Liezi's teacher sends an aura-reading shaman fleeing in fear of what he has seen. What is it? "Just now I showed him what I am when not yet emerged from my source — something empty and serpentine in its twistings, admitting of no understanding of who or what. So he saw it as something endlessly collapsing and scattering, something flowing away with every wave." (7:10; Ziporyn) With this we also understand how Liezi's subsequent conversion can be described as resulting in his being a "mass of chaos and confusion."
Needless to say, this is 'just' a story, the intent of which is to teach us that most fundamental of philosophical Daoism's points of departure, namely that we find our 'grounding' in chaos, not in essential verities. (I speak of "philosophical Daoism" quite purposefully here, for it seems to me that Zhuangzi's proto-Daoism was quickly morphed into something else quite different, something that offered a 'something'.) This is not about finding the True Self or the Universal Mind, or realizing immortality but precisely the opposite; it's about finding nothing. For all I know, those who have actually experienced either of these apparent opposites — a Something and a Nothing — if any, have had essentially the same experience. Yet, to my thinking, the most important thing is the process; but the process is most certainly determined by the 'goal'.
The pursuit of a Something is so radically different in terms of one's orientation to the world and to others, than is the acceptance of a Nothing, that it is difficult to fathom how these two could result in equally acceptable outcomes. (By "acceptable outcomes" I mean only one's personal happiness and the infecting of others with the same. I see no ultimate redemptive necessity in any way indicated by apparent reality; all things are equalized in the Whole.) Nevertheless, this seems to be the case — not that both outcomes are 'acceptable', for they rarely seem to make any substantial difference to this skeptic, but that they are the same.
One reason why this is so may be because we typically default to the pursuit of a Something even while calling it a Nothing. This is perhaps the core "human inclination" — the need to be fixed as a something. I would like to now say that were we to really follow the Daoist vision things would be different, but that would in effect be to make it a Something. Still, one must hope.
I conclude this ramble with a confession: I do not really believe in enlightenment of any stripe but only in approximations of an ideal. Or perhaps more correctly, I don't envision any such thing for myself and thus do not pursue it as such. It is enough to grow in the good stuff: happiness and thankfulness — and by coincidence, kindness and helpfulness. And the way that seems most genuine and potentially liberating to me is the way of trustful release into primal chaos.
You can check out Scott's writings on Zhuangzi here.