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In school, you learn to start with an outline but I often write mine at the end.

Here's what that looks like:

∙ Write a bunch of little paragraphs with random thoughts on a topic.

∙ Organize them into topics and sections.

∙ Once the structure is clear, I create an outline.
Starting with an outline can be problematic because it can block the creative serendipity that makes writing so productive.

Or, as @paulg once wrote: "Expect 80% of the ideas in an essay to happen after you start writing it, and 50% of those you start with to be wrong."
"I was writing and now my outline doesn't make sense anymore."

The frustration you feel is a good thing. It means you're thinking thoughts you've never thought before, which is proof of progress.

Then, once you've exhausted your ideas, create an outline

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