Here’s what happens when you try to update your Android phone if it’s low on battery (even if it’s connected to a charger):
It’s a pretty cheap error UI, a misaligned string thrown carelessly in between existing interface pieces. It doesn’t even bother explaining what “too low” means.
Compare this to what the Playdate does in the same situation:
If the device battery is depleted, the software simply charges if first to the necessary minimum (spelled out on screen), before automatically proceeding to the actual update – all without any user intervention.
We previously talked about fire-and-forget states, or interfaces which give you confidence that once the process starts, it will finish on its own. (If you don’t like military references, we could call these tap-and-walk-away.)
This is a really good example. There is even a nice corresponding version for when your Playdate needs to be plugged in first:
Once you do, the process again continues by itself right until the end.
I often link to John Gruber’s Daring Fireball posts with a nod, but this time around I want to offer an opposing point of view. About a month ago, Gruber linked to a Markdown editor written by Sean Malseed in 2026 for the early 1980s Macs, and commented:
I absolutely love that this exists. I don’t like the actual app at all. I guess “full screen” mode is the point of some “distraction free” editors, but I for one would never look twice at a Mac app that didn’t use windows. Full-screen mode just wasn’t a thing back then, except for games. ArtfulType is not a Mac-assed 1984 Mac app.
I posit: It doesn’t have to be. It’s not 1984, after all.
I actually really loved the creator of ArtfulType bringing back a few pieces from the future into the past: the fullscreen/distraction-free editing, the dark mode menu bar, the shy scrollbar. Those anachronisms felt exciting to me. They made me wonder: What if dark mode was invented decades earlier? What if Mac had a different windowing mechanism? What if we could do it all over again?
I recently linked to Sopwith, which felt interesting in the same way, and I thought I would expand on this and share a few favorite examples of similar projects that inspired me in recent years.
Playdate
Confession: I’m not a fan of Teenage Engineering. I find their products well-put mechanically, but lacking in thought and soul, a certain apotheosis of “capital D Design” that feels as incomplete as it is masturbatory. (Rabbit R1 was a perfect example, consumed by gimmicks and strange design decisions.)
Good news is that Playdate is not a Teenage Engineering project, and that it was actually initiated by the software company Panic, which gave it copious amounts of thoughtfulness and care. Playdate is a 2022 handheld game console, and a fun little device that’s intentionally anachronistic. Its design picks the best parts of each decade: the gadget excitement from the 1980s, the onscreen aesthetics of the 1990s, the social internet of the 2000s, the explosion of indie games from the 2010s, all wrapped in contemporary build quality.
Playdate is partly made out of metal and pleasant to hold and touch in a way no vintage gadgets ever were – this is where Teenage Engineering does deserve a credit – but sports an old-fashioned monochromatic display that seems to be harking back to the darkest years of the first Gameboy… which is very, very deliberate:
I love the black and white, 400 by 240 pixel Playdate screen. I kind of like don’t want to design in anything else anymore,” says [Panic designer] Neven [Mrgan]. “It is so freeing for me, personally, to not think about the color and not think too much about, like, even things like line weight and whatnot. ”
Playdate’s games are equally spread across time as if in a horrible time travel accident – some with simple mechanics utilizing the gimmick of a crank, others with much more modern or artful sensibilities. Many, confusingly, with both. Some also come packaged in a novel system of seasons, where the games drip onto your machine at a pre-determined rate, meant to mimic surprises and serendipities one could encounter in record and software stores of yore.
PICO-8
I’ve been profoundly inspired by this talk by Joseph White, explaining his “fantasy console” called PICO-8, introduced in 2015:
PICO-8 is Playdate abstracted away. It flips the world order on its head – emulators are known to emulate existing hardware, but what if they emulated imaginary ones? Why not imagine a gaming console that was never made?
The wild part of this approach is that it automatically gets rid of a lot of unnecessary nostalgia, focusing instead on crafting “hardware” and software precisely calibrated to achieve things White wanted them to achieve.
PICO-8 has a puny 128×128 resolution that makes Playdate feel like IMAX (although with very deliberate 16 colors), and many other constraints that would feel ridiculous even 30 years ago. They are, once again, brought back from the past intentionally – chiefly, to avoid “design fatigue.”
At the same time, PICO-8 doesn’t revel in the past – it also comes with built-in suite of tools, and support for modern keyboard and mouse for development. Its cartridges are not only a single file to allow easy distribution on the web or otherwise – they’re also literally baked into PNG files so the spreading can be even easier.
White’s software chimera works because he understands where nostalgia ends and the needs of modern development begin. PICO-8’s idiom, for example, is a custom subset of Lua, an easy-to-approach language likely familiar to many game programmers, whether they script emulators or use the free 2D engine LÖVE. Though PICO-8 initially ran BASIC to stay true to its ’80s pedigree, White switched because “Lua has a small footprint and is portable and quite fast. I think any language could have worked though, as long as it allowed the user to mess about in an unstructured way without worrying about programming style.” PICO-8 Lua feels snappy and sensible. There are just enough functions to get up and running quickly without the bulky overhead of complex libraries or object-oriented syntax. Need to draw a sprite? Provide an index and two coordinates. A circle? Coordinates, radius and color. It’s fast and friendly for programming beginners.
The conference talk above and the design of PICO-8 are dripping with intentionality; even the startup chime is meant to evoke a feeling. At some point White went as far as to consider whether his console would glitch nicely if its software was buggy, and then mentions “I designed a [more advanced] PICO-16 just to remind myself to not make that” – a really interesting technique to help him zero in on what he really wanted.
White also expressly states “I value design over content,” which is another thing his project has in common with Playdate.
PICO-8 saw all sorts of software developed for it since 2015 that you can all play online – from the absolute platforming classic Celeste, to a series of unofficial “demakes” like WarCraft III, complex games like SlipWays, or even tools like PicoCAD. The hardware is confusingly powerful enough for Poom (a clone of Doom) to exist, but then there’s also tons of delightful tweetcarts, cartridges whose code used to fit inside a single tweet.
Infinite Mac
PICO-8 started as an emulator for an imaginary thing. Infinite Mac, despite emulating really well-known Macs from the 1980s and 1990s, can also inspire in its imagination.
Made by Mihai Parparita in 2022, Infinite Mac is all about focusing on the right details. Emulators of vintage Macs existed before and, as a matter of fact, Infinite Mac uses those very emulators under the hood. But the glue that holds them together is Infinite Mac’s real and wonderful contribution.
If you’ve ever used an emulator, you know they are usually incredibly unpleasant to set up. You have to find a ROM that fell off of a back of a truck, set up the drives and the media inside, and fight with the poorly-designed settings and a UI that often feels like an afterthought, with the whole thing often feeling more rickety than the very 40-year-old machine it’s trying to approximate.
Infinite Mac awaits you in the browser, literally two clicks away counting this one (there is no step three!). It doesn’t show all the possible options, but curates the most useful machines instead.
The emulation is precise but Infinite Mac also – and this is my favourite thing – breaks the fourth wall in some truly useful ways. You can drag a file into the emulator and it just does the right thing with it. You also set up a magical folder that connects to the host machine both ways, in a way that was simply impossible to do back in the day.
There’s also a CD drawer underneath, and a wonderfully seamless integration with Macintosh Garden’s library of vintage software.
It’s the same story as with Playdate and PICO-8: a lot of intentionality and effort and cherrypicking so you get the best of an earlier experience without the worst of it. Pick a Mac, and use it without worry; Infinite Mac keeps the Macs both faster and more reliable than they used to be. (In a beautiful repudiation of modern software practices, I have heard of people who launch Infinite Mac to write in old word processors not just because they’re simpler, but also because they’re faster than the modern native apps.)
Parparita occasionally writes about the project on his blog; those entries are rather technical, but sometimes also highlight various design considerations (I particularly enjoyed the NeXTSTEP entry).
Epilogue
I was at the Vintage Computer Festival West recently, and for the first time I noticed how many young people were there. This got me excited. It’s one thing to revisit those old machines just to relive your own years of (likely imagined) glory, but yet another to see people see them as inspiration: to encounter computers that were simpler, unencumbered, unenshittified, and with software you could understand, remix, and own.
I hope some of those people find inspiration in the past without succumbing to it as a whole, pushing and pulling on it like the creators of Playdate, PICO-8, and Infinite Mac did.
I think that kind of push and pull is important, especially today. I don’t love using Google Sheets, but my favourite spreadsheet is not Excel 97, either. My favourite spreadsheet is some hypothetical anachronistic version of Excel 97 that also has modern high-dpi typography, and a ⌘K command palette, and today’s trackpad gestures, and support for AVIF and HEIC.
Of course, there is immense value in studying the past just so we know what was already made or just explored, what is worth being aware of, and what could deserve remixing. But it’s not great to get stuck in history.
When you venture out to do some time travelling, you get the booklet with all the rules: don’t interact with another version of you, don’t flirt with your mother, definitely steer away from any butterflies. I love that these projects, and others like them, ignore all those rules.
The software company Panic has a blog, and has had it since 2009. It has a clean, modern aesthetic that looks something like that:
However, something interesting happens as you start going back in time by clicking Older Posts at the bottom – the historical posts are rendered using their original styling:
This isn’t something that happens for free, as with any redesign every piece of content gets ported to a new framework and style by default. So, I gather this was an intentional thing that also required extra effort both to make it work like this to begin with, and to allow the old style to appear nicely within the different confines and technical realities of the new style (you can compare the above screenshot of Firewatch announcement as retrieved today with its original appearance in the late 2015).
I love this effort. I wonder if more places on the web could use that kind of thinking. As an example: what if your social posts or blog posts from long ago came adorned with the same avatar that you used when posting them, even if you updated it many times since?
Beagle Bros was a 1980s software company making apps for Apple II that is still remembered fondly for their personality.
The company had a hobbyist slant, selling various small tools and collections with fun names like Beagle Bag (in the “Indoor Sports” collection) and DOS Boss and Utility City – similar perhaps to Norton Utilities on the PC side, but with a lot more fun and charisma. This is one of their loading screens, also showing both their recognizable logo and their endearing quirkiness:
How do you understand a man who has three clocks on his wall, showing the time in three different cities-San Diego, Fresno, and Seattle-all, of course, showing the same time (″If anything changes in those cities, we’ll know about it”)?
(I find the anachronistic combination of hedcuts and dot matrix printer typography particularly fascinating.)
Some of their software was more serious; Beagle Bros released many useful tools and even text editing and presentation apps. They also made practical posters:
But other stuff…? It was just goofing off:
How does this relate to craft and quality?
There is this interesting question about how much product and marketing and vibes and lorecorrelate. Did we forgive Sierra On-Line the numerous flaws of their games because we liked the company? Do we love Panic because we like what they do, or because of how they do it? Did Google put doodles on its homepage to distract people from more nefarious things, or because it just felt like a fun way to celebrate things? Is there such a thing as pure selflessness? What is the nature of free will?
Those are, perhaps, topics for future posts.
But Beagle Bros must have been doing something right if there is still a living, elaborate catalog of their works online, 40+ years later. Jeff Atwood also argued in 2015 that it was more than just fun – or that “fun” itself can give back in great ways:
Here were a bunch of goofballs writing terrible AppleSoft BASIC code like me, but doing it for a living – and clearly having fun in the process. Apparently, the best way to create fun programs for users is to make sure you had fun writing them in the first place.
But more than that, they taught me how much more fun it was to learn by playing with an interactive, dynamic program instead of passively reading about concepts in a book. […]
One of the programs on these Beagle Bros floppies, and I can’t for the life of me remember which one, or in what context this happened, printed the following on the screen: “One day, all books will be interactive and animated.”
I thought, wow. That’s it. That’s what these floppies were trying to be! Interactive, animated textbooks that taught you about programming and the Apple II! Incredible.
Steven Frank, the co-founder of Panic, wrote this in 1999, with similar themes:
You never knew exactly what you were going to get. I remember one program listing printed on the side of a bird that, when run, produced a series of wild chirping noises from the Apple’s speaker. And this was from a program that was only five to ten lines long. As a neophyte BASIC programmer myself, I was stunned and amazed. How could you make something this cool with this small amount of code? […]
Beagle Bros’ tools were fantastic. They literally let you do the (allegedly) impossible, like change the names of operating system commands. And they always packed the disks full with extra stuff. Demos of their other products, and strange graphics hacks that existed for no reason other than the fact that they were cool, and because there was spare room on the disk. Beagle Bros. had a lot to do with why I ever wanted to learn programming in the first place. […]
I’ll never forget the book. […] The book was a huge compilation of all around interesting stuff. Weird Apple II tricks that were pointless, but endlessly fascinating. Like the fact that there were extra offscreen pixels of lo-res graphics memory that you could write to, that never got displayed. Or how to put “impossible” inverted or flashing characters into your disk directory listing. Or how to modify system error messages. Not very useful, but really fun to know and really, really cool to mess with. My dad was convinced I was going to somehow break the computer with all this hacking, but a simple reboot always fixed everything.
(I swear I did think of Panic above as a spiritual successor to Beagle Bros without knowing that their work literally inspired one of the Panic’s founders!)
The subtlety: They had utilities which would produced formatted Basic listings and they would give example output of these utlities in their ads and catalogs. It was quite a while before I realized that most of those examples were not program excerpts, but complete programs which of course contained the Beagle Bros signature weirdness. And then there were the seemingly innocent hex dumps. My favorite was from the cover of one of their catalogs, which had a classic picture of this fellow sitting in a chair. On the floor next to him is a handbag with a piece of tractor paper sticking out. On the paper is a hex dump: 48 45 4C 50 21 20 and so on, which are ASCII codes that spell out the message: “HELP! GET ME OUT! I’M TRAPPED IN HERE!----SOPHIE”
After the work the company had done on AppleWorks 3.0, Simonsen felt ready to jump into the Macintosh market with a “Mac AppleWorks” of their own – they called it Beagle Works. Unfortunately, other companies – giants in the Mac market such as Microsoft, Claris, and Symantec – had the same idea. Their resources were far greater than Beagle Bros had imagined, and the race was costly.
The gamble killed the company. It’s likely that the changing software market would anyway.
But the years before seem to still inspire some people. Check out the Beagle Bros Repository – the homepage is a bit confusing (I think it prominently shows last-updated or last-added things for some reason?), but just use the nav at the top. Maybe it will inspire you, too.
What are you favourite well-made apps or sites? Phones and computers alike.
Doesn’t have to be “pretty,” but well-made according to whatever definition works for you.
I specifically made it kind of vague, and these are the answers I got. I grouped them into categories and added links. I am excited to dig into these and study them, but wanted to share a raw list as well in case this inspires some of you, too.
Thank you to everyone who participated! (Numbers in circles like ② or ③ mean more than one person nominated a given site or app.)
Info sites:
Ian’s Shoelace Site ② “A «does one thing well» site. Great breadth and depth. Information architecture designed to help you discover/find information, not sell you something. Loads fast. Still maintained after decades.”
SCELBI Computer Museum. “Useful, tightly curated, organized, loads fast, no BS. A basic bootstrap thing, but there’s something magical about it. Small enough to be digestible in an hour, well set up for either research or just cool vibes . Partly bc subject itself is «small» but seems not only that.”
“I’m in love with Maggie Appleton’s site. The general design and the illustrations, the content (from quick notes to polished essays), the way it creates a visual and conceptual taxonomy with the #digitalgarden concept.”
Mimestream ③ “It basically stays out of my way? Which is about as good as it gets these days. Also, it has just enough customization options to handle my sometimes complex number of gmail accounts (personal/work, for various clients, etc.)”
Things ② “The fanciest, most attention-to-detail software I know of.”
Sup “Pretty niche. I’m thinking specialist interfaces for specialists here. Tools that become an extension of their users’ bodies and disappear in te use”
McMaster-Carr ④ “The best online catalog.” “Impossibly fast. Still in awe after all these years.” “It supports your cognition, including with contextual material, to find the thing you are looking for (or the thing you didn’t know you were looking for until you started looking). It helps you find the right part because of what they show, the right filters, and especially the contextual information (I think about the little scale they had to explain the different hardnesses of rubber, for example).”
Cars&Bids. “Fast, functional, and easy to use. Not stunning, just utilitarian.”
iA Writer ② “Simple and effective, using it I always wish to write more but I forget it again.” “Has been consistently great for years.”
“I’ve been using Bear ② by Shinyfrog for my notes for well over a decade now. Dependable, works great, no junk ware, and a reasonable price. Pretty to boot. The fact that in the 10+ years I’ve been using it, there’s only been a single major overhaul update is a feature, not a bug to me.”
“Notability! Haven’t found anything else that matches the flexibility for handling imported files & photographs, typed notes, hand-drawn diagrams and mark-ups completely seamlessly within a single document. Unbeatable for handling both notes in class (uni) and on site (trade).”
“Been using OmniOutliner daily for decades. Simple, focussed and matches the way I think. Lots of ways to make lists and outlines but this one works for me.”
“The radio station WFMU streams online, and also has a website where you can log in to chat with other listeners and interact with the playlist. The degree to which it does what you want it to do is stunning. It doesn’t get in your way or make you learn a new paradigm; it just makes it easy to do what you want to do. It’s a lesson in design for any UI/UX people.”
Ishkur’s Guide To Electronic Music. “This website maps out all the sub-sub-sub-genres of electronic music, with descriptions and samples. I think that the fine-grained classifications are comical, but they do an excellent job of what they’re doing.”
“Easy Metronome is a simple elegant loud phone metronome that is super easy to use even for weird time signatures.”
“Pro Metronome is also excellent. I’ve used it for over 10 years and it stubbornly refuses to abandon its skeuomorphic leather and big clicky scroll wheel”
“I really appreciate the Apple Music Classical app (even though it exists in this odd liminal space beside Apple Music) having spent many years frustrated about how traditional music streaming services handle classical recordings.”
“I‘m travelling with Deutsche Bahn quite frequently, and while their own App (DB-Navigator) is quite good compared internationally, I prefer to track trains on Bahn Experte for its bare, technical and valid information and performance.”
“The Man in Seat 61 is a goldmine for train travellers. At least in Europe, the information is really up to date and if you want to find pictures of the sleeper cars of the Romanian railway or the seat map of Prague - Berlin trains, it’s all there.”
“The kiosks in Costco’s food court aren’t the prettiest to look at but they are S tier for responsiveness. You literally just press a button and immediately the item is added to your cart. You can order a hot dog and soda in under 5 seconds.”
“WebWormhole for functionality, encrypted data transfer between your devices or to your friends without installing anything. (There’s also a similar magic wormhole CLI tool.)”
PairDrop. “Drop-dead easy file sharing on the local network.”
“LocalSend is well made, because until sofar it aleay works, even when AirDrop doesn’t. And it also works on non-Apple environments.”
Other nerdy tools:
RegExr. “A web-based tool to create or explain regular expressions.”
“The Sway compositor. A keyboard-driven tiling window manager with dynamic tiling layout. I can’t even imagine trying to use a computer with floating, overlapping windows anymore; everything lines up perfectly and adjusting layout is a matter of a few extremely quick keyboard shortcuts. They take a concept—laying out multiple windows on a display without gaps or overlaps—and build a fast, coherent interface around that concept, and it works fantastically.”
“The original HP 42S calculator packed a lot of power into a convenient and ergonomic enclosure, and Free42 is a very tasteful recreation and expansion of that device for modern platforms.”
“The Kanji Study dictionary on Android has a wild amount of polish, I’m consistently impressed by how much effort has been put into it, especially because it’s sold for a (admittedly high) one-time fee.”
