The spring of my freshman year of college, my mom sold my drum set. I used the money to buy an MP3 player. Sorry. A multi-codec jukebox.

There is a certain type of person who, when faced with a sleek, friendly, easy-to-use Apple product, will rail on about all the features it doesn’t have, all the things you can’t do with it, all the ways the walled garden is a trap.

This person has existed since the dawn of time. I used to be that guy. I still am, sometimes, but I used to be, too. And so, in the spring of 2004, when the iPod had been out for two and a half years, I spent $330 on ...