You can read countless opinions on the subject of outlining. Some writers say to do it and stick to it religiously, while other authors will say they don’t outline at all. This is one area where non-fiction writing diverges from fiction writing. If you’re writing a book about how to accomplish a particular goal, you should have a road map of concepts in your mind as a starting place. I advocate taking the moderate path: start with an outline, but give yourself permission to change the structure as you develop the content.
Define the scope of the book.
You can get stuck in endless outlining unless you are clear what the book is about—and what it is not about. For example, if you’re writing a book about how to make money selling antiques online, you might find yourself wanting to write about general web site design principles. Soon, you’ll find yourself adding a chapter about how to build a web site, then another chapter about SEO. Don’t do it!
Decide on a maximum number of chapters from the outset. I recommend no more than twelve for a single book. Also, decide on a maximum number of ideas to convey in each chapter. You might have ten chapters with ten ideas each, for a total of 100 ideas. Then, if you want to add a new idea, one of the existing ideas has to come out to make room for it. This is a simple and practical way of creating discipline.
Start with a list of questions.
You might think about writing a list of frequently-asked questions that readers are likely to be asking themselves. Write them down even if you don’t know the answers. You don’t necessarily need to phrase the chapter headings as questions, but the titles should speak to what the audience is thinking about. Finally, think about what questions your audience should be asking, but probably has never thought to ask. Write out a thorough and complete list, and you will find the chapter outline falling into place.
Having the right chapter titles is important because it keeps your audience engaged and builds anticipation. It also helps to keep your thoughts organized as you write the book. Don’t just wing it; start with a blueprint.