Trying to ditch Apple Music made me love it again

I miss those days of the iPod. It was a simple device that played music and doesn’t do anything else. No interruptions, no subscriptions, no nonsense. We now live in a world where we subscribe to music and own nothing. A few months ago I asked myself if it was possible to go back to a pure “own my music / listen to my own library” music methodology. I could rediscover songs I owned but were buried so deep in “unplayed land” I forgot about them. I could go back to embracing my own playlists I made and the “smart” ones I spent hours creating back before algorithms did it for us. And luckily, I already had the tools at my disposal.

To get a better picture of what I wanted, let’s rewind back to November of 2001 when Apple released the iPod. For a company that stuck to computers, this was a break from the norm. A small white box about the size of a deck of cards, the iPod was an odd duck. It only connected via FireWire: a Mac-Only port that PC companies didn’t include in their products. It was expensive at $399, which is $709 in today’s money. It was cool but very niche.

But then Apple opened it up to Windows machines, lowered the price, and refined it annually. And those iconic white headphones that came in the box became a status symbol. The iPod was everywhere. And for good reason. It was dead-simple to use. Rip your CD’s into iTunes, manage them however you wanted, then sync your entire music library to this small box that had great battery life and a click wheel that was also easy to use. The iPod had a lot of competition but nobody could topple it. For every feature it was missing, the whole of an iPod was better overall.

The final piece of the puzzle was the iTunes Music Store. A legal and affordable way to buy songs and they’d be yours forever. It was a genius idea to compete with Napster and piracy and it worked. I, like many others, saw the convenience to buying from iTMS and having the songs instantly in perfect quality and could use them on an iPod or burn a CD.

In 2024 I wanted to get back to this music experience nirvana. For years I’ve heard about Plexamp, the music portion of the Plex Media Server. It’s well-regarded as a fantastic music player app and experience. So I got down to business and started copying my music to places where Plex could see it. It quickly identified my music and with its built-in iTunes importer, I brought all my mid-2000 playlists over too. Within minutes it had all the art, play counts, ratings, and I was set.

Then I saw what I knew was coming. My library of music just stopped at 2017. I Feel it Coming by The Weeknd was the ‘newest’ track. That was the last song I’d purchased from any place. The hundreds of albums and songs in my Music app library were simply absent. Of course I wasn’t surprised. I don’t own all those new songs. I thought I’d be fine.

The hundreds of albums and songs in my Music app library were simply absent.

My idea to get around this restriction was to view some hard data: my listening history. I decided to filter all Apple Music songs by play count and BUY them from the iTunes Music Store to then have my own free-and-clear copies. I also decided that I would acquire the digital copies for any albums I’ve bought on vinyl, as I legally own those songs too.

Buying music in 2024 is like a time warp. Apple’s Music app hides the Music Store and you have to dig around the settings to make it visible. When you load it up, it’s the good old store but not well-modernized into the current Music app. But it works and that’s all I needed.

Before I knew it I had “new” music from The Maine, Tegan and Sara, and others added to my library and Plex picked it up. Fantastic!

The entire setup took only a couple days, but this was mainly due to me having digital music I’ve kept since the 1997. I have a lot of ‘digital baggage’ that needed to get moved over. Someone starting fresh wouldn’t have nearly the time commitment I did.

I set off to use only Plexamp instead of Apple Music. I used it on my iPhone and when I drove I used the CarPlay version of the app. It was pretty good. The app has a ‘sweet fades’ feature that does a mind-blowing job of fading songs together near perfectly. At home I added my Plex music library to my Sonos speakers and that was an easy way to listen to my tunes at home.

Everything was going great. Until I wanted to hear something new.

It didn’t take long to realize that no matter how deep my library was (I have 4200 songs), I’d hear repeats more often than not. My smart playlists would surface what I wanted to hear… for the party to be over after 10 or 15 songs. I skipped more than I wanted. I wasn’t finding what I wanted to hear. With streaming, I’d grown so accustomed to hearing songs I asked for, then letting the algorithm endlessly add more similar songs to my queue.

I skipped more than I wanted. I wasn’t finding what I wanted to hear.

Of course none of this is Plex’s fault. It can only play what I fed into it. Apple Music has 100 million songs as of 2022. My meager library can’t compete with that nor the constant flow of new songs added daily to the service.

I gave myself permission to buy more music in order to compete. If I wanted to get something new, I’d allow myself some ‘fun money’ to get it and add it in, in the hopes I would sweeten my library enough to get by another week. That was the brick wall for me.

I found with my home grown system, it was impossible to discover NEW music. Short of listening to the radio or other free music streaming services (TuneIn, Sonos Radio, things on YouTube), I was inadvertently limiting my ability to find new stuff. No matter how hard I tried, the lack of discovery was kneecapping my efforts to ditch a streaming music service.

Hours I spent on Reddit, Plex’s forums, and searching online to find how others dealt with this. Tons of websites were touted as ones I could browse to learn about new music, though to me this was more of a task I’d have to constantly perform in order to find new stuff. The ‘official’ answer was to add Tidal’s music subscription, which would hook into Plex and augment the library I owned with the subscription stuff on Tidal’s end. I could also use “Sonic Sage” to ask ChatGPT to produce playlists and it could do it with my music, Tidal’s, or a mix of both.

My quest to ditch streaming music led full circle: I’d have to add a service to get the full experience I’d so desperately wanted to get on my own.

After three weeks I threw in the towel. I want to own my music, pay artists who create that music, but also feel that the music I get is mine and usable however I want. What I discovered is that no matter how big a music library gets from our own curation, the inability to dip into a pool of 100 million songs meant finding new stuff becomes a job.

THAT is what I feel like I end up paying for with my Apple Music subscription. It’s not the access to all the songs at any time. It’s for a system built to surface stuff it thinks I’d like so I can listen to it, even when it’s from an artist I’ve never heard of.

I wanted so badly to fully live in an iPod / Music Library world and even thought I’d pick up a Tangara along the way. It was an ideal place in my mind. The reality is we’ve moved on and the world has moved on. I am so used to enjoying my own music AND discovering new music all the time, there’s no going back. It’s akin to Black and White to color, SDTV to HDTV, and any other technology that levels everything up. I can’t give it up.

I may have paid for music to own that I ‘saved’ but that’s okay. Those artists can have my $10. But it made me realize that sometimes going back home to where we started from isn’t the home we really wanted to be in the first place.

Before You Go…

TimeMachiner is my one-person project I run in my off time when I’m not working my day job in IT. If you enjoy my work, consider subscribing, leaving a tip or becoming a member. Your support is appreciated and goes a long way to keep my work going.