A thoughtful essay by Nick Heer as a sidebar to the annual Apple/Six Colors report card, in which he proposes this simple framework:

In short, the way I think about software quality is the amount of meaningful problems. […]

There are problems in Finder — resizing columns, renaming or deleting files synced with a FileProvider-based app, and different views not reflecting immediate reality. There are problems with resizing windows. AirPlay randomly drops its connection. AirDrop and other “continuity” services do not always work or, in an interesting twist I experienced a couple days ago, work fine but display an error anyway. The AirPlay and AirDrop menus shuffle options just in time for you to tap the wrong one. […]

These are the products and features I actually use. There are plenty others I do not. I assume syncing my music collection over iCloud remains untrustworthy. Shortcuts seems largely forgotten. Meanwhile, any app augmented by one of Apple’s paid services — Fitness, News, TV — has turned into an upselling experience.

As I’m reading this and thinking about my own Apple usage patterns and a similar litany of problems, I keep returning to Apple TV, which feels by far like the most stable and least troubled platform. I wish I had a better explanation for it: Is Apple magically really good at TV interfaces? Are their benefitting from it being a “hobby project”? But I think the Occam’s Razor here is this: tvOS is just a lot simpler.

And just like that, a thought appears: Is what we’re seeing overall is really just Apple losing the battle with complexity?

Apple won once, in the late 1990s, when on the hardware side all the Performas and Newtons and LaserWriters were cut ruthlessly, and on the software front Mac OS X pushed Classic away as the operating system. The situation was different then, however, because there was no other choice. Today, Apple seems successful on paper, so the pressure needs to come from inside, from someone high up enough to recognize that what Apple is doing vis-a-vis software quality is not sustainable and hasn’t been for some time now. That the bill already came due on all of the decisions where systems thinking and deep testing and focus and preventative maintenance and paying off design debt have been deprioritized in favour of another shiny launch event that stretches the teams and platforms even thinner.

When thinking about complexity, a different go-to framework I have is “can I explain a situation in a short paragraph?” This can help separate regular bugs (where the explanation is typically: I am doing the thing that used to work and it’s no longer working, so something broke), from bigger problems that require some serious long-term system-thinking approach. Off the top of my head, there are many things I can no longer explain:

• I cannot explain Apple’s widget strategy
• I cannot explain what is going on with the Fn/Globe key
• I cannot explain the long-term thinking surrounding icons in Tahoe menus

Of course, it’s not me who should be explaining those things. And I haven’t done this exercise before so I don’t know for sure if things are getting worse here. It feels like it, though. I wonder if Apple just hit a limit of some sort of being able to deal with complex things, and first course of action should be: don’t throw even more complex things on your plate.

A good thought from Dr. Drang, too:

It’s probably impossible to tell the upper echelon of Apple that it’s breaking revenue records in spite of its software design, not because of it. I hope the next regime knows better.

A good batch of history and observations by Nick Heer at Pixel Envy about ads coming to AI chatbots:

It is incredible how far we have come for these barely-distinguished placements to be called “visually separated”. Google’s ads, for example, used to have a coloured background, eventually fading to white. The “sponsored link” text turned into a little yellow “Ad” badge, eventually becoming today’s little bold “Ad” text. Apple, too, has made its App Store ads blend into normal results. In OpenAI’s case, they have opted to delineate ads by using a grey background and labelling them “Sponsored”.

Now OpenAI has something different to optimize for. We can all pretend that free market forces will punish the company if it does not move carefully, or it inserts too many ads, or if organic results start to feel influenced by ad buyers. But we have already seen how this works with Google search, in Instagram, in YouTube, and elsewhere. These platforms are ad-heavy to the detriment and frustration of users, yet they remain successful and growing. No matter what you think of OpenAI’s goals already, ads are going to fundamentally change ChatGPT and the company as a whole.

Yet another good post by Nikita Prokopov, continuing the theme of icons in Mac OS Tahoe (previously), going into more depth:

In my opinion, Apple took on an impossible task: to add an icon to every menu item. There are just not enough good metaphors to do something like that. ¶ But even if there were, the premise itself is questionable: if everything has an icon, it doesn’t mean users will find what they are looking for faster.

I always liked this kind of an exercise:

There’s a game I like to play to test the quality of the metaphor. Remove the labels and try to guess the meaning. Give it a try:

Also, this must hurt:

Microsoft used to know this.

Nick Heer at the excellent Pixel Envy, commenting on the above post, adds:

This is a gallery of elementary problems. None of this should have shipped if someone with power internally had a critical eye for consistency and detail. If Apple deems it necessary to retain the icons, though I am not sure why it would, it should be treating this post as one giant bug report.

h/t my friends Scott and Ezra.