How to Quickly and Easily Outline Your Writing

In my previous post, I discussed how to craft a thesis statement. If you have yours to hand, get it out—you’ll need it for your outline. If you haven’t written one yet, reread the previous post and write one.

Once you have a thesis, you’re ready to outline. Before I continue, I should confess that I’ve never been the kind of writer who uses detailed outlines. At school when the outline was part of the assessment, I usually wrote my paper first and then reverse engineered the outline.

Since training as a writing teacher, I’ve come to appreciate the utility of a rough outline, but still don’t create highly detailed outlines. If you’re interested in creating a more detailed outline than what I’ll walk you through in this post, please do. Many people find them useful, if you’re one of them, enjoy. In the conclusion, I explain how to use this method to create a more detailed outline.

Pre-Outline Freewriting

In my post on freewriting, I discussed how to use freewriting to get going in your writing. It’s just as useful for your outline. So, set a timer for 10 minutes and write (without stopping) about your thesis statement. Don’t judge what you write, just write whatever comes to mind when you think about your thesis. You’ll likely write some combination of phrases, rough sentences, and questions.

When the timer goes off, reread what you’ve written and underline or highlight anything that stands out as particularly useful. Keep these things in mind as you continue to the next step.

The Outline

Write your thesis at the top of the page. Below it, you’ll write questions you need to answer in order to prove your thesis.

Let’s return to the sample thesis from the previous post: People who have pet cats tend to have lower blood pressure than those who have dogs.

  1. How have scientists looked at the impact of spending time with animals on blood pressure in humans?
  2. What is the evidence that spending time with animals is beneficial in terms of lowering blood pressure?
  3. What evidence is there that dogs and cats have different impacts on blood pressure?
  4. Have the studies controlled for people who are allergic to cats? Who are allergic to dogs? Who are allergic to both cats and dogs?
  5.  How can living with a cat be better for one’s blood pressure than living with a dog, when it has been shown repeatedly that having a dog increases one’s physical activity?

The list of questions could go on, but you get the idea.

The next step is to take each question in turn and decide whether it has a place in your piece. For example, in response to question one, you could find an article (or several articles) that discuss scientific studies of the impact of spending time with animals on blood pressure. You’d likely find that some of these looked at patient records and asked the patients to fill in a questionnaire. Thus, they’d be based on doctor recorded blood pressure readings and patients’ self-reporting about the time they spend with animals.

You would likely conclude that question 1, or rather its answer, does have a place in your piece. It is vital to your thesis that you have evidence that animals affect blood pressure. If you’re writing a longer piece, you’d likely want to consider the inherent problems in studies that rely on self-reported information – to what extent can you rely on what the patients reported about themselves? Also, if the study uses medical records collected by several physicians, can you trust that the data are consistent? Is one blood pressure machine as accurate as another? Is one physician as accurate in recording patient data as the next?

After you think this through and the additional potential questions that you need to consider, it’s time to reflect on the place of this question in your larger piece. If you’re writing a blog post or an article, this might be the only point you need, but you’d then need to revise your thesis to reflect your new focus. If you’re writing a book, the exercise of thinking through question 1 as I’ve done here has shown that question one is substantial enough to warrant having its own chapter.

You would then repeat this exercise with the remaining questions. If you find a question that just doesn’t interest you, if it’s not vital to proving your thesis, cross it out. If it is vital to your thesis, consider either tweaking your thesis so it’s not, or keeping the question you’re not wild about.

Once you’ve finished working through your questions, write a one sentence answer to each question that you are keeping on a separate sheet of paper. Then think about what order they should go in; the strength of your argument, and therefore of your piece of writing, relies on the logic of your organisation. For example, if you’re writing a book, there should be a clear, obvious reason why chapter three must come after chapter two and before chapter four.

One way to test your order, is to write each statement on a separate strip of paper, mix them up (or type them out and then alphabetise them), and ask a friend to put them in order. If your friend comes up with an order that is different to yours, discuss how you each reached the order you did. Then, decide if you want to change your order. If you don’t change it, but feel your friend has some valid points, make sure you keep those in mind as you write – you’ll need to make it clear to your reader why you’re discussing things in the order you do.


If you like more detailed outlines, repeat this process with the answers to the questions you keep – those answers are the thesis statements for your individual chapters. Your answers to your chapter thesis statements will be topic sentences for your paragraphs or, for more complex issues, your section headings (the topic for a group of paragraphs). We’ll talk about paragraphing and topic sentences next month.

In the Facebook group, let us know how this outlining technique worked for you. If you have used a different technique, share that with us too!

Why do you need to brainstorm your book?

You can brainstorm before you freewrite or after. I tend to brainstorm after, hence the order of these posts. When you brainstorm after you freewrite, you can start your brainstorming session with some of the words or phrases that struck you as particularly useful in your freewriting.

Wherever you place it in relation to freewriting, brainstorming at the beginning of a project is helpful whether you have too much information or too little. As you put ideas on paper (or on the screen), you’ll be able to evaluate how much you know and identify what you still need to learn. Brainstorming is also excellent for getting the creative juices flowing.

Like freewriting, brainstorming needs to happen in a judgement free zone. It also needs to happen quickly – you don’t want to get stuck in the ‘brainstorming phase’ of your project for days or weeks.

Unlike freewriting, brainstorming can take a variety of forms, have a look at the forms I’ve listed below and choose the one that appeals to you today. If that doesn’t work, keep trying different ones until you find one that does.

1. The List

This method really is as simple as it sounds. Open a new document or take out a blank sheet of paper and list topics, subtopics, or groups of words. List things like steps in a process, aspects of a problem, or attributes of what you’re writing about. Once you have several items listed, identify topics that seem to fit together and look for patterns.

2. Similes

Think back to English class when you learned about figures of speech. You probably remember similes – they’re comparisons using like or as.

To use similes in brainstorming fill in the blanks in one or both of these sentences with as many answers as possible:

[Your topic] is like ___________.

[Your topic] is as ______ as __________.

Example: Writing a book is like planning and cooking Christmas dinner.

Once you have several similes to choose from, highlight the one that seems like the best fit for now. Then use listing (see the above) to brainstorm the second term. For planning and cooking Christmas dinner this would include things like making the guest list, choosing a main course, setting the table and so on. Now I would spend some time thinking about how the process of planning and cooking Christmas dinner is like the process of writing a book.

This method works because it makes you think about your topic in a new way. In making comparisons between different ideas, you are thinking more creatively about your primary topic. This is important because creativity is necessary for writing, whether you’re writing a novel or an instruction manual.

3. Think Like a Journalist

Whether you’ve studied journalism or not, you likely know that most news stories need to answer the following six questions: who, what, when, where, why, and how. When you’re brainstorming you can use these questions to generate a lot of ideas about your topic. Spend five minutes generating your own questions (like the ones I’ve listed below), and then spend a little time answering each one. Not all questions are created equal – spend your time and energy on the ones that quickly strike you as useful.


  • is your audience?
  • is your book about?
  • are you, the author?


  • problem does your book solve for your audience?
  • does your reader need to know about your topic?
  • does your book add to the existing body of knowledge on your topic?


  • in your reader’s life is your book helpful?
  • did you come up with your idea for the book?
  • did your topic become important to you? To others?


  • is your audience in their journey (as it relates to your topic)?
  • were you in your journey when you had a breakthrough?
  • are you trying to help your audience to go?


  • do you need to write this book?
  • does your audience need to read it?
  • is your topic important right now?


  • will your book help your audience?
  • add to our understanding of your topic?
  • does your book fit into your larger body of work?

4. Word Maps

Word maps are easier to produce on paper than on screen – you do not want to get bogged down trying to insert shapes and text into a document. These maps can take multiple forms. You can draw word clouds on a piece of paper or dry erase board:


This is probably the form you’re most familiar with. You can put your main topic in the centre and then draw lines out from the centre to the next level topic and form new webs around second tier terms if needed. You can use these maps to process the kinds of lists you produce using the first method (above), or you can use them to generate ideas from scratch. Also, don’t be afraid to use colour for different kinds of topics. For those of you who are visual learners, colour coding your word map will make it easier for you to get your creative juices flowing.

If you want to be able to quickly change the relationships between terms, write words on sticky notes and then move them around on a table or wall. If you have access to sticky notes of varying sizes, shapes, or colours, use them!



Whichever method you choose, have fun with your brainstorming. The purpose of such pre-writing activities is to get you thinking creatively about your topic. I’d love to hear more about how you like to brainstorm! Join my Facebook group and let us know: EWC Writers’ Group.

How Freewriting Can Make You a Fast and Fearless Writer

All writers fear the blank page sometimes. Freewriting helps you fill that page quickly and easily. Once you have words on the page, you can start shaping them into the final product.

What is Freewriting?

Freewriting has long been recommended by writing instructors. One of the most famous accounts of what it is and why it works is by Peter Elbow in Writing without Teachers (1973). Though this book has been around for quite a while, Elbow’s ideas still shape how we teach and think about writing now.

He describes freewriting and explains why you should do it as follows:

The most effective way I know to improve your writing is to do freewriting exercises regularly. At least three times a week. They are sometimes called “automatic writing,” “babbling,” or “jabbering” exercises. The idea is simply to write for ten minutes (later on, perhaps fifteen or twenty). Don’t stop for anything. Go quickly without rushing. Never stop to look back, to cross something out, to wonder how to spell something, to wonder what word or thought to use, or to think about what you are doing. If you can’t think of a word or a spelling, just use a squiggle or else write, “I can’t think of it.” Just put down something. The easiest thing is just to put down whatever is in your mind. If you get stuck it’s fine to write “I can’t think what to say, I can’t think what to say” as many times as you want; or repeat the last word you wrote over and over again; or anything else. The only requirement is that you never stop. (p. 3)

It really is that simple, just write (or type) without stopping for 10 minutes. The point of freewriting is to get your ideas flowing and down on paper. It gets easier with practice, but I’d suggest following Elbow’s suggestion of starting with just 10 minutes of freewriting several times a week. Doing this will help you learn to write without the fear of making mistakes.

Remember that your freewriting is just for you. Use it to help you turn off your internal editor. I agree with Elbow when he explains that one of the most useful things about developing a freewriting practice is that it encourages us to be less critical when we’re producing new material when working on longer, more organised pieces (pp. 4–7). In other words, if you commit to freewriting several times a week (for 10 minutes each time), you’ll be less likely to suffer from writer’s block.

When should you freewrite?

If you’re working on a long piece like a book, use freewriting to help you generate ideas for each chapter or section. Likely, you won’t end up using what you write in your freewriting sessions exactly as they are, but it will get you started. It’s always easier to write once you’ve begun. So, if you begin in the judgement-free zone of freewriting, you’ll get started more quickly.

Freewriting is also useful when you get stuck on something. We’ve all been there. The writing had been going well for days, or even weeks, and then all of a sudden you feel like you’ve run out of ideas. You’ve hit a block.

This is where freewriting really comes into its own. When you’re experiencing writer’s block, I always recommend changing your writing situation (if you write on your computer, switch to pen and paper or vice versa; if you’re really stuck, switch to crayon and brightly coloured paper—you can’t judge what you write in pink crayon). Once you’ve changed where and how you write, set a timer for 10 minutes and freewrite. You may be surprised by how much you now have to say.

If you’re still stuck, take a break and do something that doesn’t require a lot of concentration like taking a walk or doing the dishes. Repetitive, nearly mindless activities have a way of breaking you out of writer’s block. Then, try freewriting again—you’ll be fast and fearless again sooner than you think!

How to use your freewriting?

Once you’ve finished freewriting, you may find that you have no desire to return to the material. That’s absolutely fine. It has served its purpose, so it doesn’t need to do anything else for you.

If, however, you find that you hit upon a turn of phrase you particularly like or that you’ve written your way out of a problem, you’ll want to hang on to it and refer to it later.

When you find a phrase or an idea in your freewriting that you like, spend some time developing it. Ask yourself questions like these:

  • How does it fit into your project as a whole?
  • How does it develop or challenge your previous thinking on the topic?
  • What more do you need to do to turn it into a useable (printable) passage?
  • Do you need to do more research? Or do you just need to polish the writing?
  • If you don’t often find such hidden gems in your freewriting, why not? Have you, in previous sessions, been overly critical of what you had written? Or was there something different about how you approached the exercise this time?

Download your copy of the Freewriting Guide here. This one-page PDF will help you remember how to make the most of your freewriting sessions!