The moment I stopped outlining before writing and started writing to find the outline
For most of college I was taught to outline first, then write. The problem was I kept spending an hour on an outline that I'd completely abandon by the third paragraph anyway.
What actually worked was flipping it. Write a rough draft with no structure in mind, just get the argument out however it comes. Then read it back and ask: what is this actually arguing, and in what order does it make the most sense to argue it. The outline comes from the draft, not the other way around.
The draft is usually a mess but it has the real argument in it somewhere. The outline I wrote before starting was always a guess about what the argument would be. The outline I write after a rough draft is a description of what the argument actually is.
Curious if anyone else found that the pre-writing planning was getting in the way more than it was helping, or if outlining first genuinely works for some people.