Yeah, I had originally intended to get both at once, but my piercer was pretty adamant about only doing one side at a time for the conch. Too much risk of messing up the angle of the hole in the cartilage or other issues. They have a lot of experience and were in healthcare before, so I trusted their judgment. My hair is at a length where they're covered most of the time, and I won't be able to use rings and more noticeable stuff for a while, anyway. And yeah I'm mostly a side sleeper, so that is probably better anyway. Might check out the pillow though. I do like being able to switch sides at night so that's going to be a challenge, lol.