A month with my old iPod wasn't the nostalgia trip I expected

Key Takeaways

Reverting to an iPod for simple listening connects us to nostalgia and simpler times away from digital distractions.
I found hardware problems with song playback, highlighting the rapid evolution of technology.
Gen Z’s reliance on smartphones contrasts with the simplicity of the iPod, and a yearning to escape excessive tech access.

I’m running down Manhattan’s West Side Highway on an unseasonably warm evening in March. Despite the number of joggers, walkers, and dogs of all sizes crammed into the urban pathway lining the Hudson River, I’m cruising. Little do all these other runners know that today is unusual for more than just the weather and crowds.

After using wired headphones for 2 months, I get why old tech is new again

Going back to wired headphones offered more convenience and quality listening than I thought, but wireless buds still do one thing better.

Instead of slipping in a pair of AirPods, I followed the retro-tech comeback trend and pulled out a graying pair of wired headphones. At the end of the cord, however, you won’t find it attached to my smartphone. Rather, my fourth-generation iPod jostles in my bright pink vest pocket. And yes, I’m talking about that clunky, white-and-gray iPod you may or may not have stored somewhere in the depths of your parent’s house.

Between the sun, my retro groove session, and this powerful sense of exclusivity budding at the end of my wire headphones, I’m starting to think ‘Stepping Stone’ by The Freddy Jones Band is possibly the best song ever. One mile turns into two, soon four. And just as the sun begins to dip below the still water of the Hudson, it occurs to me that I’ve just listened to the same three songs on repeat.

Zap Mama’s oohs and aahs in ‘Wadidyusay’ are becoming akin to some sort of psychedelic experience. The song finally ends and the cheery guitar strum of ‘Stepping Stone’ rears its head once again.

For the past month, I’ve turned back to my iPod for simple listening, an homage to a digital age where listening to music was just that.

I rip the headphones from my ears. For the past month, I’ve turned back to my iPod for simple listening, an homage to a digital age where listening to music was just that. No texts, no touch screen, no phone calls. And as much as this experiment was an excuse to dive head first into a pool of nostalgia, recharging this dusty device also highlighted the all-consuming digital age we live in today.

A quest for simpler listening

The risks and rewards of going full-in on the iPod lifestyle

I wanted this iPod experiment to work, and there were many times that it did. For instance, listening to an iPod for a month was not only a personal trip down memory lane, but one that surprisingly connected me to my parents in a new way.

If you’d asked me a month ago what kind of music my dad listened to, I wouldn’t have an answer. He never seemed like a music guy. But, thanks to having him dig out the iPod from our cluttered closet, we started chatting about the jams he’d downloaded long ago from iTunes. I’m talking reggae galore, The Grateful Dead, and a whole slew of artists that aren’t on the 2024 Billboard 100. Then, there were the downloaded Italian lessons and the old podcast episodes (circa 2006) from The Onion. It was a look into a time and space in my dad’s life, making all the repeat songs this iPod churned up entirely worth it.

One major flaw to this experiment: nearly half the songs downloaded onto the 20GB of space available would not play.

There was, however, one major flaw to this experiment: nearly half the songs downloaded onto the 20GB of space available would not play. It seemed artist-specific, with bands like U2 and the Black Eyed Peas completely unavailable to me (I have never, ever wanted to hear ‘Let’s Get It Started’ more).

At first, I thought it was an ownership issue. Did certain artists take away Apple’s license on their music, thus rendering my purchase of certain songs null? No. According to Apple’s support forum, once a song is purchased and downloaded from the iTunes store, they do not expire. And ‘Let’s Get It Started’ is still available on Apple Music, so a terminated contract or license isn’t the issue.

Rather, I found that music not playing on an older iPod is more often than not a hardware issue that can be resolved via factory reset. And while glad there’s a solution, it’s one I refuse to do. The charm of this iPod experiment rests in its ability to transport me back in time, and anything that would risk erasing my library, Italian lessons, and all, is one I’m not willing to take. Even if that means reverting to my iPhone to get my Black Eyed Peas fix.

The iPod doesn’t hold up in the streaming era

I did the math, and it doesn’t add up

I still remember the thrill of receiving an iTunes gift card. For just $25, I could call some roughly 10–15 songs my own, and this was when songs cost $1.29, which Apple rolled out in 2009. The 30% hike from $0.99, originally set in 2003, to $1.29 was a controversial move from Apple, already the world’s largest music store at the time.

7 reasons why wired headphones are my personal audio choice

Getting rid of the cables seems to be the way of the future, but keeping your cords attached still has considerable advantages.

“Breaking the psychological barrier of 99 cents… [would] be the first big test of how much consumers are willing to pay to download individual songs,” wrote Dawn Chmielewski for the 2009 LA Times.

In 2024, both Apple Music and Spotify Premium cost $10.99 a month for individual accounts. That’s $131.88 a year, before tax, and translated to an iPod, only 102 songs at $1.29 a song, or 133 pre-2009 hits.

To buy the same number of songs in the bygone era of iTunes at the price I pay annually for Spotify Premium, it would take me 23 years to recreate my library.

On my current Spotify account, I have 2,378 songs spread between all the original playlists — worth anywhere between $2,354 and $3,068. This amount doesn’t even include songs in the custom features like AI DJ or Spotify-curated playlists. Ultimately, to buy the same number of songs in the bygone era of iTunes at the price I pay annually for Spotify Premium, it would take me 23 years to recreate my library. Which, given that I’m 23, is a lifetime.

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Does the ‘1000 songs in our pockets’ dream still hold in 2024?

Maybe simpler listening is the solution to our digital crisis

I was head bopping to Prince’s ‘The Word’ on the Brooklyn-bound D Train when glancing up re-branded Tinder advertisements lining the subway car, it occurred to me that the first iPod advertisement aired in 2001. I was one.

And off he goes, dancing wildly through his apartment, the music now playing from headphones connected to his iPod.

Thanks to the YouTube vortex I entered, I found the 2001 ad, featuring a man in an oversize button-down and khakis at his desk. He sits before a giant white laptop and a stack of CDs, listening to music from his MacBook speakers. He then drags and drops the file, Take California by The Propellers, into a playlist. With a cord-cluttered desk, he downloads the file onto his iPod. And off he goes, dancing wildly through his apartment, the music now playing from headphones connected to his iPod.

The tagline of the commercial was simple: “iPod, 1000 songs in your pocket. Think different.”

The simplicity of Apple’s message mirrors the iPod’s simplicity itself. Small, compact, yet limitless in unforeseeable ways. The growth of the iPod was exponential. After selling 125,000 iPods in the winter quarter of 2001, by 2003 Apple had shipped over a million devices. And in 2004, the company sold 4.4 million iPods — surpassing the sales of Macs.

Today, when I walk out of the house, with my iPhone tucked into my jeans pocket, ‘1000 songs’ really doesn’t compete with the information and content I can access.

In 2023, Apple sold over 235 million iPhones — over 20% of the market share for smartphones. Without the iPod, we would not have the iPhone. And without the iPhone, well, the list is long. Each new tech innovation spurs the quest for something greater. And Steve Jobs had a dream to get 1000 songs in your pocket. He wanted us to have music on the go.

Today, when I walk out of the house, with my iPhone tucked into my jeans pocket, ‘1000 songs’ really doesn’t compete with the information and content I can access. The dream keeps on growing.

And yet, Gen Z is still turning to retro tech

What happens when tech access is excessive?

The members of Gen Z span anywhere from 12 to 27 years old, an age range that while different, all have one thing in common: access to technology starting in the tween to teen years. The similarities don’t stop in tech — Gen Zers are more likely to be shy and risk-averse. They date less, want fewer children, and are more likely to live with their parents.

What binds Gen Z together is that we are the generation that paved the way for a childhood with smartphones. Sure, I dabbled using an iPod when I was seven or eight, but the vast majority of my life has been spent near or around touch screens, be it an iPod Touch or an iPhone.

Modern flip phones aren’t the dumb flip phone Gen Z is nostalgic for

Gen Z isn’t answering the smartphone industry’s call to make retro tech smart.

Smartphones are not the only reason Gen Z is struggling, but we live in a world where teens are experiencing higher rates of depression and suicide than ever before. Still, in 2023, Americans checked their phone an average of 144 times a day, spending over four hours online daily.

With just 1000 songs in your pocket, there are no notifications, social media wormholes, or emails to distract you. Sure, you might have to listen to the same song on repeat, but the iPod is still a testament to simpler, maybe even healthier, time. Like the guy in the 2001 Apple iPod advertisement, dancing out of your apartment with music playing in your ears meant you couldn’t simultaneously scroll through Instagram.

The end or beginning of my iPod experiment?

A comeback or a moment?

I’m not sure if I would buy an iPod if Apple suddenly released an updated version today — but I do know that I’ll be keeping my old one around. I know I need to make a conscious effort to unplug from all the tethers I have to technology, and the iPod is a step in the right direction.

So, go dig that iPod out of the dark and dusty closet back at your parents’ house. It won’t be a forever change, but nods to the past often hold nuggets of truth about our future.

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