What is great writing? A naive answer might be simply: “What is understood”. The purpose of writing is to communicate ideas; the form which most efficiently imparts them to readers is that which is best. But a cursory look at what we regard as good writing reveals anomalies with this view. A calculus textbook may be well-written, but it is never great. Many examples of great writing, particularly in fiction, are more difficult to understand than less “great” works. Perhaps it would be simpler to answer, what is bad writing? Here again the naive answer is to say: “What is not understood”. But if this is so, why are we bothered when someone misuses a word, even when we know what they mean? Someone violating a grammatical rule does little violence to our understanding of the text – what makes it worse?
We read for more than just learning. We read to understand the text, and to assess the ability of the author. It is hard to write well, precisely because that lets us weed out the exceptionally clever from the middling. To clumsily break a grammatical rule, or to misspell a word, shows that the writer is not as smart as those who can follow all the rules. To write in an unclear but difficult manner, like that of a philosopher, shows that the writer is very smart indeed. Thus, truly great writing is harder to understand than that which is “cut-and-dry”, and bad writing is bad regardless of whether or not we can understand it just fine.