The Tao says, “He who knows does not speak. He who speaks does not know.” Though Socrates praised the idea of “knowing nothing”. Should I aim to be a speaker who does not know?

Let's first look at the obvious: Socrates never "praised" the idea of "knowing nothing", quite the opposite: he quite literally laid the foundations for understanding knowledge in our modern sense and he was part of what we must call in a modern sense a "movement" that refuted a misguided idea of "knowledge" that was based on magical (or rather mythological) thinking and propagated factual knowledge.

Obligatory cultural pessimistic rant: There is a very unfortunate tendency to condense complex philosophical thoughts and ideas to snappy sound-bytes and out-of-context pseudo-profound quotations that are often misleading and always prone to misinterpretation. Half of the discussions here would be unnecessary if everyone asking could actually be bothered to first understand the connotations and implications of such statements.

We don't really know Socrates' original quote (it was later back-translated from Latin "scio me nihil scire" = "I know that I know nothing", possibly "ἓν οἶδα ὅτι οὐδὲν οἶδ"). What we do know is the context in which it was said: he was establishing his position in relation to the Sophists (wisdom teachers - we would call them "consultants" nowadays) who can be best described as "know-it-alls". And he did so in a rather provocative way.

"I know that I know nothing" in this context means: "I know the limitations of my knowledge". That phrase showed indeed a lot more wisdom (and knowledge) than what you could expect from the Sophists, who had a "business model" that was largely grounded on the claim to have an answer to anything (you see, the comparison with modern-day "consultants" is not so far-fetched!)

So in conclusion, Sokrates' "I know that I know nothing" should really be understood as "I know that my knowledge is limited while what there is that could be known is limitless." Most certainly he didn't praise the state of not-knowing as desirable, he merely tells you to be humble and realistic.

I don't know enough about Taoism to really understand the other statement (I'm sure there are others here who can provide more insight), but let me briefly touch another issue that I believe is underlying to your question:

Philosophers of all times and cultural backgrounds have made statements that explain a certain position and line of though. However, just the fact that some philosopher - even the greatest! - stated something, does not make it true, even less does that mean that it is relevant for your life or a specific situation.

We don't call somebody a "great" philosopher because all their statements are necessary true, but because they have or had interesting and original thoughts. In some cases their thoughts and assumptions stood the test of time and were confirmed by science, sometimes they laid the foundations for other thoughts, even though they themselves were refuted - and sometimes it just turned out to be complete BS. What matters is the originality of thought and the inspiration that it provided to others. In this sense, Socrates certainly was one of the greatest!

/r/askphilosophy Thread