Elegy for the Native Mac App
Remembering the boom and bust of the Mac platform — and what it means for visionOS.
The first Macintosh came out in 1984 with a familiar formula: expensive, limited, but elegant and easy to use. From the start it was something of a cult classic. Apple was struggling financially, and spent most of the 90s on hair-brained ideas: the Newton, the Pippin, the QuickTake. All of them flopped while the Mac languished, half-forgotten. A cult-ish community formed around the Mac because it needed a community just to keep it alive.
That community was still going strong in 2007 when I got an iMac and dipped my toes into Twitter — which at that point was mostly just a fun community hub for all varieties of tech nerd. It has since gone downhill.
To the old-school Mac community, installing some shitty cross-platform Java app on their pristine Macbook was an admission of defeat. Even web apps were avoided whenever possible. They saw the use of such software as a tacit acknowledgement that the PC and its “ugly but effective” mindset had won. The point of paying double the price of a PC was to buy an elevated computing experience, and that had to extend to every third-party app on the system.
So there was a small but devoted market for “native Mac apps”, often called Cocoa apps after the then-modern Mac OS X Developer API (in contrast to “Carbon” and “Classic” apps that used older APIs). Some people started referring to particularly good or beautiful Cocoa apps as “Delicious” to evoke much-loved Delicious Library.
In hindsight it seems odd to ‘organize your library of belongings’ using a bespoke piece of paid software that doesn’t even sync between devices. Today, Delicious Library would be a website, or just a shared Google Doc. It relied on the premise that even boring tasks could be made fun and playful with the right UI, and it worked! I doubt I will ever again be as organized as I was back in the Delicious days.
Of course, using bespoke apps for every task meant buying a lot of apps. An app for managing your books, an app for generating invoices, an app for drawing mind maps, an app for making shiny word-art, an app for burning DVDs, an app for organizing your font collection, and on and on.
Mac software was often expensive and niche. It spread via word-of-mouth, and buying it involved typing your credit card number into a website and hoping for the best (until 2010 there was no official Mac App Store). The Mac community could’ve created their own shared store, but boring e-commerce websites were the purview of PC enthusiasts. Instead, a wacky alternative emerged.
MacHeist
MacHeist was really just your average secret-agent-themed internet puzzle-hunt for Mac nerds. The prize at the wasn’t free Mac software but rather the opportunity to buy Mac software, in a big bundle a la Humble Bundle.
The premise: attract people with a fun game, build a community around it, and leverage that goodwill and mindshare to offer the kinds of bulk sales that weren’t otherwise available on Macs. They also donated 25% of proceeds to charity! It was, at least in theory, a win-win-win.
Even as a website whose ultimate goal was to get you to spend money, it never felt like a growth-hacking money-grab. At least, not in the slimy late-stage-capitalist way of free-to-play games or assertive subscription-plan up-sells. It was well crafted and genuinely fun, especially as later incarnations assigned every user to one of 4 color-coded teams that competed for extra prizes.
MacHeist was an example of what the web could be when not owned by massive corporations. It was the mom-and-pop-shop to Amazon’s Walmart.
That’s not to say it was perfect. Some developers were paid as little as a few thousand dollars for their participation in a bundle that likely net the MacHeist team hundreds of thousands. Mac luminaries like John Gruber and Marco Arment came out against it (although John relaxed his stance after MacHeist started paying more generous proceeds to developers in later iterations). Very few developers ever participated twice.
True MacHeist “missions” (puzzle hunts that culminated in app bundles) only happened 4 times, approximately once every year and a half, with the last one wrapping up in 2012. I remember that fourth one being pretty lackluster too, as much of the core MacHeist team had already pivoted to making iPhone apps instead. In 2016 they sold MacHeist.com to some shitty e-commerce company, and an era ended. Now you can buy outdated Excel Trainings and AARP memberships from MacHeist for some reason — a perfect encapsulation of how soulless the web has become.
A Platform for Creatives
It’s hard to overstate the importance of GarageBand and iMovie for the Mac. Not only were they free, they were installed by default. You could pull a new Mac out of its box and 10 minutes later already be mid-jam-session. For producing music or editing home movies there was nothing even comparable on the PC, at least not for novices.
Apple built a whole ecosystem of creative apps themselves, some more successful than others. Presentations made with Apple Keynote looked way better than anything Powerpoint could churn out, and iPhoto taught a generation of novice point-and-shoot photographers how to improve their craft. On the other hand: Apple Numbers has always been a laughing-stock, and iWeb’s weird newsletter-style websites revealed that Apple didn’t really understand the web at all. I suppose it’s fitting: they were great at art and marketing but absolutely flummoxed by enterprise software and the social internet.
Apple pushed hard to attract artists, filmmakers, musicians, and other creative professionals. It started a virtuous cycle. More creatives using Macs meant more potential customers for creative Mac software, which meant more developers started building that software, which in turn attracted even more customers to the platform.
And so the Mac ended up with an abundance of improbably-good creative tools. Usually these apps weren’t as feature-rich or powerful as their PC counterparts, but were faster and easier and cheaper and just overall more conducive to the creative process.
There was Comic Life for fun posters and greeting cards, iStudio for serious desktop publishing, Kinemac for 3D motion graphics, BoinxTV for live streaming, Coda for web app development. All of these were well-known to Mac users, but none really broke through to become industry-standards like Photoshop or Excel. None, that is, until Sketch.
Sketch is a vector drawing app that, at least for a time, was the de facto software for UX designers. At the time of Sketch’s launch most UX designers were using Photoshop or Illustrator. Both were expensive and overwrought, and neither were actually created for UX design. Sketch’s innovation wasn’t any particular feature — if anything it was the lack of features. It did a few things really well, and those were exactly the things UX designers wanted. In that way it really embodied the Mac ethos: simple, single-purpose, and fun to use.
Sketch took the UX world by storm. Apple started publishing official Mac and iOS design assets in Sketch format. Large companies like Google and Meta migrated their entire design workflows onto it. What started as a single developer’s hobby project now employs 140 people. And, to this day, it’s a native Mac-only app.
That’s where this story takes a turn: In recent years Sketch’s Mac-ness has become a liability. Requiring every person in a large design organization to use a Mac is not an easy sell. Plus, a new generation of “internet native” users expect different things from their software than old-school Mac connoisseurs: Multiplayer editing, inline commenting, and cloud sync are now table-stakes for any successful creative app.
So Figma has taken the baton from Sketch. Even Apple themselves, champions of the Mac platform, have recently started publishing their official design assets for Figma as well as Sketch. That’s not to count Sketch out entirely, but it’s certainly evidence of how the tides are turning.
Many of the great Mac apps are forgotten or abandoned now. MacHeist is a grotesquely reanimated corpse. The golden age is over. The question isn’t whether Sketch will succeed because it’s a beautiful Mac app, but rather whether it can succeed in spite of that.
Who Killed the Mac App?
In my days as the annoying Apple fanboy on Twitter I always figured Microsoft was Enemy #1. If anybody was going to kill the Mac and its pure ideals it was going to be Bill Gates. Well, he’s not on this list.
Instead, I think it’s safe to say it’s largely Apple’s fault. Or, maybe “fault” is the wrong word. We’ve moved on from the era of beautiful Mac software to the era of web-based apps, for better and for worse. There’s no one simple reason for this evolution, but it’s interesting to think through some of the factors.
The iPhone
When the first “I’m a Mac” ads launched in 2006 Macs accounted for a plurality of Apple’s revenue. It made sense for them to advertise hard, to attract developers to the platform, and to invest in their own example-setting Mac apps. Over the next 5 years the iPhone would become a runaway success, and Apple’s priorities would shift to support it.
As of 2023 Mac sales are reaching all-time highs, but Apple’s interest in the Mac as a platform is lackluster at best. This year’s macOS Sonoma release adds some cool new features, but also continues the larger trend of making macOS more like iOS and iPadOS. Apple’s big new ideas for Mac software: iOS widgets and progressive web apps.
Apple is still very interested in selling Macs — precision-milled aluminum computers with custom-designed chips and “XDR” screens. But they no longer care much about The Mac: The operating system, the software platform, its design sensibilities, its unique features, its vibes.
As Apple shifted its priorities, developers came along. There was a gold rush to claim territory on the hot new mobile platform, even with Apple taking a 30% cut of all app sales. Most developers didn’t outright abandon their Mac projects, but they certainly lost steam. There are only so many talented app developers in the world, and only so many hours in the day.
Jony Ive
Maybe this is an unpopular opinion but I miss when Mac apps had character. The calendar app resembled a leather calendar, the notes app resembled a college-lined notepad. Apple maintained 3 official ‘materials’ in its UI frameworks: Glossy “aqua”, brushed aluminum, and a semi-transparent “heads-up display” style. Beyond this, apps were clad in pinstripes and linen, marble and felt, wood and cork-board. Hell, restoring from a backup entailed going to space!
If Jean Shorts can become fashionable again, why not over-the-top software designs? The term-of-art for this style is “skeuomorphism”: modern designs inspired by their antecedents — calculator apps that look like calculators, password-entry fields that look like bank vaults, reminders that look like sticky notes, etc.
This skeuomorphic playfulness made downloading a new Mac app delightful. The discomfort of opening a new unfamiliar piece of software was totally offset by the joy of seeing a glossy pixel-perfect rendition of a bookshelf or a bodega or a poker table, complete with surprising little animations.
This era of Mac app design was helmed by Scott Forstall, Apple’s then-head of software. He and Steve Jobs had worked together since NeXT computer, and had returned to Apple on a mission to make computing more fun and approachable. OS X’s software design paired perfectly with bondi blue iMacs and iBooks, and everything made sense.
Increasingly though, the hardware design team helmed by Jony Ive headed a different direction. Apple became a luxury brand, thanks mostly to the iPod and the iPhone. Mac hardware ditched its colorful plastics for precision-milled unibody alumin(i)um. Meanwhile the software design stayed resolutely ornate, rejecting Ive’s minimalist high-fashion. Purportedly the two teams began to resent each-other.
Ultimately Jony Ive and his hardware team won. Forstall left Apple in 2012 and Ive absorbed control of software design. The very next release of iOS featured a top-to-bottom redesign: the skeuomorphism was entirely gone, replaced by a flat typography-centric design language. The only material left was a Windows-Vista-esque matte glass.
It was controversial. Let’s call it the Cybertruck of its day. Some people loved its clean lines and no-nonsense layout, while others (like me) found it soulless and boring. To be honest, I never grew to like it. I avoided upgrading to Mac OS Yosemite (which introduced the new design language to Mac) as long as I could. Eventually I conceded defeat.
Sure, after almost a decade of refinement the flat UI is perfectly usable and pleasant on the eyes. But it’s no fun! As third-party apps adopted this new design language they lost all differentiation. It became hard, if not impossible, to distinguish native Mac apps from web apps or ports of Windows apps — at least from a UI perspective. The difference between Mac and Windows was no longer fun-versus-dull but rather “Dull™ Deluxe” versus “Dull™ Enterprise”.
Now that Jony Ive has left Apple, part of me hopes for a return to skeuomorphism, but I also know it’s a bit … much. The screenshots I’ve included here haven’t necessarily aged well, nostalgia aside. Still, I think Jony Ive swung the pendulum too far in one direction. There’s room for computers to be just a little bit more fun again.
Practicality
Back in the olden days most people had only one computer, if any. Today, partially thanks to Apple’s marketing department, it’s not uncommon to have a phone and a tablet and a laptop and a watch. Maybe you have a personal laptop and a separate work laptop, or a Mac and a separate gaming PC. It’s reasonable to want your same apps and files to be available across all of them.
Making software is hard. Developing separate apps for iPhone and Android and iPad and Mac and PC and Chromebooks is prohibitively expensive for pretty much any indie developer. There are literally dozens of ways to develop cross-platform apps, including Apple’s own Catalyst — but so far, none of these tools can create anything quite as polished as native implementations.
So it comes down to user preference: Would you rather have the absolute best app experience, or do you want the ability to use an acceptably-functional app from any of your devices? It seems that users have shifted to prefer the latter.
The most famous recent example is 1Password, which began life as a beloved Mac-only password manager. As people got more devices, syncing passwords between those devices became a critical feature. So the company started building 1Password implementations for more and more different platforms until eventually the situation got untenable. In 2020 they set out to rewrite everything around a single shared codebase. Ultimately that meant abandoning their native Mac app for Electron (which is basically just a web app with some extra abilities). There was outcry among some die-hard Mac fans, but for most people: it’s good enough.
Advertising
Apple may have a semi-infinite ad budget, but they use it to tell a cohesive story: what Apple is all about, why it’s cool, why it’s the brand to buy. The Mac and the iPhone tell different stories: the former a story of creative personal computing, the latter a story of an internet-forward luxury lifestyle. Apple had to focus on one to avoid diluting their brand, so they (obviously) chose the more profitable one.
Unfortunately the appeal of native Mac software was, at its core, driven by brand strategy. Mac users were sold on the idea that they were buying not just a device but an ecosystem, an experience. Apple extended this branding for third-party developers with its yearly Apple Design Awards.
In a sense, Apple’s marketing department was so strong that it served as the marketing department for third-party apps as well. And then it stopped. I haven’t seen an Apple ad touting macOS in ages, and no Mac-exclusive app has won an Apple Design Award since 2015.
There is no more “I’m a Mac” Guy. Without the force of Apple’s “Reality Distortion Field” the culture of hard-core fandom has faded.
I no longer am a Mac. I use a Mac, usually — they’re good computers! But that’s just it: for the first time since the introduction of the original Mac, they’re just computers. Yes, they were technically always “just computers”, but they used to feel like something bigger. Now Macs have become just another way, perhaps the best way, to use Slack or VSCode or Figma or Chrome or Excel.
What about visionOS?
The first Vision Pro will come out in 2024 with a familiar formula: expensive, limited, but elegant and easy to use.
VisionOS, the operating system of the Vision Pro, has the potential to be the next Mac. I mean that both metaphorically (the two have a lot in common) and literally — visionOS might entirely replace macOS as the de facto platform for creative digital professionals.
It also might not. I don’t have a crystal ball. But I can at least imagine a future where desks full of bulky monitors and desktop towers are replaced with nothing but a keyboard and a headset. The “Pro” branding implies that this is Apple’s (ahem) vision for the product too. It is not a workout device or a gaming rig or a fashion accessory. It is a face-mounted Mac.
In the last 15 years Apple has created 3 new developer platforms: iOS, iPadOS, and watchOS. Each caused developer gold-rushes, and each has a relatively lively developer community to this day. However, looking at the App Stores for each one, the top apps are mostly bland corporate products. The early days of the iPhone were fun, but in the Jony Ive days post-iOS7 the platform became, well, mainstream. There’s little room for playful indie developers with so much money involved (see last week’s Apollo drama).
VisionOS might be different. First of all, it’s niche. Really really niche. The Vision Pro is extremely expensive and, let’s be honest, mostly pointless. But I’m probably going to buy one anyway, as are hundreds of thousands of other gadget-obsessed nerds. What are those nerds going to do other than develop cool apps for their new toy? After all, buying a $3500 headset just to run normal 2D desktop apps on it is a bit self-defeating.
More importantly: visionOS, and spacial computing more broadly, mark the first time in recent memory that developers will be given more space to work with. The story of frontend software in the 21st century has so far been a story of shrinkage — of fitting apps onto smaller and smaller screens, sacrificing features and playfulness along the way. There’s simply not all that much a developer can do to build a novel piece of software for your wristwatch.
I think developers are going to have a field day with visionOS. Not only can apps be big, they can be 3D! Everything Apple’s demoed so far has been rather flat and grey (Jony Ive’s legacy lives on), but for indie developers it could be the Wild West. Who’s to say this brand new computing paradigm shouldn’t sport 3D bookshelves made of textured wood, or whiz-bang page-flip animations? And who knows what kinds of creative workflows could be unlocked given so much room?
That said, we don’t know the full extent of what’s possible on visionOS yet: whether it will adequately support VR games, or custom hand gestures, or bluetooth controllers. For that matter, we don’t know whether it will allow side-loading of apps outside of Apple’s proprietary App Store (it probably won’t).
This is where visionOS’s story diverges from that of the Mac. Apple is no longer a scrappy upstart. Rather, they’re the largest company in the world by market cap. It’s not so much that Apple doesn’t care about indie developers anymore, it’s just that indie developers often end up as the ants crushed beneath Apple’s giant corporate feet. Or, to use a less cliché and more relevant analogy, Apple is a GMC Sierra pickup and indie developers are small children playing in the road.
Indie Developers just don’t matter to Apple’s bottom line anymore. When they want to show a cool third-party demo at WWDC they can call up industry titans like Bob Iger and Hideo Kojima. So big corporate software developers get sweetheart deals on Apple’s App Store commission while indie dev’s can’t even get their bugs addressed. Plus, if an indie developer has a good idea and finds success, Apple is likely to just copy them.
In short: it’s never been more risky to build a career developing software for any Apple platform, including visionOS.
I think we’ll see a lot of cool indie software for visionOS, but also I think most of it will be small utilities or toys. It takes a lot of effort to build and support apps that people rely on for their productivity or creativity. If even the wildly-popular Mac platform can’t support those kinds of projects anymore, what chance does a luxury headset have?
