I’ve been using my iTunes playlist strategy for over five years now in order to keep my songs fresh. But it’s a bit inevitable that I will begin to tire of my collection since I’m adding new songs much less frequently than I did in the past. The past little while when I have been listening to my music, I’ve felt that I’m beginning to tire of some songs even if they are good/great songs. In encountering this, I realize that there should be two different metrics for a song – its rating and its freshness.

The rating is easy to understand, you either really like or really hate a song or somewhere in between. I don’t think a song rating should change (unless something drastic happens such as you associating the song with a tragic event).

Freshness describes how frequent you want to hear the song, and that changes over time. When you hear a great top40 hit for the first time, it will be very fresh (say 5/5) and you want to hear it very often – maybe every day. After two weeks or so, you may still enjoy listening to the song but it will drive you crazy if you hear it all the time, so let’s say the freshness is 3/5. Then after a few months, you may still want to hear the song on occasion, but you’ve moved on to newer songs – then its freshness could be 1/5.

A smarter playlist would actually sort and pick songs based on the freshness rather than rating. You could have some 1 or 2 star songs that you want to listen to a bit more frequently for a time (say Christmas songs around Christmas) so you would adjust to freshness higher. The only problem with this approach is that there is no mechanism to record freshness in iTunes (unless you reuse the rating field or add the freshness into the actual metadata of the file). So I’m kind of stuck in how I would actually implement this.

The second problem is that when you have a large collection, it is very time consuming to keep accurate freshness of your music. There probably needs to be an automated system that would adjust freshness of songs based on your listening frequency.