Yes, you read that headline right, might there be times when you shouldn’t outline first? I would say yes, but they are few and far between. I subscribe to the camp of those who outline first, and then ignore the outline for the rest of the writing process. That means I will add or drop scenes, and usually end up with a pile of extra fights that were not in the original outline. Alright, I admit it, I like fight scenes… 
Reason One: Any type of plan or step by step process makes you want to do the opposite, and/or shuts down your creativity because you don’t want to do it wrong. In this case, you will not want to outline as it will shut you down mentally. A way to escape this, and still keep your story straight, is to create a story-board and as you introduce plot threads, characters, and events, you add them to the board. This will help keep the plot straight and known, so you don’t have any plot-bunnies escaping to chew plot holes in your carefully woven story. All without outlining once.
Reason Two: You have no clue where the story is going but the character is engaging enough to follow blindly. Okay, well this might be a good reason to avoid an initial outline, it could create havoc later with innumerable plot threads and twists. Use the above story-board method to help keep track of plot threads. Or, do a character interview and see what your character can tell you about their story. Maybe they will give you an outline through the interview.
Reason Three: You have always outlined and want to try novel writing by the seat of your pants. Have fun, and enjoy your adventure. National Novel Writing Month is a good time to try this technique, since it’s hard to forget things if you are writing daily for 30 days. Of course, keeping notes can help even if you don’t outline first.
Reason Four: You are writing short stories about the same person over a period of time. Short stories do not need an outline as much as a novel does. I’ve never outlined for a short story, usually because my short stories are less than three thousand words long. I love challenging myself to write a short story within the NaNoWriMo daily word-count limit, 1667 words. It can be lots of fun, and a good way to practice story arc, rising and falling action, and experiment in different genres.
Back To You:
What do you think? Would you write with an outline or without one?
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