The Book of Zhuangzi ends with the words, "How sad!" This is, of course, simply an accidental consequence of editing, but still it makes one think.
The author who brushed these words was referring to the life of Hui Shi; he had so much potential, came so close to understanding something of the implications of Dao, and yet he preferred to be someone. How sad. Hui's particular form of trying to be someone involved proving to others that he was smarter than they, but the endeavor is universal among us and can take many forms. "He was like a man", the author tells us, "trying to outrun his own shadow." "Hui Shi's talents were fruitlessly dissipated running after things and never returning to himself." (Ziporyn)
To return to oneself is, from a Daoist perspective, to discover and embrace one's essential emptiness; in this is fullness of a genus entirely other than the supposed fullness sought in the pursuit of fame. This latter seeks to fill what cannot be filled; it is running from one's own shadow. The former surrenders identity into universality, where fullness abides and nothing need be filled.
Zhuangzi applies a similar assessment to the lot of humanity when considering the decaying of the body and the disappearance of the mind in death. "Can this be called anything but an enormous sorrow? Is human life always this bewildering, or am I the only bewildered one? Is there actually any man, or anything in a man that is not bewildered?" (2:11) How sad! is an expression which can easily be applied to humanity as a whole. Zhuangzi did not gloss over the cold facts of our tenuous existence in the world, or our failed attempts to fill the unfillable void. And yet....
Hui Shi failed in his bid to be free. So do I. And so, probably, do you. How sad! And yet, So what!? All is well. I am not sure the author of this final chapter, "The World Under Heaven", actually understood the implications of that point of view; he seems to think the failures he reveals matter to "Heaven". They do not. And if they do not matter to Dao, they ultimately do not matter at all. How sad! So what!? All is well. From the perspective of Dao, these are all the same. And from the perspective of Daoism, all the sadness intrinsic to our existence is thankfully affirmed as an opportunity to soar above all sadness; to deny the sadness would be to clip our wings.
You can check out Scott's writings on Zhuangzi here.