First of all, bear in mind this is a high-end monitor meant (presumably, like the Westone UM3X) mostly for performing musicians. This means ideally these should be worn over the ear to get the best fit, seal and SQ; this, BTW, also helps to prevent microphonics.
My first experience with over-the-ear IEMs was the Shure SE530. I found the over-the-ear aspect quite daunting and a real turn-off at first but I kept reading in several online places that you get used to it. So, at first I found it VERY awkward but after 2 weeks or so things made more sense and later I found it awkward to wear IEMs any other way! Really. As time goes by you won't really need to use both hands - as you do initially - to get the right fit, and even if you do, it'll all soon become second nature even when you're out and about.
Wearing customs is even more awkward at first. In my case for about a year I've been using one hand to put them on and take them off - something unthinkable when I first got them.
Edited by music_4321 - 7/30/10 at 6:00am