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How to Outline (Without Dreading It) [Originally published June 23, 2021]



Warning! This may give you a flashback to your terrible memories of school. You're in English class, your teacher explains that you have an assignment, and then she says what you were praying she wouldn't say, "Before you start writing your essay, you must write an outline." In school, we are told that before you start writing anything, you must map out your thoughts with Roman numerals for your main points, letters for your sub points, and numbers for your supportive arguments. Now there are certainly pros to outlining like this, and I personally outline every sermon I write just like that. But there is a problem to insisting that when you outline a book or any other writing, it must be like that. What is the problem? Most writers don't think like that! If you're like most writers, you have an idea, a message, or a story that you just need to write on paper before you lose your hankering to write down that thought. When you fall into the trap of "I must outline," you often start an outline, lose the desire needed to get the thought down on paper, and leave that brilliant thought as a half-done outline. Why? Because you only had the great thought. You didn't have all the sub points and arguments thought out – just the message. I'll give you a little secret. I didn't outline this blog before I started writing. That's right. I didn't outline a blog about outlining! But I did have something just as good. I had a starting place (where I wanted to start the conversation) and an outcome (where I wanted it to end). In this case the starting place was terrible memories of outlining in school, and the outcome is a better way to outline. An outline is simply a tool to help you with a process. The process is writing your content in a way that flows from point A to point B (from the starting place to the outcome). So rather than forcing yourself to outline in a traditional sense, simply write down where you are starting, and where you want it to lead. Rather than using a traditional outline for your book, try an outcome outline. Ask yourself a few questions about each topic of your book. These topics will become your chapters, and the order of the chapters will be determined by the answers to these questions.

  1. What is the point of this chapter? What problem are you solving or message are you conveying? Where is the reader's understanding when you start the chapter?

  2. What is the outcome of this chapter? What will the reader learn or be doing by the end of the chapter?

  3. How do you connect this chapter to the next? The outcome from question 2 should lead you to the point of the next chapter. For example, because of what the reader learned in chapter 4, you will address the following point in chapter 5.

The best part of this method is that it encourages you to write down your thoughts when you are thinking, "I've got to write that!" Afterwards, you can answer these questions about it and map out your thoughts. Or if you're stuck, and you don't know what to write, you can answer these questions, and they'll help you decide what to write next. Answering those three questions will automatically map out your book for you, which was the whole point of outlining. You can take this a step further by dividing your chapters into topics, answering these same three questions, and mapping out your thoughts for the individual chapters. If you don't like to outline your writings, I suggest you outline your outcomes by writing the point, the outcome, and the connection of each chapter. I prefer this as a spreadsheet with the chapters being the rows and the columns being the point, outcome, and connection. I'm not here to tell you what way to outline your book, but rather, I'm here to show that there are many ways to map out your thoughts – just make sure you do it. If you don't, your readers will be able to tell. Make sure your writing leads the reader on a journey of learning – not an unorganized collection of facts and tips. Joel Collison is the founder of Now Written Christian Books, and now provides editing and coaching for aspiring authors through Authorize.


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