I didn't encounter the Dao de Jing until later in life, but the opening bit has always seemed straightforward to me. I first saw it as "the way that can be described is not the Way", but also "the way that can be traveled is not the eternal Way". That is, the eternal (spiritual) Way cannot be concretized, just as a name is not the real thing. Or, given that this is HN, "the software development methodology that can be executed like a program is not software development methodology". ("The Agile that can be PM'd is not Agile.")
However, I think it might require some life maturity to recognize that. Certainly a recovery from Englightenment rationalism. My person experience is that an understanding that "the name that can be named/identified is not the eternal Name" and "the way that can be walked is not the eternal Way" took me until around my 40s to appreciate.
Daoism also appears to have taken a literalist turn (ironically). The book "Taoism: the Parting of the Ways" [1], by (former) Harvard Professor Holmes Welch, interprets the text as being a guide to a mystical way of living, similar to St. John of the Cross (minus the Christian part), which is fascinating. Then he describes how the two main factions took the text literally, and how that evolved.
[1] I have a summary at http://geoffprewett.com/BookReviews/TaoismThePartingOfTheWay...
However, I think it might require some life maturity to recognize that. Certainly a recovery from Englightenment rationalism. My person experience is that an understanding that "the name that can be named/identified is not the eternal Name" and "the way that can be walked is not the eternal Way" took me until around my 40s to appreciate.
Daoism also appears to have taken a literalist turn (ironically). The book "Taoism: the Parting of the Ways" [1], by (former) Harvard Professor Holmes Welch, interprets the text as being a guide to a mystical way of living, similar to St. John of the Cross (minus the Christian part), which is fascinating. Then he describes how the two main factions took the text literally, and how that evolved.
[1] I have a summary at http://geoffprewett.com/BookReviews/TaoismThePartingOfTheWay...