[whswhs]

Giving advice on this is a little difficult; I tend to think of "do an outline" as the solution to a problem, not as a problem in its own right. (My sister tells me that i was giving her advice on how to structure a paper when she was in high school!) But let me try to reflect on how I go about outlining.

I look for major issues that have to be addressed in treating a question. This usually includes an overview of the general subject, with discussion of preliminary issues, which serves as an introduction. Then I break the subject up into general areas; for example, I broke "electricity and electronics" up into laboratory equipment and tools, electrical devices, analog electronic devices, and digital electronic devices. There may be a subtopic that's convenient to split off into its own chapter, such as military and adventuring electronics, or the transition between social interaction and combat.

I start listing all the subtopics I can think of for each major topic. If possible, I group several narrow subtopics into one broad subtopic; for example, in Template Toolkit 2, I had a subsection on physical traits of races, with subsubsections on things like movement, manipulation, attack, and defense. Sometimes I may decide that a subtopic belongs in a different chapter; occasionally this may even mean reconceiving what a chapter is properly about. Once in a while, I may even change the order of the chapters; the current first chapter of Social Engineering started out as the final chapter, but I decided that a guide to how social mechanics fits into play style would be more helpful as an introductory section.

I look for incidental issues that aren't part of the main flow of a chapter, but are relevant to it, and give them boxes.

Once the list of topics is stabilized, I count how many there are, and divide that number into the number of pages to get a page length per topic. Then I go through and assign estimate page lengths to major sections and then to chapters. I go over this a few times, thinking about whether a section needs to be longer than average or can be shorter than average. This is a hard part, and you'll probably misjudge the first few times you do it; after you've written a few books you'll have a better feel for how long sections will be.

If I'm writing for SJ Games, I send the outline to Kromm, and revise according to his comments. You won't have that option if you're self-publishing, but I encourage you to find a volunteer with a good sense for document structure, if you can. Remember, no one can edit their own writing!

I hope this is some help.