Your Story Isn’t Working? Here Are 6 Problems to Troubleshoot

If you’re here because you feel your story isn’t working, you’re not alone. Most writers feel that way about most of the stories they write. The good news is you can probably salvage your current story by troubleshooting a few key areas. One way to learn how to accomplish this is to learn what didn’t work in certain stories.

Today, I’m offering myself up as a guinea pig. A few years ago, I wrote a post I called “Lessons From a Lost Novel,” in which I talked about a story that hadn’t worked out for me and what I was later able to realize were its stumbling blocks. Today, it’s time for Round 2. If you’re a regular reader, you know I recently moved on from a novel I struggled with for years before admitting it. just. didn’t. work. Today, I want to analyze some of the missteps I made early on in writing this story and what the advantage of time now tells me I could have done to avoid all its problems. Almost all these mistakes could happen in any type of novel. My hope is that, with the benefit of my experiences with this story, you may be able to catch some of these problems much earlier on in your own manuscripts.

First, a little background. The story I was working on was intended to transform my already published standalone portal fantasy Dreamlander into a trilogy. This story is about a man from our world who is the only person in his generation with the ability to “wake up” in his dreams—in a fantasy-esque world parallel to our own. Without spoiling the ending too much, I will say that I tied off the loose ends in a way that made a sequel difficult. But then one night, while daydreaming at a campfire, I came up with an idea that would allow my hero to return to his lost love in the land of dreams for another apocalyptic adventure.

Right away, however, I was already in deeper water than I would usually be when plotting a new story, since I had to somehow create a resonant full trilogy out of a story that not only was intended to be a standalone but that had really tied off its own loose ends. Still, I was excited to return to the characters, and I swam ahead. I plotted, outlined, and wrote the entirety of what would be the second book in the trilogy. I called it Dreambreaker. So far, pretty good. But then it came time to write Book 3 and finish off the trilogy. I dove in—only to realize I had written myself into an unsolvable tangle. Whoops.

Before long (due also in part to larger life circumstances), I had major writer’s block. After struggling along with the story for several years, I ended up taking a conscious sabbatical of nearly two more years before finally returning to take another look at my outline for Book 3. Happily, enough time had passed for me to see (and admit) to the six major reasons the story wasn’t working. Not so happily, this led to the subsequent realization that, in order to create a solid conclusion for my trilogy, I would have to completely rewrite the already completed second book. I decided that was more than I wanted to commit to at the time and put the book back on the shelf so I could pursue a new idea.

6 Tips to Look at When Your Story Isn’t Working

Today, I want to share with you the six big pitfalls I fell into when writing Dreambreaker and its sequel. None of them are surprising; all of them are obvious. But all of them are also surprisingly easy for even experienced writers to overlook. Whether or not you currently feel your story isn’t working, double-check you’ve ticked all of these important boxes in writing a cohesive story that works.

1. Know the Ending

The Problem: Specifics are important. It’s one thing to know your story’s general ending and another to know the specifics of how your characters will get there, how their motivations will influence their final actions, and how the theme will prove out.

As an avid outliner, I always know how my stories will end before I start writing. But because this particular story was split into two books, I didn’t follow my own game plan as I usually would have. I did not outline Book 3 before writing Book 2. My outline for Book 2 worked out just fine. But by the time I sat down to outline Book 3, I realized what I had set up in Book 2 would not properly create the necessary payoff by the end of Book 3. I worked for months trying to get around this, but my attempts to explain my characters’ motivations and the mechanics of the magical finale became more and more convoluted as I tried to make sure plot, character, and theme all pulled together to create a cohesive whole.

The Fix: Had I outlined my series all the way to the end, I could have avoided this trouble altogether. I could have made sure Book 2 properly built into Book 3 before I spent so much time and effort writing it.

I realize timing on this one will vary from writer to writer. Some writers prefer to discover their ending in the writing. Personally, however, I have always liked to figure out my endings early on when outlining, for the very reason that I when I start writing the first draft, I can make sure everything builds sensibly toward that all-important Climax.

Regardless of whether you prefer outlining or discovery writing, as soon as you do know your ending, you will need to look back over the book-long build-up to that point and ensure it all makes sense. It’s far too easy to accidentally create a build-up and pay-off that are not two parts of a cohesive whole, but rather two separate entities altogether.

A Full Post I’ve Written About This: 

2. Keep the Plot Simple, So You Can Focus on Character Interactions

The Problem: I deliberately decided I wanted to write a Very Complex Novel. As my father would put it, I got too big for my britches. I wanted to magnify everything from the first book, going wide and deep with the history, culture, politics, and geography of my fantasy world. I drew complicated family trees for my royal characters, created twisty conspiracy theories that trailed centuries into my backstory, and crafted the plot around a complicated magical mystery the characters would have to unravel.

It had its good bits to be sure, and I thoroughly enjoyed concocting it all. But I kept tripping over the troubling sense that my story was getting away from me. The word count was geysering (even for me), and I knew I was spending an inordinate amount of time explaining all these complexities.

When reading Matt Bird’s The Secrets of Story, I cringed at his pointed question:

Is the concept simple enough to spend more time on character than plot?

For that matter, could I even reasonably describe my complicated plot in a simple concept? I tried and tried and tried, but the answer was always, “Uh, no.”

The Fix: Bird went on to encapsulate (in appropriately simple language) what I was reminded of the hard way:

…a good plot should be simple enough that both the characters and the audience understand it just by looking at it.

And:

[Characters need] to talk about something other than the plot at least once per scene.

Here’s how it’s supposed to work: the backstory and world lore in stories such as Lord of the Rings, Harry Potter, and Game of Thrones may be elaborately and deliciously complex, but they never take away from the simplicity of the plot and therefore never (or rarely) get in the way of the development of the characters and their relationships. So if, like me, you are tempted by complexity, stop and ask yourself these two questions:

1. When you add a new element (such as a character’s family tree), is the plot reliant on it? (Sometimes that’s fine; other times, it’s a sign you’ve unnecessarily complicated your plot concept.)

2. If not, does the explanation of it distract from the plot itself unnecessarily?

Full Posts I’ve Written About This:

3. Know Your Antagonist’s Motivation

The Problem: One of the secrets to creating a tight plot is understanding your antagonist’s role. Antagonists have always been hard for me. I just… don’t care enough about them. I always struggle to integrate them into the plot and theme in a way that lifts them above mere plot devices. The trouble is I like epic, world-ending stakes, and the kind of antagonists who drive those stakes are usually unavailable for the more interesting relational-level scenes that humanize both them and the protagonist.

In this story, I created a shadowy group of “elites,” who were secretly pulling all the strings behind the scenes. Intrinsic to the problem that this is probably the single most difficult type of antagonist for me to personally understand, I struggled to come up with solid reasons why anyone would be motivated to create the kind of world-ending events I wanted for my story. After all, these dudes have to live in my story world too—so why would they want to blow it up?

Cue more over-complicated attempts at explanation and rationalization. My antagonists and their motivations just kept getting more and more far-fetched. Even I didn’t believe in them.

The Fix: When I went back to my story after my long break, I knew the only way to fix it would be to change the role of the antagonists. Not only did their current iteration make no sense, but their defeat in the Climax had no thematic resonance. So I completely ripped them out of the story and replaced them with a single character who wasn’t unbelievably all-powerful, who had much more primal and relatable motivations, and who was already a player in the first book—and therefore carried much more weight and resonance in the sequels.

Unfortunately, this alone was enough to make me realize I would have to pretty much entirely rewrite the finished second book (something I wasn’t currently willing to do). This is because a solid antagonistic force will never just be tacked on to the overall plot. Even if that character isn’t present in most of the scenes, his or her influence must be integral to every structural beat of the story.

The easiest way to double-check your antagonist’s cohesion within the story is to examine his or her role in the Climax—and then work backwards to set that up. And if you find your current antagonist isn’t really all that crucial to the mechanics of your Climax, you may realize you’ve chosen and/or focused on the wrong antagonistic force.

Full Post I’ve Already Written About This:

4. Double-Check Your Story’s Thematic Resonance

The Problem: Because my antagonistic force was too separate from my main characters’ personal journeys and because I had over-complicated the plot to the detriment of my characters’ relational development, my story’s thematic resonance inevitably suffered as well. The “shape” of a story is important. Plot structure and character arc play a role in this. But ultimately, “shape” comes down to thematic resonance. What overall image is emerging from all the individual puzzle pieces?

In my story—as in many problematic stories—the answer wasn’t clear. The more I worked on it, the more it just seemed like a rehash of every other fantasy story about brave heroes making difficult sacrifices. Don’t get me wrong: that is and will always be one of my favorite themes. But this time around, it just felt… fake. It didn’t feel as if the characters’ actions offered any deeper symbolic insight or import. My messy plot, my messy fantasy lore, and my messy magic system were all combining to create a cohesive effect—and that effect was, in a word, messy.

The Fix: Good complexity arises out of simplicity—out of going deep with a few cohesive elements. Bad complications arise out of a bunch of random pieces that never quite pull together. Particularly in a genre like fantasy that, however realistic it may seem, is deeply symbolic, it is important every piece makes sense as part of a larger whole. Thematic resonance is where this will prove out: your plot, your character arcs, your theme, and your overall symbolism will all create a larger whole.

For me, the good news in all this messiness was that in my attempts to create thematic resonance, I dug deep into archetypal studies and ended up with a new book on the subject (Writing Archetypal Character Arcs–coming very soon)! The not-so-good news was that, once again, I realized I would have to streamline my story’s elements to the point that I would have to rewrite the finished book altogether. This is yet another reason why it can be so valuable to know your story’s ending before you begin the first draft—so you can make sure every piece is pulling together toward the same end result.

Full Posts I’ve Already Written About This:

Bonus for Writers of Fantasy: Understand Your Magic System

The Problem: Fact #1: I write fantasy.

Fact #2: Most of the best-known fantasies these days incorporate elaborate magic systems.

Fact #3: I don’t really care about magic systems.

For me, magic systems generally fall into that same Plot Trope bucket as antagonists. Not saying this is a good thing, but it is me recognizing it’s difficult for me to write what I don’t care about. In most of my stories, this has never been much of a problem because the fantasy element has always been relatively simple and catalytic. In the original Dreamlander, the magic system is pretty much relegated to the protagonist’s ability to live in both the real world and the dream world; in Storming, the speculative element is limited to the “science” of a weather-controlling dirigible; and in Wayfarer, the only magic is the superpowers gained by two people from the same simple source.

But true to my commitment to a Very Complex Novel, I decided to go big or go home with the magic system in these new sequels. (Needless to say, I went home.) I created a comparatively big magic system that was really just a big mess. It made no “scientific” sense, even though I kept throwing explanations at it. And it lacked thematic resonance, in that it didn’t symbolize anything pertinent or cohesive.

The Fix: To fix my story’s magic system, I knew I would have to do three things:

1. Simplify the magic system, by stripping it down to a handful of very specific, simple, and sensible rules so everything the characters did with it did not require oodles of on-the-spot explanations from me.

2. Pay strict attention to the magic system’s thematic import. Not only did I want the magic system to seem like an extension of the overall theme and the characters’ growth within it, I also wanted every piece to be a part of its own thematic motif (in this case, I decided to re-center it around water motifs).

3. Identify what I needed the magic system to accomplish in the story’s Climax and build everything around that.

Since then, I’ve also read and appreciated C.R. Rowenson’s The Magic System Blueprint, which I would use if I ever attempt another complex magic system.

Bonus for Writers of Series: Make Sure Sequels Add to All Aspects of the Existing Story

The Problem: This whole adventure was my first foray into the world of sequels and series. The fact that I was trying to create a trilogy out of a first book that had already been published as a standalone only complicated the task further.

As I wrestled with my sequels, one thought I kept circling back to was how much I hated, as a reader, when an author wrote sequels that seemed to forget what was best about the original or even what was the point of the original. I did not want to do that to my own readers, who already had a relationship with my original book Dreamlander.

I finally had to admit the sequels I’d created did not properly honor the original. Just as with certain series that I had felt personally let down by as a reader, I knew the sequels I was creating were not so much adding to the vision of the original as subtly changing and retrofitting elements in attempt to overall cohesion. (I did figure out how to fix that, but, again, it would require starting from scratch with the sequels.)

The Fix: Sequels and series are all the rage these days, for so many reasons—including the fact that they generally sell better and also that authors often love revisiting and expanding upon their own creations. But many sequels not only fail to add to their predecessors, they end up taking away from them, either simply because of their comparatively poor quality or because they change the original story and characters readers loved so much.

The simplest solution here is just to ask: does this sequel really need to be written?

If the answer turns out to be yes, then ask: how can I make sure every new element within these sequels adds to the original?

Of course, many of the potential pitfalls of writing sequels and series can be eliminated simply by planning the entire thing upfront, knowing the ultimate ending, and making sure everything in every book builds toward that end.

Full Posts I’ve Already Written on This:

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There’s knowing how to troubleshoot when a story isn’t working and there’s knowing. The frustrating part of my experience with these “lost novels” is that I consciously knew all six of these guidelines before I started writing them.

Writing a story, however, is never a simple experience. Even the most straightforward story requires the author to keep track of hundreds of different ideas and techniques all at the same time. It’s easy to forget, lose track of, or simply miscalculate the effect of any one decision you may be making about your story.

The more often we recognize these six important guidelines, the more likely we are to instinctively catch ourselves whenever we veer off-track when writing a story. And if we do get so far into the weeds that we must admit we wrote something unsalvageable, I can promise you the experience will make sure you never forget to check these points again.

Wordplayers, tell me your opinions! Have you ever felt like your story isn’t working? What did you do to fix it? Tell me in the comments!

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