When you’re not sure your story will work, it’s easy to assume that uncertainty means something is wrong with the story.
There’s a moment in almost every book where the writer gets scared for a very good reason.
They’re not sure it’s going to work.
And that’s a moment when a lot of writers make one really dangerous assumption.
They think, “I’m not sure, so it must mean something is wrong with this story.”
And here’s where I want to bring in Sting.
Yes, Sting, the famous pop singer who used to head up the rock band The Police.
Recently, I was listening to him talk about his musical The Last Ship, and he said something that hit this exact problem. The interviewer, Mark Phillips, posed the question about the risk involved in this project. Sting is a hugely successful pop artist, and here he is venturing into the world of theater and musicals.
Was he taking a risk?
And Sting said this: “You need to put yourself in a slightly uncomfortable position in order to produce something new. Without uncertainty, there is no art.” [Emphasis mine.]
So in this post, we’re going to talk about how to tell the difference between a story that needs help and a story that’s just asking you to take a risk.
When You’re Not Sure Your Story Will Work, Start Here
What we need to be careful of is this: Feeling uncertain about your story is not automatically a sign that it’s no good. It’s just a signal.
And like any signal, we have to learn how to interpret it.
Sometimes uncertainty is telling you this part of the story needs more structure. Maybe the character doesn’t want something clearly enough. Or maybe the ending is too vague.
And that kind of uncertainty is useful because it points you toward something you can fix.
But sometimes uncertainty is telling you something else. Sometimes it’s just saying you’re stepping into a story you don’t know how to write yet.
That’s a different kind of uncertainty—the kind Sting was talking about. The risk of stepping into a form, a project, or creative challenge where the outcome is not guaranteed.
And writers hit this all the time.
Maybe the book is asking for more emotional honesty than you expected, or the structure is more complicated than you thought it was going to be.
So being unsure of your story doesn’t mean you should quit or give up. It means you should pause and ask a better question:
“Is this story missing a piece I need to fix? Or is it challenging me to do something I haven’t done before?”
Because if the story is missing something, you can work on a craft problem.
But if the story is challenging you and pushing you past what you already know how to do, you don’t want to run from that because that’s where growth happens.
So what do you do instead?
We’re going to get into that, but first, let’s figure out how we can tell if this is a structure problem or a challenge problem.
When You’re Not Sure Your Story Will Work Because the Structure Is Missing
A story with structure is like a road trip. Somebody’s trying to get somewhere. And they may know exactly where they’re going, or they may only know what they’re trying to get away from, but there’s some kind of direction to the story.
Then something gets in their way, and that’s what creates conflict. And conflict creates a story.
So if a person gets in the car because they need to drive across the state to see their sister before she moves away, and then the car breaks down, and they have to decide how badly they want to get there, well, that’s a story.
But if a person just drives around the block ten times with no destination and no reason, then nothing really changes. That’s not a story yet. That’s just a person using gas.
Same thing with a simple adventure story.
If a kid wants to find their lost dog before dark, and the storm is coming, and every wrong turn makes it harder to get home, that’s a story.
But if the kid just walks around the neighborhood looking at trees and flowers and then eats a snack and finds the dog in the neighbor’s yard and goes home, then there may be nice moments in there, but there’s no real structure yet.
Or think about a friendship story.
If two friends have had a fight and one of them wants to fix it before the other one moves away, but they’re too embarrassed to say what they really feel, that’s a story.
But if two friends are just hanging out and talking and nothing is pushing them toward a choice or a change, the story doesn’t have enough direction.
Check Your Story
So here’s a concrete way to check your own story. Ask yourself, “What is my character trying to do?”
And then ask, “What’s making that harder?”
And finally, ask, “Will something be different by the end because they tried?”
If you can answer those questions, you probably have at least the beginning of a structure.
If you can’t, then your uncertainty may be pointing you toward a structure problem.
The story may need a clearer destination, more pressure, or a more visible change in your main character before you can tell whether it’s really working.
When You’re Not Sure Your Story Will Work Because It’s Challenging You
So let’s say that you do have structure. Your character is trying to do something, and something or someone is making that hard. The story is definitely going somewhere, and you can feel that it has a path.
But you’re still unsure, and you’re worried that maybe you’re wasting your time with this book.
That’s when we might be dealing with a different kind of uncertainty—the kind that shows up when the story is pushing you past what you already know how to do.
So maybe you’ve written easier stories before, but this one has a deeper emotional center. Or maybe the character has to face something that you don’t quite know how to write yet.
That’s a challenge problem.
And that’s where a lot of writers panic because they think, “If I were better at this, I would feel more certain.”
But that’s not necessarily true.
When a story starts pushing you into new territory, you may have to learn something new while you’re writing it.
Or, more likely, you may have to stretch yourself emotionally, technically, or creatively to be able to figure out what the story is asking you to do.
The Best Kind of Stories
In my opinion, those are the best kind of stories, because they are the ones that make you a better writer.
But how can you tell?
Well, for one, when a story challenges you, it often creates a very specific kind of discomfort. You may have a sense that this book could work, but you don’t quite know how to pull it off yet. You may feel drawn to the story and intimidated by it at the same time.
Or you might keep thinking about it even when part of you wishes you could choose an easier idea.
That’s different from a structure problem. A structure problem feels like, “I don’t know where this is going.”
A challenge problem feels like, “I can see where this needs to go. I’m not sure I know how to get it there.”
So if this story is taking you somewhere new, then you don’t want to quit. You want to stay close enough to it that you can learn what it’s trying to teach you.
So how do you do that?
When You’re Not Sure Your Story Will Work, Follow the Energy
The first thing you want to do is follow the energy, not the guarantee.
So here’s what I mean: If you’re unsure about a story, your brain usually wants one thing—certainty. It wants that guarantee.
You want someone to come down from the sky with a clipboard and say, “Yes, this book is going to work. Yes, readers will like it. Yes, you’re not wasting your time. Please continue.”
And sadly, the sky clipboard person is usually booked.
So instead of asking, “Can I guarantee this whole book will work?” ask a different question.
“What part of this story still pulls at me?”
Because even in the middle of being uncertain, there’s often something that still has energy.
So maybe there’s one character you can’t stop thinking about, or a scene you’re nervous to write, but you keep coming back to it.
Or there could be a question inside the story that still bothers you, or an ending you can almost feel even though you don’t know how to get there yet.
Focus on that energy. It usually hums inside you and makes you eager to get back to the book.
It’s not going to prove that the book’s going to work. But we’re not looking for proof here.
We’re looking for life.
So instead of demanding certainty from the whole story, just move toward the part that still feels alive.
When You’re Not Sure Your Story Will Work, Ask What It Needs Next
The second thing you can do is stop asking whether the whole story will work and just ask what the story needs next.
Because “Will this whole book work?” is usually just too big of a question. Your brain can’t answer that when you’re standing in the middle of the book with all these loose pieces around you that you’re not sure where they go.
It’s like asking, “Will this entire house stand?” when you’re just holding one board, a bucket of nails, and half a sandwich.
Of course you don’t know yet.
So bring the question down to something you can actually work with.
Ask, “What does this story need next?”
Maybe it just needs you to write the scene you’ve been avoiding. Whatever that is, just give it a try. Sketch the ending. Try the conversation. You may still feel uncertain afterward, but now you’re not frozen. You’re working with the story again.
And that’s important because uncertainty becomes much scarier when you stop moving. It starts to feel like you’re giving up and the story is toast.
But when you take the next step, uncertainty just becomes part of the process. You’re not deciding the fate of the entire book today. You’re just giving it another chance to show you where it wants to go.
When You’re Not Sure Your Story Will Work, Try This
Take the story you’re unsure about and make a simple two-column chart.
On one side, write: Signs this may be a structure problem.
And on the other side, write: Signs this may be a challenge problem.
Potential signs this may be a structure problem:
- “I’m not sure what my character is trying to do.”
- “The story feels like it’s wandering.”
- “It’s getting boring.”
- “I don’t know what’s making the character’s goal harder.”
- “I’m not sure what changes by the end.”
On the other side, signs this may be a challenge problem:
- “I do know what my character is trying to do, and I do know where I’m going, but I’m nervous because I don’t know if I can pull it off.”
- “The story feels bigger, deeper, or riskier than anything I’ve written before.”
- “I keep thinking about it even when part of me wants to choose an easier story.”
- “The story has a path, but I’m scared I won’t be able to write it well enough.”
Once you have those two columns filled out, here’s the quick win for you.
Circle the side that has more true statements.
If the structure side has more circles, your next step is to strengthen the story path. If the challenge side has more circles, your next step is different.
You simply narrow your focus and ask what the story needs next.
Then be willing to work with that, even while you’re feeling uncertain, until the story is finished.
Note: If you want more help, this is exactly the kind of thing we work on inside Writer’s Brain Studio, where I teach regular masterclasses to help us dig into writing problems like structure, procrastination, self-doubt, momentum, and the places where the brain starts making the story feel harder than it needs to.
Featured image by lookstudio on Magnific.