Zhuangzi asks rhetorically, "What if we depended on . . . nothing?" He answers, "Then our wandering would indeed be free and unfettered." Perhaps his entire message could be encapsulated in this. There are, of course, many other themes which we could choose to explore the depths of his way, but this one offers some very clear and present realities by which to gain traction toward transcendence. If "imaginative meditation" is a useful tool toward that end, then exploring the ways in which we do depend on things and how it would be to not do so would be most helpful.
But wait, are we not absolutely and utterly dependent on . . . everything? Our spirituality in fact opens us up to this incredible mutual interdependence of all things. Yes, and what would it be like to not depend on that? Would not our non-dependence free us to rejoice more fully in our complete dependence? Is not love just this — affirmation without co-dependence?
Zhuangzi's primary focus is on the psychology of dependence, not the actuality of dependence. The mighty bird Peng, symbolic of all things extant, depends on forty thousand feet of air beneath his wings in order to complete the journey of existence from oblivion to oblivion. Is he then in bondage to air? Only if he is dependent on existence. But the air is there; the impetus to existence is there; so, without striving and clinging he lets existence happen. Existence happens; and he rejoices and glories in it because he does not need that it should happen. To need it would be to depend upon it; and to depend upon it would be to fear its loss. Fear is the absence of freedom.
The tiny quail scoffs at dependence upon so much air; he only needs a few feet to accomplish his goal of reaching the next bush. Yet it is not the amount of air that matters, Zhuangzi tells us, but the dependence. In this they are the same. And for this reason, their possible freedom is also the same. The greatest and the least are able to participate in the same vast freedom.
There are those who find a certain worth and self-affirmation in the roles they play, Zhuangzi tells us. They are 'someone'. Perhaps they are leaders, and people in their village look up to them. They are model fathers; their children affirm them, and so they can affirm themselves. They are successful businesswomen; people praise them, acknowledge their virtue in 'getting ahead' and accumulating stuff. They are thought wise and sagacious; they can hold their heads a little higher than the rest of the herd.
All these palpable dependencies are opportunities to imagine the freedom of non-dependence, and in doing so, perhaps to get a taste of that freedom. To the extent that we depend on our 'successes' we are not free, for they are contingent, we can lose them, or what's worse, we can come to realize that they are all empty whether lost or saved.
This, I believe, is Zhuangzi's way: releasing into our utter dependency, letting it be, and not requiring that it should be. Existence? Who needs it? This is the freedom of non-dependence.
You can check out Scott's writings on Zhuangzi here.