Some very smart and insightful people I know have bounced off Zhuangzi with the impression that the book is full of self-contradictory nonsense. This is in some sense true, but misleading.
Most philosophical works seek to make deep points via extended argument, building up ideas over whole pages or chapters, leading to some capstone idea. Looking for that kind of thing in the Zhuangzi will do your head in. If most philosophical works are like textbooks, the Zhuangzi is like a cookbook.
Zhuangzi's usual mode plays out like this: "Here's something interesting to consider. What does it mean? Hmm..." If you're expecting a conclusion or thesis, this is very disorienting, because a lot of the time there is none! Zhuangzi constructs situations and turns away from them ambiguously, often leading the reader in one direction and then undermining them. Zhuangzi isn't presenting a point, Zhuangzi is presenting a point of view.
Compare these passages on death:
From chapter 18:
When Zhuangzi's wife died, Hui Zi went to mourn with him, but found Zhuangzi sitting on the floor with his legs stretched out in front of him, banging on a drum and singing.
Hui Zi said: "You lived with this woman, raised your children with her and got old together. That you don't cry about someone dying is one thing, but to be banging on a drum and singing shows complete lack of affection for her!"
Zhuangzi said: "Not at all. When she first died, how couldn't I react to it! I thought back to the time before she was born. Not only before she was born, but to the time before she had any shape whatsoever. Not only before she had any shape, but to the time before she had any spiritual essence. So many different pieces blended together between the time when she was nothing at all and the time when she came into existence. As they evolved, so did her spiritual essence. As her spiritual essence evolved, her shape arose. As her shape evolved, she was born, and now the evolution has resulted in her death. Just like there are spring and autumn, summer and winter, the four seasons naturally progress from each other. For the time being she is lying down and appears to be sleeping in a huge room, and I started out rushing around trying to follow her while crying my eyes out. Then I realized I was simply trying to obstruct destiny, so I stopped."
Zhuangzi was taking part in a funeral procession when he passed the grave of Hui Zi. He turned around to face those behind him and said:
"There was a man from Ying who had a speck of plaster on the tip of his nose sitting there like the wing of a fly, so he requested that Carpenter Shi chop it off. Carpenter Shi swung his ax making a sound like hissing wind and chopped off the piece of plaster without causing any harm at all to his nose while the man from Ying just stood there without losing his composure. When Duke Yuan of Song heard about this feat, he summoned Carpenter Shi and said: 'I'd like you to try doing that on me.' Carpenter Shi said: 'As your servant I'm able to carve things. However, what I used as the substance for doing that particular feat died long ago.'"
"My own dearest friend has died. I no longer have any substance to act upon! I no longer have anyone I can share in discussions with!"
Chapter 18 again:
On his travels through the state of Chu, Zhuangzi noticed a hollow skull. Even though it was old and covered with dirt, he could still make out its shape. Zhuangzi poked it with his riding crop and then asked it:
"My friend, was it because you lost your principles and were corrupt in your life that you ended up this way? Or was it because you had no loyalty to the affairs of your country and your head was chopped off that you ended up this way? Or was it because your behavior was so horrendous you brought shame to your parents and wife that you ended up this way? Or did you end up this way simply because you found yourself cold and hungry out here in the wilderness? Or did you just die a natural death when your time was up?"
When he was finished speaking, he went to sleep using the skull as a pillow. In the middle of the night the skull came to him in a dream and said: "It's obvious from what you said that you're an eloquent and educated speaker. Everything you said shows the ways people exhaust themselves while they're alive. After you're dead, there's no need for all that. Do you want me to tell you about what it's like to be dead?"
Zhuangzi said: "Yes."
The skull said: "In death there's no ruler above you nor a servant below. Also, you're not affected by the four seasons. You can be as spontaneous as the heavens and the earth, and simply flow along naturally. Even the happiness of the highest king couldn't be any better than this."
In disbelief, Zhuangzi said: "If I could control destiny and bring you back to life again in your previous body with bones, flesh and skin, and you could return to your parents, wife, friends and neighbors, would you like that?"
The skull gave an angry glare and said: "Why in the world would I want to give up happiness comparable to the highest king and return to the toils of human life?"
(All translations by Nina Correa: http://www.daoisopen.com/ZhuangziTranslation.html)
What's the Zhuangist philosophy of death? That's something interesting to consider. What does it mean? Hmm...