You know where your story starts. You know where you want it to end. Your outline is all the “stuff” that goes in between. Don’t make it harder on yourself than it needs to be. Everyone does it a little differently. I usually write my outline like a very boring short story.
Hairy short man is given a magical ring
He must take it to the elves to dispose of it
The elves aren’t any help.
Others join him on a dangerous mission to destroy said ring.
There are obstacles a long the way (think trolls, evil wizards, and creepy creations)
The others crave the ring for themselves and the group is disbanded.
One, a true friend stays and my MC reluctantly accepts.
Together they take off and fight more obsticles. And there are some people who will help and die.
My MC goes crazy and wants to keep the ring, but something happens the ring is destroyed anyway. (come on you know that Tolkein didn’t know that a creepy toad of a man would bite off Frodo’s finger and fall into the one thing that could destroy the ring)
At this point you know the bones of your story. These things will likely never change.
Now break them apart.
Hairy short man gets a name. Frodo. You figure out what motivates him. (he envies his uncles adventures. He likes food. He likes pipe weed – we all know he is a pot head) So he is little bit of a lush. It would take something powerful to get his ass out of the shire. Ohh.. How about a shiny ring that could be the end of all? Sounds dark. Has potential. I’d say go with it.
No story is complete with outside kicks. figure them out a little. They are motivated by different things. Maybe one likes adventure. Another loves Frodo. The third does whatever the other two do. they set out.
It is strange and dangerous. Insert creepy dead horse men. Let the readers know the stakes. They would totally fail on there own. Hello they are a bunch of pot head fooddies. Better give them someone who knows what the hell they are doing. Make him dark and mysterious.
He’s helpful just in time, because something even more dangerous comes along. Epic battle. We have to knock the short man down to size. He gets hurt in the battle. Wouldn’t it be cool if the person that stabbed him used some kind of poison? Up the stakes. the Elves will know how to heal him.
See… this is like writing a short story, but it leaves room for things to change. Some of it are basic ideas (some sort of poison) others you will get excited about and will be more detailed like the characters being foodies and pot heads. Different things will speak to you. Write them down. Trust yourself to let the words come to you later and just focus on plot points, character bios (especially motivation) and things that need to be layered (The hobbit wouldn’t have gotten far if the ring was never given to him… and that it couldn’t be destroyed by anything man made… it is the driving force behind the book.