9 Ways To Undermine Your Characters’ Best Laid Plans

Remember in elementary school, back in the good old analog days, when writing a report meant pulling out your trusty encyclopedia, looking stuff up and then – this was the maddening part – rewriting it “in your own words,” even though the words in the encyclopedia were perfectly fine? I mean, since you weren’t being asked to do more than give info, why couldn’t you just copy it over? And sometimes you did. Especially if you had a lot of other homework, plus band practice, play rehearsal and your paper route.

Why am I bringing this up now? Um, because I have a lot of homework – who knew it didn’t end when school did. So this month, instead of writing a column from scratch, I’m cribbing some info from my book, Wired for Story. Hey, if you can’t steal from yourself, who can you steal from?

So with that full disclosure, let’s talk about how to make sure you’re up to speed when it comes to really, truly, torturing your protagonist enough to make sure she actually earns her “aha” moment. After all, that’s what the reader comes for. Here’s why . . .

There’s an old saying: good judgment comes from experience; experience comes from bad judgment. The trouble is, bad judgment can be deadly. It can lead you to ignore that funny squeak every time you hit the brakes, put off checking out that funny-shaped mole on your big toe, decide to invest every penny with that clever guy whose hedge fund always turns a hefty profit. Even worse, bad judgment can derail your social life—which is a much bigger deal than we often realize. [pullquote]Story lets us sit back and vicariously experience someone else suffering the slings and arrows of outrageous fortune, the better to learn how to dodge those darts should they ever be aimed at us. [/pullquote]

So, since there are countless tricky situations in which good judgment comes in awfully handy, often the best—not to mention safest—experience to learn from is someone else’s. Could this be where story came from?

Story lets us sit back and vicariously experience someone else suffering the slings and arrows of outrageous fortune, the better to learn how to dodge those darts should they ever be aimed at us.  Since we’re wired to feel what the protagonist feels as if it were happening to us, when it comes to experience, it’s as close as we’re going to get to having our cake and eating it too. Which, of course, is precisely the point.

This means the protagonist is a guinea pig, and whether we like it or not, guinea pigs suffer so we don’t have to. But although guinea pigs have PETA to champion their rights, protagonists are on their own—and trouble really is their middle name.

There’s no way around it:  your protagonist really truly does have to suffer—otherwise not only will he have nothing to teach us, but we won’t have much reason to care about what happens to him, either. Like everything in life, this is much easier said than done.

And while punching, shooting, stabbing, and otherwise roughing up your protagonist can be difficult, there’s something even harder to get them to do: embarrass him. After all, a punch is a punch; it’s physical, external—once the sting fades, the wound heals, it’s usually gone and forgotten. What’s more, physical pain is something one can keep to oneself. No one else has to know. But to embarrass someone? That’s public. It’s no surprise the word “mortify” originally meant “to die.” Because that’s often exactly what we want to do when we’re embarrassed.

However, it also tends to be the only thing that spurs growth.

So it’s a pity that embarrassment, mortification, and shame are often the last thing writers want to put their protagonist through. We don’t need to read Pygmalion to know writers and artists have a tendency to fall for their creations. So, without meaning to, we’re always smoothing the way, pitching ’em softballs. Do not do this. ‘Cause it undermines your protagonist in the one way you never want to: it robs him of the ability to grow, and show what he’s really made of.

Constantly upping the ante gets the protagonist in shape, which is crucial since the final hurdle he’ll have to sail over will be impossibly high. Thus the more you put him through before he gets there, the better. After all, as Emily Dickinson points out, “A wounded deer leaps the highest.” If you want your protagonist to be up to the test when he gets to that last hurrah, you’ve got to toughen him up along the way.

Keeping in mind that your reader must know what your protagonist’s plan is before you begin to dash it, here’s a crash course on how to torture your protagonist—for his own good, naturally:

Nine Do’s and Don’ts for Undermining Your Characters’ Best Laid Plans

1.  Don’t Let Your Characters Admit Anything They Aren’t Forced To, Even To Themselves.

Remember when you were a kid, and someone was trying to get you to do something you didn’t want to do? You’d yell, “Oh yeah? Make me!” Well, in a story, when it comes to admitting anything, ever, that’s your characters’ mantra. No one in your story should ever divulge anything they aren’t forced to—either by a gun to the head or, far more likely, circumstances beyond their control. Information is currency. It has to be earned. Your protagonist needs a compelling reason to admit anything.

2.  Do Allow Your Protagonist to Have Secrets—But Not to Keep Them

We keep secrets for one reason: because we are afraid of what will happen—that is, change—if they’re divulged. But that doesn’t make it easy. A secret is “the result of a struggle between competing parties in the brain. One part of the brain wants to reveal something, and another part does not want to,” writes neuroscientist David Eagleman in Incognito: The Secret Lives of the Brain.

Thus it’s comforting to know that ultimately forcing her to divulge her secret will actually be a kindness. You don’t want her to have a heart attack from the stress of keeping it in, do you? So no matter how fervently she may want to keep her secrets close to the vest, you can’t allow it. In fact, the more the protagonist wants to keep mum, the more the story will try to make her sing.

And one more thing: don’t keep her secret a secret from us—let the reader in. We love being insiders. Our delight comes from knowing what the protagonist is holding back and why; we revel in the tension between what she’s saying and what we know she’s really thinking.

3.  Do Make Sure Everything That Can Go Wrong, Does

But don’t let your protagonist in on your agenda. Let him start out believing all he has to do is ask and voilà, all the riches in the world will be delivered by FedEx before nine the next morning. It’s not that he’s delusional; it’s human nature. In the beginning no one ever spends more than the minimum effort required to solve a problem. But honestly, can you remember the last time the smallest amount of effort solved anything? In fact, it’s practically guaranteed to make things worse, and hopefully in ways the protagonist never imagined.

4.  Don’t Forget That There Is No Such Thing as a Free Lunch–Unless, of Course, It’s Poisoned

This is another way of saying everything must be earned. Which means that nothing can come to your protagonist easily—after all, the reader’s goal is to experience how he reacts when things go wrong. The only time things come easily is when they are the opposite of what is actually best for him.

5.  Do Encourage Your Characters to Lie

While in real life we don’t want people to lie to us, in a story, characters who lie are the ones who catch our interest. A provocative lie can make even the most bland character intriguing. Because we then wonder, Hmmm, I wonder why she lied. What’s she got to hide? Maybe she’s not so bland after all.

This, of course, means you need to let us know the character is in fact lying. If we don’t know it’s a lie, how can we anticipate what will happen when the truth is discovered? Because like secrets, lies, once told, must eventually be exposed. In fact, a big part of what keeps the reader turning pages is imagining the lie’s possible consequences.[pullquote]There is one accessory that no antagonist should leave home without: a ticking clock. Nothing focuses the mind—not to mention the actions of the protagonist—better than a rapidly approaching deadline.[/pullquote]

6.  Do Bring In the Threat of a Clear, Present, and Escalating Danger–Not a Vague Facsimile Thereof

Everyone knows you need a force of opposition. Without one, the protagonist has nothing to play against, making it damn near impossible for him prove his worth, no matter how hard he tries. Which is why the force of opposition must be well defined–and present. It can’t be a nebulous threat that never really materializes, or an antagonist, no matter how potentially dastardly, who merely hovers meaningfully on the edge of the action but never actually does anything.

To that end, there is one accessory that no antagonist should leave home without: a ticking clock. Nothing focuses the mind—not to mention the actions of the protagonist—better than a rapidly approaching deadline. This not only keeps the protagonist on track, but keeps the writer on track as well, by constantly reminding her that as much as she’d love to send the protagonist off on a soul-searching weekend in Tuscany, unless he finds Uncle Milt’s will by midnight, all will be lost when the wrecking crew arrives at dawn.

Of course, the force of opposition doesn’t have to be a person. It can be conceptual, like the straitjacket of strict social conformity, the dehumanization of unchecked technology, or the tyranny of the letter of the law. But–and it’s a big but–it can’t stay conceptual. Because, as we know, concepts are abstract; they don’t affect us, either literally or emotionally. What does affect us is a concept made specific, and thus concrete. This means the concept needs to be personified by specific characters who try to force the protagonist to bend to their will.

7.  Do Make Sure Your Villain Has a Good Side

As counterintuitive as it seems, the villain has to have a good side, however fleeting and minuscule. After all, no one is all bad. Or, if they are, they rarely see themselves that way. The majority of history’s bloodthirsty, despicable despots, not to mention elected officials, thought they were doing a good thing, often in the name of God and country. But even more to the point, black-and-white characters—whether all bad or all good—are tedious. Not to mention impossible to relate to.

Plus, a character who’s 100 percent bad isn’t likely to change, which renders him one-note. When it comes to “what you see is what you get,” what you tend to get is bored. Whereas a villain with a couple of good qualities just might be redeemable, instilling suspense. Not that your bad guy has to be redeemed, mind you, but both he—and the story—are far more intriguing if the possibility is open.[pullquote]As Thomas Carlyle said, “By nature man hates change; seldom will he quit his old home till it has actually fallen around his ears.”[/pullquote]

8.  Do Expose Your Characters’ Flaws, Demons, and Insecurities

Stories are about people who are uncomfortable, and nothing makes us more uncomfortable than change. Or, as Thomas Carlyle said, “By nature man hates change; seldom will he quit his old home till it has actually fallen around his ears.”

This means that a story is often about watching someone’s house fall around their ears, beam by beam. Thus it’s your job to dismantle all the places where your protagonist seeks sanctuary and to actively force him out into the cold. Writers tend to be softies, so when the going gets rough, they give their protagonist the benefit of the doubt. But a hero only becomes a hero by doing something heroic, which translates to rising to the occasion, against all odds, and confronting one’s own inner demons in the process. It’s up to you to keep your protagonist on track by making sure each external twist brings him face-to-face with something about himself that probably he’d rather not see.

9.  Do Expose Your Demons

There’s another, trickier reason writers sometimes shield their protagonists and let them duck the really thorny questions. Rather than protecting the protagonist, sometimes it’s the writer who’s uncomfortable with the issue the protagonist faces. By allowing the protagonist to sidestep it, the writer, too, gets to avoid it. Because just as you “out” your characters, so will they out you. After all, if you make them do things propriety frowns on, you’re revealing that you’re no stranger to the uncivilized side of life yourself—that is, all those things we do and think when we’re pretty sure no one else is looking. This, of course, is precisely what the reader comes for. We all know what polite society looks like—no one needs to explain it to us, we get it.

But beneath our very together, confident public persona, most of us are pretty much a raging mess. Story tends to be about the raging mess inside, the one we struggle to keep under wraps as we valiantly try to make sense of our world. This is often the arena the real story unfolds in, and what causes the reader to marvel in relieved recognition, Me too! I thought I was the only one! And so, to both the writer and the protagonist, Plutarch offers this sage advice: “It must needs be that those who aim at great deeds should also suffer greatly.” Often in public.

It reminds me of something I once heard the novelist Meg Wolitzer say. She’d just published a novel called The Position, about a couple who write a bestselling book ala The Joy of Sex, much to the endless mortification of their four children. She was on Fresh Air, and Terry Gross asked her whether it embarrassed her that her fourteen-year-old son might read the book. With missing a beat she said, “Nope. I learned a long time ago that you have to write as if everyone you know is dead.”

What about you? Have you ever flinched when holding your protagonist’s feet to the fire? How do you keep from pulling punches?