I loved my Sony Discman, but the nostalgia for CDs is overrated


Back in the day, I wanted a Sony Discman for a long time, and when I finally got one, I fell in love. The experience was far from perfect, however. Devices such as iPods and smartphones made it easy to forget just how bad using CDs could actually be.

A red SUV driving on a road and a hand holding a CD in the foreground.


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I was really excited to buy my first Discman

CDs were replacing my cassettes

Sony Walkman WM-AF58 Credit: Joe Fedewa / How-To Geek

The first portable music player I ever had was a portable cassette player, a cheap knock-off of the hugely popular Sony Walkman. I absolutely loved it. I used it until the feeble foam pads of the crappy headphones were almost worn through.

Then CDs arrived. The sound quality was so much better that I started buying CDs instead of cassettes when I bought new music. For a long time, if I was on the move, I had to stick to my portable cassette player, as I couldn’t afford a Sony Discman.

Eventually, however, I found one in a second-hand electronics store for a reasonable price. It had been used, but I tested it out in the store, and it seemed to work fine. It was a Sony Discman D-141 that included a Mega Bass boost feature, and I instantly fell in love with it.

The skipping was really annoying

Motion and CDs are not a good mix

The sound quality from the Discman was so much better than my knock-off Walkman. Gone was the constant hiss and muddy sound, replaced with crisp, clear music and some serious bass thanks to the Mega Bass feature. When I was lying on my bed, listening to music, the experience was perfect.

The trouble is that portable music players are designed to be used when you’re moving around. I’d always listen to my portable cassette player whenever I was walking anywhere, and the same became true of my Discman. This was when the problems started.

The D-141 didn’t include any form of shock protection. Some models included electronic skip protection (ESP) that would buffer audio data into RAM so that if the CD skipped, the music would play uninterrupted from memory.

Since my model lacked this feature, every time my Discman got jolted, the music would skip. When I was out walking with my Discman, this would happen a lot. This is something that never happened with my cassette player, and it quickly became very annoying.

Bringing your music with you was a chore

CDs were far easier to damage

A storage bag for CDs isolated on a white background. Credit: Imagentle/Shutterstock.com

Another major annoyance when using my Discman was that if you wanted to listen to more than one album when you were out, you’d have to bring multiple CDs with you. CDs aren’t small, so you couldn’t just shove one in your back pocket like you could with a cassette.

I ended up with a CD wallet full of discs that I would carry around in a shoulder bag, but even this wasn’t ideal. To save space, the CDs were stored in a wallet with no CD trays, and it was easy to scratch them when taking them out or when they jostled around in the bag. A scratched CD would skip even when the player was completely still, making the problem even worse.

CDs could also hold less music than cassettes. I could fit two entire albums on the two sides of a blank cassette, but a CD could only fit up to 80 minutes. It meant I needed to bring more CDs with me than I did with cassettes.

Making mix tapes was a chore

Burning CDs was harder than you remember

A laptop CD-R drive. Credit: Wachiwit/Shutterstock

This was the real issue when I first got my Discman. I’d been making mixtapes for years using a tape-to-tape cassette player. While the process was laborious, anyone with a dual-cassette player could do it, and blank cassettes were cheap and could store up to 120 minutes of music.

Burning CDs was a different story. You needed an entire computer with a CD burner, and early CD burners weren’t cheap. Some of the models could only burn at 1x speed, making the process slower than using a tape-to-tape machine with high-speed dubbing.

Blank CD-R discs were also fairly expensive in the early days in comparison to cassettes, and you could only fit up to 80 minutes of music on them.

Using CDs wasn’t as good as you remember

There’s a reason they were superseded

A selection of nostalgic retro late 2000s gadgets including an iPod, MiniDisc player, digital SLR, and Nintendo DS. Credit: Tim Brookes / How-To Geek

One of my favorite cassettes included a live version of The Way We Were / Try to Remember by Gladys Knight and the Pips. This song is about how everything in the past always seems better, even if that wasn’t actually the case. This is definitely true of using my Discman.

When I look back, I have fond memories of using my Discman. I have a powerful memory of walking through the streets of Sydney at sunset with Revolver by The Beatles playing on my Discman and feeling that life couldn’t get much better.

Then I remember all the times that my Discman would skip as I walked or the albums that I couldn’t listen to all the way through due to the scratches on the disc. Modern music streaming is so flawless that it’s hard to remember a time when it wasn’t perfect. I loved CDs at the time, but I don’t miss them at all.​​​​​​​

CDs were great for their time

I loved CDs, but there’s no way I would return to using a Discman now, even if I could buy one with skip protection. We may be spoiled by the ease of use of modern media players, but honestly, using CDs would drive me insane.



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Recent Reviews


There’s something oddly brilliant about outsourcing your curiosity to an AI that doesn’t get tired or awkward. After all, if an AI agent can call thousands of pubs and build a Guinness price index, why stop there? Why not send one loose into the wild to track the cost of your daily caffeine fix or your late-night ramen cravings?

I’m sold — I want one of those

That’s exactly the kind of domino effect sparked by a recent experiment inspired by Rachel Duffy from The Traitors. A developer built an AI voice agent that sounded natural enough to chat up bartenders and casually ask for Guinness prices, compiling the data into a public index. It worked so well that most people on the other end didn’t even clock that they were speaking to a machine. And just like that, a slightly chaotic, very clever idea turned into something surprisingly useful.

Now imagine applying that same idea to coffee and ramen. Because if there are two things people are oddly loyal and sensitive about, it’s how much they’re paying for a flat white or a bowl of tonkotsu.

A “CaffIndex,” for instance, could map out the price of cappuccinos across cities, highlighting everything from overpriced aesthetic cafés to hidden gems that don’t charge $3 for foam. Similarly, a “Ramen Radar” could track where you’re getting the most bang for your broth, whether it’s a premium bowl or a spot that somehow gets everything right. Don’t giggle, I’m serious.

The appeal isn’t just novelty. It’s scale. Calling up a handful of places yourself is tedious. Getting real-time, city-wide data? Nearly impossible. But an AI agent doesn’t mind dialing a thousand numbers, repeating the same question, and logging every answer with monk-like patience. What you get in return is a living, breathing map of prices.

It’s not all sunshine and roses

Of course, it is not all smooth sipping and slurping. There is a slightly uneasy side to this, too. Questions around consent and transparency start to creep in, and you cannot help but wonder if every business would be okay with being surveyed by an AI that sounds just a little too real. In the original experiment, the AI was designed to be honest when asked directly, but let’s be real: most people aren’t going to question a friendly voice casually asking about prices. It feels harmless in the moment, and that is exactly what makes it a bit tricky.

Still, there is something genuinely exciting about the idea. Not in a scary, robots-are-taking-over kind of way, but in a way that makes you pause and think, this could actually be useful if handled right. Prices are creeping up everywhere, from your rent to that comforting bowl of ramen you treat yourself to after a long day. Having something that keeps track of it all feels like a small win.

Maybe that is the real takeaway here. Today it is Guinness. Tomorrow it could be your morning coffee or your go-to ramen spot. It makes you wonder how long it will be before your phone steps in, calls up a café, asks about their espresso, and saves you from spending more than you should. Because honestly, if AI is willing to do the boring work for you, the least it can do is make sure your next cup and your next bowl actually feel worth it.



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