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Pips is a daily puzzle from The New York Times, one of the top video game companies on the planet (they also meddle in journalism). It’s fun, frustrating, and recently taught me something important. 

In Pips you need to place a number of dominos on a board while following certain rules. Some groups of spots need to add up to a particular amount, for example, and there are individual spots that require a specific number. 

To win the game, particularly on the hard puzzles, you typically need to look at the dominos you have and find pieces that, logically, have to go in a particular place. If there’s only one six, for example, and there’s a place on the board that requires a six, you know your six needs to go there. Placing one piece allows you to find another piece that logically has to go somewhere, which eventually cascades until you place the final piece. 

The best games make you feel smart—Pips excels at this. Working out why a particular piece has to go somewhere is extremely satisfying, especially when doing so requires thinking ahead.

But sometimes it feels just as good to be wrong.

Anyone who plays Pips has, at some point, made a confident assumption about where a particular piece must go. It gives you the exact same feeling—of progress and of being smart. For a while. 

What’s actually happening is that your initial bad assumption is cascading into more bad assumptions, until you get to the final few pieces and realize you’ve played yourself into a corner. Then you need to figure out where you went wrong, go back to that point, and work out the actual way forward. 

In the short term, being confidently wrong about something feels just as good as actually being correct. 

Life isn’t as clear-cut as a Pips board, unfortunately—sometimes being confidently incorrect is rewarded seemingly indefinitely (insert your own political joke here). Generally, though, bad assumptions lead to bad outcomes, even if they feel useful for a time. Eventually you need to look back and figure out where you went wrong, then correct for that. 

This idea goes against the grain at the moment. American society believes that backing down on something you believe is weak, even if it turns out your belief isn’t true. But changing your mind when bad ideas don’t work isn’t weakness—it’s strength. It’s how you learn to be better. It’s a skill we’re all going to need.

Lately I’ve been wanting to write a newsletter and realizing that, for the most part, I don’t feel like I have much to say. 

I sometimes wonder if it’s depression, but I’m not sure it is. My life is pretty good. I have a great wife, the best cat, and fantastic friends. I’m secure. I get to write for a living, in a world where that feels like a miracle.

So I don’t think I’m depressed, exactly. I just think I’m not sure what my contribution to the conversation is supposed to be right now. It feels like the only way to get attention, at this point in history, is to say dumb shit and harvest the outrage. I’m not built for that, so I’m mostly not talking. 

It’s been a few months since I sent out a newsletter, and I barely post on social media anymore. I guess I just don’t see the point. Where once I’d share links, these days I just send them directly to a few friends and talk about them privately. It feels more personal, and I’m less likely to be interrupted. 

Plus, what do you even say to the world right now? Every day the news is a cavalcade of the dumbest, cruelest shit you’ve ever imagined being presented as though it’s normal, followed by a predictable cycle. The stages:

1. The president says something stupid, cruel, and/or evil. 
2. His party, afraid to ever contradict him, repeats the thing he said.
3. The media somewhat calls out this new stupidity in the most milquetoast language imaginable. 
4. The right accuses the media of being biased and uses the attention that generates to repeat the thing several times. 
5. Everyone gets bored until the cycle repeats with some other stupid thing.

This whole thing happens every couple days, and sometimes even faster. It doesn’t seem like there’s any beneficial way to engage with all of that. Reacting to the ridiculous thing feels like taking the bait, giving the people who say awful things the attention they don’t deserve. Ignoring it doesn’t feel much better, though, because they just keep on saying it anyway, which over time makes the horrible thing feel normal. 

I can’t find anything to hold onto in this ecosystem, is what I’m saying, and I guess I’ve kind of dropped out for a bit to maintain my sanity. I’m still writing for work, though, focusing on promoting small, useful bits of software made by independent producers. It feels useful in a way that commentary just doesn’t right now. 

It all leaves me wondering how to best use this space, though, which I’ve traditionally used for commentary. What kinds of subjects would you like to hear me talk about? And what’s a productive way to engage with the world right now? That’s what I’m going to be thinking about going into the new year, and I hope we can think about it together. Keep in touch. 

Stuff I wrote lately

• wBlock Is the Best Way to Block Ads on Safari Lifehacker Mac, iPhone, iPad—there’s no reason to see ads ever again. 
• Missing Launchpad in MacOS 26? Here’s How to Bring It Back WIRED Not a feature I used, granted, but a lot of people were sad to see it go. 
• Your Friend Asked You a Question. Don’t Copy and Paste an Answer From a Chatbot WIRED Thoughts on remaining human. 
• 4 common cat myths, debunked PopSci Always nice to have an excuse to write about cats. 

Stuff you should check out

• You Have Invested Billions in Generative AI A “game” where you pretend to be a very smart person who invested billions in a technology that is for sure not a bubble. 
• Rubio stages font coup: Times New Roman ousts Calibri Humeryra Pamuk/Reuters The State Department switched to a worse font to make…a point? About political correctness? Or something? Very stupid but pretty funny. 
• AI can steal crypto now Matt Levine/Bloomberg All I can say is “let them fight”. 

Mira went missing during a party; multiple people searched for her for quite a while and couldn’t find her. This is her casually walking downstairs a little bit later. “Hey guys!”

Anyone who has ever edited me will tell you I have a few…quirks. My worst habit is leaving unfinished sentences it the end of my 

…paragraphs. Like that. I regularly do this without noticing, even after I re-read an article multiple times. 

You could argue that I’m an idiot, and I do argue that to myself every night when I’m trying to fall asleep. But I’m not stupid—at least, not for this reason. Research suggests it’s harder to edit your own writing than the writing of other people. 

If you’re reading someone else’s writing it’s presumably because you want to understand the ideas that are being conveyed. In that context a typo can trip you up—the mistakes come between you and understanding the ideas. This makes them stand out to you. Compare that to the experience of reading your own writing—you already know what you’re trying to say. Because of this your brain is more likely to skip over typos—you don’t need the context that precise language provides. 

There’s a lot more psychology at work here, more than I could break down, but the basic problem is that it’s really hard to edit your own work. This is why I’m grateful for all the editors I have to work with at various publications, and for my wife Kathy who edits this newsletter (hi Kathy). 

Even with that help, though, I occasionally try to catch my own typos. I’ve tried various grammar checkers over the years, and sometimes they help. But nothing has been as effective, for me, as listening to my writing. When I’m finished with a draft I get my computer to read it back to me. It’s much easier for me to notice a computer voice failing to finish a sentence than it is for me to notice the unfinished sentence while reading. The same goes for typos: hearing my computer say the wrong word, or be unable to pronounce a word, makes it immediately obvious that I need to change something. 

I could go on. I always catch multiple things I want to change after listening to my articles, and it’s easier to do than you’d think. There are built-in tools for this on the Mac and in Microsoft Office, meaning you can start doing this right now with just a couple of clicks. Give it a try the next time you find yourself editing your own work. 

Stuff I Wrote

• How to (Mostly) Get Rid of Liquid Glass WIRED Distracted by all the transparency, or just wish your device wasn’t running so slow? These tips can help. 
• You should wash your clothes with cold water Popsci Modern detergent is chemically engineered to work with cold water, meaning you don’t have to waste energy heating up your laundry. 
• You Can Now Read Instapaper Articles on Your Kobo Lifehacker Mozilla shut down Pocket, which sucks, but at least I can read articles on my e-reader again. 

Stuff You Should Check Out

• A rich person with awful taste is more of an ‘average’ consumer than you now Mike Pearl/Mike The majority of spending in America is done by the top ten percent of earners, which is skewing the entire economy. 
• America’s Dumbest Crop Climate Town/YouTube America uses more water growing useless grass than any other crop. Hilarious breakdown of a depressing situation (with a few potential solutions). 

Last week we talked about how mediums—like film and novels—have their own built-in rules, and how those rules necessarily shape the way you can tell stories and express ideas. We made this point, naturally, by talking about Tom Bombadil. This week we’re going to see how the same principles apply online. 

A social media network is a medium; the choices made by the designers set the framework for how the medium works. Maybe the most obvious example of this is Twitter. 

I was a real Twitter addict in the first half of the 2010s, and I don’t entirely regret it. I built friendships and a career on that site, and I’m nostalgic for a version of it. I wrote last year about how I hate the zombie Twitter that’s still roaming the earth. But it was a lot of fun for a time. 

The limitations of the medium—mostly that you only had 140 characters to work with—meant there was a real incentive to be efficient with your words. It demanded a certain creativity to communicate something interesting. It was a place where a certain kind of nerd who was good with words could make the right joke and become briefly famous. 

To be good at Twitter meant mastering the art of hinting at complex ideas using as few words as possible. This meant depending on in-group knowledge—in jokes, sure, but also stereotypes and other cultural shorthand. And mixing in a little bit of absurdity to connect with the sort of audience you were likely to find there.

This wasn’t a website where you could make a complete, complex, nuanced point, but you could certainly jokingly point at such things, preferably with ironic flair. And that was basically fine when Twitter was mostly just a video game played by a few internet weirdos. The problem is, instead of staying that way, it became the main platform for political discourse.

I don’t have to re-litigate the rest here, but over time Twitter became a force that boiled every political and cultural conversation down into a competition to say the most absurd thing possible in order to get attention. We all know what happened next (and it’s very stupid). It’s unclear, in 2025, if we’ll ever recover from the political consequences of that media environment. 

This isn’t to say that nothing good happened on Twitter. There really were social movements that started on the platform and prompted valuable conversations. But as a whole, the rules and logic of Twitter created the political and cultural framework we all live in now. 

Neil Postman, in the 1980s book “Amusing Ourselves to Death”, wrote that he didn’t have a problem with TV as entertainment—his problem was with anyone who would claim that TV could be used to inform people. From the book: 

What is happening here is that television is altering the meaning of ‘being informed’ by creating a species of information that might properly be called disinformation. I am using this word almost in the precise sense in which it is used by spies in the CIA or KGB. Disinformation does not mean false information. It means misleading information—misplaced, irrelevant, fragmented or superficial information—information that creates the illusion of knowing something but which in fact leads one away from knowing. In saying this, I do not mean to imply that television news deliberately aims to deprive Americans of a coherent, contextual understanding of their world. I mean to say that when news is packaged as entertainment, that is the inevitable result. And in saying that the television news show entertains but does not inform, I am saying something far more serious than that we are being deprived of authentic information. I am saying we are losing our sense of what it means to be well informed. Ignorance is always correctable. But what shall we do if we take ignorance to be knowledge?

I think everything Postman says here applies as well to Twitter in the late 2010s as it did to TV in the 1980s. Twitter was at its best when used as a source of entertainment. It became a place people went to find information and proved to be horrible at delivering it. The results are the political hellscape we find ourselves in. I would go so far as to argue that it doesn’t matter much what people posted on Twitter—the design of the website led inevitably to certain outcomes. The values embedded in the system itself—”get as much attention as you can in as few words as possible”—led us to Brexit, Trump, and whatever comes next. 

Other social media outlets—Facebook, YouTube, Reddit, TikTok—are similar. Each has its own innate rules. When I talk about “rules” I’m not pointing at things like moderation policy—I’m talking about how things like design decisions and incentives subtly shape what kind of content can be successful, which in turn shapes the world in ways that can be hard to predict. 

Which is all to say that the channels we use to express our ideas matter as much as the ideas themselves, because the medium is ultimately going to shape which ideas can and cannot win. The design of the systems we use to communicate have an impact on what kinds of ideas can be expressed successfully, and the systems we have now aren’t doing a good job at bringing us together so we can solve problems (or even agree on what our problems are). 

But this doesn’t have to be doom and gloom. We can build a better world if we keep this in mind while designing what will replace the crumbling social media ecosystem—but only if we’re intentional about it.

Featured image, a photo from the long closed Thurderbeast Park in Chiloquin Oregon, is via Public Domain Review

Stuff You Should Check Out

• A prominent OpenAI investor appears to be suffering a ChatGPT-related mental health crisis Joe Wilkins/Futurism One problem with large language models is that they rarely tell you you’re wrong. This means, if you have delusions, they will happily tell you that they’re real. 
• The binder George Evans/Crossplay A grown man’s memories of his strict parent’s limits on video game times—rules that affect him negatively to this day. 
• Clues by Sam A logic game with new puzzles every day, best played over breakfast. 

One of the most profound lessons you can learn about media literacy is that it isn’t enough to talk about the content—you need to talk about the medium. People far smarter than me have written books and dissertations about this, but let’s start with an example that’s easy to grasp: the differences between the Lord of the Rings books and the movies.

I’m in the middle of re-reading these books for the first time in decades, time during which I’ve seen the movies several times. There are so many details in the books that aren’t present in the movies. The most famous example is Tom Bombadil, an ancient creature who is seemingly unconcerned with what’s happening in the outside world. He’s the only character in the books to wear the One Ring and be completely unaffected—he basically laughs and then gets back to his gardening. 

While reading the book, Tom Bombadil serves several purposes. He introduces you to the idea that there are all kinds of forces at play in the world, and some of them aren’t involved in the conflict at all. He leaves the characters, and the reader, feeling comforted and a little bit unsettled. 

But he also temporarily puts a stop to all forward momentum in the story. That can be interesting in a book, where you as the reader have time to reflect on what’s happening and put it into context on your own. Film doesn’t give you the kind of time you need to do that. Films are built on momentum—on one scene leading to the next, all constantly building toward a climax. Tom stopped that momentum and, as such, needed to be removed from the script even though his feathered cap, yellow boots and bright blue eyes would have been an engaging visual. Instead the hobbits go from the Shire to Bree in an on-screen instant. Film, built around visuals, requires constant forward momentum in order to capture the imagination.

Media theorists like Marshall McLuhan argue that this isn’t simply a choice that directors make—it’s something that’s baked into the medium of film itself. “The medium is the message,” the most famous quote attributed to McLuhan, is pointing at this truth—that the design of a medium itself shapes what can be said using it and, to a point, is a statement in itself. 

Understanding how film works, and how that function differs from the way a novel works, can help you see why Tom Bombadil was left out of the movies. But it can also give you critical insights about the world. A TV newscast, for example, must cover a news story differently than a newspaper article or podcast does, and you can generally work out why if you think about how the different mediums work. A TV newscast needs to keep your attention at all costs. You can’t put it down and come back later, or re-read a sentence you didn’t catch the first time. The visual imagery and on-screen text are essential to accomplishing that task. Fewer words will be used to tell the same story, and in most cases there will be more appeals to emotion. 

Paying attention to these media differences can help you think critically about what you’re taking in and, potentially, make it just a little bit easier to understand the world. This sort of media literacy is vital right now, so I’m going to spend a little more time on it for the next few weeks. First I’ll try to unpack what message is implicit to social media and how that got us into the mess we’re in now. Then, after that, I’ll talk a bit about how I use AI in my work (sparingly) and how my understanding of the way it works as a medium shapes that. I hope you’ll join me.

Tom Bombadil Fan Art by GoldeenHerself

Stuff I Wrote

• Get the macOS Finder to do just about anything by typing natural language commands  WIRED I think this is a pretty cool use of AI. 
• This site lets you browse Instagram without an account Lifehacker At some point I’m going to set up my browser to do stuff like this automatically and I will never need to open a website owned by Meta ever again. 
• Don’t fall for these 4 cybersecurity myths  PopSci I’m having so much fun writing these myth articles—here’s the latest one. 

Stuff You Should Read

• Compression culture is making you stupid and uninteresting Maalvika/learning-loving and meaning-making I’m not going to summarize this because that would completely defeat the point—just read it. 
• The ladder is burning Matthew Hughes/What We Lost Entry level jobs are a thing of the past and it’s only going to get worse. 
• My school banned phones for the year. Here’s what happened. Gilbert Schuerch/After Babel One teacher’s story about how much easier it is to teach when students no longer have the most compelling entertainment device in history in their pockets.