If you’ve been diligently working on your timeline or outline, you’ve probably noticed the middle (and longest) section of your story is a little sparse. Lots of writers panic when it comes to the middle because they automatically think they’ll never be able to come up with enough interesting stuff to happen. Lies! Stuff happens all the time!
If you understand what the function of the middle is, you will have no problem torturing your characters.
Think of the middle of your story as one of those really bad days when everything seems to go wrong.
Your external goal is to get that promotion at work. And in order to do that, you have to nail a presentation to a bunch of Japanese business men. Great! We’ve already established your goal in the beginning of your story, which probably took place the day or night before when we first met you and your cat family.

Here’s where the middle starts:
You oversleep, wake up in a panic, jump out of bed and land in a pile of cat puke. “Damn, cats!”
You fling the bezoar off the bottom of your foot and hop into the kitchen where you start the coffee maker before hitting the shower.
Someone in another apartment flushes her toilet and your water turns scalding. Curses abound.
While pouring your coffee, you drop the pot, breaking it and spilling more scalding liquid all over your power suit.
You’re cranky because you don’t have time to stop for Starbucks and losing self-confidence because you have to wear a different outfit.

Of course there’s a traffic jam. Some idiot got in an accident. You’d go around but cars are blocking you in. The only thing you can do is lay on the horn and scream obscenties.
Phew! You finally get to work (late) but still in plenty of time to make the presentation. After grabbing a cup of sludge in the breakroom, you head into the conference room to set up before the others arrive.
Fire up the computer, take a deep breath, access the file.
The presentation you worked so hard on and stayed up all night perfecting is gone. Hard drives, soft drives, thumb drives; it’s nowhere to be found. Your blood pressure rises, you start hyperventilating, and the thoughts in your brain start to swirl. You look for it again. You try another way. You go through a back door. Fuck! you scream silently.
You sweat, you feel weak, you sink into the chair and ask yourself how you’re going to tell your boss you screwed up.
And then you remind yourself that even though the promotion is out of the question, you still need a job or your cats will go hungry.
Hmm, less food means less barfing…
No, that’s just cruel.
And then you start drawing from memory your diagrams, graphs, and charts on the whiteboard. And you give the worst presentation of your life.
Okay, so that’s the end of the middle of your story. Easy peasy.
If you look closely a each of the scenes or events in my outline, I started with small events that are easily overcome:
Oversleeping, stepping in barf, scalding shower, coffee break (literally).
They start small; annoying, but you can move past them. You don’t really have a choice.
To increase tension, I added some conflicts that are outside of your control or that you can’t readily get around:
Traffic jam; sorry, you’re stuck there, so deal with it.

Presentation file gone. There is nothing you can do to retrieve it except drive all the way back home, and that is so not going to happen.
You hit rock bottom, your lowest moment. You want to give up. You failed. You will never reach your goal. Everything you’ve worked for up to this point has been for nothing.

But you don’t give up because your cats depend on you. Because you’re not a quitter and neither is your main character. He has to see it through to the end, regardless of obtaining that goal. It’s a matter of fulfilling something bigger. And that something bigger is your internal need. What do you need to make yourself truly happy, fulfilled? Seeing a tough situation through to the end, the sense of accomplishment you get when you try no matter what, the increased self-confidence that you can go out there and face those Japanese business men without a shred of technology. Your dignity. Your courage in the face of adversity. A sense of humbleness and humility. Whatever it may be, you have achieved it because you did your best in a losing situation.
To recap in the middle of things: an event or conflict happens that tries to thwart your main character from reaching his goal (coffee spills all over his power outfit). He reacts to the conflict (spends a few seconds cursing) then devises a new plan (changes from his power outfit into one that makes him less confident but is still going to make the presentation anyway).
Repeat this sequence as many times as you want, increasing the difficulty level with each new conflict thereby increasing the tension (will he make it to work on time? will he be able to pull off the presentation without his file? will he get the promotion? will he get fired?), really making it difficult for your protagonist to reach that goal. Because after all it’s not really the goal that matters, it’s what he learns about himself through overcoming obstacles, what he gains internally, that is the real prize.
You know that quote about, “God only gives us as much as we can handle?” Well, you’re God and it’s your job to bring your character to that breaking point and then make him try one last time. Insert your climax here.
So as you work through your timeline/outline for the first time, don’t worry too much about not having enough conflicts. Just aim for a few events, keeping in mind what it will take to bring your protagonist to almost quit and how you want your climax to play out. How does your character react to those conflicts? What new tactics will your character use to get through all those barriers?
And remember, this is just one of many passes you and I will take as we continue to outline our stories.
Next time we’ll visit The End.
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