He mentions being forced to write an outline before the essay, and doing it the other way around. I've heard this so many times that it makes me wonder, why is that even a thing? Like, where did that practice come from, and why are we still using it in schools?

Are there really people who prefer to do it that way? Is it even possible to do it that way? It sounds like, first you come up with the software architecture, and then you write the software, and of course the architecture is perfect the first time! Whereas, in reality, any time you build something nontrivial, the process of building it inevitably reveals flaws in your initial best guess about how to build it... just as nontrivial writing will reveal gaps in your knowledge, or flaws in your logic.

In my professional life, I’ve found that I do start with outlines, but only for specific forms of writing. I spent a bunch of time writing instructional/tutorial content. Stuff like “How to achieve <outcome> using <feature(s)> in <product>”.

I was starting from a position of having expert product knowledge and having to boil that down into a useful post for people who were either beginners, or had knowledge of the product, just not how to achieve <outcome>.

Starting with outlines helped me think about what things this audience would find most useful before diving into the writing process. But that was just a starting point, and the outline would evolve quickly as I got into the actual writing process.

Outside of this, I’ve never found outline-before-writing useful, and see this as an iterative or post-writing exercise if I want to see a high level overview/arc of the content.