> I like to think I'm getting better at being generally skeptical and slowly layering together a coherent, mutually supportive set of usefully accurate mental models of how the world works
I remember running across that site a few months ago when it was posted on HN. I really like his basic description of meaning as a nebulous, contextual, and participatory dynamic. I also remember some good points about how the universe is one cohesive thing, but the stuff inside varies immensely in the degree of connectedness, and that these connections are often quite nebulous.
You may be interested in the Meaningness project: http://meaningness.org