Six impossible things

The Worst Possible Thing

“Ask yourself what the worst possible thing is that you can do to your characters” is an often-repeated piece of advice that is a lot less helpful than it looks. If you follow it literally, about 99% of the time the answer is going to be “torture the character to death after torturing all their loved ones to death in front of their eyes.” Since the number of novels that involve the death-by-torture of the protagonist is nowhere near 99%, not even if you limit yourself to the Horror genre, I think it is fair to say that the advice is not meant to be taken literally.

To most experienced writers, that seems obvious. One of my writer friends has pointed out that at the very least, there’s an implied “…that the character can survive and possible learn/grow from” tacked on to the end of that sentence. You can also make a good argument for making it “…the worst possible thing from this character’s point of view at the moment…” because having to eat seaweed and bugs to survive on a desert island might be especially awful for a gourmet, but having died in the shipwreck would really have been worse, wouldn’t it?

Too many writers, though, do take “do the worst possible thing to the character” literally, and then make it a requirement for writing a decent story. They don’t even look for smaller questions like “What would my character really hate to have happen right this minute?” or “What screw-up will cause this character the most inconvenience for the next hour or so?”

Any good novel, though, is a combination of both small and large moments, good and bad. And the classic stories that get told and retold seldom involve “the worst possible thing that could happen” by objective standards. It’s pretty easy to think of a lot worse things that tornado could have done besides dumping Dorothy in Oz. And was getting taken in by Fagin really the worst possible thing that could have happened to Oliver Twist as an unprotected and easily missed child in the slums of 19th century London?

From an objective standpoint, the answer is obviously “no,” but the alternative possibilities would lead to very different stories from the ones that Baum and Dickens wrote. Too often, though, writers are so focused on the “worst possible thing” that they lose sight of the character, the context, and the constraints of the story they set out to tell, and they don’t stop to consider small things. Objectively, the “worst possible thing” that could happen to a character might be to be hit by a car and crippled as he leaves the cafe to rush to his important business meeting, but in a story about a desperate attempt to get investors for a fledgling Silicon Valley business, a more believable and useful “worst thing” might be having the character spill ketchup on his shirt out of nerves.

In a similar vein, looking for the “biggest challenge” or “greatest obstacle” that a character can face is not useful, if one takes it literally. I’m a writer; for any given character who isn’t a totally invulnerable Superman, it is trivially easy to come up with a challenge or obstacle that is too much for them to plausibly overcome. It’s only slightly harder, in most cases, to come up with a challenge/obstacle that is impossible for any character to overcome. Which is fine, if you want to write a tragic story of a character overreaching and failing, but no help at all if you want a more successful ending.

Focusing on superlatives (the best option, the worst happening, the hardest choice) can be useful if one is the sort of writer who has to force oneself not to write about happy people happily being happy. (In my experience, such writers tend to present their characters with easy to solve “problems” like “My hair is too long and looks horrible and the wedding is tomorrow!” [Hint: call a hairdresser] and need to really push themselves to get to a “biggest challenge” like “Somebody in the parking lot put a huge dent in my car and my spouse is going to be really upset!”) For most writers, though, insisting on superlatives makes it difficult to present the results believably.

It’s hard (though doable) to get a reader to believe a totally-out-of-the-blue-coincidental-hit-and-run car accident that prevents the hero from making his/her meeting. It’s fairly easy to get a reader to believe that a nervous person would spill ketchup on themselves right before an important meeting, or even that somebody else in the restaurant would trip and cover the character in spaghetti at just the wrong moment. Using the smaller, more believable incident allows the writer to save extreme measures for things that are really plot-necessary but tough to get readers to buy.

To put it another way, Occam’s Razor applies to writing more often than you might think. You don’t need the worst possible biggest challenge or the best hardest choice; you need the smallest thing that will do the job you want done. If you want the character to miss the big meeting entirely, you don’t need to have him hit by a car and put into a coma for three days; you can have his car towed while he’s in the restaurant. But do think about the ketchup thing – it might actually work better for your plot if he shows up in his ketchup-stained shirt and therefore manages to make a thoroughly bad impression in person.

This works for defeating villains, too – find the smallest possible thing that, if it can be accomplished, will derail or completely foil the villain’s plan. If that makes it too easy, figure out the villain’s precautions that keep that small thing from working, and move to the next-smallest possible thing. If there’s an obvious worst-possible-thing, too, that’s fine; you then get to decide which of the options sends the book in a direction you’re interested in writing.

  1. I’ve always thought the “worst possible thing” advice implied a lack of imagination. Because, y’know, I can think of a host of really awful things that could happen to my characters… but most of them would make for a very short book. Whereas “What would really f’ up my character’s day” contains a world of possibilities, and “What does my character really not want to do, and how can I maneuver her into having to do it?” — well, come to think of it, that’s the plot of my first book.

    Maybe it’s just that “worst possible thing” implies a lack of sadism. It’s so much more fun to play with your toys for extended periods than to break them right out of the box. 😉

  2. When I used that line (dratted interviews), the problem in later out-of-context quotations was that the italics dropped out. My version being, “What’s the worst possible thing that could happen to this character?” I was talking about matching characters to their quintessential plots. Standard thought experiment about which goes, “Imagine Hamlet dropped down in Othello’s plot, and Othello in Hamlet’s.” You’d get very different stories indeed from Shax’s.

    So it wasn’t intended to be an exhortation to character torture, but rather, about finding the plots that would reveal the most interesting things about a particular character.

    Ta, L.

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