

I got a front row seat to these acts of creation. At the time I was working on Movable Type, which was the most popular tool for publishing “serious” blogs, and helped popularize the medium. Two of my good friends had built the tool and quickly made it into the default choice for anybody who wanted to reach a big audience; it was kind of a combination of everything people do these days on WordPress and all the various email newsletter platforms and all of the “serious” podcasts (since podcasts wouldn’t be invented for another few months). But back in those early days, we’d watch people use our tools to set up Gawker or Huffington Post one day, and Daring Fireball or Waxy.org the next, and each of them would be the first of its kind, both in terms of its design and its voice. To this day, when I see something online that I love by Julianne Escobedo Shepherd or Ta-Nehisi Coates or Nilay Patel or Annalee Newitz or any one of dozens of other brilliant writers or creators, my first thought is often, “hey! They used to type in that app that I used to make!” Because sometimes those writers would inspire us to make a new feature in the publishing tools, and sometimes they would have hacked up a new feature all by themselves in between typing up their new blog posts.

A really clear, and very simple, early example of how we learned that lesson was when we changed the size of the box that people used to type in just to create the posts on their sites. We made the box a little bit taller, mostly for aesthetic reasons. Within a few weeks, we’d found that posts on sites like Gawker had gotten longer, mostly because the box was bigger. This seems obvious now, years after we saw tweets get longer when Twitter expanded from 140 characters to 280 characters, but at the time this was a terrifying glimpse at how much power a couple of young product managers in a conference room in California would have over the media consumption of the entire world every time they made a seemingly-insignificant decision.

The other dirty little secret was, typing in the box in that old blogging app could be… pretty wonky sometimes. People who wanted to do normal things like include an image or link in their blog post, or even just make some text bold, often had to learn somewhat-obscure HTML formatting, memorizing the actual language that’s used to make web pages. Not everybody knew all the details of how to make pages that way, and if they made even one small mistake, sometimes they could break the whole design of their site. It made things feel very fraught every time a writer went to publish something new online, and got in the way of the increasingly-fast pace of sharing ideas now that social media was taking over the public conversation.

Enter John and his magical text files.

Marking up and marking down

The purpose of Markdown is really simple: It lets you use the regular characters on your keyboard which you already use while typing out things like emails, to make fancy formatting of text for the web. That HTML format that’s used to make web pages stands for HyperText Markup Language. The word “markup” there means you’re “marking up” your text with all kinds of special characters. Only, the special characters can be kind of arcane. Want to put in a link to everybody’s favorite website? Well, you’re going to have to type in <a href="https://anildash.com/">Anil Dash’s blog</a> I could explain why, and what it all means, but honestly, you get the point — it’s a lot! Too much. What if you could just write out the text and then the link, sort of like you might within an email? Like: [Anil Dash’s blog](https://anildash.com)! And then the right thing would happen. Seems great, right?

The same thing works for things like putting a header on a page. For example, as I’m writing this right now, if I want to put a big headline on this page, I can just type #How Markdown Took Over the World and the right thing will happen.

If mark_up_ is complicated, then the opposite of that complexity must be… markd_own_. This kind of solution, where it’s so smart it seems obvious in hindsight, is key to Markdown’s success. John worked to make a format that was so simple that anybody could pick it up in a few minutes, and powerful enough that it could help people express pretty much anything that they wanted to include while writing on the internet. At a technical level, it was also easy enough to implement that John could write the code himself to make it work with Movable Type, his publishing tool of choice. (Within days, people had implemented the same feature for most of the other blogging tools of the era; these days, virtually every app that you can type text into ships with Markdown support as a feature on day one.)

Prior to launch, John had enlisted our mutual friend, the late, dearly missed Aaron Swartz, as a beta tester. In addition to being extremely fluent in every detail of the blogging technologies of the time, Aaron was, most notably, seventeen years old. And though Aaron’s activism and untimely passing have resulted in him having been turned into something of a mythological figure, one of the greatest things about Aaron was that he could be a total pain in the ass, which made him terrific at reporting bugs in your software. (One of the last email conversations I ever had with Aaron was him pointing out some obscure bugs in an open source app I was working on at the time.) No surprise, Aaron instantly understood both the potential and the power of Markdown, and was a top-tier beta tester for the technology as it was created. His astute feedback helped finely hone the final product so it was ready for the world, and when Markdown quietly debuted in March of 2004, it was clear that text files around the web were about to get a permanent upgrade.

The most surprising part of what happened next wasn’t that everybody immediately started using it to write their blogs; that was, after all, what the tool was designed to do. It’s that everybody started using Markdown to do everything else, too.

Hitting the Mark

It’s almost impossible to overstate the ubiquity of Markdown within the modern computer industry in the decades since its launch.

After being nagged about it by users for more than a decade, Google finally added support for Markdown to Google Docs, though it took them years of fiddly improvements to make it truly usable. Just last year, Microsoft added support for Markdown to its venerable Notepad app, perhaps in attempt to assuage the tempers of users who were still in disbelief that Notepad had been bloated with AI features. Nearly every powerful group messaging app, from Slack to WhatsApp to Discord, has support for Markdown in messages. And even the company that indirectly inspired all of this in the first place finally got on board: the most recent version of Apple Notes finally added support for Markdown. (It’s an especially striking launch by Apple due to its timing, shortly after John had used his platform as the most influential Apple writer in the world to blog about the utter failure of the “Apple Intelligence” AI launch.)

But it’s not just the apps that you use on your phone or your laptop. For developers, Markdown has long been the lingua franca of the tools we string together to accomplish our work. On GitHub, the platform that nearly every developer in the world uses to share their code, nearly every single repository of code on the site has at least one Markdown file that’s used to describe its contents. Many have dozens of files describing all the different aspects of their project. And some of the repositories on GitHub consist of nothing but massive collections of Markdown files. The small tools and automations we run to perform routine tasks, the one-off reports that we generate to make sure something worked correctly, the confirmations that we have a system email out when something goes wrong, the temporary files we use when trying to recover some old data — all of these default to being Markdown files.

As a result, there are now billions of Markdown files lying around on hard drives around the world. Billions more are stashed in the cloud. There are some on the phone in your pocket. Programmers leave them lying around wherever their code might someday be running. Your kid’s Nintendo Switch has Markdown files on it. If you’re listening to music, there’s probably a Markdown file on the memory chip of the tiny system that controls the headphones stuck in your ears. The Markdown is inside you right now!

Down For Whatever

So far, these were all things we could have foreseen when John first unleashed his little text tool on the world. I would have been surprised about how many people were using it, but not really the ways in which they were using it. If you’d have said “Twenty years in the future, all the different note-taking apps people use save their files using Markdown!”, I would have said, “Okay, that makes sense!”

What I wouldn’t have asked, though, was “Is John getting paid?” As hard as it may be to believe, back in 2004, the default was that people made new standards for open technologies like Markdown, and just shared them freely for the good of the internet, and the world, and then went on about their lives. If it happened to have unleashed billions of dollars of value for others, then so much the better. If they got some credit along the way, that was great, too. But mostly you just did it to solve a problem for yourself and for other like-minded people. And also, maybe, to help make sure that some jerk didn’t otherwise create some horrible proprietary alternative that would lock everybody into their terrible inferior version forever instead. (We didn’t have the word “enshittification” yet, but we did have Cory Doctorow and we did have plain text files, so we kind of knew where things were headed.)

To give a sense of the vibe of that era, the term “podcasting” had been coined just a month before Markdown was released, and went into wider use that fall, and was similarly a radically open system that wasn’t owned by any big company and that empowered people to do whatever they wanted to do to express themselves. (And podcasting was another technology that Aaron Swartz helped improve by being a brilliant pain in the ass. But I’ll save that story for another book-length essay.)

That attitude of being not-quite-_anti_commercial, but perhaps just not even really concerned with whether something was commercial or not seems downright quaint in an era when the tech tycoons are not just the wealthiest people in the world, but also some of the weirdest and most obnoxious as well. But the truth is, most people today who make technology are actually still exceedingly normal, and quite generous. It’s just that they’ve been overshadowed by their bosses who are out of their minds and building rocket ships and siring hundreds of children and embracing overt white supremacy instead of making fun tools for helping you type text, like regular people do.

The Markdown Model

The part about not doing this stuff solely for money matters, because even the most advanced LLM systems today, what the big AI companies call their “frontier” models, require complex orchestration that’s carefully scripted by people who’ve tuned their prompts for these systems through countless rounds of trial and error. They’ve iterated and tested and watched for the results as these systems hallucinated or failed or ran amok, chewing up countless resources along the way. And sometimes, they generated genuinely astonishing outputs, things that are truly amazing to consider that modern technology can achieve. The rate of progress and evolution, even factoring in the mind-boggling amounts of investment that are going into these systems, is rivaled only by the initial development of the personal computer or the Internet, or the early space race.

And all of it — all of it — is controlled through Markdown files. When you see the brilliant work shown off from somebody who’s bragging about what they made ChatGPT generate for them, or someone is understandably proud about the code that they got Claude to create, all of the most advanced work has been prompted in Markdown. Though where the logic of Markdown was originally a very simple version of "use human language to tell the machine what to do", the implications have gotten far more dire when they use a format designed to help expresss "make this **bold**" to tell the computer itself "make this imaginary girlfriend more compliant".

But we already know that the Big AI companies are run by people who don't reckon with the implications of their work. They could never understand that every single project that's even moderately ambitious on these new AI platforms is being written up in files formatted according to this system created by one guy who has never asked for a dime for this work. An entire generation of AI coders has been born since Markdown was created who probably can’t even imagine that this technology even has an "inventor". It’s just always been here, like the Moon, or Rihanna.

But it’s important for everyone to know that the Internet, and the tech industry, don’t run without the generosity and genius of regular people. It is not just billion-dollar checks and Silicon Valley boardrooms that enable creativity over years, decades, or generations — it’s often a guy with a day job who just gives a damn about doing something right, sweating the details and assuming that if he cares enough about what he makes then others will too. The majority of the technical infrastructure of the Internet was created in this way. For free, often by people in academia, or as part of their regular work, with no promise of some big payday or getting a ton of credit.

The people who make the real Internet and the real innovations also don’t look for ways to hurt the world around them, or the people around them. Sometimes, as in the case of Aaron, the world hurts them more than anyone should ever have to bear. I know not everybody cares that much about plain text files on the Internet; I will readily admit I am a huge nerd about this stuff in a way that maybe most normal people are not. But I do think everybody cares about some part of the wonderful stuff on the Internet in this way, and I want to fight to make sure that everybody can understand that it’s not just five terrible tycoons who built this shit. Real people did. Good people. I saw them do it.

The trillion-dollar AI industry's system for controlling their most advanced platforms is a plain text format one guy made up for his blog and then bounced off of a 17-year-old kid before sharing it with the world for free. You're welcome, Time Magazine's people of the year, The Architects of AI. Their achievement is every bit as impressive as yours.

The Ten Technical Reasons Markdown Won

Okay, with some of the narrative covered, what can we learn from Markdown’s success? How did this thing really take off? What could we do if we wanted to replicate something like this in the modern era? Let’s consider a few key points:

1. Had a great brand.

Okay, let’s be real: “Markdown” as a name is clever as hell. Get it it’s not markup, it’s mark down. You just can’t argue with that kind of logic. People who knew what the “M” in “HTML” stood for could understand the reference, and to everyone else, it was just a clearly-understandable name for a useful utility.

2. Solved a real problem.

This one is not obvious, but it’s really important that a new technology have a real problem that it’s trying to solve, instead of just being an abstract attempt to do something vague, like “make text files better”. Millions of people were encountering the idea that it was too difficult or inconvenient to write out full HTML by hand, and even if one had the necessary skills, it was nice to be able to do so in a format that was legible as plain text as well.

3. Built on behaviors that already existed.

This is one of the most quietly genius parts of Markdown: The format is based on the ways people had been adding emphasis and formatting to their text for years or even decades. Some of the formatting choices dated back to the early days of email, so they’d been ingrained in the culture of the internet for a full generation before Markdown existed. It was so familiar, people could be writing Markdown without even knowing it.

4. Mirrored RSS in its origin.

Around the same time that Markdown was taking off, RSS was maturing into its ubiquitous form as well. The format had existed for some years already, enabling various kinds of content syndication, but at this time, it was adding support for the technologies that would come to be known as podcasting as well. And just like RSS, Markdown was spearheaded by a smart technologist who was also more than a little stubborn about defining a format that would go on to change the way we share content on the internet. In RSS’ case, it was pioneered by Dave Winer, and with Markdown it was John Gruber, and both were tireless in extolling the virtues of the plain text formats they’d helped pioneer. They could both leverage blogs to get the word out, and to get feedback on how to build on their wins.

5. There was a community ready to help.

One great thing about a format like Markdown is that its success is never just the result of one person. Vitally, Markdown was part of a community that could build on it right from the start. Right from the beginning, Markdown was inspired by earlier works like Textile, a formatting system for plain text created by Dean Allen. Many of us appreciated and were inspired by Dean, who was a pioneer of blogging tools in the early days of social media, but if there’s a bigger fan of Dean Allen on the internet than John Gruber, I’ve never met them. Similarly, Aaron Swartz, the brilliant young technologist who’s known best known as an activist for digital rights and access, was at that time just a super brilliant teenager that a lot of us loved hacking with. He was the most valuable beta tester of Markdown prior to its release, helping to shape it into a durable and flexible format that’s stood the test of time.

6. Had the right flavor for every different context.

Because Markdown’s format was frozen in place (and had some super-technical details that people could debate about) and people wanted to add features over time, various communities that were implementing Markdown could add their own “flavors” of it as they needed. Popular ones came to be called Commonmark and Github-Flavored, led by various companies or teams that had divergent needs for the tool. While tech geeks tend to obsess over needing everything to be “correct”, in reality it often just doesn’t matter that much, and in the real world, the entire Internet is made up of content that barely follows the technical rules that it’s supposed to.

7. Released at a time of change in behaviors and habits.

This is a subtle point, but an important one: Markdown came along at the right time in the evolution of its medium. You can get people to change their behaviors when they’re using a new tool, or adopting a new technology. In this case, blogging (and all of social media!) were new, so saying “here’s a new way of typing a list of bullet points” wasn’t much an additional learning curve to add to the mix. If you can take advantage of catching people while they’re already in a learning mood, you can really tap into the moment when they’re most open-minded to new things.

8. Came right on the cusp of the “build tool era”.

This one’s a bit more technical, but also important to understand. In the first era of building for the web, people often built the web’s languages of HTML, Javascript and CSS by hand, by themselves, or stitched these formats together from subsets or templates. But in many cases, these were fairly simple compositions, made up of smaller pieces that were written in the same languages. As things matured, the roles for web developers specialized (there started to be backend developers vs. front-end, or people who focused on performance vs. those who focused on visual design), and as a result the tooling for developers matured. On the other side of this transition, developers began to use many different programming languages, frameworks and tools, and the standard step before trying to deploy a website was to have an automated build process that transformed the “raw materials” of the site into the finished product. Since Markdown is a raw material that has to be transformed into HTML, it perfectly fit this new workflow as it became the de facto standard method of creation and collaboration.

9. Worked with “View source”

Most of the technologies that work best on the web enable creators to “view source” just like HTML originally did when the first web browsers were created. In this philosophy, one can look at the source code that makes up a web page, and understand how it was constructed so that you can make your own. With Markdown, it only takes one glimpse of a source Markdown file for anyone to understand how they might make a similar file of their own, or to extrapolate how they might apply analogous formatting to their own documents. There’s no teaching required when people can just see it for themselves.

10. Not encumbered in IP

This one’s obvious if you think about it, but it can’t go unsaid: There are no legal restrictions around Markdown. You wouldn’t think that anybody would be foolish or greedy enough to try to patent something as simple as Markdown, but there are many far worse examples of patent abuse in the tech industry. Fortunately, John Gruber is not an awful person, and nobody else has (yet) been brazen enough to try to usurp the format for their own misadventures in intellectual property law. As a result, nobody’s been afraid, either to use the format, or to support creating or reading the format in their apps.

500,000 tech workers have been laid off since ChatGPT was released

2026-01-06 08:00:00

One of the key points I repeated when talking about the state of the tech industry yesterday was the salient fact that half a million tech workers have been laid off since ChatGPT was released in late 2022. Now, to be clear, those workers haven’t been laid off because their jobs are now being done by AI, and they’ve been replaced by bots. Instead, they’ve been laid off by execs who now have AI to use as an excuse for going after workers they’ve wanted to cut all along.

This is important to understand for a few reasons. First, it’s key just for having empathy for both the mindset and the working conditions of people in the tech industry. For so many outside of tech, their impression of what “tech” means is whatever is the most recent transgression they’ve heard about from the most obnoxious billionaire who’s made the news lately. But in many cases, it’s the rank and file workers at that person’s company who were the first victims of that billionaire’s ego.

Second, it’s important to understand the big tech companies as almost the testing grounds for the techniques and strategies that these guys want to roll out on the rest of the economy, and on the rest of the world. Before they started going on podcasts pretending to be extremely masculine while whining about their feelings, or overtly bribing politicians to give them government contracts, they beta-tested these manipulative strategies within their companies by cracking down on dissent and letting their most self-indulgent and egomaniacal tendencies run wild. Then, when people (reasonably!) began to object, they used that as an excuse to purge any dissenters for being uncooperative or “difficult”.

It starts with tech, but doesn’t end there

These are tactics they’ll be bringing to other industries and sectors of the economy, if they haven’t already. Sometimes they’ll be providing AI technologies and tools as an enabler or justification for the cultural and political agenda that they’re enacting, but often times, they don’t even need to. In many cases, they can simply make clear that they want to enforce psychological and social conformity within their organizations, and that any disagreement will not be tolerated, and the implicit threat of being replaced by automation (or by other workers who are willing to fall in line) is enough to get people to comply.

This is the subtext, and sometimes the explicit text, of the deployment of “AI” in a lot of organizations. That’s separate from what actual AI software or technology can do. And it explains a lot of why the majority AI view within the tech industry is nothing like the hype cycle that’s being pushed by the loudest voices of the big-name CEOs.

Because people who work in tech still believe in the power of tech to do good things, many of us won’t just dismiss outright the possibility that any technology — even AI tools like LLMs — could yield some benefits. But the optimistic takes are tempered by the first-hand knowledge of how the tools are being used as an excuse to sideline or victimize good people.

This wave of layoffs and reductions has been described as “pursuing efficiencies” or “right-sizing”. But so many of us in tech can remember a few years back, when working in tech as an upwardly-mobile worker with a successful career felt like the best job in the world. When many people could buy nice presents for their kids at Christmas or they weren’t as worried about your car payments. When huge parts of society were promising young people that there was a great future ahead if they would just learn to code. When the promise of a tech career’s potential was used as the foundation for building infrastructure in our schools and cities to train a whole new generation of coders.

But the funders and tycoons in charge of the big tech companies knew that they did not want to keep paying enormous salaries to the people they were hiring. They certainly knew they didn’t want to keep paying huge hiring bonuses to young people just out of college, or to pay large staffs of recruiters to go find underrepresented candidates. Those niceties that everybody loved, like great healthcare and decent benefits, were identified by the people running the big tech companies as “market inefficiencies” which indicated some wealth was going to you that should have been going to them. So yes, part of the reason for the huge investment in AI coding tools was to make it easier to write code. But another huge reason that AI got so good at writing code was so that nobody would ever have to pay coders so well again.

You’re not wrong if you feel angry, resentful and overwhelmed by all of this; indeed, it would be absurd if you didn’t feel this way, since the wealthiest and most powerful people in the history of the world have been spending a few years trying to make you feel exactly this way. Constant rotating layoffs and a nonstop fear of further cuts, with a perpetual sense of precarity, are a deliberate strategy so that everyone will accept lower salaries and reduced benefits, and be too afraid to push for the exact same salaries that the company could afford to pay the year before.

Why are we stirring the pot?

Okay, so are we just trying to get each other all depressed? No. It’s just vitally important that we name a problem and identify it if we’re going to solve it. 
Most people outside of the technology industry think that “tech” is a monolith, that the people who work in tech are the same as the people who own the technology companies. They don’t know that tech workers are in the same boat that they are, being buffeted by the economy, and being subject to the whims of their bosses, or being displaced by AI. They don’t know that the DEI backlash has gutted HR teams at tech companies, too, for example. So it’s key for everyone to understand that they’re starting from the same place.

Next, it’s key to tease apart things that are separate concerns. For example: AI is often an excuse for layoffs, not the cause of them. ChatGPT didn’t replace the tasks that recruiters were doing in attracting underrepresented candidates at big tech companies — the bosses just don’t care about trying to hire underrepresented candidates anymore! The tech story is being used to mask the political and social goal. And it’s important to understand that, because otherwise people waste their time fighting battles that might not matter, like the deployment of a technology system, and losing the ones that do, like the actual decisions that an organization is making about its future.

Are they efficient, though?

But what if, some people will ask, these companies just had too many people? What if they’d over-hired? The folks who want to feel really savvy will say, “I heard that they had all those employees because interest rates were low. It was a Zero Interest Rate Phenomenon.” This is, not to put too fine a point on it, bullshit. It’s not in any company’s best interests to cut their staffing down to the bone.

You actually need to have some reserve capacity for labor in order to reach maximum output for a large organization. This is the difference between a large-scale organization and a small one. People sitting around doing nothing is the epitome of waste or inefficiency in a small team, but in a large organization, it’s a lot more costly if you are about to start a new process or project and you don’t have labor capacity or expertise to deploy.

A good analogy is the oft-cited need these days for people to be bored more often. There’s a frequent lament that, because people are so distracted by things like social media and constant interruptions, they never have time to get bored and let their mind wander, and think new thoughts or discover their own creativity. Put another way, they never get the chance to tap into their own cognitive surplus.

The only advantage a large organization can have over a small one, other than sheer efficiencies of scale, is if it has a cognitive surplus that it can tap into. By destroying that cognitive surplus, and leaving those who remain behind in a state of constant emotional turmoil and duress, these organizations are permanently damaging both their competitive advantages and their potential future innovations.

AI Spring

When the dust clears, and people realize that extreme greed is never the path to maximum long-term reward, there is going to be a “peace dividend” of sorts from all the good talent that’s now on the market. Some of this will be smart, thoughtful people flowing to other industries or companies, bringing their experience and insights with them.

But I think a lot of this will be people starting their own new companies and organizations, informed by the broken economic models, and broken human models, of the companies they’ve left. We saw this a generation ago after the bust of the dot-com boom, when it was not only revealed that the economics of a lot of the companies didn’t work, but that so many of the people who had created the companies of that era didn’t even care about the markets or the industries that they’d entered. When the get-rich-quick folks left the scene, those of us who remained, who truly loved the web as a creative and expressive medium, found a ton of opportunity in being the little mammals amidst the sad dinosaurs trying to find funding for meteor dot com.

What comes next

I don’t think this all gets better very quickly. If you put aside the puffery of the AI companies scratching each others’ backs, it’s clear the economy is in a recession, even if this administration’s goons have shut down reporting on jobs and inflation in a vain attempt to hide that reality. But I do think there may be more resilience because of the sheer talent and entrepreneurial skill of the people who are now on the market as individuals.

How the hell are you supposed to have a career in tech in 2026?

2026-01-05 08:00:00

The number one question I get from my friends, acquaintances, and mentees in the technology industry these days is, by far, variations on the basic theme of, “what the hell are we supposed to do now?”

There have been mass layoffs that leave more tech workers than ever looking for new roles in the worst market we’ve ever seen. Many of the most talented, thoughtful and experienced people in the industry are feeling worried, confused, and ungrounded in a field that no longer looks familiar.

If you’re outside the industry, you may be confused — isn’t there an AI boom that’s getting hundreds of billions of dollars in investments? Doesn’t that mean the tech bros are doing great? What you may have missed is that half a million tech workers have been laid off in the years since ChatGPT was released; the same attacks on marginalized workers and DEI and “woke” that the tech robber barons launched against the rest of society were aimed at their own companies first.

So the good people who actually make the technology we use every day, the real innovators and creators and designers, are reacting to the unprecedented disconnect between the contemporary tech industry and the fundamentals that drew so many people toward it in the first place. Many of the biggest companies have abandoned the basic principle of making technology that actually works. So many new products fail to deliver on even the basic capabilities that the companies are promising that they will provide.

Many leaders at these companies have run full speed towards moral and social cowardice, abandoning their employees and customers to embrace rank hatred and discrimination in ways that they pretended to be fighting against just a few years ago. Meanwhile, unchecked consolidation has left markets wildly uncompetitive, leaving consumers suffering from the effects of categories without any competition or investment — which we know now as “enshittification”. And the full-scale shift into corruption and crony capitalism means that winners in business are decided by whoever is shameless enough to offer the biggest bribes and debase themselves with the most humiliating display of groveling. It’s a depressing shift for people who, earlier in their careers, often actually were part of inventing the future.

So where do we go from here?

You’re not crazy.

The first, and most important, thing to know is that it’s not just you. Nearly everyone in tech I have this conversation with feels very isolated about it, and they’re often embarrassed or ashamed to discuss it. They think that everyone else who has a job in tech is happy or comfortable at their current employers, or that the other people looking for work are getting calls back or are being offered interviews in response to their job applications. But I’m here to tell you: it is grim right now. About as bad as I’ve seen. And I’ve been around a long time.

Every major tech company has watched their leadership abandon principles that were once thought sacrosanct. I’ve heard more people talk about losing respect for executives they trusted, respected, even admired in the last year than at any time I can remember. In smaller companies and other types of organizations, the challenges have been more about the hard choices that come from dire resource constraints or being forced to make ugly ethical compromises for pragmatic reasons. The net result is tons of people who have lost pride and conviction in their work. They’re going through the motions for a paycheck, because they know it’s a tough job market out there, which is a miserable state of affairs.

The public narrative is dominated by the loud minority of dudes who are content to appease the egos of their bosses, sucking up to the worse impulses of those in charge. An industry that used to pride itself on publicly reporting security issues and openly disclosing vulnerabilities now circles its wagons to gang up on people who suggest that an AI tool shouldn’t tell children to harm themselves, that perhaps it should be possible to write a law limiting schools from deploying AI platforms that are known to tell kids to end their own lives. People in tech endure their bosses using slurs at work, making jokes about sexual assault, consorting with leaders who have directly planned the murder of journalists, engaging in open bribery in blatant violation of federal law and their own corporate training on corruption, and have to act like it’s normal.

But it’s not the end of the world. The forces of evil have not yet triumphed, and all hope is not lost. There are still things we can do.

Taking back control

It can be easy to feel overwhelmed at such an unprecedented time in the industry, especially when there’s so much change happening. But there are concrete actions you can take to have agency over your own career, and to insulate yourself from the bad actors and maximize your own opportunities — even if some of those bad actors are your own bosses.

Understanding systems

One of the most important things you can do is to be clear about your own place, and your own role, within the systems that you are part of. A major factor in the changes that bosses are trying to effect with the deployment of AI is shifting the role of workers within the systems in their organization to make them more replaceable.

If you’re a coder, and you think your job is to make really good code in a particular programming language, you might double down on getting better at the details of that language. But that’s almost certainly misunderstanding the system that your company thinks you’re part of, where the code is just a means to the end of creating a final product. In that system-centric view, the programming language, and indeed all of the code itself, doesn’t really matter; the person who is productive at causing all of that code to be created reliably and efficiently is the person who is going to be valued, or at least who is most likely to be kept around. That may not be satisfying or reassuring if you truly love coding, but at least this perspective can help you make informed decisions about whether or not that organization is going to make choices that respect the things you value.

This same way of understanding systems can apply if you’re a designer or a product manager or a HR administrator or anything else. As I’ve covered before, the purpose of a system is what it does, and that truth can provide some hard lessons if we find it’s in tension with the things we want to be doing for an organization. The system may not value the things we do, or it may not value them enough; the way they phrase this to avoid having to say it directly is by describing something as “inefficient”. Then, the question you have to ask yourself is, can you care about this kind of work or this kind of program at one level higher up in the system? Can it still be meaningful to you if it’s slightly more abstract? Because that may be the requirement for navigating the expectations that technology organizations will be foisting on everyone through the language of talking about “adopting AI”.

Understanding power

Just as important as understanding systems is understanding power. In the workplace, power is something real. It means being able to control how money is spent. It means being able to make decisions. It means being able to hire people, or fire them. Power is being able to say no.

You probably don’t have enough power; that’s why you have worries. But you almost certainly have more power than you think, it’s just not as obvious how to wield it. The most essential thing to understand is that you will need to collaborate with your peers to exercise collective power for many of the most significant things you may wish to achieve.

But even at an individual level, a key way of understanding power in your workplace is to consider the systems that you are part of, and then to reckon with which ones you can meaningfully change from your current position. Very often, people will, in a moment of frustration, say “this place couldn’t run without me!” And companies will almost always go out of their way to prove someone wrong if they hear that message.

On the other hand, if you identify a system for operating the organization that no one else has envisioned, you’ve already demonstrated that this part of the organization couldn’t run without you, and you don’t need to say it or prove it. There is power in the mere action of creating that system. But a lot depends on where you have both the positional authority and the social permission to actually accomplish that kind of thing.

So, if you’re dissatisfied with where you are, but have not decided to leave your current organization, then your first orders of business in this new year should be to consolidate power through building alliances with peers, and by understanding which fundamental systems of your organization you can define or influence, and thus be in control of. Once you’ve got power, you’ve got options.

Most tech isn’t “tech”

So far, we’re talking about very abstract stuff. What do we do if your job sucks right now, or if you don’t have a job today and you really need one? After vague things like systems and power, then what?

Well, an important thing to understand, if you care about innovation and technology, is that the vast majority of technology doesn’t happen in the startup world, or even in the “tech industry”. Startups are only a tiny fraction of the entire realm of companies that create or use technology, and the giant tech companies are only a small percentage of all jobs or hiring within the tech realm.

So much opportunity, inspiration, creativity, and possibility lies in applying the skills and experience that you may have from technological disciplines in other realms and industries that are often far less advanced in their deployment of technologies. In a lot of cases, these other businesses get taken advantage of for their lack of experience — and in the non-profit world, the lack of tech expertise or fluency is often exploited by both the technology vendors and bad actors who swoop in to capitalize on their vulnerability.

Many of the people I talk to who bring their technology experience to other fields also tell me that the culture in more traditional industries is often less toxic or broken than things in Silicon Valley (or Silicon Valley-based) companies are these days, since older or more established companies have had time to work out the more extreme aspects of their culture. It’s an extraordinary moment in history when people who work on Wall Street tell me that even their HR departments wouldn’t put up with the kind of bad behavior that we’re seeing within the ranks of tech company execs.

Plan for the long term

This too shall pass. One of the great gifts of working in technology is that it’s given so many of us the habit of constantly learning, of always being curious and paying attention to the new things worth discovering. That healthy and open-minded spirit is an important part of how to navigate a moment when lots of people are being laid off, or lots of energy and attention are being focused on products and initiatives that don’t have a lot of substance behind them. Eventually, people will want to return to what’s real. The companies that focus on delivering products with meaning, and taking care of employees over time, will be the ones that are able to persist past the current moment. So building habits that enable resiliency at both a personal and professional level is going to be key.

As I’ve been fond of saying for a long time: don’t let your job get in the way of your career.

Build habits and routines that serve your own professional goals. As much as you can, participate in the things that get your name out into your professional community, whether that’s in-person events in your town, or writing on a regular basis about your area of expertise, or mentoring with those who are new to your field. You’ll never regret building relationships with people, or being generous with your knowledge in ways that remind others that you’re great at what you do.

If your time and budget permit, attend events in person or online where you can learn from others or respond to the ideas that others are sharing. The more people can see and remember that you’re engaged with the conversations about your discipline, the greater the likelihood that they’ll reach out when the next opportunity arises.

Similarly, take every chance you can to be generous to others when you see a door open that might be valuable for them. I can promise you, people will never forget that you thought of them in their time of need, even if they don’t end up getting that role or nabbing that interview.

It’s an evolution, not a resolution

New years are often a time when people make a promise to themselves about how they’re going to change everything. If I can just get this new notebook to write in, I’m suddenly going to become a person who keeps a journal, and that will make me a person who’s on top of everything all the time.

But hopefully you can see, many of the challenges that so many people are facing are systemic, and aren’t the result of any personal failings or shortcomings. So there isn’t some heroic individual change that you can make when you flip over to a new calendar month that will suddenly fix all the things.

What you can control, though, are small iterative things that make you feel better on a human scale, in little ways, when you can. You can help yourself maintain perspective, and you can do the same for those around you who share your values, and who care about the same personal or professional goals that you do.

A lot of us still care about things like the potential for technology to help people, or still believe in the idealistic and positive goals that got us into our careers in the first place. We weren’t wrong, or naive, or foolish to aspire to those goals simply because some bad actors sought to undermine them. And it’s okay to feel frustrated or scared in a time when it seems to many like those goals could be further away than they’ve been in a long time.

I do hope, though, that people can see that, by sticking together, and focusing on the things that are within our reach, things can begin to change. All it takes is remembering that the power in tech truly rests with all the people who actually make things, not with the loudmouths at the top who try to tear things down.

What about “Nothing about us without us?”

2025-12-08 08:00:00

As I was drafting my last piece on Friday, “They have to be able to talk about us without us”, my thoughts of course went to one of the most famous slogans of the disability rights movement, “Nothing about us without us.” I wasn’t unaware that there were similarities in the phrasing of what I wrote. But I think the topic of communicating effectively to groups, as I wrote about the other day, and ensuring that disabled people are centered in disability advocacy, are such different subjects that I didn’t want to just quickly gloss over the topic in a sidebar of a larger piece. They're very distinct topics that really only share a few words in common.

One of the great joys of becoming friends with a number of really thoughtful and experienced disability rights activists over the last several years has been their incredible generosity in teaching me about so much of the culture and history of the movements that they’ve built their work upon, and one of the most powerful slogans has been that refrain of “nothing about us without us”.

Here I should start by acknowledging Alice Wong, who we recently lost, who founded the Disability Visibility Project, and a MacArthur Fellow, and a tireless and inventive advocate for everyone in the disabled community. She was one of the first people to bring me in to learning about this history and these movements, more than a decade ago. She was also a patient and thoughtful teacher, and over our many conversations over the years, she did more than anyone else in my life to truly personify the spirit of “nothing about us without us” by fighting to ensure that disabled people led the work to make the world accessible for all. If you have the chance, learn about her work, and support it.

But a key inflection point in my own understanding of “nothing about us without us” came, unsurprisingly, in the context of how disabled people have been interacting with technology. I used to host a podcast called Function, and we did an episode about how inaccessible so much of contemporary technology has become, and how that kind of ruins things for everyone. (The episode is still up on Spotify and Apple Podcasts.) We had on Emily Ladau of The Accessible Stall podcast, Alex Haagaard of The Disabled List, and Vilissa Thompson of Ramp Your Voice. It’s well worth a listen, and Emily, Alex and Vilissa really do an amazing job of pointing to really specific, really evocative examples of obvious places where today’s tech world could be so much more useful and powerful for everyone if its creators were making just a few simple changes.

What’s striking to me now, listening to that conversation six years later, is how little has changed from the perspective of the technology world, but also how much my own lived experience has come to reflect so much of what I learned in those conversations.

Each of them was the "us" in the conversation, using their own personal experience, and the experience of other disabled people that they were in community with, to offer specific and personal insights that the creators of these technologies did not have. And whether it was for reasons of crass commercial opportunism — here's some money you could be making! — or simply because it was the right thing to do morally, it's obvious that the people making these technologies could benefit by honoring the principle of centering these users of their products.

Taking our turn

I’ve had this conversation on various social media channels in a number of ways over the years, but another key part of understanding the “us” in “nothing about us without us” when it comes to disability, is that the “us” is all of us, in time. It's very hard for many people who haven’t experienced it to understand that everyone should be accommodated and supported, because everyone is disabled; it’s only a question of when and for how long.

In contemporary society, we’re given all kinds of justifications for why we can’t support everyone’s needs, but so much of those are really grounded in simply trying to convince ourselves that a disabled person is someone else, an “other” who isn’t worthy or deserving of our support. I think deep down, everyone knows better. It’s just that people who don’t (yet) identify as disabled don’t really talk about it very much.

In reality, we'll all be disabled. Maybe you're in a moment of respite from it, or in that brief window before the truth of the inevitability of it has been revealed to you (sorry, spoiler warning!), but it's true for all of us — even when it's not visible. That means all of us have to default to supporting and uplifting and empowering the people who are disabled today. This was the key lesson that I didn’t really get personally until I started listening to those who were versed in the history and culture of disability advocacy, about how the patronizing solutions were often harmful, or competing for resources with the right answers.

I’ve had my glimpses of this myself. Back in 2021, I had Lyme disease. I didn’t get it as bad as some, but it did leave me physically and mentally unable to function as I had been used to, for several months. I had some frame of reference for physical weakness; I could roughly compare it to a bad illness like the flu, even if it wasn’t exactly the same. But a diminished mental capacity was unlike anything I had ever experienced before, and was profoundly unsettling, deeply challenging my sense of self. After the incident I’d described in 2022, I had a series of things to recover from physically and mentally that also presented a significant challenge, but were especially tough because so much of people’s willingness to accommodate others is based on any disability being visible. Anything that’s not immediately perceived at a superficial level, or legible to a stranger in a way that’s familiar to them, is generally dismissed or seen as invalid for support.

I point all of this out not to claim that I fully understand the experience of those who live with truly serious disabilities, or to act as if I know what it’s been like for those who have genuinely worked to advocate for disabled people. Instead, I think it can often be useful to show how porous the boundary is between people who don’t think of themselves as disabled and those who already know that they are. And of course this does not mean that people who aren't currently disabled can speak on behalf of those who are — that's the whole point of "nothing about us without us"! — but rather to point out that the time to begin building your empathy and solidarity is now, not when you suddenly have the realization that you're part of the community.

Everything about us

There’s a righteous rage that underlies the cry of “nothing about us without us”, stemming from so many attempts to address the needs of disabled people having come from those outside the community, arriving with plans that ranged from inept to evil. We’re in a moment when the authoritarians in charge in so much of the world are pushing openly-eugenicist agendas that will target disabled people first amongst the many vulnerable populations that they’ll attempt to attack. Challenging economic times like the one we’re in affect disabled people significantly harder as the job market disproportionately shrinks in opportunities for the disabled first.

So it’s going to take all of us standing in solidarity to ensure that the necessary advocacy and support are in place for what promises to be an extraordinarily difficult moment. But I take some solace and inspiration from the fact that there are so many disabled people who have provided us with the clear guidance and leadership we need to navigate this moment. And there is simple guidance we can follow when doing so to ensure that we’re centering the right leaders, by listening to those who said, “nothing about us without us.”

They have to be able to talk about us without us

2025-12-05 08:00:00

It’s absolutely vital to be able to communicate effectively and efficiently to large groups of people. I’ve been lucky enough to get to refine and test my skills in communicating at scale for a few decades now, and the power of talking to communities is the one area where I’d most like to pass on what I’ve learned, because it’s this set of skills that can have the biggest effect on deciding whether good ideas and good work can have their greatest impact.

My own work crosses many disparate areas. Over the years, I’ve gotten to cycle between domains as distinct as building technology platforms and products for developers and creators, enabling activism and policy advocacy in service of humanist ideals, and more visible external-facing work such as public speaking or writing in various venues like magazines or on this site. (And then sometimes I dabble in my other hobbies and fun stuff like scholarship or research into areas like pop culture and media.)

What’s amazing is, in every single one of these wildly different areas, the exact same demands apply when trying to communicate to broad groups of people. This is true despite the broadly divergent cultural norms across all of these different disciplines. It can be a profoundly challenging, even intimidating, job to make sure a message is being communicated accurately, and in high fidelity, to everyone that you need to reach.

That vital task of communicating to a large group gets even more daunting when you inevitably realize that, even if you were to find the perfect wording or phrasing for your message, you’d still never be able to deliver your story to every single person in your target audience by yourself anyway. There will always be another person whom you’re trying to reach that you just haven’t found yet. So, is it hopeless? Is it simply impossible to effectively tell a story at scale if you don’t have massive resources?

It doesn’t have to be. We can start with one key insight about what it takes to get your most important stories out into the world. It’s a perspective that seems incredibly simple at first, but can lead to a pretty profound set of insights.

They have to be able to talk about us without us.

They have to be able to talk about us without us. What this phrase means, in its simplest form, is that you have to tell a story so clear, so concise, so memorable and evocative that people can repeat it for you even after you’ve left the room. And the people who hear it need to be able to do this the first time they hear the story. Whether it’s the idea behind a new product, the core promise of a political campaign, or the basic takeaway from a persuasive essay (guess what the point of this one is!) — not only do you have to explain your idea and make your case, you have to be teaching your listener how to do the same thing for themselves.

This is a tall order, to be sure. In pop music, the equivalent is writing a hit where people feel like they can sing along to the chorus by the time they get to the end of the song for the first time. Not everybody has it in them to write a hook that good, but if you do, that thing is going to become a classic. And when someone else has done it, you know it because it gets stuck in your head. Sometimes you end up humming it to yourself even if you didn’t want to. Your best ideas — your most vital ideas — need to rest on a messaging platform that solid.

Delivering this kind of story actually requires substance. If you’re trying to fake it, or to force a narrative out of fluff or fakery, that will very immediately become obvious. When you set out to craft a story that travels in your absence, it has to have a body if it’s going to have legs. Bullshit is slippery and smells terrible, and the first thing people want to do when you leave the room is run away from it, not carry it with them.

The mission is the message

There’s another challenge to making a story that can travel in your absence: your ego has to let that happen. If you make a story that is effective and compelling enough that others can tell it, then, well…. those other people are going to tell it. Not you. They’ll do it in their own words, and in their own voices, and make it theirs. They may use a similar story, but in their own phrasing, so it will resonate better with their people. This is a gift! They are doing you a kindness, and extending you great generosity. Respond with gratitude, and be wary of anyone who balks at not getting to be the voice or the face of a message themselves. Everyone gets a turn telling the story.

Maybe the simple fact that others will be hearing a good story for the first time will draw them to it, regardless of who the messenger is. Sometimes people get attached to the idea that they have to be the one to deliver the one true message. But a core precept of “talk about us without us” is that there’s a larger mission and goal that everyone is bought into, and this demands that everyone stay aligned to their values rather than to their own personal ambitions around who tells the story.

The truth of whomever will be most effective is the factor used to decide who will be the person to tell the story in any context. And this is a forgiving environment, because even if someone doesn’t get to be the voice one day, they’ll get another shot, since repetition and consistency are also key parts of this strategy, thanks to the disciplined approach that it brings to communication.

The joy of communications discipline

At nearly every organization where I’ve been in charge of onboarding team members in the last decade or so, one of the first messages we’ve presented to our new colleagues is, “We are disciplined communicators!” It’s a message that they hopefully get to hear as a joyous declaration, and as an assertion of our shared values. I always try to explicitly instill this value into teams I work with because, first, it’s good to communicate values explicitly, but also because this is a concept that is very seldom directly stated.

It is ironic that this statement usually goes unsaid, because nearly everyone who pays attention to culture understands the vital importance of disciplined communications. Brands that are strictly consistent in their use of things like logos, type, colors, and imagery get such wildly-outsized cultural impact in exchange for relatively modest investment that it’s mind-boggling to me that more organizations don’t insist on following suit. Similarly, institutions that develop and strictly enforce a standard tone of voice and way of communicating (even if the tone itself is playful or casual) capture an incredibly valuable opportunity at minimal additional cost relative to how much everyone’s already spending on internal and external communications.

In an era where every channel is being flooded with AI-generated slop, and when most of the slop tools are woefully incapable of being consistent about anything, simply showing up with an obviously-human, obviously-consistent story is a phenomenal way of standing out. That discipline demonstrates all the best of humanity: a shared ethos, discerning taste, joyful expression, a sense of belonging, an appealing consistency. And best of all, it represents the chance to participate for yourself — because it’s a message that you now know how to repeat for yourself.

Providing messages that individuals can pick up and run with on their own is a profoundly human-centric and empowering thing to do in a moment of rising authoritarianism. When the fascists in power are shutting down prominent voices for leveling critiques that they would like to censor, and demanding control over an increasingly broad number of channels, there’s reassurance in people being empowered to tell their own stories together. Seeing stories bubble up from the grassroots in collaboration, rather than being forced down upon people from authoritarians at the top, has an emotional resonance that only strengthens the substance of whatever story you’re telling.

How to do it

Okay, so it sounds great: Let’s tell stories that other people want to share! Now, uh… how do we do it? There are simple principles we can follow that help shape a message or story into one that is likely to be carried forward by a community on its own.

  • Ground it in your values. When we began telling the story of my last company Glitch, the conventional wisdom was that we were building a developer tool, so people would describe it as an “IDE” — an “integrated development environment”, which is the normal developer jargon for the tool coders use to write their code in. We never described Glitch that way. From day one, we always said “Glitch is the friendly community where you'll build the app of your dreams” (later, “the friendly community where everybody builds the internet”). By talking about the site as a friendly community instead of an integrated development environment, it was crystal clear what expectations and norms we were setting, and what our values were. Within a few months, even our competitors were describing Glitch as a “friendly community” while they were trying to talk about how they were better than us about some feature or the other. That still feels like a huge victory — even the competition was talking about us without us! Make sure your message evokes the values you want people to share with each other, either directly or indirectly.
  • Start with the principle. This is a topic I’ve covered before, but you can't win unless you know what you're fighting for. Identify concrete, specific, perhaps even measurable goals that are tied directly to the values that motivate your efforts. As noted recently, Zohran Mamdani did this masterfully when running for mayor of New York City. While the values were affordability and the dignity of ordinary New Yorkers, the clear, understandable, measurable principle could be something as simple as “free buses”. This is a goal that everyone can get in 5 seconds, and can explain to their neighbor the first time they hear it. It’s a story that travels effortlessly on its own — and that people will be able to verify very easily when it’s been delivered. That’s a perfect encapsulation of “talk about us without us”.
  • **Know what makes you unique.**Another way of putting this is to simply make sure that you have a sense of self-awareness. But the story you tell about your work or your movement has to be specific. There can’t be platitudes or generalities or vague assertions as a core part of the message, or it will never take off. One of the most common failure states for this mistake is when people lean on slogans. Slogans can have their use in a campaign, for reminding people about the existence of a brand, or supporting broader messaging. But very often, people think a slogan is a story. The problem is that, while slogans are definitely repeatable, slogans are almost definitionally too vague and broad to offer a specific and unique narrative that will resonate. There’s no point in having people share something if it doesn’t say something. I usually articulate the challenge here like this:Only say what only you can say.
  • Be evocative, not comprehensive. Many times, when people are passionate about a topic or a movement, the temptation they have in telling the story is to work in every little detail about the subject. They often think, “if I include every detail, it will persuade more people, because they’ll know that I’m an expert, or it will convince them that I’ve thought of everything!” In reality, when people are not subject matter experts on a topic, or if they’re not already intrinsically interested in that topic, hearing a bunch of extensive minutia about it will almost always leave them feeling bored, confused, intimidated, condescended-to, or some combination of all of these. Instead, pick a small subset of the most emotionally gripping parts of your story, the aspects that have the deepest human connection or greatest relevance and specificity to the broadest set of your audience, and focus on telling those parts of the story as passionately as possible. If you succeed in communicating that initial small subset of your story effectively, then you may earn the chance to tell the other more complex and nuanced details of your story.
  • Your enemies are your friends. Very often, when people are creating messages about advocacy, they’re focused on competition or rivals. In the political realm, this can be literal opposing candidates, or the abstraction of another political party. In the corporate world, this can be (real or imagined) competitive products or companies. In many cases, these other organizations or products or competitors occupy so much more mental space in your mind, or your team’s mind, than they do in the mind of your potential audience. Some of your audience has never heard of them at all. And a huge part of your audience thinks of you and your biggest rival as… basically the same thing. In a business or commercial context, customers can barely keep straight the difference between you and your competition — you’re both just part of the same amorphous blob that exists as “the things that occupy that space”. Your competitor may be the only other organization in the world that’s fighting just as hard as you are to create a market for the product that you’re selling. The same is true in the political space; sometimes the biggest friction arises over the narcissism of small differences. What we can take away from these perspectives is that our stories have to focus on what distinguishes us, yes, but also on what we might have in common with those whom we might otherwise have perceived to have been aligned with the “enemy”. Those folks might not have sworn allegiance to an opposing force; they may simply have chosen another option out of convenience, and not even seen that choice as being in opposition to your story at all.
  • Find joy in repetition. Done correctly, a disciplined, collaborative, evocative message can become a mantra for a community. There’s a pride and enthusiasm that can come from people becoming proficient in sharing their own version of the collective story. And that means enjoying when that refrain comes back around, or when a slight improvement in the core message is discovered, and everyone finds a way to refine the way they’re communicating about the narrative. A lot of times, people worry that their team will get bored if they’re “just telling the same story over and over all the time”. In reality, as a brilliant man once said, there’s joy in repetition.
  • Don’t obsess over exact wording. This one is tricky; you might say, “but you said we have to be disciplined communicators!” And it’s true: it’s important to be disciplined. But that doesn’t mean you can’t leave room for people to put their own spin on things. Let them translate to their own languages or communities. Let them augment a general principle with a specific, personal connection. If they have their own authentic experience which will amplify a story or drive a point home, let them weave that context into the consistent narrative that’s been shared over time. As long as you’re not enabling a “telephone game” where the story starts to morph into an unrecognizable form, it’s perfectly okay to add a human touch by going slightly off script.

Share the story

Few things are more rewarding than when you find a meaningful narrative that resonates with the world. Stories have the power to change things, to make people feel empowered, to galvanize entire communities into taking action and recognizing their own power. There’s also a quiet reward in the craft and creativity of working on a story that travels, in finding notes that resonate with others, and in challenging yourself to get far enough out of your own head to get into someone else’s heart.

I still have so much to learn about being able to tell stories effectively. I still screw it up so much of the time, and I can look back on many times when I wish I had better words at hand for moments that sorely needed them. But many of the most meaningful and rewarding moments of my life have been when I’ve gotten to be in community with others, as we were not just sharing stories together, but telling a united story together. It unlocks a special kind of creativity that’s a lot bigger than what any one of us can do alone.