“Wow,” a man said to me recently on the subway, “I haven’t seen one of those things in years.” He gestured toward the scuffed-yet-still-sleek, aluminum-colored rectangle in my hand — a 160GB sixth generation iPod Classic. I blinked for a moment. We were not talking about, say, a quill pen, a monocle, or a bottle of Crystal Pepsi, but an electronic device I had purchased in 2010.

I knew what he meant, though. Technology moves at hyperspeed. Apple has created and helped universalize a particular kind of planned obsolescence — its products have to go out of fashion and/or break every few years, to ensure you’ll buy a newer one — and as a result, in the eyes of the general public, Last Year’s Model has never looked like more of an antique. The Museum of Modern Art recently hosted an exhibit called “Making Music Modern: Design for Ear and Eye,” which showcased the successive innovations in music players over the past century or so. As I strolled through, the piece that stopped me in my tracks and made me think, wow, look at that dinosaur! was not an old Victrola or a bulkily primitive jukebox — but a first generation iPod, circa 2001, complete with a clunky pre-touch click wheel and (get this) a FireWire port. “Nothing in the world,” writes Ben Lerner in his 2014 novel 10:04, “is as old as what was futuristic in the past.”

On September 9, 2014, Apple announced that it would no longer be making the iPod Classic. For a seemingly all-powerful corporation, its reasoning was uncharacteristically defeatist: “We couldn’t get the parts anymore, not anywhere on Earth,” Apple CEO Tim Cook later explained. “It wasn’t a matter of me swinging the ax, saying ‘what can I kill today?’ The engineering work was massive, and the number of people who wanted it very small.”

Well, relatively small. He was not wrong about the low sales numbers — especially when compared to a product like the iPhone, which essentially ended the need for a separate mobile music player. But in the weeks after Apple killed off the Classic, something unexpected happened: Used iPods started selling for double, triple, even quadruple their original retail price on eBay. By December, a characteristically melodramatic Daily Mail headline enthused: “iPod Classic which is THREE YEARS OLD is Apple’s hottest item this Christmas.” The Apple Watch never stood a chance.

Who would fork over up to $1,000 (or more; a factory-sealed seventh gen is listed for $1699 on eBay right now) for an old, obsolete MP3 player except a stick-in-the-mud Luddite, resistant to our inevitable progress toward a cloud-based future? I’m not sure. But I think these people were onto something.

“When I’m searching for something to listen to on Spotify, I feel like I end up listening to the same albums and artists again and again,” my friend Becca wrote in an email, after I asked a handful of acquaintances about their post-iPod listening habits. “My brain by itself isn’t good at cataloguing everything I love.”

The psychologist Barry Schwartz has written (or, if you don’t have too much time on your hands, has TED-Talked) about a related phenomenon he calls “paradox of choice” — the notion that, although we tend to think of freedom of choice as an inherently good thing, too much choice can leave us feeling paralyzed and anxiety-ridden. “With so many options to choose from,” he says, “people find it very difficult to choose at all.” I personally have proven this theory many times over in the past few months, when I’ve stared for a few moments at the infinite void that is the Apple Music search bar and decided, “I guess I will just listen to Pablo or Lemonade again.” Another friend I emailed summed up the Paradox of Digital Music Listening succinctly: “With device-bound listening, I absolutely feel limited by [storage] space. With streaming, I feel limited by my own memory.”

Catherine Moore, an adjunct professor who studies music technology and digital media at the University of Toronto, agrees with this assessment. “People just don’t know where to start,” she says of listening in the streaming era. Moore also pointed me to Harvard Business School professor Anita Elberse’s much-discussed 2013 book Blockbusters, which explores the business decisions behind massive entertainment hits. “Her findings showed that this enormous proliferation of choice has actually made big, giant hits even bigger.”

Schwartz’s theory posits that there’s a sweet spot: “Some choice is better than none, but it doesn’t follow from that that more choice is better than some choice. There’s some magical amount, I don’t know what it is.” Streaming services are currently on a quest to find that magic number: Think of the new fixation on “discovery,” curation, and tastemaker-created (or algorithm-created) playlists. Last month, The Ringer’s own Victor Luckerson wrote a piece about Spotify’s popular “Discover Weekly” feature, noting that the company “initially tested a 100-song version of the feature but found that combing through that many songs was exhausting for users.” It took off once Spotify whittled that down to a more manageable 30 songs.

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In terms of device storage capacity, I think the magic number was, for me, 160GB — the size of my iPod Classic. Large enough that I was never worried about running out of room, but small enough for my device to feel manageable and personally curated. Ryan, another friend who I emailed, remembered iPod libraries as “great conversation starters.” He mused, “It was nice to feel like you could showcase your curated collection of music to friends via an iPod … often someone had a Neil Young rarity or a friend’s unreleased record, so each one seemed pretty intimate and personal.”

I’m already dipping a toe into the realm of nostalgia and sentimentality — so let’s just dive in. My still-functional iPod bears the grubby fingerprints of the person I was from roughly 2010 until the end of 2014 (when my old laptop kicked the bucket and I stopped updating my device). It contains 323 songs by the Mountain Goats, 153 by Pavement, and, solely for the purpose of impromptu living room dance parties, one by the Quad City DJ’s. (You’ll never guess which!) There are playlists for specific crushes and specific breakups, titled so cryptically that only I will ever know who they’re about. (One begins with Hole’s “Violet” and ends with Kelly Clarkson’s “Since U Been Gone,” as every breakup playlist should be legally mandated to.) Glitches and imperfections in the files have fused with my remembered melodies of these songs; in my mind, the opening bars of Katy Perry’s “Firework” contain the foreign-language radio tag from the sketchy Japanese website I illegally downloaded it from. Certain hastily assembled On-the-Go playlists conjure, so vividly in my mind, exactly Where-I-Was-Going the day I made them.

Sure, our phones might hold some of this sentimental junk, but unless we’ve sprung for one with a massive amount of storage space, we’re constantly having to clear them out to make room for the new. And in a larger sense, we’re now fully immersed in the Snapchat era, in which our digital footprints are becoming more and more ephemeral — if only to make room for the humongous amount of data we all generate in any given day. At the risk of sounding like a total geezer, I can’t help but feel that we’ve long since crossed the threshold of that magic number, into the realm where there’s simply too much music, too many tweets, too much stuff out there to feel anything but overloaded and paralyzed almost all of the time.

“The best thing about the iPod was that when I was listening to music, that was all I was doing,” wrote my friend Miriam. “When I’m listening to something really beautiful [on my phone] and it fades out for a phone call, I get a little upset at whoever called me.” (There is, of course, the iPhone’s Do Not Disturb button, but in my experience that can be flicked off just as easily as it can be flicked on.)

In the tech world, everything is moving toward multifunctionality. This shift, in some sense, is physically liberating: If your smartphone can play music and send/receive phone calls and texts (get you a phone that can do both), what’s an iPod but one more device weighing down your bag? At the same time, this shift makes immersive, distraction-free listening feel, more and more, like a thing of the past. A few years ago, Pulp frontman Jarvis Cocker observed this dynamic in an interview with The Guardian. “People still listen to [music],” he said, “but it’s not as central. It’s more like a scented candle. It sets the mood… I think people like things that just make the right kind of noise, but leave your brain free to do something else.”

Moore says something is lost in this shift. “It makes it harder for new music — especially new music that is a little unusual — to get people’s attention,” she says. Listening on multifunction devices favors repetitive, unchallenging songs that you don’t need to use much of your brain to process — Cocker’s “scented candle” music. Moore, though, notes that it’s that more challenging, less predictable music (like, say, Kendrick Lamar’s To Pimp a Butterfly) that over time provides listeners with the greatest rewards. “Often, of those types of songs, people will say that when they first listened to it they didn’t get it, or didn’t particularly like it, but then as they listen more, it becomes their favorite song,” she says. “And those songs take some concentration.”

When I listen to my iPod these days, it gives me the small but subversive thrill of going against the grain — not only rejecting the hectic, multitasked rhythm of smartphone life, but also pushing back against a digital marketplace that’s trying to instill in me loyalty toward certain streaming services rather than the music and the artists themselves. When I’m listening to my iPod I am, at least for the moment, opting out of the Streaming Wars, which — as services like Apple Music and Tidal compete for “exclusive” songs walled off to subscribers of their competitors — increasingly feels like a losing game for the listener. (Let’s conveniently put aside the fact I gave Apple Music’s parent company a couple hundred bucks to buy the device in the first place.) It would have seemed insane to suggest this in the early-aughts, when the iPod seemed like an emblem of our cultural overload (“1,000 songs in your pocket!”) but using an iPod in the age of the smartphone almost feels like an act of meditation. I’m slowing down, tuning out, placing my life — for the length of an album or even a single song — in Do Not Disturb mode.

To plenty of people, the desire to do that will seem silly, absurd, even old-fashioned. Fair enough. In my brief survey, I noticed that the ones who expressed the most nostalgia for the iPod Classic were — and this is a term I use with both love and self-identification — the music nerds: Friends I made at my college radio station, as well as other people who make, listen to, or write about music for a living. And unless Tim Cook stumbles upon an elephant graveyard of unused iPod parts anytime soon, this niche group will be the ones who still evangelize the iPod long after its death, and even pay through the nose for new or refurbished ones when their own needs replacing.

The iPod Classic is now becoming what vinyl was a decade or two ago — not when vinyl became cool again, but during the CD era, when it seemed obsolete to everyone but collectors and music snobs. Which is to say that the iPod’s “vintage” resurgence is probably inevitable. Rest in peace, sweet iPod Classic. See you at Urban Outfitters in 2036.