I do it a bit differently, but in a way similar, too. I do not have a grand collection, nor do I use CDs in practice (in fact, I have most of my discs, software and media alike, stuffed away in a box). I do not prepare what to listen for for the day, it is more like picking something every once in a while if I am in a certain mood. That is a problem with my portable player, as I want to have something for most occasions with me, yet I listen to a certain subset often enough to get bored of it - which means I consume 8 GB for about an hour or two of songs I actually listen to.