I've never understood how people can wear IEMs in the cup of their ear like that. I've tried that with my E4Gs, but it just doesn't work. I think my ear canal is shaped funny, because they stick out no matter what.
So, I just shove the entire thing in. (Not to mention, my left ear doesn't have a cup like that. Only my right.)

This is the way IEMs were meant to be worn. Or maybe I just have cavernous ear canals.
I could almost fit the entire SF5P into my ear as well, although it was very uncomfortable to do so.