I love tools that make it easier to do things. We just discovered a simple web app that will help you plan and organize your book. It's called Thoughtboxes. The app will allow you to brainstorm ideas and organize them into categories and subcategories. This is exactly what an author does in developing an outline for a book. Let's look at how that might work.
You begin by creating a "Train of Thought" which is simply the overarching idea of your project. Make it simple, call it "My Book" to start. You can change it when you develop a working title for the book.
Next you create "Thoughtboxes." These are simply categories of information you want to include in the book. In our workshops we advise participants to begin with three categories - People, Events, and Ideas. These might be the titles you give your three thought boxes. You can make each box a different color for easy visual recognition.
Once you've created your boxes, you can use them to brainstorm the items you want to include in your book in that category. Thoughtboxes calls these items "Thoughts." This is simply brainstorming. List all the people, events or ideas you think belong in your book. Don't worry about the order in which they appear. Just get they listed in one of the three categories.
When you are happy with your lists, you can begin to organize your thoughts. For example, you may notice that you have two or more lines of your family listed in the People box. Create a separate new box for each line and move the people you have listed to the appropriate box. Thoughtboxes makes it easy to move thoughts from one box to another.
As you begin to manipulate the boxes and thoughts you'll probably begin to get ideas about how to organize the material you've decided to use. In looking at your Thoughtboxes does it appear to make better sense to organize things chronologically, or might it work better to organize topically around themes like love, religious faith, patriotism and military service, the value of education or work ethic and entrepreneurship. You can create new boxes and move thoughts around to try them out.
Eventually you will have arranged your thoughts into categories and subcategories that you want to include in your book. The Train of Thought you have created will morph into an outline for your draft and emerge when your manuscript is completed as it's table of contents.
Thoughtboxes looks like a great tool, simple and easy to use. Check it out!