For me, it was really the process of learning how to listen to different styles of music that helped me move into new listening realms.
Like ambient is a good obvious choice. You donāt listen to ambient in the same way or for the same reasons as you would pop music. Ambient tends to be more of a textural thing, which makes long drawn out minimal tracks a positive. This also works for techno and experimental music listening. Dub music in a lot of ways as well.
Then thereās jazz. Jazz can cover a lot of different styles of listening from harsh noisy free jazz to almost ambient to funky fusion to the more ātypicalā bop sound and many more.
Once I discovered these ideas it occurred to me that being able to understand music or sound is largely a function of how you approach it in your own head.
Once I got beyond the kind of exploratory period where I searched out as many different sounding musics as I could so I could teach myself how to listen to them, I got more into trying to listen to styles or types of music to match my mood. And from that I got into trying to use other styles to alter my mood.
Not coincidentally this was around the time I became very good at DJing.
These days I really like listening to music played from vinyl over my hifi. This is the ideal manner of listening. I rarely to never use headphones. I listen in the car as well. I donāt have music playing all the time. I enjoy the sounds of my environment as well as silence.