This part of the answer in particular speaks to me on an emotional level:

neil-gaiman:

I don’t. Sometimes I’ll jot things down before I start, though. But normally I only find out what it’s about and what’s happening when it’s being written. 

…normally I only find out what it’s about and what’s happening when it’s being written. 

I recently found out this approach is called “pantsing” in the NaNoWriMo and writing community; in layman’s terms, it’s just plain flying blind. 

This is how I write everything. I don’t recommend it. But I do recommend it.

Imagine you’re going on vacation. You know where you’d like to go, and you know what you’d like to get out of the trip, but you do ZERO planning in advance. You don’t pack, you don’t make reservations, you don’t even check if there’s an outbound flight or train to where you want to go. You just go. 

This sounds awful, right? You might run out of gas on the way to the airport. You might have to wait hours for your flight. You’ve got to buy clothes and toiletries when you get to your destination. You need to find a place to stay, too. You know what kind of touristy things you want to do when you get there, but you don’t know where anything is in the city, so how will you get there?

Now, think about this in terms of writing. Maintaining momentum writing like this can be INCREDIBLY difficult. It’s easy to feel like you’re getting bogged down in events, like your pace is suffering, like you’re just not getting anywhere and you’re never going to finish. First drafts are hard enough, and no preplanning makes them even harder. You might get some ideas when you’re 5k, 10k, 15k words in–ideas that impact the beginning of the story, or the story’s theme, or your characters. Do you go back and change it, or do you push on and make a note to come back and make changes later? 

So, yeah, it sounds horrible. I don’t recommend it. But let me tell you a thing…

Going back to our travel analogy, sure your trip is going to be haphazard. Sure, it will probably be exhausting. Sure you might feel like you’re constantly lost. But think about it–every place you make it to will be a pleasant surprise. Every person you meet will be a stranger you never meant to meet–a friend you never expected to make. You’ll get lost looking for a tourist attraction, and end up finding a bookstore where they had a book you had been looking for forever. You’ll ask a nice lady for directions to a restaurant, only to have her give you directions to an even better restaurant where you’ll eat the best meal of your life. You won’t feel rushed for time or pressured to get to one place or another, because you have no plans to be there to begin with.

That’s what writing without an outline can be like! You might know your main character’s name and you might know their final destination, but you have no idea how they’re going to get there. You meet your Main Character and get to know them by writing them; eventually you find out what they’re likely and not likely to do, what choices they’ll make, why they’ll make them, what their fears are, what their favorite food is, etc. And you meet every other character that way. You don’t plan them out; they sort of just show up in front of you and tell you, “I’m a part of this story now, and I’ll tell you how it goes.”

Some of the best elements of my own writing haven’t come from any planning on my part, but have come from my characters wandering around on rooftops or down alleys or between bookcases and stumbling across an item or person that they mess with for a few hundred words–and that same item or person comes in handy a few thousand words later when my character needs backup in a fight or needs to use that unorthodox item as a method of self-defense. 

So yeah, writing without an outline can be tough. It can take literal years to put your story down on paper. You can end up with a little 40k word first draft ‘cause you didn’t plan enough to flesh it out, or a 250k word monolith because you rambled a lot and you’re going to need to edit the draft to death to get it where it needs to be. Things can feel clunky, or rough, or even cringe-worthy. Writing professors and creative writing classes will teach you it’s a BIG NO-NO to write without an outline, and I agree it’s definitely not for everyone. 

But, for me, writing with an outline feels like having Siri tell me exact directions on how to get somewhere, or walking down a sidewalk already set in stone. 

For me, writing without an outline feels like going on a journey with nothing and no one to guide me. And that’s how I want my readers to feel when they read what I’ve written. So, why wouldn’t I want to feel that way when I’m writing?