Some stories take a while to get started. Others suffer from a rushed or poorly thought out ending. Yet the place where a lot of stories I’ve read stumble is in the middle. The middle is also where a lot of beginning writers start to run into problems, lose steam and confidence, and are tempted to abandon their story altogether. The worst part is that the middle is the longest section of the story – the majority of it. So getting the middle right is vital to writing a consistently enjoyable story.

The middle is very simple in theory. It’s a string of obstacles. Once you’ve determined an end goal for your characters, you just need to arrange multiple obstacles in their path. Your typical short story will have a few, while a series of novels can hundreds spread over the grand story arc. The exact number of obstacles popping up at break-neck pace, while a slice of life drama dwells on a handful of obstacles.

Alright. But how do I come up with obstacles? How do I know if they’re good or not?

Good questions, reader, and you’ve brought up a good point. If you’ve been writing and analyzing stories for a while, everything I’ve said is old news. So enough theory. Let’s dig into the execution.

What particular obstacles you set in front of your characters will depend on them and the overall plot you are shaping. Each story is its own beast, so it’d be impossible for me to go over all of the possibilities that are available. However, I’ve found a useful structure for planning out the scene or sequence where a particular obstacle is presented.

I sub-divide the obstacle into four stages: Introduction, Conflict, Resolution, and Consequences. You can think of these stages as the mini-arc the story progresses through to move from one plot point to the next. Going through each of these stages will give the scene or sequence some sense of completeness as well as give you a general idea of where your story should go beyond this obstacle.

  • Introduction: This is your set-up phase, showing how the characters arrive at the obstacle. If the characters discover this obstacle on their own – say, finding an enemy lair guarded by minions – your introduction will include the initial discovery as well as any preparations the characters make. For the guarded enemy lair example, this would likely involve gathering reconnaissance, observing patrol patterns, working contacts to get inside information, and acquiring the tools they’ll need for a successful infiltration. If the obstacle comes to the characters – a rival approaching the protagonist at a party, for instance – then the introduction stage is condensed to describing the how, where, and when of the scene.

  • Conflict: This stage is the obstacle itself and how the main characters respond to it. It is the fight, the chase, the argument, or whatever shape the struggle between protagonists and antagonists takes. With our enemy lair example, this is how the protagonists infiltrate it. With our rival example, this is them and the protagonist trading words or blows, depending on the kind and/or amount of tension you want at this point in the story.

  • Resolution: Here is where you wrap up the conflict and present the outcome of the characters’ efforts. This is where you show the characters succeeding or failing. In the infiltration scenario, our protagonists can succeed in taking out their enemy’s first line of defense and gain entry into the lair. Or the protagonists are caught in the act, and they are the ones who get beaten by the enemy guards. In the party scenario where the rival confronts the protagonist, the rival could expose some the protagonist’s dirty secrets thus ripping the protagonist’s social standing out from underneath them. On the other hand, the protagonist could skillfully dodge the rival’s incriminating questions and leave the party with their reputation intact. This scenario could also end in a stalemate. Maybe the protagonist and their rival do throw punches, but the host quickly breaks up the fight. There is no success or failure in this case, but it is an opportunity for both sides to prove their strength to each other.

  • Consequences: This is the aftermath of the characters’ confrontation with this obstacle. Think of it like the rewards for success or the punishments for failure. These rewards/punishments establish the direction the story will take moving forward. If the infiltration ends successfully, the biggest reward is entry into the lair. The characters could also gain keys for greater success or disguises in the form of the downed guards’ uniforms. If the infiltration was a failure, punishments could be wounds sustained in the fight and the enemy beefing up security, moving their base, or even retaliating against the protagonists. I’ve already touched on the rewards and punishments of the party scenario: the protagonist losing their reputation or maintaining it (along with the frustration on their rival’s face). Consequences from the stalemate ending would be a bit subtler, since it wasn’t a true success or failure. Yet even here, the protagonist could leave with greater determination to fight and new insight into their opponent.

The best way to know if you’ve chosen the right obstacle for your characters and have made the resulting bit of story interesting to read is to get feedback on your draft. But if you’re reading this post, then you likely want a bit more encouragement than what the blunt statement of “Just do it!” provides. So here are some tips and tricks that can help you craft interesting obstacles.

  1. I’ve always found it helpful to adopt a philosophy of nothing comes easy and all of the things you want come with a price when writing. Attaching a price tag onto each of the protagonist’s moves and victories keep them challenged and struggling. This constant struggle makes sure that the plot is constantly moving forward to my desired ending. The move or victory I’m attaching the price to also inspires me to come up with obstacles that would logically spring from it.

  2. If you’re writing an outline or plot sketch, stick to the major obstacles at first. You can add minor ones later. For instance, infiltrating an enemy base is a multi-step operation and would likely have minor obstacles embedded within it. There’s the guards outside to take care of, unlocking the front door, and then the minions directly inside to subdue without alerting the entire base.

  3. Rewards can be as simple as opening the way forward or as elaborate as obtaining the shiny MacGuffin. Likewise, punishments can be as simple as a delay or as elaborate as losing an ally. Scale the consequences according to the difficulty of the obstacle.

  4. Don’t forget about failing forward – failures that come with benefits. Let’s go back to the infiltration example one more time. Suppose that the protagonists failed and the enemy decides to move to a different base. This means that the enemy will be temporarily vulnerable while they’re traveling and perhaps easier for the protagonists to attack. Or the enemy may leave behind valuable clues on their way out of the old base. In either case, the protagonists’ failure has opened up new opportunities for them.

  5. You may have a scenario that has multiple rewards or punishments. Perhaps even a mix of both. You finally defeat that powerful wizard who’s been making you and your friends’ lives hell, but not before they finished summoning one pissed-off demon.

  6. The scenario may play out differently for different characters. One of your protagonists might get captured by the big bad. Naturally, this is quite the setback for their allies. But the captured protagonist has the chance to pick up useful insider knowledge about the big bad and their plans – a bleak situation that is ultimately advantageous.

  7. Don’t forget about shades of success and failure. Shade the consequences accordingly. When you land in the gray area between success and failure, it’s useful to think of them in terms of costs and compromises instead of rewards and punishments. You can have the shiny MacGuffin, but you must give up something equally valuable. The protagonist destroys their archnemesis but is fatally wounded in the process.

Do you find the middle of stories easy or hard to write? Have any of these tips helped you? Do you have tips of your own to share? Drop your answers down in the comments.