Two anecdotes: I don't know if either of them are true.
One is about a famous artist. He'd sneak into museums with his pallet of paints and "fix" the works of his that were hanging there.
Another is about Isaac Babel, who would trim his stories until nothing was left. In desperation, his editor would sneak into his home and steal the manuscripts.
Sometimes brilliance and obsessive behavior come together. There is a tendency to hang onto works, hoping that one more revision will bring them to perfection. Poets, who rarely make a living with their poems, are famous for "never finishing, just abandoning."
Those writers fortunate enough to make a living with their work usually face the discipline of deadlines. It doesn't always work. In high school, I heard, Guy Owen, the author of The Ballad of the Flim-Flam Man (which became a film), speak because he had to get the on lecture circuit to pay off an advance for an undelivered novel. And Douglas Adams famously said, "I love deadlines. I like the whooshing sound they make as they fly by.”
Of course, conceding that a work is done when the deadline arrives doesn't mean much to writers who are working on spec (either because they are still unpublished or because they can only sell finished works — maybe). How do they know when they're done?
I use a task-based approach, meaning that I always have specific steps that need to be completed before I even imagine that the work is finished. Now, once I have gone through all those steps, I'm still likely to have misgivings. But the good news about having tasks is that steps that were completed (but not to my satisfaction) tend to stand out. When none stand out, I know that, despite my gut feelings, I won't be embarrassed if I hand it to someone I trust to take a look. Outside views usually provide what I need to discover and fix what needs to be taken care of.
At times, I've completed a draft and realized that revision isn't the right choice. When one piece of the manuscript inspires me and directs me to do a new story based on it, I usually trust my instincts, throw out 90% of what I have, and work on the 10% that's golden.
Another realization I've had is that changing the protagonist offers rich possibilities I haven't explored. A manuscript I just completed had two previous versions — one finished decades ago – that didn't satisfy me. So I had these two proto-novels that led to something that, at last, feels right.
I'm a big believer in Heinlein's rule, "You must finish what you write." Not only does this suppress the urge to initiate too many projects, it also enhances learning. I have many stories sitting on the shelf that I like, but don't see much prospect for. There is not one of them that hasn't taught me something important about writing — something I would not have learned if I hadn't gotten to "the end." In addition, I'm amazed at how many times I'm working on a story nowadays and I'll remember a scene from one of these works. To a surprising extent, these scenes fit right in, as if they were created for the new work.
I think a sure sign that a work is finished is when the corrections become trivial (to the point where often fixes are put back to their initial states). After a cooling off period, if writing time ends up being devoted to minor tweaks, let it go. Don’t be Isaac Babel.
Similarly, if you get to "the end" and there is no passion left the project, it's time to put it on the shelf. You may get back to it, but your muse is telling you there's something else to work on. That manuscript has (at least for now) done all it can for you as an artist.
One question that rarely comes up is, are you calling it finished when it's not? I suspect this happens far too often with best-selling writers. No one is there to tell them "no," so they turn in works that are beneath their capabilities. For some people, raising the bar is very difficult. (Of course, you don't have to be a successful writer to stop growing as an artist.) It's challenging and sometimes painful to move to a new, higher level of ambition.
Here's what I do to challenge myself. Once I have a draft, I look to see if I'm missing an important part of its potential. Sometimes, my muse gets ahead of my understanding and gives me gifts I don't recognize. So I write down the theme and some of the major points of the story and explore them with questions, and often a lot of lists. That usually shows me if I'm shortchanging the content.
The shape of the work is more difficult to appreciate. The beauty of the language or the opportunities for symbols and metaphors or reinventing the structure so the story has more impact means asking less obvious questions. I found that listing works other people that seem to be related to what I've written forces me to imagine my story in different ways. It's a very right brain, intuition-driven approach, but it works for me.
One that I also depend on that is likely more generally applicable is approaching people who have provided good feedback and explicitly asking them for their thoughts on beauty and language and symbols and structure. A good reader may not have the exact answer, but he or she can push you in the right direction.
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