A Few Thoughts on the Learning of Literary/Classical Chinese (Comments for the Beginning Learner):
for Marielle, and for Laura
I'm not going to say that literary Chinese is not difficult -- having now formally learned thirteen languages (five to native or near-native level fluency and the rest literate/conversational), literary/classical Chinese presents unique challenges which are virtually nonexistent in other languages and other types of language learning. That said, the language (as we know it, none of us have a time machine) is actually relatively small in scope when one considers the number of graphs and range of sounds generally required, and the grammar is actually not that difficult when you get used to it (it's somewhat difficult, mainly due to different modes of writing and the ways word usages developed over time -- see #1 below -- but this is not Latin, where you could easily spend ten years just trying to figure out the grammar). Literary Chinese will likely seem extremely daunting at first, mainly because rather than sticking to one text or type of text, we tend to try to teach the language as we have it preserved in its different forms over 2000+ years all together. The nice thing is that after two or three years, the difficulty curve levels off significantly, and everything becomes easier (or at least more straightforward) after that.
Here are some general thoughts on the learning process:
1) Literary Chinese is not one language. This presents special problems for the beginner. The language used by Confucius, Mencius, the histories, and in religious/philosophical texts are all quite different from each other -- different grammar and usage, different vocabulary (even if they're using the same characters, they're often not the same words), different styles, different modes of thought and argumentation. Here's the nice thing: There are only so many really different modes of composition in this language, and as you get better and better, you begin to understand how a single character can be used for what seems at first like totally different meanings, but in fact those meanings are often closely interrelated. (Use of homophones and word borrowing complicate this significantly, but those tend to have been well-discussed in the commentaries -- see #3 below.) It's not really close to Modern Chinese, either (except for characters and some archaisms which have survived) so if you thought Modern Chinese would be of great help here, I'm sorry to say, it's really a different language. But that means it's hard for native speakers of Chinese as well -- their advantage is actually pretty minimal, what really matters is one's exposure to classical Chinese.
2) Vocabulary: It seems daunting and crazy at first, but the overall numbers of commonly-used words in classical texts is actually very manageable. With a good understanding of the 2000 most common classical Chinese words/characters in your vocabulary (yes, you will just have to memorize them, and their main ranges of meanings/connotations), you should be able to get the general gist of most prose texts, no matter the time period, the subject matter or the author. As I said above, each text has its own "mode" of composition, and when you get used to it, it tends to be internally consistent -- when you get very good at one mode or type of text, it actually becomes relatively easy. (Though it never really becomes that easy, except perhaps after decades working closely with one mode/style.) Proper names (of people, characters, places, book titles etc.) will continue to be strange, difficult and surprisingly changeable (I know of one author who is referred to by over 30 totally different names in his own works and others'), but these are clearly marked in most well-edited modern editions of texts, so that's not so hard -- and that's a great segue to #3.
3) Commentaries: Literary Chinese is no modern person's first language. It can be, at times, so inscrutable that even our greatest scholars will argue vociferously, disagreeing radically about the meaning of a phrase or a word, and there are even some words/characters which we basically all agree we have no idea what it really means, and we're just making educated guesses. (And some guesses are definitely more educated than others.) The texts you will see in the first two years of Literary Chinese will tend to be those where scholars have argued back and forth for millennia (this is China, after all -- they've been explicating texts in different ways for a good 3000 years now), and at this point we have more or less come to a general consensus about what the text says (or is trying to say), what all the words most likely mean, and even the underlying thought processes (sīxiǎng 思想) which went into and underlie its composition. If you really work hard at figuring out why and how a great text says what it says, it is generally not easy, and a very deep rabbit hole. Really -- this is hard stuff, and that's actually part of what makes it so fun. (Poetry is usually especially pregnant with meaning, but can be totally inscrutable -- check out "Tiān Wèn" 〈天問〉 in the Chǔ cí 《楚辭》 if you want to see a poem that nobody understands completely, and we probably never will.) So -- what do we do? We use commentaries and the interpretations of great scholars (and even some not-so-great ones; in the most ancient periods, we have to take what we can get) from the past and present to help us figure out what the text is saying. If you're lucky, the text you're reading will have at least four or five great commentaries, both ancient and modern, to help you. And they will probably disagree with each other -- reading commentaries is a skill of its own, which you will need to develop at some point, but they're actually pretty straightforward (with some notable exceptions -- some of the early commentaries to Taoist texts are fully-developed cosmological schemes of their own, and can seem just plain crazy -- but who are we to judge, they're all products of their own time, place and sīxiǎng 思想).
4) Fun: Here's the real kicker -- Literary Chinese can be so fun and crazy and brilliant and awesome I don't even have words to describe it. The Lǎo zi 《老子》 may have said it best: "玄之又玄，衆妙之門。" ["More profound than the profound, the gateway to the myriad subtleties." = my translation off the top of my head]. So, hold on, how can something be "more profound" than that which is already "profound/inscrutable/so-deep-you-can't-understand-it"? What the heck are these "myriad subtleties/mysteries"? I don't think any of us really knows, but this stuff is very deep and often brilliant -- but that doesn't mean it's easy to understand. Or, in the Zhuāng zi 《莊子》, whenever Confucius shows up, the text describes him as a buffoon and a simpleton -- I'm not sure the Confucians liked it very much, but it's often laugh-out-loud hilarious. On that note, the Zhuāng zi 《莊子》 may well be the most "fun" text in all of early Chinese -- highly, highly, highly recommended for anyone; but read it with a good translation alongside so you can get the jokes and feel the playful spirit of the text.
In general, the texts which have been passed down to us have been preserved because they're special in one way or another. You're not reading the daily newspaper from 2000 years ago, you're reading (usually) the greatest classics of literature, history, philosophy/religion and discourse/rhetoric that Chinese civilization produced in its first two millennia. But because of this, they're often playing with language, making very deep and important/influential statements, and telling stories which mean something on the level of Shakespeare, Dante, or Faulkner. Think about giving Macbeth to a young learner of English -- that's what you'll be reading. This is deep, deep, hard stuff. But like Shakespeare, when you really "get it", it can be staggeringly beautiful.
So -- here's the trick -- go with your gut instinct. As you read more and more classical/literary Chinese, your instincts will get better and better. If you don't understand what a word is doing (and that will happen more than you think, no matter how long you spend at it), then be honest. Give it your best guess. Put in question marks if you like; what the heck are the "衆妙"?
Lastly, I would recommend using dictionaries, but wisely. Start with something like this:
because it will give you the most common ways the words were used in Literary Chinese, and as a beginner, you need to know these. If it still makes no sense to you, go to the commentaries. Pulleyblank for grammar is usually excellent. And when you get better at it, I'd say using Mathews' dictionary (which is based on the most well-known texts in Literary Chinese), digital applications like Wenlin, and the Hànyǔ dà cídiǎn 《漢語大辭典》 will begin to give you better and better insights into how these words worked and changed and diverged over time, and when paired with good training to build good instincts, after 5-10 years you can basically just read and get at least the gist of almost any early Chinese text. Yes, it does take that long to get good at it -- but anything this deep and brilliant is not going to be easy, and that's partly what makes it worth it (again, Shakespeare). It can change how you think (and help as you develop your own sīxiǎng 思想), if you spend the time to learn it well.
This was lots more than I had planned to write -- you caught me at an interesting point in my own learning. Mostly, I hope this all helps, at least in some small way.