Colaborative Writing with AI
How to plan your story without turning it into homework.
For a lot of writers, the word “outline” triggers flashbacks to high school English class—Roman numerals, forced indentations, and the feeling that you’re supposed to know Chapter 14 before you’ve written Chapter 1.
If you outline a story so rigidly that A must lead to B, which must lead to C, and perfectly conclude at D, E, and F… you aren’t writing a story anymore. You are filling out paperwork. You drain the story before it’s even had a chance to breathe. Leaving no room to discover that maybe the story naturally wants to flow into a D1, a D2, and throw in a little bit of H.
But staring at a completely blank page is its own kind of terror.
Over the course of writing projects like Astral Rob and Second Chance, I developed a different approach. I call it the “Half-Lit Outline.” It gives you enough of a map to feel safe stepping into the dark, but leaves enough shadows for the story to surprise you. And it is the absolute perfect place to bring an AI collaborator into the mix.
Here is how the workflow actually operates.
Step 1: The Bare-Bones Map
I always start with a tool like Workflowy (which ports beautifully into Google Docs later) to build a minimal, overarching map. I only want the key points: the beginning, the middle threads, and a general sense of where the conclusion leads.
(A quick note on Flash Fiction: The rules change for very short stories. For flash fiction, I always flesh out the beginning, middle, and end completely, usually starting with the end clearly in mind first. But for longer narratives, keep it loose).
Step 2: The Pre-Prose Stress Test
This is the most important step, and it happens before a single line of prose is written.
I take that bare-bones map and hand it to my AI collaborator, Cg. But I don’t ask it to write the chapters. I ask it to act as a structural engineer. I ask Cg to aggressively look for plot holes, broken logic, or impossible mechanics in the world-building.
This is where the entire approach flips. You get to find out if a bridge is going to collapse before you spend 40,000 words building it.
Step 3: Fleshing Out (Only to the Midpoint)
Once the overarching structure survives the stress test, I start filling in the details. I will map out the plot beats, chapter by chapter. If I have a piece of dialogue that I absolutely know must be said, I drop it in.
But here is the trick: I stop outlining just past the middle of the story—right where things usually start to get interesting.
I leave the entire last third of the outline incredibly minimal. I still have a resolution in mind, and I am still working toward it, but by leaving the final act in the dark, I allow the story to remain fluid.
As you write, characters evolve. Themes emerge that you didn’t plan for. If you force those evolved characters to hit an old, rigid plot point, the story feels plastic. The Half-Lit Outline ensures that when your story inevitably beckons toward a different, more natural trajectory, you have the flexibility to follow it.
Try This:
Take your current idea and write a three-point outline: beginning, midpoint shift, and ending. Then hand it to your AI and ask one question: “Where does this break?”
It doesn’t have to be a complicated outline, just bullet points like the following example.
Here’s what an unfinished outline looks like in practice. Notice that I haven’t decided how it ends.
Working Title: How to Pickpocket a Kangaroo
- Know Your Hopper
Outside of the exclusive iHop restaurant, Darrell, a wallaby, sees Mantee, a kangaroo, go into the restaurant. He’s been stalking her for a few hours.
- Opening
- Darrell’s been stalking Mantee Roo and sees her going into the iHop
- He decides to go into the restaurant
- Greeted by iHop Hopstess
- Sorry, but this is a Roo’s only restaurant.
- Darrell snaps angry look
- Excuse me
- Gives Darrell the Manger dealing with a Karen look
- Did my words go over your head. They serve Wallaby’s at Skip Instead Diner across the way.
- Darrell leaves back to the parking lot.
- Middle act
Darrell took a bench outside of the iHop to wait for Mantee
- Eddie the Emu sneaks up on Darrell
- Can you spare some change for a war amputee.
- Darrell looks at Eddie smirking at his panhandle attempt
- But Eddie, you were born without arms
- Eddie looks back at Darrell madder than hell
- Didn’t say I was the amputee
- End of Middle
- Mantee leaves the restaurant and hops to her Toyota Outback
- Mantee sees Darrell approach
- Can I help you???
- Darrell hops over to intercept
- Mantee stealily reaches for her can of Wallaby Gone
- Darrell smiles
- I’m from Kid Protective Services, I have a warrant to inspect your Kid’s living conditions
- Mantee gives a confused look
- But I don’t have a Kid
- Darrell smiles
- We at KPS look after future Kids needs, now if you don’t mind, I need to inspect the pouch.
- Darrell grabs the bill-fold out of her pouch and books it.
- Resolution
- Police called?
- Wallaby gets away with it?
- Mantee belongs to a Mob (kangaroo pun) and gets her own vengeance?
This is the actual response from Cg for the above example story. I simply asked it to pressure test this story.
This has a wonderfully daft comic engine, but a few things need tightening before you write it.
First, make it clear early that Darrell is a wallaby. The “Roos only” rejection then becomes part of his motive, rather than a joke readers have to decode later. Second, his KPS claim needs to buy him just enough time to reach Mantee’s pouch. As written, she’s already reaching for Wallaby Gone, so she seems too alert to let him inspect anything.
The biggest choice is the ending. I’d go with Mantee belongs to a mob: Darrell gets away with the billfold, thinks he’s pulled off the perfect theft, then discovers he’s stolen from someone whose entire mob can out-hop him. That pays off the kangaroo premise and lets Mantee have the last laugh.
One more thing: decide how dark you want Darrell’s weeks of stalking to feel. If this is pure cartoon caper, a shorter, more foolish obsession may fit the tone better.
The Takeaway
An outline should be a compass, not a straitjacket.
Use your AI to test the ice before you step out, map just enough of the lake to get moving, and trust that the story will show you where the far shore really is.
Writing short, short stories?
Or writing Episodal fiction?
Do you still need an outline?
Check out my post on Foxxfyrre’s Honk’n’Holl’r called “The Googly-Eye Outline & The Red String Map” for it addresses these questions. And pokes a little fun at the whole process.
TTFN
Frank