Outlines serve two purposes: a way of formatting my arguments (not unlike in philosophy with premises P1, P2, P3 leading to conclusion C, etc) and as a jumping-off point. But there's a thousand ways to write a certain statement, tell a part of my story or explain a concept. I usually figure those out during the writing process and can't imagine knowing that beforehand. It's like guessing where to put your furniture when you haven't built a house yet - the details matter, but they are dependent on the larger structure that it's very hard to get right so early on. Plus, I often think of new arguments or points of view during my writing, necessitating restructuring or rewriting of parts. Do you not have those issues, or are they not significant for you? InDesign so far has been me attempting to cobble together a few booklets. If I embed all the assets, I don't break everything. Its logic is kinda weird and I don't know whether that's because of my low skill level, because I confuse concepts with Illustrator and Photoshop, because it's just weird or all of the above.Well, technically, if you are going back and forth between your outline and your first draft, then you haven't outlined it properly, or you have started writing too soon. You need to re-think the purpose and content of your outline.
But it is a bottomless black hole pit of despair unless you get professional training on it.
I agree with everything you said... ten years ago. Nowadays, writing is a system for me. It is a woodworkers shop. The logs come in over here, they get shaped into planks, the planks get honed here, individual pieces get made here, the pieces get fit together over there, and at the end, the piece is sanded and finished at that last table near the door. When I moved from a "creative" writing mindset to a "production-writing" mindset, I realized that there is no "magic" in writing. You don't need candles burning, and the lighting just so, and quiet, and all that. Now, I align the tools and the steps, and the writing happens. I think I have reached a state like Stephen King talks about in "On Writing" where you get all the mechanical bits lined up, and then you let the creativity flow via those tools. The "system" is in place to produce great work... you just insert the creativity. This is why I don't return to my outlines. Because when I write my outline I am thinking about how I am going to consume that outline at the next step. So when I get to the next step, I consume the outline, and out comes the first draft. When I get to the second draft, I consume the first draft, and output the second draft. It's a linear process for me. And it works for me. (Clearly doesn't work for KB, though!)