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. ”

The quote is from a long read about the Playdate’s inception (also available as a well-made podcast ep), which is worth checking out.

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.

From a 2016 AV Club article:

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 title of the post comes from the Playdate’s making of essay.