In a thread over at Hacker News, someone pointed out how the "simplification of any complex subject has limits". There's only so much you can boil a subject down before you start to do it injustice. The original discussion revolved around software tools, and how some kinds of programming can only be made so simple before they become constraints on further learning. At some point you gotta take the training wheels off.
The same thing happens with writing. There comes a point when all the books, all the advice of teachers or peers, all the things (ALL THE THINGS!!!) have to be shelved in favor of making an effort on one's own.
The way I once put this to someone else was, "I know when someone's arrived if they can write something where I don't agree with a single word, but I can still admire every impeccably-assembled syllable of it."
Now, I've thought for a long time about why I put it in those specific terms -- that is, why did I use such a negative, contrary example? Why say that instead of, say, "I know when someone's arrived when they write something I can't wait to show all my friends"?
Well, okay, that's often a sign someone has arrived, too, but I pick the contrary example first because my own tastes are often deeply at odds with most other peoples'. I have to do a little more work than most people might to offset it. In other words, that's the critic in me talking rather than the creator, both of whom are picky as hell for totally different reasons.
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