Rethinking iTunes

More than a textbook case in how not to design usable software though, iTunes has for me come to represent all the things that Apple is doing wrong, even as the company’s profits continue to snowball.
— Khoi Vinh
iTunes is like having your hand held by a robot who wants to walk into the ocean and die.
— Jon Bois


iTunes, like Microsoft Office, or Slack, is one of those pieces of software that is so ubiquitously used and relied upon that it’s hard to think of a world without it. But that world is starting to exist for many many people. Services like Spotify, Netflix, and Amazon Prime, are eating into the space - digitally distributed entertainment - that Apple once singularly dominated.

It has turned out that iTunes’ approach to content feels bloated and overly complex. This is both because of old models of purchasing and a resistance to adopt information architecture paradigms that have worked extremely well on it’s iOS devices.

The idea for this concept is to explore what a world would look like where Apple completely rebuild’s its vision of what iTunes is, from the ground up. Just like my other concepts, these ideas are extremely unlikely to pan out. I’m just one guy with basically no insight into how people are actually using product I’m critiquing. But that hasn’t stopped me before.

iTunes is dead. Long live digitally distributed entertainment.

The first sweeping update to iTunes is that iTunes doesn’t exist. Instead, there is a suite of cohesive apps which take its place: Music, Videos, Books, Podcasts, Apple U, App Store, and Device Manager. Each app adopts and expands on an experience which was once a section of iTunes. This new structure allows each app to have an information architecture which is much more forgiving to it’s content, and a user experience which need make no compromise.

Syncing and storage

In this new set of content apps, I’ve come up with what I think is a more reliable and coherent system for moving data from one device to another: iCloud Library, AirSync, and Lightning.

iCloud Library

Right now, Apple Music and Photos use what are called “iCloud Libraries” to store data in the cloud so that they don’t have to be stored on a single device. This is the most obvious way to sync data because it’s optimizing local storage and it means that you don’t have to worry about losing data when your iPhone falls in a river. This paradigm would be used for all of the content apps listed above. You might be thinking that apps like Videos, Podcasts, Books, and Apple U are already doing this kind of iCloud syncing. And you’d be partially right. But, explicitly having an iCloud Library means that you can add your own content in addition to the content you get from Apple’s databases. Want to sync your PDFs in Books between devices? You’ll need a Library for that.

For storing this kind of personal data, an self-organizing iCloud Drive folder would be automatically created which you could manually add items to outside of the context of the app.


For some apps, like Videos, you might have home movies from iMovie that are north of 1 GB that you don’t want sitting on Apple’s servers, costing you some money every month. You’d rather that kind of content just stay on your Mac. So the devices would sync using a technology like BitTorrent, which allows devices across the globe to sync with each other directly. So no need to be on the same network as your Mac. Your Mac would still need to be turned on or plugged in for syncing to happen. This feature would be called AirSync, and it would let users avoid increasing their iCloud storage limit. This would expand on the WiFi syncing capability that iTunes has now.

Eventually, AirSync could be used in conjunction with iCloud to reduce latency. So if you saved a new bookmark in Safari on your iPhone, rather than needing to send that data to a server 100 miles away and back down again to the iPad across the room, the data would be sent directly to the iPad and the server at the same time (or for large files, sent to the server when battery life is ideal). This would mean that you wouldn't necessarily need an internet connection to share content between your devices.


For use cases like setting up a device for the first time where you want to load all of your music onto your iPhone at once, you would still have the option to use a fast cable to directly sync between devices. This would also be useful for things like backing up an iOS device to your Mac more quickly. It's important to note that the interface for managing your devices and content would be the exact same, no matter which of these syncing technology was being used behind the scenes. 

Connect for everything

There’s quite a bit of shade being thrown at Connect on Apple Music, which I partially understand. But there’s also an argument to be made that Connect doesn’t go far enough. Being able to follow not only musicians, but all directors, actors, podcast hosts, and authors would be fantastic. More details on this as I jump into each of the apps.

iCloud as a social network

I have a strong belief that iCloud has the opportunity to become the largest and most successful social network in the world. This probably sounds crazy, but when you think about the number of people with iPhones (700 million units sold as of March 2015), that idea isn’t as crazy. Apple just has to execute on making it easy and comfortable to share within their iCloud connected apps.

Because of Ping’s devastating failure and the “It’s a social network. For music!” ringing in the head of Eddie Cue and company, I don’t see them going down this path lightly. But they need to remember Spotify. Spotify, the company that’s overtake Apple’s music offerings for most people my age, did it on the backs of you, the social animal that you are. After f8, the Facebook developer conference of 2011, Spotify’s daily active users blew threw the roof because of one small feature: seeing what your friends were listening to.

I’m not saying that all of your friends should see that you’re watching the last episode of Gilmore Girls for the 4th time today. What I am saying is that if my roommate publicly recommended a documentary about a water crisis in Somalia, I would probably watch it. Connecting my Twitter account could open a flood gate of immediate activity.

This gets to a three pronged strategy for recommending content:

  1. Thoughtful selections by professional curators
  2. Algorithmic recommendations and groupings
  3. Recommendations from people you know and trust in your personal life

Each method has it’s own attributes, but giving people all three in a delightful package is what could set Apple apart. Especially if they nail it on every one of these content apps.

Going to the platforms that matter

iOS, OS X, watchOS and tvOS are the platforms that will matter most to Apple in the foreseeable future, but some of the lessons that Apple learned with iTunes should carry through to this next iteration as well. Music, Videos, Books, Podcasts, Apple U, App Store, and Device Manager should have corresponding apps on Windows, Android, and the web. Yes, the web. 

If Apple wants the average customer to take their products reliable to the average customer, the customer needs to know that whether they have an Apple product or not, they’ll be able to take their content with them.

So these are some of the core features that I think would make the next versions of these apps make more sense to the user. But what do the apps actually look like?


Music consists of the following sections:

  • Discover
    • For You
    • New
    • Explore
  • Radio
    • Apple Radio
    • Internet Radio
    • Listen In
  • Connect
  • My Music
  • Playlists
    • Apple Music Playlists
    • My Playlists
    • Shared Playlists
    • Genius Mixes


Access and Payment

Music has a paid subscription service, Apple Music, and a store called Apple Music Store where you can buy songs and music videos that aren’t available for streaming. Those purchasing methods are layered on top of the the discovery features listed above. Subscribing? You can listen and save stuff to your library. Not subscribing? That’s fine too, you can purchase the songs and they’ll be saved to your iCloud Music Library. Of course, even if you’re subscribing you can still buy songs to keep after your subscription ends.

But the idea of a separate store would go away. There would be an option to only show songs available for streaming so you could hide all other music, but even in that case if you did a search there would be a prompt to see options from the store at the end of your search results.

If you have songs from a CD that aren’t in the Apple Music database, you could also upload those songs to your iCloud Music Library, but they would - understandably - count against your iCloud storage.

iCloud social enhancements

Playlist Sharing

Users could also share their playlists in the same way that you can share photos on Photos. Create a “Shared Playlist” and add any music you want to it. Depending on the payment method of choice from the playlist’s subscribers, they’ll have the option to stream or buy the songs in the playlist. Unlike iCloud Photo Sharing, which is limited to 100 people, iCloud Playlist Sharing wouldn’t have any limits. This means that eventually, for people who make their playlists public, they could be featured as part of the Discover section.

Loves, Following, and Sharing

Turned on by default, you can share what pieces of content you have “Loved” and which artists you have followed. You’d get a feed of what you’re friends have been up to in Connect right next to the content from artists. And you’d be able to see which friends loved a piece of content when you see it anywhere in the app.

You could also explicitly share any piece of content to the Connect feed.

Listen In

Turned off by default, Listen In would let your friends see what you’re playing, when you’re playing it. These streams of audio would appear in the Radio section of the app.


Videos consists of the following sections:

  • TV Shows
    • For You
    • New
    • Explore
  • Movies
    • For You
    • New
    • Explore
  • Connect
  • My Videos
    • TV Shows
    • Movies
    • Home Videos


Access and Payment

Just like you can subscribe and buy in Music, you can subscribe and buy in Videos. With Apple Video, you can access TV shows and movies which you can add to your iCloud Video Library. The store, Apple Video Store, let’s you purchase TV shows or movies that aren’t available for streaming. They would appear in the same interfaces where you can find movies for streaming.

Just like with Music, you’d have a few options for syncing your content that isn’t part of the Apple Video database. You could store your videos in iCloud Video Library, which would count against your iCloud storage, or you could sync them directly to your device using AirSync or Lightening.

Connect for TV

If you want to keep up with people in the film industry, you can use the Connect section of the Videos app. It’s basically the same as the Connect section in Music, but could give you behind the scene shots of TV shows, movies, documentaries, etc. When you go review content in Apple Video, those reviews could appear in Connect if you wanted them to.

The loves, following, and sharing functionality would exist in the Videos app as well.


Books consists of the following sections:

  • For You
  • New
  • Explore
  • Connect
  • My Books
    • Books
    • Audiobooks


Access and Payment

Just like you can subscribe and buy in Music and Videos, you can subscribe and buy in Books. With Apple Books, you can access books, audiobooks, magazines, journals, and comic books from the Apple Books database. You can also buy books from the Apple Books Store.

Syncing your content across the iCloud Books Library is probably the most useful part of the Books upgrade. Most of my books are ePub and PDF files from different sources across the web, which don’t have counterparts in the Apple Books database. So this would mean that you could sync your books to any device, with the source of truth being iCloud, rather than the hard drive in your Mac.

Connect for Books

I’d love to know when Kim Stanley Robinson starts working on his next novel, and I’d love to share which books I’ve read with my friends. Think Goodreads, but with an app that’s properly supported, and made with the thoughtfulness that Apple gives it’s products rather than the questionable “engagement” methods of Amazon.

Because of the nature of books, you could say whether you’ve read a book, and that would be noted and added to the Connect stream. You could even say that you’ve read a book more than once.


Here’s the sections of the Podcasts app:

  • New
  • For You
  • Explore
  • Connect
  • My Podcasts
  • Stations



This is where the model of subscription + store falls apart a bit. But since Podcasts are free, I think that makes sense. Podcasts actually don’t need to change very much from the app that exists for iOS.  

Since there’s no need to historically store a user’s collection of podcast episodes, a iCloud Library is probably overkill. What’s more important is syncing the podcasts themselves, knowing which episodes have been listened to, how much of an episode has been listened to, etc. But, to help users understand what’s happening, the user’s set of podcasts could be referred as an iCloud Library.

Connect for Podcasts

Again, the most important part of Connect on the Podcasts app would be the ability to see what your friends listen to. Being able to connect your Twitter and Facebook accounts to Podcasts would completely change the value of the app and would mean that podcasts could go viral way more quickly.

Apple U

iTunes U would be rebranded as Apple U and the Mac version would have the same power as the iPad app. It would have the following sections:

  • New
  • For You
  • Explore
  • Connect
  • My Courses


The app would have the same power as the iPad Apple U app, giving the you the ability to complete a course right from your Mac. This update would just be an exercise in consistency. Courses would be stored and synced in an iCloud Courses Library.

App Store

The App Store app would replace both the App Store section of iTunes and the Mac App Store app. App Store consists of the following sections:

  • New
  • Explore
  • My Apps
  • Updates


Universal App Stores

This App Store app would have the same content from the iPod Touch to the Mac, and would allow you to remotely install apps on your devices from any other device. So products like Tumblr would have a single app page where you could remotely install the app on your Mac, iPad, iPhone, iPod Touch, Apple Watch, or Apple TV in addition to installing it locally on any of those devices.

On the “New” section, the apps and content would be optimized for the device that you’re using. In the “Explore” section, your device would be selected automatically in a device filter, only showing apps that work on the device that you’re on. But if you wanted to, you could also switch to one of your other devices on your iCloud account.

Device Manager

Device Manager would replace and expand the device management functionality  of iTunes. It would have the following sections:

  • My Devices
  • Brent’s iPhone 6S (any device connected through Lightening or AirSync)
    • Settings
    • Apps
    • Content


Device Manager would let you control everything in the Settings app of a devices from basically any other device. You’d also be able to remotely uninstall and re-arrange apps. The content section would let users manually manage content the old school way, bypassing iCloud all together. This app would let Apple continue to sell or support the iPod nano and iPod shuffle.

Not all at once

With Apple Music and Photos, has set up an infrastructure that makes most of what I’m talking about possible. Part of me thinks that they’re just waiting for the iPod to die before they move to this kind of model. Then they would be in a position where they might not need a Device Manager app at all. There is a paradox within Apple between very hardware centric approaches to software, and tendencies to push for fast WiFi connectivity and virtually no IO.

To me, the future is simple, social apps that are connected through the cloud. It’s a future that’s real for many many people. I hope the users of iTunes will get to join in the fun soon.