I've seen Tao Te Ching's translation on the HN front page for several times. It seems people are interested in it. The thing with Tao Te Ching is it's too ambiguous because: 1) The Chinese language is very overloaded and thus very ambiguous. 2) Classical Chinese is even more so. 3) Tao Te Ching is intentionally filled with clever puns which makes it more ambiguous. The problem with translations is the translator has…
There was a period in my life in my early 20s when I dabbled heavily in taoism. The book was a staple read for me and I tried to adjust my Outlook accordingly for a long time. Finally though, i dropped it and went back to who I was. Your comment makes me wonder if the specific translation of the book I read was a big factor.
I do feel like I have a respect for such things where before I just considered it all manipulative woo or self-delusion. I also think it paved the way to my being able to appreciate Wittgenstein's ideas (the ones I can grasp anyway).
I read through a few different translations of the TTC, two of which had commentaries. Both the text and the translations had somewhat different takes. So it's definitely worth trying a few versions.
Two I recommend: DC Lau's translation and Philip Ivanhoe's.