So, not what I'm listening TO, but what I'm listening WITH...
I just bought a pair of Tozo open ear-ring headphones and they're a revelation for me. Both over-the-ear headphones and earbuds begin to cause physical pain to my ear after about 30 minutes to an hour due to the physical pressure of the over-the-ear headphones pressing against my ear and the earbuds never fitting well in my concha.
These little babies are nice and small and nestle in there, then clip around the back of the ear. I can wear them for hours and it's like they're not even on, they're just night-and-day more comfortable for me. For anybody who has earbud/headphone comfort issues, these are definitely worth a try! Obviously there are other brands with this same open ear-ring style, I got the Tozo because of good reviews and a mid-level price point to balance between overpaying for professional stuff and buying junk.