As you’ve probably gathered from previous articles, I’m not one to chase after the latest technology.  However, I can be convinced to upgrade to a new wave of gadgets if I can see how I can save time, money, or effort.  And so, in 2009, I purchased a 4th generation iPod nano in my favorite color of orange.

I started the ongoing process of initiation to the mysteries of iTunes.  I digitized all my CDs and learned how to download music.  I figured out how to edit the length of songs to cut out long intros.  I made up my own names for genres of music.  I messed around with creating playlists to act as the soundtrack to my life.  

The learning curve was enabled by the fact that I had a Macbook at the time.  But once it started to go belly up, my usual cheapskate nature kicked in and I opted for an off-brand budget PC laptop.  I was able to get all my music transferred to my new device and I was ready to fire up the music (circa 2018).

But somehow I now had multiple copies of some songs.  The edits I had made to songs no longer applied.  All my creative music genre names were replaced with default settings.  It seemed like a high price to pay for saving money on my new computer.  But I persevered and after chipping away at the issue for months, I finally had everything organized, categorized, and accounted for.

Remember the part about me buying a cheap computer?  Last summer (2021) it started running as slowly as the drain in my bathroom sink.  According to a tech guru of my acquaintance, I needed to back up my files and have the laptop purified from all uncleanliness (I’m paraphrasing, but that’s the gist).

So I know the drill.  Music saved to external drive, then transferred back—and once again surveyed the wreckage of my music collection with all the disorganization, misclassification, and general chaos.  I worked on it here and there but without the vim and vigor of the first time around.  

I just didn’t seem to have the heart to go through each song with laser precision and decide which of two dozen different categories it belonged in.  Especially considering that so many songs and artists could hold claim to different genres.  I had an inkling that I was spending more time on sorting my music than I was listening to it.

Have you ever had one of those moments when you realize that you’re one with the universe?  Me either, but I did have the revelation that none of these categories matter.  It’s all my music that I’ve specifically chosen because I want to listen to it.  So why not just throw it all together and embrace randomness?  

Enter iPod roulette.  I could say “digital mixtape” or “musical salad” but this makes my life sound more exciting than it is.  (I need to say this concept doesn’t always work.  I remember once hearing about someone who had a chili luncheon at work.  Everyone was asked to bring their own chili speciality.  Then they dumped all the different kinds together in one pot for an utterly disgusting stew.)

My point is that it’s freeing to have this flash of insight.  You’ve spent all this time redoing a task over years that you didn’t need to do in the first place.  It’s like thinking about life instead of living it.  And worrying about categorizing everything instead of appreciating uniqueness.  So let the music play as it will, and head out into the world.