I have been doing something similar on Spotify. I've been curating a playlist called "Jam of the Week" and each Thursday, I look back on the week and pick one song that best represents that week. What did I listen to on repeat? What song just dropped that I loved? What song did a friend share with me that I loved? Pick one and add it.

I've been running it for 460 weeks now - almost 9 years of memories. Not every song means something important, but a lot of them bring me right back to the time when I added it and makes me smile. I put the playlist on shuffle when I don't know what to listen to.