Brace yourself. I’m about to get all “Back in my day” on you.

You see, back in my day, road trips were different. Most notably when it came to music selection. Due to limited space in our family car my brother and I each acquired a small travel suitcase that could hold exactly 12 cassette tapes (It looked like this), and before each road trip we had to go through our hundreds of tapes and rapture a chosen few to be our companions along the way.

Picking the music for a trip was a big ordeal, one that started several weeks before our scheduled departure. There are a lot of factors to consider when one can only listen to 12 albums for about 2 weeks on the road. For example, you can’t just pick music based on how you feel on the day you’re making your choices. Who knows how many different moods you’ll go through while you’re stuck in a car with 3 other people for days on end? So you have to choose happy music, sad music, and everything in between.

An album’s length is also important. You can’t have a bunch of 35 minute albums in the case — that’s a lot of dead air that could be filled with musical sounds. This introduces another trade-off, though. It doesn’t help to have a 55 minute album but you only like 2 of the songs on it. Then it would be better to pick that 40 minute album with 30 minutes of great music on it.

Here’s another thing — my brother and I didn’t want to duplicate efforts. So we would start our work independently, but then compare suitcases so that there would be no overlap, and to make sure that our selections were evenly spread out over all the moods we might find ourselves in.

And on and on it goes. Choosing road trip music was agonizing art, with very little room for error. The disappointment of being halfway across the country when you realize you’re just not into that Belinda Carlisle album any more can be pretty devastating. But man, when it worked — when you listened to Pink Floyd’s The Division Bell over and over and over, and you know you made the right choice? Nothing could beat that feeling.

Road trips are different now. Our little family took a drive from Portland to Bend for Memorial Day weekend (past Smith Rock, pictured above), and I didn’t give music a single thought before we got in the car. I had a charger, a phone with an LTE connection, and access to any song our hearts might desire through the magic of Spotify. In fact, we didn’t even have to figure out what kind of music would match our moods — Pandora did that for us.

Look, I’m not complaining. These new tools have done wonders for our music discovery. Just last weekend we went to a live show because Songkick went through my Spotify library and noticed that one of the artists on my playlists were in town. That’s amazing. But I do miss the meticulousness that music selection used to require. We always talk about how boundaries spark creativity, and it’s true here as well.

Without the boundaries imposed by my little tape suitcase I don’t have to work hard to figure out what music to listen to next. There’s no friction, but here’s the thing: there’s also no victory. The glory (and sometimes the agony) of closing that suitcase for the last time the night before the road trip begins — hoping and praying that you made the right tradeoffs — is just not there. And I wonder if the loss of analogue boundaries hurt our appreciation of art just a little bit. Not enough to make me stop using Spotify, but enough to make road trips that fraction less fun than it used to be.