Very nice writup about different ways to engage in music listening and all the different paths that engagement can lead you down.
Regarding the above quote, I find that roon’s integrated metadata and recommendations are a great way to explore. Sort of like liner notes.
You can look at album notes/artists bios, and there are links to other artists they have worked with, similar artists/albums, similar genres, suggested albums/artists, etc. Each of those links leads to other connections and so forth. You can do that all day, and probably get from Delta Blues to Beethoven eventually.
Much of that can found online in Wikipedia and Allmusic and the like, but roon’s integration and standardized presentation makes it easy and fun. I haven’t found any other software or streaming app that does it so well.