How to prevent outlines that make you stuck

detailed planning outline can make you stuck
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Somewhere in the invisible recesses of cloud storage, a book outline exists.

Complete with title, it’s a 3-page Word document with 10 sections.

It’s gorgeous. Organized. Easy to read.

I spent hours on it.


I never wrote it.

When I was done with the outline, I felt repelled to see it. I lost all motivation and interest in the topic.  

If you’ve created a detailed plan for a project yet never carried it through, this might look familiar. How frustrating to put all the time and energy into planning your project without following through.

Why did this happen? 

Mystery is important

Spoilers are called spoilers for a reason.  When the ending of a story is spoiled, do you want to watch the movie? 

How is it to read a book when you already know the key details or destination?

When you’re feeling creative, there’s likely something you’re wanting to explore.  Some mystery you’re trying to solve.  Questions you’re seeking answers to.  

When there’s no mystery, you lose your curiosity.  When you’re not curious, you lose the drive to turn the page. You no longer need to take the effort to find out what’s going to happen next. 

It’s about the big picture, not the details

Imagine looking at a map, like Google maps.  Think of the difference between scrolling around the image of the map to see the route, versus reading the step-by-step turn details.  

I don’t know about you, but those detailed instructions are tedious when I’m choosing a route.  I want to be told the next turn when I’m ready to turn, not before I even start driving!

I’d rather look at the big picture and scroll around that map to get a sense of the directions before I start.

Your outline is like that map.  It shows the milestones to turn at.  You can see the general beginning, middle, and end. 

You’re planning a route to the destination.  

But it’s not the only way to get there.  

The mistakes I made, and why they kept me from the writing

I immediately realized why I’d outlined myself into the wall.  I’ve seen these issues keep my clients from writing as well.

With all the effort put into making a detailed outline, there was no more magic and mystery.

In adding details, I had no room to explore further.

In making the outline pretty, I was using creative energy that could have been going into the actual writing.

The result? Boredom and depletion.

Below are principles you can apply to your own outlines to create plans that stimulate your creativity:

  1. Use bullet points, not complete sentences.
  2. Use a few words to capture the key concepts.
  3. Try to fit the outline on one page.
  4. The outline doesn’t need to be pretty.  It’s not likely something anyone but you will see.  Don’t expend too much creative energy exhausting yourself in the planning phase.  
  5. Think of the outline as the bones of your piece.  It’s the foundation.  All it’s doing is helping to create a structure. The creativity and fun comes in the act of writing.
  6. It’s okay to stray from the outline a bit. Refer to it, but don’t be tied to it.  You don’t need to be attached.  If you’re moving completely away from the outline, this can be an issue.  But you don’t need to know everything before you start writing.
  7. Keep the outline and brainstorm separate.  The brainstorm contains extra ideas that may not be used. The outline has limited information.  It’s about choosing an arc deliberately.  You’re making choices based on all the ideas you brainstormed.
  8. When you start writing, write the words out, even if they’re written in your outline verbatim. Copying and pasting from your outline interrupts the flow of writing and prevents new creative insights.

As an example, here is my outline for this article:

  • Struggling to write a detailed outline. (e.g. that book outline I never wrote)
    • Plan, but don’t use up all creative energy.  Keep openness.  
    • Mystery important.  
      • E.g. If know book ending, curiosity lost.  Map–details tedious.
    • How to
      • Don’t get caught in details. 
      • Bullet points. 
      • Few words to capture concepts. 
      • Fit in one page. 
      • Outline = big-picture look.

Pretty boring, right? Outlines don’t need to be pretty, just functional.

You might notice that I don’t stick to this outline exactly.  There’s some rearranging. 

Your outlines don’t have to look exactly the same as this. Keeping the principles above in mind can help in making plans that support you with your actual writing.

I hope instead of a bunch of stale documents piling up on your hard drive, your ideas are transformed into the stories you want to create. Please reach out if you’d like help with this.

Good luck, and happy writing.