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.

Something different for today: a one-hour episode of a podcast A Life Well Wasted from 2025. (I can’t link to it directly, but it’s the most recent episode, called “Game Over.”)

It’s a human story whose beats might be familiar to some of you: a long software project that ultimately failed despite the enormous effort. And it did so in an industry – high-budget videogames – where failures might feel particularly brutal: the projects take multiple years but the defeat can be swift, the servers get shut down and the game instantly evaporates, and instead of employees being reallocated to other games, the studio gets disbanded and people let go.

There are some nice moments in the podcast’s interviews with about a dozen people, hearing about personal pride and responsibility, working together with others, and a certain camaraderie not just with other people, but with their software that develops:

I think the best part about it was being able to play with my coworkers and then cutting loose, and being silly, and really enjoying what we made together, as a unit. That experience alone made it worth it.

There are also questions about the management’s role in all of this – this part we might never get to know fully – and the worry about game preservation.

This is not mentioned in the podcast, but it seems widely understood the story is about Concord, a AAA live-service game that is rumored to have cost a staggering $400 million dollars and taken 8 years to develop, only to be shut down mere 12 days after its launch in the late 2024. (AAA means a blockbuster with highest budgets seen by the industry, and live service means a game like Fortnite, which is expected to make money over time from add-ons and upgrades.)

Learning about Concord’s macro view adds a lot of color to the boots-on-the-ground podcast above, but one has to be careful exploring it; the online discourse about the game felt similar to the 2016 reboot of the movie Ghostbusters where sure, the product might have been subpar, but also a lot of commenters seemed eager to arrive to the conversation carrying truckloads of bad faith, gatekeeping, and misogyny.

Some good articles? Keza MacDonald in the Guardian has a nice summary of the whole situation:

This is a brutal sequence of events. Sony bought the makers of Concord, Firewalk Studios, in 2023. Concord had been in development for eight years, and it was an expensive game, with bespoke cinematics and a long-term plan that would have cost $100m or more to develop. In its two weeks on the market, it sold fewer than 25,000 copies, according to estimates. This is a shocker, even compared with the year’s other bad news for developers and studios.

MacDonald also adds:

Speaking personally, I do not want a game that takes years to play. I want one with something to say, an experience to impart, and one that eventually ends. A game whose artistry comes before its business model.

This is partly a matter of taste. Self-evidently, there is an enormous market for live-service multiplayer games; it’s just that most of those people are already playing one. I highly doubt that there are untapped millions of players desperate for a hero shooter or battle royale game who just haven’t found the right one yet. It’s time that publishers try something new instead.

An article by Matt Kim at IGN adds to this notion:

With so many games now taking close to a decade from the beginning of development to release, we’re starting to see the financial and creative consequences of an overlong development cycle. Spend too much time in development and ideas that were once novel are no longer in vogue. Furthermore, the time and money spent over those years has to be recouped somehow, which leads to decisions like the $40 cost of entry for Concord when many of its peers are free to play.

The cost of coming late to the party means you must bring something new to the table. Unfortunately, Concord is neither particularly innovative nor content-heavy. That said, it does have a level of polish at launch that was often absent from its hero shooter peers when they were first released. Indeed, Concord’s weekly animation story drops are fully motion-capture, and Firewalk’s time spent on crafting its lore has helped secure Concord an episode of this winter’s video game animation anthology series, Secret Level.

But well-established hero shooters like EA’s Apex Legends launched almost bare bones and still managed to make a splash thanks to its intriguing central concept which combined hero loadouts with a battle royale match format. Valve’s Deadlock doesn’t even have finalized assets or art but has still caused a huge burst of excitement among the PC community, thanks to the way it changes up the classic 6v6 hero formula with its heavy lane-and-minions MOBA [Multiplayer Online Battle Arena—ed.] mechanics. By contrast Concord appeared with an all-too-familiar offering and, frankly, the time spent on finessing its presentation – the graphics, motion capture, performance, and so on – likely lead to a later release date which in turn meant it lost valuable time establishing itself among its peers. If it had been released four or five years ago, when the PS5 first came out, maybe its launch would have been an entirely different story.

I think this is important to quote on this blog that often talks about “finessing” and implicitly – or sometimes explicitly – about the value of taking time to get the details right. We can’t forget that there are such things as overdesigning and overproducing, and that ultimately there is no way to polish your way out of something that lacks a soul.

This 25-minute segment on MKBHD’s Waveform podcast (video or audio, segment starts at 40:21) is from November 2024, and is a nice counterpart to the post about favourite well-made apps and sites.

The original theme is “what is an app that you use all the time, and like to use, but is actually a bad app?” but it quickly moves to a more general conversation about good and bad mobile apps.

It’s always interesting to me to see what themes emerge and what other people think is important. Here’s the list where I linked to relevant apps as long as I could find them:

Bad apps:

• Google Messages – dinged for unreliable spam and lack of organization/​filtering
• Notion (on mobile) – hard to orient yourself and some direct manipulation is wonky
• many smart home accessory apps – bad and redundant with Google Home, but have to keep for emergencies
• Netgear Orbi (network router) – specific functionality and bad password recovery
• Hatch (white noise machine for babies) – simple things are hard to discover
• Nest app/Nest Yale Smart Lock – bad integration
• Goodreads – stale

Good apps:

• ButterflyMX (smart building lock app) – reliable
• UDisc (score keeper for disc golf) – good functionality, great in a free version
• New York City ferry
• New York City ticket payment – reliable and has many payment options
• Greenwich, CT and San Francisco parking apps – live activities
• The StoryGraph – cool graphs and stats about your book reading patterns

Found listening to this 2-hour episode of The Talk Show podcast with Daniel Jalkut very enjoyable, and more thoughtful than just “bitching about Tahoe.”

One particular thing that stood out to me was a discussion of shame and embarrassment and pride that all come with shipping software. And looking to Apple itself for direction that the company is not really providing, as many of their apps are not using the new Liquid Glass interface – or when they do, they use it in ways that are inconsistent or disappointing.

Some other good themes:

• it’s okay not to change something if the alternative is change for the sake of change, a posture Apple’s hardware team feels more comfortable with than Apple’s software team
• internal Apple politics and the story of the Control Strip
• loved this phrase from Gruber about the macOS’s Tahoe release: “they vandalized it.”

Also, this:

A fair criticism of Apple over the years is that sometimes fixing 50 little misaligned text boxes or divider bars… using your time to do that, is time better spent than adding another user feature.