Fixing iTunes I: To the iCloud!

iTunes was originally based on SoundJam MP, an MP3 player and sync app Apple acquired in 2000. The launch of iTunes in 2001, alongside the iPod and, eventually, the iPhone, drove Apple's resurgence and led to the greatest financial comeback in the history of... history. Yet our greatest strengths are often our greatest weaknesses, and while iTunes continues to serve more people in more ways than ever before, it's now become the poster app for Apple's "software problems".

So, what can be done about it?

The impossible job

I've previously called the job has been given "impossible". There are simply too many different use-cases, for too many different services and devices, for any single app to elegantly handle them all.

Because hundreds of millions people alone depend on use cases that end with an offline iPod syncing via USB to a Windows PC, and involve huge libraries of content downloaded and ripped from non-Apple sources, shows both the depth and breadth of the problem — how do you move forward without leaving those people behind? And how do you do it without threatening the billions and billions of dollars of transactions that go through iTunes every year?

Certainly everyone inside the Apple feels the same pains as we do on the outside. We have the luxury of complaining about it, though. They have the equally impossible task of actually doing It.

There are simply too many different use-cases for too many different services and devices for any single app to elegantly handle them all.

All it takes to say "reboot iTunes!" or "break it up like on iOS!" is frustration and a keyboard. Fixing it takes a ton of engineering and expectation management.

Apple has done the former several times already. iMovie, Final Cut X and Logic X, the iWork apps and Photos were all rebooted. The Mac App Store and iBooks for Mac were broken out like on iOS. That all of those reboots and breakouts have causes as much vocal frustration as keeping iTunes monolithic should immediately dispel any misguided belief in either alone as a panacea.

As much as we all say we want change, the vast majority of us are still going to hate it in whole or in part. Because it will be different. And it will hurt.

iTunes of iCloud

When you need to replace a bridge, you don't simply blow up the old bridge and then start work on a new one. Not unless your goal is absolute disaster. Instead, you start building one or more new bridges first and then you carefully start redirecting people onto them.

The first new bridge for iTunes feels like it needs to be iCloud.

The iTunes Store has always been an online service providing digital downloads. The infrastructure is likely old and needs to evolve as much the app does — a topic for a future installment — but in concept it's always been where it needs to be.

What has to move to iCloud now is the iTunes media interface. Sure, I'd love to be able to access my iTunes music, movies, and TV shows from any web browser, but the primary reason for this is to start removing the need to port iTunes to Windows.

Apple never made Mail, Calendar, Contacts, Notes, or Reminders for Windows, the company simply made Likewise, Apple never made the iWork apps for Windows. The company brought them to

Making iTunes music, movies, TV shows, podcasts, and the rest available from any web browser means iTunes would no longer need to be as easily and singularly portable to Windows, and that means it would no longer need to be so monolithic.

Syncing older, offline iPods and making backups of purchased content would still have to be addressed, but that's the topic for the next installment.

Products vs. services

App Store not withstanding, iTunes music, movies, and TV shows have reportedly always run at break even or at a very low (for Apple) profit. The content wasn't meant to be a huge revenue generator but to make the iPod, and now iPhone and iPad, more valuable.

Thanks to the digital rights management (DRM) mandated by the media companies that own the content Apple provides, it also creates a lock-in. Music may have gone DRM-free years ago, but movies and TV shows absolutely have not.

So, some might think there'd be a concern at Apple that letting go of that lock-in by making iTunes content available on the web would lessen the value of iPods, iPhone, and iPad.

The truth is, Apple doesn't want or need third-party lock-ins. The company fought for DRM-free music despite it lessening the lock-in. My guess is they'd be just as happy with DRM-free video. Netflix, Amazon, Hulu, Google, and others have already made ubiquitous alternatives, reducing video to a commodity you can get with or without iTunes. If Apple really wants a video lock-in for the future, a streaming service seems a more likely direction.

Either way, Apple has enough first-part lock-ins, like iMessage and Apple Pay, that third-party lock-ins shouldn't be a concern.

Baby leaps

With the positioning of the iMac as "digital hub", Apple sought to solve for content by putting everything you owned all in one place — locally on a machine that would sync it to all your Apple devices. With the advent of iCloud, Apple started to allow some of that burden to move from local to online.

Moving slowly is a smart strategy — when you need to build a new bridge, you can't blow up the old one until you're finished.

Most of it was management — buying, downloading, and re-downloading from any device on your account to any device on your account. With iTunes Preview, web pages were made for all the items in the iTunes store. With Apple started to provide access to data and even some apps like iWork right from the browser. With Apple TV and Apple Music, the company even began to breakdown the traditional buy-and-download model, offering streaming and subscriptions.

The steps, tentative as they may be, have been taken. The pieces, as they say, are slowly moving into place.

Moving slowly is a smart strategy — again, when you need to build a new bridge, you can't blow up the old one until you're finished. Often, not until long after you've finished. There are still today hundreds of millions of people who sync local content from a PC to an iPod or iOS device using iTunes and they'll need to be able to keep doing that today, tomorrow, and for a while to come.

The rest of us, though, the ones not only ready but waiting for the Cloud, would be able to begin the transition. And that's all it takes to start lessening Apple's almost Microsoftian legacy burden.

Next steps

Even when iTunes moves to there's still a lot of work left to be done. There's syncing offline devices, backing up purchased content, integrating local content, and more. We're talking about pixels and bits that handle irreplaceable personal music collections and billions of dollars of transactions.

'Fixing iTunes' requires more care, consideration, patience, and ingenuity than any other product in Apple's portfolio.

There are signs — including iTunes Match for moving music collections to the cloud and Apple Music for making us less dependent on collections — that the transition is already underway.

Still, at some point the bigger switch will need to be flipped, and we'll need to enter the post-iTunes era. All I plead is that they do it on the back of a giant neon "beta" sign.