My friend and creative colleague Steven Savage has published several books about creative processes and tooling. The latest of these is actually a sequel to a previous book about worldbuilding. Way With Worlds 2, as it is called, can be read standalone, but it works best when paired with its predecessor, since it expands on and provides additional discussion for many of the ideas in the original.
The book has been hugely useful to me as of late. This is less because it taught me things that were strictly new, more because it reacquainted me with things I did know but had allowed to slip from view, and allowed me to reconsider them in the context of my current writing project.
The first reminder was something Steve phrased this way: "Stop thinking 'good and evil'. Start thinking 'why and how'. ... Few people seem to think "I wish to be an awful person" in real life, yet many do awful things." The awfulness is about lack of perspective, or about conceitedness, but rarely about the actions themselves. It's about the motives and the methodology.
My own story has a few characters who run the risk of becoming cackling-evil stereotypes. Some of that is present in the first draft I'm still working on, and I know it. The trick will be to look at all that the next time around and say: If I were writing a new story as a response to this one, how would I do it? How would I take something that could end up as sterotypical evil and make it nuanced, convincing, something that doesn't lend itself to an easy category, something where you have to take the person in their entirety?
Another thing Steve brings up as a corollary to this: in order to know the people in question, you have to be willing to get close to them. Sometimes we end up with stereotyped bad guys because we're not comfortable with the idea of trying to know evil intimately.
Dalton Trumbo was at the time of his death working on a novel called Night of the Aurochs, about an unrepentant Nazi. He wanted to use the novel to show people what it was about Nazism that was appealing, empowering, even sexy, to a great many people both then and now. Trumbo struggled with mightily with the book, but it remained unfinished at his death, and eventually the unfinished manuscript was published along with a sheaf of letters, notes, and other material. The very last note from him was this "Oh god, don't let it dribble out like this. Just let it come in one big lump." (My heart collapses every time I even so much as think about that line.)
There are any number of reasons why Trumbo wasn't able to finish the book — his own conflicting and mutating plans for it, or the various circumstances of his life at the time, what have you. But I wondered if one of the more prominent, unacknowledged reasons was that he simply couldn't do it — he just couldn't lower himself all the way into that cauldron. Some think they can, but aren't able to follow through when they realize what it costs them psychically.
It would be cruel of me to make the argument that anyone who can't go coalwalking in the name of their art is just a wimp. What I will say is that anything that attempts to do more than merely distract us for a little bit needs to come from a deeper place than many of us are accustomed to going.
Before you dive into deeper places, check out my (new!) novel Welcome To The Fold, and showing your support for it by registering at Inkshares and adding the book to your "Follow" list! Failing that, you can always buy one of my existing books, available on Amazon Kindle and in dead-tree format.