For a quick summary of the Dao, here is an excerpt of what it is in the book Effortless Action: Wu-wei as Conceptual Metaphor and Spiritual Ideal in Early China
The culmination of knowledge is understood not in terms of a grasp of abstract principles but rather as an ability to move through the world and human society in a manner that is completely spontaneous and yet still fully in harmony with the normative order of the natural and human worlds—the Dao or "Way."
However, in order to reach that spontaneity and yet still fully in harmony, it is necessary to pass through the abstract stage. This is simply how our brain works. If we insist to pass the abstract stage to jump to the spontaneity stage, I think the harmony is just an illusion created by our sense of pride that we know the Dao. Since pride is a self-conscious emotion, this is not Daoism because it advocates selflessness. Another article that illustrates this is There’s more to mathematics than rigour and proofs.
Question 1: Is my understanding correct? Am I missing something?
Still, the scholars feel that what they do can't never be Daoistly satisfied. This is best illustrated in the article Zhuang Zi: A funhouse mirror for the soul
Here too I’m running into problems, however. In speaking for the Zhuang Zi, I’m somewhat uncomfortable, just as I would be uncomfortable speaking for a friend. I’m not alone in my discomfort. [...] Master Zhuang [...] appears to have engineered his work to resist definitive interpretation. [...] ‘Whenever I sit down and try to write seriously about Zhuang Zi,’ he explained, ‘I seem, somewhere in the back of my head, to hear Zhuang Zi cackling away at the presumption and futility of such an endeavour.’
Question 2: If the author can't explain to his friend Zhuangzi that what he does is what his friend wants him to do, then how can he justify his action?