I try not to think about the grueling process of cleaning out my iPod, but sometimes I come across a really ugly jam on shuffle and I'm all, "Why god, why do I own this song?" I have an 80g iPod. You'd think I'd want to fill that shit up, but no, I use my space sparingly. My iTunes library holds selection of carefully curated rooms, each filled with artifacts from specific genres. I have everything from 90s to hardcore to Turkish psychedelic music. In total, there are 5777 songs to this day on my iPod. That's over 15 days of music.
Collecting, organizing and labeling is crucial with the iPod. Some albums you store away, removing from your shuffle queue in silence. Others you highlight in newly designed playlists that scream, "I'm new to your iPod. Listen to me before you forget about me!" I study each album prior to uploading to see if it will "make the cut".
Cleaning out your iPod is a difficult process. You may hate yourself for liking that John Mayer song, but if you DARE delete it, the song will come crawling back to you in some way. Is the lesson to store everything as often as possible and be a music hoarder? If anything, it's the incessant amount of options I have given myself that make this whole process of choosing the soundtrack of my life undesirable.