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Originally Posted by MrBritish
I was also wondering whether it would be within my best interest to at one point in my life try at a personal translation.
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I agree with the gist of what everyone else has already replied, but I will add a few quick thoughts.
One, yes, most definitely learn the ancient (pre-200 B.C.) version of the written Chinese language, and then do your own translation. A bit of foreknowledge: to adequately grasp useful concepts of the ancient Chinese wording may require the translating of numerous other ancient Chinese books so that you can learn how specific words are used. Zhong Yong, Da Xue, and Xunzi's books are extraordinarily useful of being translated prior to taking a stab at Dao De Jing.
Two, in my own personal experience, English-Chinese dictionaries may be fine for modern phonetic Chinese, but the dictionaries fail rather badly with historical word meanings. There are many Chinese words that have no parallels within the English language (requires the use of descriptive phrases), and so since the needed words do not exist in English, then the English dictionaries cannot offer words that do not exist.
Three, there are many Chinese words that rely on the reader to mentally assemble two or more concepts simultaneously. It is not common in European languages for individuals to be accustomed to assembling concepts, and so some individuals are unable to grasp the words' intentions. Nevertheless, some multiple concepts are easy, like 'monkey' plus 'heart' which could be playfully (and accurately) interpreted as 'monkey brains' or 'dumb'.
Four, many ancient Chinese words also rely on one's firsthand experiences with a topic. If a person does not first have the life experience, then the words cannot be comprehended. Example: a plumber may speak of sweating pipe; unless a person has actually sweated pipe, then the person cannot grasp what it means. 'Float points on a car' is another example. Extremely important relative to Dao De Jing is the self-awareness that enables an individual to self-observe one's own creation of virtue. If an individual has not yet learned self-awareness, and the person has not yet self-observed, then the person will not grasp what virtue is (western philosophy has debated virtue for three-thousand years, and still does not know what it is).
A good and very simple self-test: when an individual is able to enter into a lengthy (verbose) and intricate description of what 八 (divide) means, then that individual will be ready to begin translating Dao De Jing.