It's Too Hard to Manage Music Now: Why It's Okay to Miss the Old iPod

As albums disappear from Spotify and the smartphone hard drives becomes crowded, it's becoming clear that simpler really was better for many listeners.

Jae C. Hong/AP

Recently I had a fairly pedestrian thought, a thought I've been having on and off for 10 years: "I want to put some music onto my portable music listening device." This used to be a relative cinch: I'd put the music on iTunes, plug in my iPod, and drag the songs over. Now, anytime I dare hook my iPhone up to a computer, there's software that needs updating, apps and photos I need to clear away for extra room, and esoteric rules regarding what is allowed to "sync." After finally getting an album onto my phone, another software update a week later reverted my music library to its previous state, putting me back at square one and making me long for my iPod, the last device I owned that was just for music.

Apple discontinued the "iPod Classic" (the click-wheeled hard drive that changed the way much of the world listened to music) two months ago. Last weekend, The Guardian found absence was making hearts grow fonder. "With a storage capacity double the size of any current iPods still being made, versions of the 160GB Classic—which can hold around 40,000 songs—are being sold as new via Amazon for up to £670," or more than $1,000, Paul Gallagher wrote.

The price is a little lower in America, but an iPod Classic still retails for $493 on Amazon Prime. You can get an iPhone 6 Plus, with 128 gigabytes of storage, for pretty much the same price—and that sucker can browse the Internet, watch movies, use Spotify, and do a zillion other things. It also shackles you to a cellular contract, pesters you with notifications, and commits the unavoidable sin of trying to manage all of the stressful aspects of daily life. The smartphone is a miracle, to be sure, but it might not be making things simpler.

If I'm out and about and listening to music via headphones, those songs get interrupted by text message notifications and email dings all the time. I'm so used to it, but when I think about it for a second, I realize how crazy that is (and yes, I know I can turn my phone sounds off, but sometimes I have to be alerted to things quickly). Apologies if I sound like Andy Rooney, but the truth is I’m not railing against newfangled tech or yearning for a distant past—I’m frustrated to have to abandon a recent solution. It wasn’t long ago that I’d get annoyed when music skipped on Discman as I walked to school. The iPod was the answer. That's when we fixed all these problems.

It's not hard to get conspiratorial about just why Apple doesn't want us to have iPods. I buy music directly from my phone, just so I don't have to deal with iTunes, a program that somehow gets more hellishly slow and unusable with every software update. That's vertical integration for you. The stated reason for the iPod Classic's demise was that its parts were no longer easily available to Apple for manufacturing, and that demand wasn't high enough to create new ones. And I'm sure part of the mad scramble for iPod Classics is their perceived rarity. If Apple brought them back, sales would remain at low.

But I remain on the hunt for something new, dreaming of downgrading my phone to a smaller hard drive that I just use for photos and games. Meanwhile, my bloated music library can move to an easier-to-manage brick. Remember the Zune? That was also discontinued, but has a cult following as a cheaper option to the iPod. Other long-running companies like Creative Zen and SanDisk have always had functional mp3 players, and Sony has revived the Walkman brand for the high-end audiophile crowd (to little fanfare, it seems). There's also this strange PonoPlayer, a Kickstarted device created by Pono Music (owned by Neil Young!) that boasts a weird triangular shape and the option to buy high-quality versions of the albums you already own.

It all feels very imperfect, which means I'm probably stuck getting increasingly frustrated with iTunes and groaning audibly when an album I want to listen to isn't streaming on Spotify. But the surge of demand for old iPods suggests what I've long been thinking: There's a hole in the market here. Something has to rush in and fill it eventually. The question is whether Apple will realize its mistake or some other company will do it for them.