I usually prefer to have a story outlined to within an inch of its life before I start writing. The reason is that, if I don't, then I tend to wander off on tangents. Before I now it, the story has morphed into something very different from what I intended. Usually that means that I've written myself into a corner. That's the main motivation for outlining: to prevent yourself from writing the story into a corner.
Right now, though, I'm living on the wild side a bit. I've got the bare bones of a story outline, but only vague stuff, not the usual detailed scenes. And I've started writing the story.
The good news is that I've got over 10k words, and I'm not in a corner yet. It's usually somewhere between 10k and 20k that "the corner" happens. So I'm cautiously optimistic.
The bad news is that I've still got lots of unknowns to tackle. But for now, I'm willing to face them head-on.
In the meantime, I'm putting words on the page. I'm doing what writers do. I'm cool with that.