The biggest ongoing problem in my technological life is when, where, and how to easily listen to music. There are two reasons why this is a problem: 1) music is a vital part of my life - I need a steady stream of new tracks and artists to listen to, and I need to be able to cue up my old favorite songs at crucial moments - and 2) I strongly suspect there is no perfect way to listen to music.
But sometime in the mid-aughts, I came close. The system I developed then represents the most fruitful and healthy relationship I’ve ever had with music. I spent money on used and new music — a good Amoeba haul would sometimes set me back $40 or $50 — but as a college student in a post-Napster world, I did my fair share of pirating, too, and ripped countless CDs borrowed from the college radio station I worked at. I uploaded my entire music library to my fourth-generation iPod, while still continuing to use the CDs in my stereo at home and in my friends’ cars. Part of my collection was based off recommendations, part of it was made up of canonical must-listens, and some of it was completely random. Some songs I only listened to once; others became my favorite songs of all time. It was during an afternoon of idle browsing at the station that I found the album Wonder Wonder by alt-country singer-songwriter Edith Frost. Most of that album wasn’t really my style, but the fifth track, "Cars and Parties," became a sturdy old friend to me in my first transitory years living in Los Angeles.