I too have struggled with the same issues. I'm sure we all have. Reality makes living an "ascended life" extremely difficult, almost impossibly so. Society and "wisdom" are in constant conflict. We cannot uphold the values of both simultaneously, at least not in their present state. One tells you to that money and status matters, the other says to forget them.
Can't they both be right?
The way I see it, choosing one is more difficult in an environment dominated by the other. In the U.S., we're gonna be upholding our national values, usually that of production, progress and capitalism. In the mountains of Alaska and Tibet, we can view a more isolated way of life as the "down-to-earth," "natural," and "wise" way of life which may ignore whatever superficialities we become aware of in our culture. Proponents of our way of life will denounce a Buddhist monastery for not being wise enough to break free of old cultural dogmas. Even going by your distinguishing of society and wisdom, its up to us which we choose, and they can't both be right because you're implying our society lacks total wisdom.