> Could you elaborate on your process for outlining? What level of detail do you go into?
It depends on how developed the idea is. When I have give a lot of thought to something, especially the very moving and important points, I often know exactly how I want to phrase something poignant. In that case, I may write a full sentence, and if a great idea strikes me at this moment I might continue writing a full paragraph, but I ONLY do this if the inspiration is flowing and I don't want to lose it. Whenever possible, I will channel that flow into additional bullet points and work on the phrasing later.
> Do you nest bullets or stick to one top-level list?
I don't usually nest with formatting, unless the order of the sub points are really important; I usually list related ideas below each other. I do this because when I'm playing with the plot, sometimes I'll move those related points to come earlier in the story, even though they happened later in chronological time -- especially if I'm trying to pull in the reader during the first or second paragraph with something that is interesting, but is not an important event in the story.
> Do you try to lay out the substance of your argument?
The main points are usually the first items in the list and then I insert the connecting ideas and points in between. In terms of how substantive those list items are, I try to keep them short and stay high level in the brainstorming/outlining mode.
Other suggestions on process:
I delete a lot at the end. I scrub every word and phrase that isn't absolutely necessary.
The last paragraph I write is the first paragraph of the article/essay -- it's so much more natural to create a map of where you're going after you've already been there. This also takes the pressure off of getting started because you can start anywhere, and it makes writing the introductory paragraph so easy it feels like cheating.
The last thing I write is the title.