I don't listen to my own music collection anymore!
Lately I've been listening to most of my music in the form of various internet radio stations, mostly in the kitchen, through Airplay! I do have a great collection of music - various MP3s that I've collected over the years, converted from my CD collection, bought from iTunes or just downloaded... But it's just too much hassle to manage.
Usually, I prefer to have someone else do the heavy lifting. I love variety, almost every genre and the more indie or obcure, the better. That's why a good DJ is still my best friend, CBC Radio 3 and KEXP are both longtime favourites around the studio.
Maybe this obcure new iOS6 feature will encourage me to curate more of my own listening again... With "sync over wifi" enabled, you can just drag songs right onto your iPhone, wirelessly! They've created a great how-to over at OSXDaily.