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Fear of failure keeps a lot of writers inside the story they first imagined. Asking “what’s the worst that can happen?” is a practical way to test that fear, take bigger creative risks, and push a draft past the limits you’ve set for it.

On our first trip together to Europe, the hubs and I had mapped out a trip from Florence to the Cinque Terre region in Italy, where we’d spend the first three days of our vacation. But when our plane was unexpectedly delayed and diverted to Bologna, the airline planned to bus travelers on to Florence—backtracking us south.

What if we just took a train from Bologna and went on to our destination? we asked ourselves. What’s the worst that could happen?

Ah, well…

Bologna, unlike Florence, is a city where English is not nearly as commonly spoken, so we had to figure out getting from the airport to the train station, and from the station to a small coastal region, with only my very remedial Italian to help us, navigating an unfamiliar city and an overwhelming train station and schedule to find the line that would get us there. At night. Where we would now arrive well past when the little B&B we were staying at would be manned by a desk attendant. Without our luggage, which—no surprise—was headed to Florence without us.

But my husband and I frequently find ourselves using this phrase, especially when we travel: hopping onto public transportation, getting lost down unmarked alleys, trying experiences we know nothing about. Things may veer off plan, but how bad could it be?

Generally we trust that we’ll figure things out if they go awry, and that there’s not too much that’s going to lead to consequences that are world destroying or can’t be fixed or at least bettered. That night in our unexpected Bologna detour we managed to find the right train, contact the B&B and arrange for a key to be left, and wash our underwear in the bathroom sink until our luggage could be delivered the next day.

I’ve been thinking about this approach in terms of writing lately. In a recent editing consultation I offered feedback that would have meant a pretty substantial revision for the author if he agreed with my observations. Eventually, once he sat with the idea, it turned out he did, realizing that part of the story wasn’t serving the whole, but still the idea of wide-ranging cuts and rewrites was daunting—not just because of the work it entailed, but because he worried it might make the rest of the manuscript fall apart.

“What’s the worst that can happen?” I asked him. “Take out the parts in question in one big excision and move it to another document, then save the original manuscript as a new document.” If things don’t work out, I told him, he could easily revert to the old version, and if he wanted to incorporate any of the excised material, it existed in a handy separate file he could mine from.

Taking a looser approach to our writing and revision can open up pathways neurologically and on the page that might infuse our stories with surprises and originality we could never have envisioned.

Writing, for all its difficulty and facets and complications, is not brain surgery. A slip of the scalpel isn’t going to cost anyone their life. Taking a looser approach to our writing and revision can open up pathways neurologically and on the page that might infuse our stories with surprises and originality we could never have envisioned while bearing down hard to make sure everything comes out just right or the way we intend it.

The “what’s the worst that could happen?” approach involves one of my other favorite phrases: What if? What if instead of having the character end up with the love interest you originally intended, you have her end up with the disruptor you thought was just the antagonistic force? What if she zigs left when you intended her to zag right? What if he fails at the crucial climax moment when he is tested instead of triumphing, as you may originally have intended or as the reader expects?

Might your story be infinitely more interesting and original and engaging in these unexpected scenarios? Might you discover something beyond the limited boundaries of your initial ideas? I’ve worked with authors who faced each of these situations and took the road less traveled (or at least one they hadn’t intended to travel) and found unexpected treasures—like those dreams where you discover extra rooms in your house you never knew were there.

This is part of the unexplained magic of writing—where the work takes on its own life and moves in directions you didn’t guide it. It’s where we can discover facets to our stories we didn’t imagine and never even realized existed. There’s no risk involved in this kind of a leap—modern technology means you always have a safety net. So why not take chances in your writing—explore the unknown road?

Start by asking yourself—and your characters—that key question:

What’s the Worst That Could Happen?

In this case I mean the question literally, rather than hypothetically. Give your character’s situation, personality, and objectives, what is the very worst thing that could happen right now to throw a wrench in their plans?

This is a “rescue question” that can help unstick stuck stories (especially in the dreaded saggy middle), get characters out of dead ends, add greater levels to your story, and heighten stakes and suspense and reader investment.

Sometimes authors play things a little too safe—I’ve worked on many stories where every time the protagonist gets into trouble, the author mitigates it, pulls their punches, or resolves things too quickly.

I get it—most of us live our lives working hard to avoid worst-case scenarios of all stripes, so it goes against the grain to plunge your characters into the soup. But that’s what makes for compelling, engaging stories. In life we get plenty of “medium.” In story we want full-frontal catastrophe, the lowest lows—but those can also lead to the highest highs.

Read more: “Most of Your Life Is Medium”

What is the thing you least want to inflict upon your characters—that messes up their plans (and yours) the most? What’s the thing that scares you to write? Do it. At least try it; see where it takes your characters and your stories.

Running your characters through the wringer lets readers imagine our own “what-ifs” if we had to live through “the worst that could happen”—but safely and vicariously. It gives us the extreme emotions and experiences we crave…but with the prophylactic protection of experiencing it through your characters. (“Books! The Condoms of Life”—my new tagline I just created for a reading campaign…)

There’s every chance you won’t use these wild leaps into the unknown and unplanned—but trying them, taking your story and characters in the most aversive direction possible, can help unlock levels and directions you may not otherwise have discovered in your work. And it may create an original, fresh, compelling approach that sets your story apart.

Key places for worst-case scenarios

• At the inciting event: What is the worst thing that could happen right now to not only force your character onto a path they’ve been hesitating before, but to do it in the most uncomfortable or risky or undesirable way possible? Andy Defresne goes to prison for a murder he did not commit in The Shawshank Redemption. Spock’s planet is destroyed and his mother killed in the 2009 Star Trek remake. Aliens destroy countless lives and cities in Independence Day. Take a bad situation and make it infinitely, hopelessly worse for characters we are invested in and you suck readers in and jack stakes sky-high.
• In upward trajectories: Things are going well for your protag—they’re moving toward their goal, experiencing character growth, triumphing over obstacles and challenges. Now how might they drop the ball? Is there an unexpected setback? A massive failure? A crippling crisis of confidence? A terrible loss? Mark Watney is surviving on Mars alone against all odds—until a ruptured airlock destroys half his shelter and almost all his food. Obi-Wan is killed; Gandalf dies. Countless main and beloved characters are killed off just when viewers are expecting the heroes to triumph in Game of Thrones and the final two Marvel movies. No one expected that shit, and it blew audiences away. What horrible thing can you do to your characters to complicate their journey?
• In downward trajectories: You’ve chased your characters into a tree and are throwing rocks at them, but how can you take it further? Fire missiles instead; cut the tree down; send a platoon of feral zombie rats up there after them and infest it with snakes. I speak metaphorically, of course (though I’d read that story), but there’s nothing to risk and everything to potentially gain by taking things further than you currently are, plunging the characters into more trouble, writing them into corners even you may not see the way out of. Does that scare you? Good—then you’re challenging yourself as a writer and storyteller, and maybe creating a story that will keep readers on the edge of their seats biting their nails, hearts pounding as they tear through the pages to see how the hell the character can possibly extricate themselves from this impossible situation. E.T. dies. Princess Buttercup marries Prince Humperdinck before Westley can rescue her. (Even little Fred Savage has to yank his grandfather out of telling the story to protest this seemingly irretrievable all-is-lost moment.)
• At the climax: This is where you can—and should—torture your characters as much as you possibly can. They are so close to getting what they’ve been striving toward all this time. Don’t just yank it away from them; make it threaten to cost them everything anyway, even in defeat. Katniss and Peeta, against the odds, have survived—and now the rules have changed and one has to kill the other. Jack and Rose stave off death together as the Titanic sinks from under them until only one of them can escape the freezing waters before rescue comes. If you can’t see a way out of the situation, readers likely won’t either, elevating stakes, suspense, and their investment, and demanding even greater reserves of strength from your characters.

The upside of “the worst that can happen”—in story as in life—is that deep suffering often calls upon the most profound wells of strength and resourcefulness and fortitude we possess, and almost always results in the greatest growth. And that is the delicious chewy center of effective story, especially the ones that move and change us and linger with us long after the final page.

Our impromptu midnight detour in Italy remains one of our favorite travel stories—and one of the adventures we most enjoyed and are proudest of.

The times I took the greatest chances—the ones that terrified me—are also the ones where I’ve grown the most. The ones that changed and shaped me into someone with more resilience, strength, and wisdom than even I knew I had. The ones that gave me the confidence in myself to keep moving down unfamiliar roads, instead of sticking to the same old safe ruts.

Take the chance. Do the crazy thing. Try the wild idea. Go down the weird untrammeled path you can’t find on any map and see where that sucker leads. If it’s nowhere good, you can (usually) just turn right back around and retrace your steps.

But if it is, what an adventure you’ve had—and taken your characters and your readers on—by stepping off the known road…in story and in life.

What’s the worst that can happen?

How about you, authors–do you find yourself playing it too safe in your stories, sticking to the script…skating along the “medium”? How do you break out of those confines to explore parts of your story you might not have imagined until they begin to come to life on the page?

FoxPrint Editorial helps writers strengthen their manuscripts through developmental editing, education, and practical writing guidance. Explore more articles on revision, storytelling, and the publishing process.

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