Which translation of the Tao Te Ching is your favorite?
SecularFuture
-------------------------------------
I'd be very careful about how to read the Daodejing or any other of those early Chinese texts. The DDJ is in a very archaic form of Chinese that only specialists can read - most of the "translations" floating about are transliterations or paraphrases of other translations. For some reason everyone seems to think they can interpret the DDJ for themselves. I'd look at translations by scholars (e.g. Hendricks, LaFargue) before taking the popular ones seriously.
It was likely the product of a school of thought and practice, rather than the philosophical expatiation of a Great Man. Some of the terms used, as always with these kinds of texts, are "jargon" terms related to psychosomatic exercises or practices, and their results, and in the absence of living traditions, we can't be exactly sure what was originally meant. But then again, Chinese thinkers have themselves reinterpreted the text many times - because of the brevity and obscurity of the text, everyone tends to see what they want to see in it. It's a kind of philospohical Rorschach blot

Having said that, I don't think the "pop" versions of the " philosophy" are all that far off the mark, it's just that they mostly don't give a good sense of the text in its historical and social context. Basically the philosophy is a kind of non-dualism, somewhat akin to Advaita Vedanta or the non-dual forms of Buddhisim like Zen and Dzogchen; but there are also other philosophies mixed in, such as primitivism. It may be that the apparent contradictions aren't cute paradoxes but simply contradictions arising from the fact that the text is a bit of a grab-bag. (The same goes for the other famous text often lumped in with the DDJ, the Zhaungzi or Chuang Tzu) Nevertheless, there is a certain kind of consistency in the bulk of the passages and it does seem to point to non-dualism.
(One cliche to watch out for is the notion that there was originally this pristine school of "philosophical" Daoism that got corrupted into "religious" Daoism. That's now thought by some scholars to have been a misunderstanding perpetrated by 19th century Protestant scholars and their Confucian interlocutors. In reality, there was no such distinction, and "religious" Daoism is just as ancient as the "philosphical" variety - they have always been interlinked. The DDJ is as much a manual of kingship as it is a practice text for meditation and a philosophical text.)