Saturday, February 12, 2022 [Tweets] [Favorites]

Improving macOS Widgets

Stephen Hackett:

Apple killed off Dashboard at exactly the wrong time. Just one year after Catalina killed Dashboard, Apple started allowing developers to bring their iOS widgets over to the Mac in macOS Big Sur. Sadly, they all got stuffed into the slide-out Notification Center user interface[…]

Notification Center is a real mess. Even on a Pro Display XDR, you get three visible notifications. That’s it.

They’re narrow, too.

I was not a heavy user of Dashboard, but I miss it because the new iOS-style widgets are a huge regression. They’re not interactive. They generally have fewer features or display less information than their iOS counterparts, despite having access to the Mac’s larger display. And they’re unreliable. My Mac frequently forgets all my widgets. I configure them all again. They persist for a few reboots, then sometime in the middle of the day they’ll spontaneously disappear again.

Steve Troughton-Smith:

Widgets need a permanent home in the Mac UI, not hidden off in a Notification Center nobody looks at anyway. Alternative would be massively improving Launchpad to work much more like SpringBoard, and allow you to set that in place of your desktop

John Gruber:

But forcing them into Notification Center on MacOS is poorly considered. The Mac has bigger displays than any iPad, yet has less screen real estate for visible widgets than an iPhone.

Nick Heer:

At WWDC 2007, when Steve Jobs announced the “sweet solution” for iPhone apps, Dashcode was envisioned as a way to build those web apps. The idea was that developers could take their existing Mac OS X widget and convert it to work as an iPhone web app. That, obviously, was not well-received, and an official SDK for native apps was launched the following year. Dashboard withered and died, but not before Dashcode bit the dust. Yet, it took until just a couple of years ago for widgets to once again be a multi-platform effort, now with SwiftUI and, as Hackett wrote, without interactivity. Curious.

BasicAppleGuy:

When Mac OS X 10.7 launched in 2011, Dashboard stopped being an overlay and became a separate page accessed via a swipe gesture, hotkey, or the LaunchPad. By OS X 10.10, Dashboard was disabled by default, and in macOS 10.15, it was removed from the OS entirely.

[…]

Many factors contributed to the success of widgets in iOS 14. First, Widgets became more customizable and provided users with the content they care about. Second, Widgets became more prominent; rather than being relegated to the side panel, Widgets adorned a user's Home Screen however they liked (a 'however they liked' that remains strictly restrained by Apple as to the placement and size of said Widgets). And lastly, third-party apps flooded the App Store allowing for the creation of custom Widgets which furthered the degree of personalization available. This personalization for content, coupled with increased visibility and an enthusiastic developer base, propelled Widgets to popularity. With Dashboard on Mac OS X, Apple did little to promote or enhance the platform beyond its initial release, and widgets were slowly set adrift into a sea of forgotten features.

JF Martin:

This is what we get: a small, vertical, cramped band of widgets. The interface is complex, slow even of fast Macs. I don’t know why Apple is confining them in this small and constrained space, maybe for the sake of some sort of cohesive visual experience to Apple’s other hardware platforms. This design is based on arbitrary rules that we, the users, cannot be related to anything as we have the big screen has a reference. I don’t think Apple had to create such an experience just to make it easy to select a widget and its size. I find it surprising that nobody thought of mocking up a better way of managing widgets in the modern era.

Previously:

Update (2022-02-16): Stuart Breckenridge:

For all of the reasons in this article—and more—we decided not to implement widgets in #NetNewsWire on macOS.

Riccardo Mori:

The usefulness of Dashboard and the concept of the ‘desk accessory’ or widget started waning for me as soon as I got my first iPhone in 2008. Ironically enough, for many quick tasks and quick information retrieval, the iPhone has become the tangible desk accessory. In a way, fetching the smartphone to check things like the weather forecast, the status of a package that I should receive soon, or to make a calculation or unit conversion, is less disruptive of the workflow I’m having on the Mac than having an overlay or a dedicated space within the Mac UI itself.

[…]

Konfabulator’s approach was to embed the widgets in the desktop itself, where they remained, beneath all open windows and apps, always ready to be glanced at when needed, and existing rather unobtrusively when not. If you needed to customise them, you could do so by using the Konfabulator menu extra or by right-clicking on them directly.

[…]

A similar approach can also be seen in Panic’s Stattoo, an app developed in 2004–2006 that certainly didn’t want to replace Konfabulator or Dashboard, but whose idea was to offer a limited selection of widgets that could be placed on your desktop and display useful information like weather, date/time, battery status, song playing in iTunes, email headers, even RSS feeds.

24 Comments

The problem with OS X is that it has no home screen. Apple needs to kill the desktop folder, which is just a dumping ground for uncategorized files, and turn it into a proper home screen for apps and widgets, and for shortcuts to file that the user added with intent, and that have a permanent place of residence elsewhere.

Please god no to replacing the desktop with a homescreen.

The MacOS equivalent of the iOS “Springboard” already exists: it’s the app called Launcher. Maybe that would be the best place to reintroduce good ol’ floating Dashboard widgets.

Apple should never get rid of the Desktop folder as a location for storing files… it’s convenient, and intuitive. Even if too many folks use that functionality improperly, and allow icons to pile up. Maybe the OS could make it easier for users to keep it organized (by which I mean, encouraging users to sort their files in an appropriate subfolder under Home, other than the desktop).

The desktop is where my screenshots end up, and that's it. Surely there could be a better use for it?

It's kinda funny how nobody has nailed this on the desktop.

Microsoft had the Longhorn/Vista Windows Sidebar with widgets; when that didn't prove popular, they changed those widgets to work right on the desktop in Windows 7; then by Windows 8, they removed that API altogether (and prevented 7 from downloading those widgets, too) in favor of Live Tiles on the new Start Screen; that didn't work either, so they changed the Start Screen back into a Start Menu with Windows 10; those, too, are gone by Windows 11 in favor of a different widgets API.

Apple went through a similar journey. 10.4 Tiger introduced Dashboard as an overlay; 10.7 Lion (optionally, I think?) made it a separate Space; 10.15 Catalina removed it altogether. Meanwhile, incompatible widgets in the Notification Center were introduced.

So both OSes have experimented full-screen overlay, separate virtual desktop, sidebar.

Another thing that's striking is how modal all of these approaches are: all three largely prevent you from using any other app until you're done using the widget. Not very multitasking-friendly.

I imagine part of the answer is that widgets just aren't as appealing on desktop OSes. We already have windowed apps for one extreme and status items/menu extras/notification area icons for the other; widgets are somewhere awkwardly in between. That's not the case especially on iOS, where widgets are basically the only way for a third party to show status (beyond an unread badge), other than running the app as a whole.

The other part could be that quickly glancing at information might be a more common use case on a phone than on a desktop.

I can't help but wonder what usage statistics are for Launchpad. It's there in the Dock by default, I think? And it's also F4/fn-F4 on my MacBook keyboard. (There's also a gesture, but I seem to have disabled it at some point.) About 11 years in, how many relatively new Mac users have always used their Mac this way? How many old-timers have migrated to it? If the answer is: quite a few, then Apple should indeed expand Launchpad by adding widgets support. But for everyone whose Mac workflow doesn't involve Launchpad (it really doesn't fit my concept of a Mac at all), I'm not sure what the solution is. Perhaps Dashboard originally got it right — have an entirely separate overlay.

Right: the utility I was thinking of is called Launchpad. “Launcher” is the name of the somewhat similar utility that was part of the good ol’ “classic” Mac OS.

I’ve always thought that the new-style widgets that appear in the Today sidebar would be more useful if you could make the sidebar “sticky”, and let it stay visible and active while using apps. Instead, the sidebar steals focus.

I miss Dashboard, now that I've been forced to upgrade to Catalina on my work Mac. Trading Dashboard for daily kernel panics feels unfair, and Notification Center has always been a waste of main menu real estate (although at least I finally stopped accidentally hitting it instead of Spotlight).

Anyway, as a Mac user for the better part of 40 years, I don't care if anyone thinks I'm using the Desktop improperly to store files and the dozen or so projects I'm working on at any given time.

Go away and play with your single-window tablets and gridded icons sorted by name, and leave the Mac-using adults with spatial memory alone. Launchpad reminds me of Launcher from classic Mac OS: garish and useless, except for grade schoolers.

Dashboard devmode let widgets float above your Desktop, on top of your apps. This wasn't a final destination for the UI interaction, but it was a path that should have been explored.

Konfabulator (https://apple.fandom.com/wiki/Konfabulator; https://daringfireball.net/2003/02/konfabulous)was the best widget-ing system because you could place them anywhere on your desktop and set what layer they sat on, e.g. behind apps, floating, desktop only, etc. The widgets were all written in Javascript with HTML and CSS to mod their UIs. Then Apple released Dashboard, a sub-par experience from the beginning with more flash than substance and Konfabulator was dead of course. Dashboard copied/stole/enshrined (depends on your POV really) everything about Konfabulator except its finesse and flexibility.

Dashboard would always be wonky. Things improved slightly when Apple made Dashboard a space, but kept the option to be an overlay too. I resisted Catalina mostly because Dashboard still worked and was/is a major part of my workflow with the conversion, weather, clocks, and ASCII table widgets being the most useful. The weather widget died two years ago. The conversion widget died in 2021. The clocks and the ASCII table widgets still work but Dashboard is so much less useful that it was under Sierra which was the last time anyone paid it any love.

The brokenness of Dashboard, only one 32bit app left (iViewMediaPro anybody?), and the rise of software updates that require a minimum of Catalina, bcoz universal code bases, will drag me kicking and screaming into the three-years-ago future with a Mojave virtual machine.

I hate Notification Center for the sole reason that the Growl team wrapped up their project upon Notification Center's release and of course, Growl had the finesse and flexibility that the other does not. Notification Center alerts either linger for-freaking-ever or disappear before-I-can read them. There is no per app fine tuning. I cannot control where the alerts appear or style the appearance of the alerts.

Both Notification Center and Dashboard are bland offerings from an increasingly bland company that, but for the rare reminder, shows off flashy hardware with subpar or ill-conceived software.

"leave the Mac-using adults with spatial memory alone"

Spatial? Oh, so you're still using System 8? That's great, then you don't have to worry about what the evil kids are doing in OS X, yeah?

I've never seen a single Mac whose desktop wasn't either completely empty, or so full of garbage that the person using it plainly had declared desktop defeat, and essentially stopped using it other than as an accidental dumping ground for files that will hopefully later be found again by Spotlight.

The problem here is that this is not the outcome these people desired, but it's the outcome OS X created for them through sheer lack of competent UX design.

Perhaps I should screenshot this thread, so I can use it as an illustration for loss aversion in the economics textbook I'm writing. Even the worst thing will find its defenders, once they consider the possibility that it might go away.

I navigate the few files I have on my MacBook by pressing cmd + Space and then typing the name of the file or folder I want to interact with.

I'm no longer fully aware of where my folders are, I just worry about what the files are called. Alas, most of it is in Chrome.

So my files consist of well named Keynotes basically.

@ Foobat

The widgets were all written in Javascript with HTML and CSS to mod their UIs. Then Apple released Dashboard, a sub-par experience from the beginning with more flash than substance and Konfabulator was dead of course. Dashboard copied/stole/enshrined (depends on your POV really) everything about Konfabulator except its finesse and flexibility.

This isn’t really true. Konfabulator widgets were written in a custom XML language. It was Dashboard that introduced the idea of “hey, they can just be a small HTML page”, and years later, Konfabulator added WebKit so it could support HTML widgets as well.

It’s true that Dashboard wasn’t as flexible, but I think that’s exactly the right approach to sherlocking: have the OS vendor cover the basics, and leave more specialized use cases to third parties. What’s the alternative? a) Apple doesn’t ship Dashboard at all (not great, and Microsoft was gonna ship a widgets system in Windows) b) Apple ships Dashboard with as many features as Konfabulator (terrible for competition). I suppose Apple could’ve bought Konfabulator instead of rolling their own, but that’s also not great for competition. A healthy platform can survive more than one piece of software of a kind.

I hate Notification Center for the sole reason that the Growl team wrapped up their project upon Notification Center’s release and of course, Growl had the finesse and flexibility that the other does not. Notification Center alerts either linger for-freaking-ever or disappear before-I-can read them. There is no per app fine tuning. I cannot control where the alerts appear or style the appearance of the alerts.

I miss Growl, kind of, though really more for its playfulness than practicality. (One Growl visualization filled the bottom quarter-or-so of the screen, which made sense for things like “what’s the current song playing”. Maybe we should get that sort of thing back?)

But, again, I’m not sure what you want Apple to do here. Not provide system-wide notifications in macOS? That would make macOS look very dated in 2022. Buy Growl? Maybe, but some of the options are really quite nerdy, and IMHO don’t make sense for a mainstream implementation.

I get it: you’re making the case that Dashboard and Notification Center sucked the air out of the room and kept Konfabulator and Growl from thriving. But I’m not really sure what the suggestion is.

@ Plume

I’ve never seen a single Mac whose desktop wasn’t either completely empty, or so full of garbage that the person using it plainly had declared desktop defeat, and essentially stopped using it other than as an accidental dumping ground for files that will hopefully later be found again by Spotlight.

Guilty as charged, but between a folder hierarchy, decent support for tagging, and Spotlight (which IME worked poorly for many years but started working fine for me around Yosemite), I’m not really sure what more Apple can offer, and “let’s just kill off the desktop altogether and make it a big fat grid of app icons to launch” is… maybe the right approach for many people, but not for me. I never liked that about my iPhone, and I wouldn’t like it for my Mac.

"I’m not really sure what more Apple can offer"

They should start by offering less. If people are not going to organize their files, and are just going to spotlight them, Apple should just put them all in one place, probably in the Documents folder. Then at least people know where their files are, and there's only one place that needs to be backed up and synced.

Then Apple can add more features, maybe give people the ability to star files they're currently working on, so they appear on their home screen, or maybe provide a calendar-like view of files, so people can easily reopen the document they worked on last Wednesday, stuff like that.

But as long as Apple still pretends that organizing files into hierarchies of folders all over people's hard disks is a reasonable approach for the vast majority of their customers, or that "the spatial Finder" still exist or is workable in a world where people have thousands of documents on their computers, often spanning back a decade or more, people are going to continue dumping their files in random places, and never finding them again unless they happen to chance upon the right words to put into Spotlight.

Apple's approach to file management was designed for 800K floppies, and still doesn't scale much further than that.

Then Apple can add more features, maybe give people the ability to star files they’re currently working on

I guess? But that’s really no different than a tag. You can already do that in various ways, and the result will automatically show up in the sidebar.

(Which doesn’t mean they won’t do it. They introduced “likes” as a simpler alternative for stars in Apple Music, so maybe we’ll get them in Finder as well.)

Apple’s approach to file management was designed for 800K floppies, and still doesn’t scale much further than that.

I don’t disagree that there’s a problem (and, given how different they’ve tried to approach it in early iOS, they seem to agree as well), but I don’t think that’s fair. The search capabilities since 10.4 Tiger and tagging capabilities since 10.9 Mavericks (and, before that, labelling since 7.0) stand out as approaches that were unthinkable in the 800K floppy era.

I don’t think this is an easy needle for Apple to thread. You want fewer places to store things, but I imagine many have the opposite point of view.

Sure, Apple has made improvements, but the fundamental concept remains the same it was on the Lisa: users are supposed to manually build folder structures, and then put their documents in the one correct place, preferably in Icons view, so people can identify their documents based on their positions, and their icons, not just their names. That's a great system if you have 800K of space, which limits you to having to managing a max of maybe 100 documents at a time.

Today, we're still mostly using the same system, except that now we have thousands of documents. This problem initially started to become obvious all the way back in the 90s, as evidenced by BeOS. You'd think that Apple would have come up with a proper solution by now, but no. It's the same thing, but with added search. So the only realistic option for most people is to just try to dump everything into one place, and then hope that spotlight will find it again.

People want more places to store things? That's fine, but then they should probably use an operating system that caters to highly technical users. Try out the newest KDE release, that's made exactly for this kind of person. Millennials, who grew up on iPhones, definitely aren't going to learn how to create hierarchial folder structures on their Macs, so the percentage of people who want more places to store stuff isn't exactly going up.

BTW, I found this an interesting read:
https://www.theverge.com/22684730/students-file-folder-directory-structure-education-gen-z

Quote:

Peter Plavchan, an associate professor of physics and astronomy at George Mason University, has seen similar behavior from his students and can’t quite wrap his head around it. “Students have had these computers in my lab; they’ll have a thousand files on their desktop completely unorganized,” he told The Verge, somewhat incredulously. “I’m kind of an obsessive organizer ... but they have no problem having 1,000 files in the same directory. And I think that is fundamentally because of a shift in how we access files.”

I don’t get these gripes. At all. Ultimately it’s up to users to figure out that they need to organize their files in a useful way. What more can Apple do? Not much.

There’s a very handy “All My Files” view in Finder, which can be set as the default view. In this view, files can be grouped according to how recently they’ve been modified, etc.

There’s also the Recent Documents menu. And there’s a hidden Dock setting to create a Recent Documents ‘Stack’ in the Dock… (that setting should be more prominent for sure; I turn on the setting using third-party app TinkerTool).

If desktop icons get out of hand, Apple provides a context menu option, ‘Clean Up By’.

Yes we live in the age of thousands of files, not the 800K floppy era. Ultimately users have to decide if they should bother taming their files by taking a few seconds to sort them properly when saving/downloading. Basic computer literacy. Not Apple’s fault if users don’t bother to do this. Mac is 1,000x better than Windows in this regard—Windows Explorer is a nightmare when it comes to orienting the user and making it clear how drives/folders are organized.

"Ultimately it’s up to users to figure out that they need to organize their files in a useful way. What more can Apple do?"

By that logic, there's no difference between using DOS and Mac OS X, because it's exclusively the user's fault if they don't have "basic computer literacy," not the system's.

"Mac is 1,000x better than Windows in this regard"

Wait, so now you're saying that it is *not* up to the user, and that the system you use actually *does* make a difference?

So I guess your point is that Apple has already achieved absolute file management perfection, and that further improvement is entirely impossible?

It just hit me that I love the fact that my desktop is nothing but a nice picture of my choosing. Whenever i share my screen in meetings, whenever I start my computer, peeking out behind my myriad of windows (I rarely run things full screen)

I've done a 180. The desktop is perfect as it is, and whilst a separate screen full of widgets is fine, I'm never going to replace the current thing for that if I have a choice

Millennials, who grew up on iPhones, definitely aren’t going to learn how to create hierarchial folder structures on their Macs, so the percentage of people who want more places to store stuff isn’t exactly going up.

This is an aside, but I’m a millennial, and I grew up on a Commodore 64 and later Macintosh LC, certainly not an iPhone. ;-)

Peter Plavchan, an associate professor of physics and astronomy at George Mason University, has seen similar behavior from his students and can’t quite wrap his head around it. “Students have had these computers in my lab; they’ll have a thousand files on their desktop completely unorganized,” he told The Verge, somewhat incredulously. “I’m kind of an obsessive organizer … but they have no problem having 1,000 files in the same directory. And I think that is fundamentally because of a shift in how we access files.”

I think what happened here is: 1) in the 1990s, various computer companies recognized the growing complexity of file hierarchies as a problem, finding that users are confused and annoyed by them. BeOS saw additional metadata as one approach to tackle it. 2) in the 2000s, search increasingly became another way to handle it. Both macOS and Windows increasingly emphasized it. 3) with iOS and Android, Google and especially Apple saw it as a chance for a more radical shift in how we think about files, largely eliminating them from the user interface altogether. But then 4) this only further accelerated how users were baffled by files.

I just don’t think Apple nailed it with iOS. I get what they were going for, kind of, but their attempt to hide complexity was a very leaky abstraction.

Ultimately it’s up to users to figure out that they need to organize their files in a useful way. What more can Apple do?

I don’t think that’s quite right. We’re talking about machines; the entire point is to make our lives easier. Anything that feels like we’re becoming digital janitors is a problem waiting to be solved.

Which doesn’t mean the solution is easy. But, just spitballing: one thing Apple can do is apply machine learning to figure out how you usually handle files, and make suggestions based on that.

Mac is 1,000x better than Windows in this regard—Windows Explorer is a nightmare when it comes to orienting the user and making it clear how drives/folders are organized.

A bit hyperbolic, but yes.

I think Mac OS X was a significant regression in that regard, though, and macOS has never quite recovered since. Classic Unix folders like /usr should not exist. The $TMPDIR hierarchy is bananas.

There was an attempt to make ~/Library/Containers more user-friendly, but then you scroll down and wonder why Mail is in there six times and Notes thrice. You can Get Info to figure out why, if you’re nerdy enough: one is the app itself, the second the SharingExtension, the third the WidgetExtension, but hang on a second, right next to that are (fake) folders named Notes QuickLook Extension and Notes Spotlight Index Extension, so why aren’t those labeled Notes as well? Why aren’t all five of these grouped in a single folder instead? Who at Apple looked at this folder and thought, “yup, that’s as good as it gets”? Probably no one; at best, this (leaky) abstraction feels like a half-finished feature that may or may not improve in macOS 13, 14, 15.

The Mac App Store has also made this worse, not better. It teaches users, Windows-style, that there’s some kind of magical step involved in installing an app, rather than encouraging them to drag it to where they want it to be.

Still, Windows is a lot worse in that regard. But it doesn’t mean Apple’s work here is done.

Very interesting discussion on file management, indeed.

In the past, I spent a few years doing tech assistance, either remotely or by making house (or office) calls. When it comes to file management, I have seen everything, including people with two university degrees who believed that the Trash emptied itself automatically, or that the files put in there stopped occupying physical space and kept existing only as names so you could remember which files you deleted. I've seen people extremely well organised, with their files neatly archived in different folders and folder structures; people who dumped everything in one bucket, but claimed to always find everything because they named their documents like "Financial forecast for June 2016 to be delivered to ACME inc on 18 May.doc"; and many different degrees of order or mess along this spectrum.

My takeaway from all that experience is that file management is just too variable, too personal, and there is no simple way to solve it. Some people have terrible organisational habits and demand that the computer do all the heavy lifting for them — but how? Talking about using AI/machine learning to help people file their documents is cool, but when any kind of organisational habit is absent, and the person just puts everyhting on the Desktop or leaves everything in the Downloads folder, what can the machine learn from the user? Then we have those who 'have their system' and get mad if the computer dares add certain tags automatically, for instance, and would get mad if e.g. the AI suggested putting all Excel files in an automatically-generated 'Spreadsheets' folder.

At this point I could say "Yes, file management is hard", and maybe it is, but I've grown cynical over time, and people who can't even learn or bother to create descriptive folders where to put their documents — and then complain that "they can't find anything" — just irritate me. I absolutely endorse the principle that machines should adapt to people and not viceversa, but this isn't a matter of constantly babysitting your buggy system, or arcane and abstruse user interfaces people need to decipher in order to operate their computers. It's a matter of learning absolutely basic organisational blocks. And I have no sympathy for those who refuse to do so.

Talking about using AI/machine learning to help people file their documents is cool, but when any kind of organisational habit is absent, and the person just puts everyhting on the Desktop or leaves everything in the Downloads folder, what can the machine learn from the user?

They don’t pay me the big machine learning bucks, and there’s always a certain creepiness vs. privacy factor to it, but one thing that comes to mind is: if you’re often editing one particular file at the same time as another file, or if you have a certain combination of apps running while working on that file.

For example, if I have research project X, and whenever I mention that project to someone on SomeMessenger, I also have files RemainingBudget.numbers and ProgressReport.pages open, then maybe those messages, that spreadsheet, and that document all fit in a suggested bucket “Project X”. There’s certainly false positives to that (I personally find myself often talking about a project X not because I’m working on it, but so I can get it out of the way in order to focus on project Y, so maybe that’s what the RemainingBudget is actually about), but maybe they still need to try.

It this isn’t a matter of constantly babysitting your buggy system, or arcane and abstruse user interfaces people need to decipher in order to operate their computers. It’s a matter of learning absolutely basic organisational blocks. And I have no sympathy for those who refuse to do so.

I think there are huge swaths of people who see computers as both a blessing and a curse, and there’s even a case to be made that solving this was part of the origin story of the Macintosh. They see how it’s helpful for tasks, yes, but they also feel they need to pamper it too much.

I get your point that organization isn’t babysitting. But from a user’s perspective, this isn’t organizing your own house, or your office desk. It’s organizing a digital, intangible thing that ideally shouldn’t even exist, because the whole point of a tool is to make things easier. Yes, you need to sharpen a knife and eventually replace it when it has become too dull and/or thin, but you don’t need to organize its inner workings. That’s the disconnect: software updates, security best practices (including some that are conflicting: should you rotate passwords, or is that counterproductive? Should you install an antivirus, or does that slow down your system and not help much?), keeping the disk from getting full, etc. already place undue burden on the user.

There’s certainly false positives to that (I personally find myself often talking about a project X not because I’m working on it, but so I can get it out of the way in order to focus on project Y, so maybe that’s what the RemainingBudget is actually about), but maybe they still need to try.

Maybe. But I fear this kind of digital assistant would end up being as useful as Siri — not much, that is. You know, that kind of 'help' that ultimately needs even more supervision on the part of the user. When someone or something else labels things for you, chooses folders for you, etc., you're even more removed from your stuff in the end. Going from 'Where did I put that file?" to "Where did the Mac's 'File Assistant' put that file?" isn't that great of a progress. Sure, there's always Search, but then… what problem has the 'File Assistant' actually solved? The supposed removal of the organisational burden / cognitive load has little benefits if it just comes back with the retrieval of information at a later moment, which ends up being the same process as before.

I don't believe the current file management tools are inadequate. People are getting lazier, and more dependent on machines for any sort of task. File management and organisation is something that should pertain to the user and be carried out by the user. General machine maintenance and security is something that should pertain to the machine and be carried out by the machine. In an ideal world. The problem is, again, that machine maintenance and babysitting becomes yet another task that requires the user's attention and intervention. No wonder users feel overwhelmed. It shouldn't be like this. I would very much prefer that the computer took care of its business automatically without me having to worry about it, and that it let me drive with manual transmission (for the most part) when I need to organise my stuff. What we have now is a sort of mediocre middle ground that ultimately makes users feel distrustful of most instances of automation within a system.

I get your point that organization isn’t babysitting. But from a user’s perspective, this isn’t organizing your own house, or your office desk. It’s organizing a digital, intangible thing that ideally shouldn’t even exist, because the whole point of a tool is to make things easier.

The computer is a tool, yes, but it's also a space, no matter how tangible or intangible. And the nomenclature is clear: 'files', 'folders', 'documents', 'storage', etc. Whether we're talking of actual paper documents inside cardboard folders inside file cabinets inside storage rooms, or their digital counterparts, these are still entities that have to be organised. The computer can help you organise them, but the preferable way to do so (for me) is not through some kind of automated tools that work in mysterious ways (from the user's perspective), but through a clean and clear user interface, and through an efficient, reliable, crystal clear information search & retrieval system. Meanwhile, automation (hopefully done well) should take care of all the things you listed at the end of your comment, those things that are already placing 'undue burden on the user'.

[Full disclosure: I am the sort of person who has an 'organised mess' in their home office, but keeps everything meticulously organised in the digital space. It's a good habit I have developed since I started working with computers in the late 1980s, and that has made my life very easy over time. I handle a lot of computers and devices on a daily basis, with thousands of files across all of them, plus the manual backups. Most of the time I know exactly where to look when I'm searching for something, and use tools like Find Any File by Thomas Tempelmann (better than Spotlight) only when I really can't remember where I've put something.]

I think you're overestimating how intuitive the concept of a nested, hierarchical file system is to most people, Riccardo. That's a thing that doesn't really exist in the natural world. Even well-organized people put their real-world documents inside a folder, and their folders inside a filing cabinet, and that's it.

There's no distinction between an actual document and its iconic representation in the file system, there's no infinite folders inside folders, there's no file names file name extensions and file types, there's no "accidentally putting my document in the Applications folder", there are no file paths, and so on.

I'm not complaining that my doctor didn't learn how hierarchical file systems on computers work, I want this guy to further his education on medicine, not go take a course on tech topics. That's not lazy, that's just doing his job. The thing that isn't doing its job here isn't the doctor who doesn't learn how file systems work, it's the computer.

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