Tao Te Ching

Some disclaimers:
1. I'm new to reading texts like this and this is waaay out of my comfort zone.
2. There's a good chance I'm just not at a place in life to comprehend/understand the text properly.
3. There was a language barrier, as I didn't find a good translation in my native Bulgarian.

With this in mind, here's some notes to hopefully help you if you're in my shoes.

tl;dr
1. Read Gia-Fu Feng and Jane English's version
2. Give it a chance, there is some wisdom to be found in the book

First, which translation you pick up matters.. A LOT! And it doesn't help that there's a ton of them. I started with Ursula Le Guin's version, but I quickly discarded it. It felt too prescriptive and like it romanticizes the source material. I don't think this is Tao Te Ching, this is what Ursula Le Guin wants to believe (or wants you to think?) Tao Te Ching is.

I jumped over to James Legge's version - and this time read the whole book. This version, and especially forewords, gave me a lot of good context on the history of the book, various ancient translations, a general explanation for how Laozi thinks of the Tao, and the approaches to translating and interpreting the source material. My understanding is that this translation tries to be as close to the source material as possible.
And... it seemed like a complete mess intertwined with some good ideas and a lot of gibberish. There are numerous instances where Legge admits in notes that Laozi is contradictory, doesn't make sense, etc. Some times Legge says things like “I will not attempt to explain this” (paraphrasing).

After that, I read (~80% of) Gia-Fu Feng and Jane English's version. This seems somewhere in between Ursula Le Guin and James Legge. It's written in more accessible English, and comparing to Legge's version it seems close-ish to the source material most of the time. The translators did change the tone a lot, but this allowed them to showcase the ideas more clearly. However, I cannot help it - if I assume Legge's version is closer to the source, I feel this version does a decent amount of gymnastics to give the text deeper meaning (I even wanna say “force deeper meaning into the text”). It almost completely replaces some of those gibberish-y/hard-to-translate/very abstract passages with alternatives I feel are interpretations of the source rather than the source itself.

Here's an example of why the translation you pick matters:

Fifty Six (James Legge):
He who knows (the Tao) does not (care to) speak (about it); he who is (ever ready to) speak about it does not know it.
He (who knows it) will keep his mouth shut and close the portals (of his nostrils). He will blunt his sharp points and unravel the complications of things; he will attemper his brightness, and bring himself into agreement with the obscurity (of others).

Fifty Six (J. English):
Those who know do not talk.
Those who talk do not know.
Keep your mouth closed.
Guard your senses.
Temper your sharpness.
Simplify your problems.
Mask your brightness.
Be at one with the dust of the earth.

—

Some thoughts on the Tao itself:
1. The book does not explain a lot. Laozi seems even kinda protective of the knowledge, like he deliberately doesn't want to share it. He mostly teaches you in the style of ‘if you followed the Tao, this is what you would've done'. The Tao is amazing, all-knowing, and you should follow it, of course. If you do, everything will be great, if you don't - bad stuff happens. “My words are very easy to know, and very easy to practice; but there is no one in the world who is able to know and able to practice them”. Sure.

2. The book teaches humility and humbleness, and reiterates on those to burn them in your head. This I appreciate very much, and the author found various ways to explain why humility and being humble is a good way to live life. It teaches about being kind to others and not being greedy. Good stuff.

3. The book teaches that not acting is good, and not knowing is good. You should strive to do nothing and learn nothing. This I cannot comprehend.

I will most likely go back to Gia-Fu Feng and Jane English's version sometime in the future, after some time passes. There is wisdom to be found in this version - even if their interpretation is not really what Laozi wrote, does it really matter?

Laozi says “The wise student hears of the Tao and practices it diligently. The average student hears of the Tao and gives it thought now and again. The foolish student hears of the Tao and laughs aloud”.
I guess I'm okay with being average.