Being an overly analytical person myself, I can understand where you are coming from. I only started understanding how to be the detached observer by being the detached observer. What I mean is that at some point I made myself stop the analysis; stop trying to figure this whole thing out. You're not going to get the answers that you're seeking by being the analytical scientist (if you will). Just have a seat, relax, calm yourself, your breathing, your body, and just let it go. It should only take a few times before you suddenly realize that you were doing just what you tried so hard to understand. Then, of course, you've strayed from the exercise due to excitement, but it only gets easier with each attempt. I find the less time I spend worrying and analysing things to death, the more time I spend actually understanding things from the inside out. Let it go.