"Tao Te Ching" can (apparently) be very loosely translated as "Book of the Way and Virtue". Ching is fairly straightforward, though the more pretentious sometimes prefer "tome" or "classic" to book. Tao does actually mean "way", both in the meaning of "fashion" or "method" and in that of "road".
Te is already a little more complicated. It's some kind of amalgamation of "virtue", "power" and "excellence". Apparently it's quite similar to the ancient Greek concept of "arete", for which I've linked a wikipedia article I haven't myself read, and it can also be likened to the concept of "Quality" which a certain Robert M. Pirsig spent a whole Zen and the Art of Motorcycle Maintenance trying to demonstrate.
The Tao Te Ching is about harnessing the power of the Tao for, among other things, the purposes of Te. Te appears to be the active and insistent aspect of a generally passive and indulgent philosophy.
So what is this so-called Tao anyway? It's the name given to the supposed spiritual force behind everything that's alive in the world, also sometimes known non-specifically as God or Buddha-nature, but appealingly absent any attaching dogmatism.
The Tao is the organic fuel that moves everything. It's not that things can't be moved without it, but the idea is that they're then not moved nearly as well. Possibly the major notion in Taoism is the attempt to keep the Tao unpolluted. You observe how it works, and you try to emulate it. It is "The Way" - the more you try to follow it, the more you'll get to where you need and ultimately want to be.
The Tao Te Ching is basically a collection of musings about the Tao. I have tried to identify the major recurring themes and have separated them into three different categories, which will take three separate posts. Today we talk about the nature of the Tao - what it's like in relation to itself, even before it actually affects and interacts with anything else. This is about its composition, and the things important to know about it before we go into its actual significance, which in effect makes this a second introduction. Whaddayagonnado.
Obliqueness and Paradoxes - "The Tao that can be spoken is not the eternal Tao / The name that can be named is not the eternal name"
So opens the Tao Te Ching, generally causing a reaction either of adulation and self-important consecration of this impenetrable mystery as institution, or of disdain and irritation at this book effectively proclaiming that it has nothing to say and that reading it will be a waste of time.
As you may have guessed, I agree with neither approach. It seems to me, based on several passages from the book, that the abstruse nature and sometimes paradoxical aspects of the Tao are unfortunate and serious difficulties that are mentioned so that they may be overcome, rather than to rub in our faces how little we can know about the truly important and how small and useless we are.
It seems to me less about an innate mysteriousness and ambiguity than about the fact that the Tao of people is different from the Tao of the world, and the Tao of people sucks. We've been raised speaking the wrong language, as it were, and we need to learn a new one in order to harness the Tao.
The first issue in dealing with the Tao is that of dealing with any spiritual concept - it is difficult to fully internalise its lack of corporeality. It's more than not being able to physically grasp it - Taoism, like the Indian religions, suggests that it is impossible to even mentally grasp it. You have to make do with a spiritual grasp of it.
This is one of the most problematic points though for generally discerning people with Taoism, and largely where Eastern and Western philosophy part ways, so I'll forgive you if you don't accept it just yet. It smells of religious charlatanism, but Taoism's obvious and complete benignity as well as its complete lack of dogma managed to put at least my mind at rest on this point.
The second issue with the Tao is how inconspicuous and even underwhelming it is, on an emotional level, when it does show up. It demonstrates a complete failure in calling attention to itself. It will make things better, but it will not make them bigger and brighter and louder.
The third issue, as extending the first two, is to do with the general behaviours that Taoism considers conducive. It is a good thing to follow the Tao even to places that seem to contradict your understanding or your emotional reactions. You'd sometimes - not always - find yourself doing the opposite of what you'd have thought you should do.
The fourth issue, which I only remember mentioned twice but seems to me significant enough to warrant a mention, is that this paradoxical relationship with the world and society also takes its toll. Only in the striking 20th chapter (or for a better translation scroll to 20 here) does the author seem to let go and talks of loneliness, alienation and weariness before concluding that the Taoist lifestyle is worth it anyway, which I find noteworthy mainly because it seems you very rarely find these kinds of admissions of difficulty with the lifestyle in religious texts. The actual effort itself is painful. It is important to recognise this. More after this monkey:
Oneness/Holism and Dynamism - "Do not wish to be shiny like Jade / Be dull like rocks"
Western life is all about distinguishing yourself. Excellence is measured by and synonymous with "distinction". It is very very important to be different. I'm not sure Taoism would outright oppose this inclination, but it would emphasise that, however different you try to make yourself from other people, you will remain essentially the same, because we all have the same Tao flowing through us.
More than that, though - the artificial severance and division of what is essentially one contradicts the Taoist mission and lays obstacles in its path. Whether it's trying to make yourself distinct, or veneration of the extraordinary in others or in nature or whatnot, it amounts to a delusory preoccupation with shiny things, under the assumption that anything that doesn't call attention to itself - anything that's "dull" - is not worth considering.
It is exactly this "dullness" (by which, I must clarify emphatically, I do not mean "bore" or "lack") that Taoism promotes and supports - in which the Tao itself germinates and flourishes. The moment you cleanse yourself from egocentrism and dichotomism, you open yourself to the cosmic harmony and its accompanying dynamism, because you are connecting to the Tao at its source.
It is this "dynamism" then, when harnessed, that Taoism claims outdoes any "shininess" in terms of utility and eventual satisfaction. Through the cosmic harmony and the Tao (which are the same thing), you can do and thereby become more than you ever could by personal distinction. A kind of transcendent practicality, if you like. The practicality is crucial, as we'll see when we go on.
Yin and Yang - "Know the masculine, hold to the feminine"
The masculine being yang and the feminine being yin. This is probably the most famous Taoist concept and the one I feel I understand the ramifications of the least. What we are definitely talking about, though, is two complementary opposites - interconnected and interdependent essential parts of the same whole. This touches again on the paradoxicality I spoke of earlier. Despite and against intuition, the disparities merge into a coherent whole, as popularly represented by this the "taijitu" (white representing yang and black yin, if it matters):
The Tao appears to be a result of the dialectic between these two forces, the masculine pushing for power, utility, and complexity, while the feminine pushes for softness, connectedness, and simplicity. The guidance appears to be to know the yang/masculine/white as a supportive construct and means of damage control, but to hold to the yin/feminine/black as the thing itself - the means to spiritual exaltation. It's somewhat analogous to the concept of body and soul. Not much use having one without the other.