Of course it never works. The self has to have some kind of existence independently of the stuff or the stuff could as easily be said to be looking at the self, which is circular, the stuff reflecting on the self and the self on the stuff. There's no static point of reference, just interdependence, and the stuff is tainted by association with the insecure self.
What did Groucho say about not wanting to belong to any club that would have him? So the insecure self can never be reassured, since it is looking for reassurance in the wrong place. And it has to always have "more" in an attempt to fill up something that is losing ground out the other end because the acquired stuff loses its power and becomes diminished.
The circle must be broken.
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