I’ve never been good at playlists, but I dipped my toe in the water a few months ago by starting what’s now become a tradition.
On the first of the month, I create a new playlist. Then I play it on shuffle the whole month.
Now I have a place to put new music I want to try out (MusicBox wasn’t working for me) and a place to re-find songs I was listening to recently. And a snapshot of how I was feeling any given month!