I don't really have much issue. Here are the two choices:
I sleep with normal headphones that push into my ears when I lie on my side. So I put my hand under my head to the left to hold my face slightly off of the pillow and relieve any pressure on my ear. The bad part about these guys is they come out during the night if I roll about and wrap around my neck and stuff so I get up in the morning all jumbled into my headphones.
Then I have a pair like this: 
If I put those on, the same problem of irritating me when lying on my side is present, but has the same solution. I put my hand under my head or position my head on the edge of my pillow so my head lies on the pillow while my ear hangs slightly off the side. Those usually stay on straight up until the morning when I wake up to take them off, regardless of how much rolling I do.
But all in all, neither the sound nor the feeling keep me awake for any longer than usual. If the sound is disturbing you so much, turn the volume down a bit! I have had instances where I couldn't sleep for the sound, and that was fixed by just turning it down until it was barely audible. As soon as you become more tired, the volume will begin to sound as if it's all the way up again.
If you leave your volume at what seems like a comfortably loud area before you go to sleep, after you fall asleep, it will seem way, way, way too loud, and will wake you straight back up.
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