Pushing beyond what you know how to do

I'm getting ready to forward a difficult email to a friend who's a writer. I've many comments for his novel and I suspect he's not going to like what I have to say. In preparation, I was reading Leonard Bishop again: his brief commentary on "Completing Impossible Scenes." This little gem of advice is mislabeled for it's really about pushing ourselves as writers.

By the time most of us start writing, especially those of us who come to the craft at midlife or later, we have already absorbed many writing techniques through all the reading we've done. But that doesn't mean there isn't an infinite amount to learn ahead of us. Bishop enourages us to write the scenes we don't know how to write, to keep pushing the idea or the character or the plot deeper, further. Of course, we risk writing something that doesn't work, but all artists have to do that, create junk that teaches us something.

Too many writers, he says, get pretty good and then rearrange what they already know how to do. That's the place I think that my friend has fallen into. He knows how to write clever sentences, and introspective first-person narration, but he hasn't pushed the plot into an original place. I'm hoping I'll find the right words to encourage him to do so.