Creative writing can be such a difficult activity to estimate. Some would say that plan creativity, and time restricting creative writing, goes against its principals. Strict planning of other artistic and creative processes (films, music, etc) does occur and helps focus the participants in on the value of their time.
Therefore, treat writing ebooks with the same approach you would create a physical project (e.g. building a wooden chair). With this approach first brainstorm as many ideas as you can, focus in on ideas that interest you and prototype them. Prototyping ebook ideas can be as simple as white-boarding as many ideas as you can, delving deeper into the ones that interest you and coming up with a story line or chapter guide for your book.
After prototyping your eBook ideas you are ready to start into the execution phase of producing and writing your eBook. The stages mentioned below are formed in such a way that the overall goal of your eBook filters down into each activity.
Define the books goal/objective.
Set the goal or goals for your book. Don't try to muddy the waters with a multitude of goals. Think of any of your favourite books and they probably have a small amount of objectives and one central goal.
Break down the writing into sizeable chunks.
You could start with defining each of the chapters (finishing a chapter can be a good milestone). Add tasks for designing the book, proof-reading, research, etc. You'll know best what tasks authoring a book will involve. Define a level of effort for each job, preferably in man-days or half-day units.
Analyze the list for external dependencies (third parties) and arrange this work early on.
Planning to use a personal assist to do some research for your book? Intending interview some industry leaders to add some real world insight? Well, then you'll need to front load booking their time and add this to your list of jobs/schedule.
Sum up the level of effort and add in contingency time.
Add an extra ten to twenty percent to the overall duration of your project for those unforeseen things which may arise. The percentage will vary and only experience can guide the individual into knowing their own contingency level.
This completes the planning phase. You now have a list of tasks, with estimated level of effort. Add these to a diary/spreadsheet/calendar to establish what duration your writing project will have. Use any tool to visualize the plan that you are comfortable with - the tool is primarily there to help gain a high level view of the plan. Factor in holiday time and other work commitments. You now start writing, finally!
Keep on top of things as you implement your plan so that you always know if you are on track.
Writing ebooks involves the daily graft of putting in the work producing X words per day. Revert back to your plan each evening to establish how the day went, any contingency that was used up, unforeseen issues that arose and the plan for the following day.
Report milestones.
Any project plan should have natural minor and major milestones. These can be chapters/sections/paragraphs. Work each day with a goal of the next milestone to keep motivation levels up. It is easier to think of only have 1,000 words to an end of chapter milestone, rather than the ominous prospect of 20,000 words to the end of the book. Track these milestones in a simple report/document.
Keep going until all tasks are complete. Congratulate yourself and run a review of your plan.
You're done! Now you have completed your plan, take a look back at what was done right/wrong and how accurate your estimates were. Note down items you had not planned for which affected your time-lines (delays with research/other work commitments/etc.) so that your next eBook will have more predictable time-lines of delivery. Gauge what direction your own eBook business is taking and if there are smarter ways of creating your content.
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