Writing in Reverse: How Planning, Checklists, and Outlines Can Improve Your Writing

a writer making a checklist before writing

Writing isn’t a linear process with a specific set of tools that a writer must use to succeed. It’s more like the messy, disjointed process of putting together a puzzle, where you don’t find the missing pieces until the end. Only after it has taken shape do you see it more clearly. But just because the act of writing is non-linear, doesn’t mean that the process has to be unstructured.

That’s where writing in reverse comes in—start with the end and work your way backward using reverse planning, pre-writing checklists, and reverse outlines. Here’s how you can make the most out of working in reverse.

Reverse Planning: What do You Want to Achieve?

Reverse planning is a common approach to managing large tasks and projects. It may seem counterintuitive, but it can show you what you need to achieve at each stage of your project and what mistakes to avoid.

Reverse planning is goal-setting: Define your goal and identify what you must do to achieve that goal. You may already use reverse or backward planning in your own life! Think about when you coordinate a holiday meal, organize a vacation, or set a training schedule for a sporting event.

Reverse planning can even improve perception, motivation, and outcomes. The process triggers “future introspection,” which allows us to imagine the goal as if we’ve already achieved it. Reverse planning helps people visualize the outcome and necessary steps, which increases confidence about starting the project.

How to Use Reverse Planning for Writing

Taking a backward approach can be an effective method when writing. If you’re writing a paper, here are a few questions to consider when reverse planning:

  • When is my deadline?
  • When should my first draft be ready?
  • When should I finish research?
  • What milestones will help me stay on track?

When you focus on defining your goals and creating your action plan, you’ll have more confidence and conviction to write. It will help you avoid getting stuck in brainstorming mode or staring at a blank page as your focus and motivation fade. Get the words out and worry about editing later.

Pre-Writing Checklists: Start with End Quality in Mind

Have you ever consulted a checklist before writing? Most people think of checklists as a list of tasks you mark off once you’re done. But the main purpose of a checklist is to help you remember critical tasks and help you focus on completing those tasks.

Reviewing a pre-writing checklist (or rubric) will set you up for success by helping you to stay mindful and avoid mistakes you make when writing on autopilot.

Why Use a Pre-Writing Checklist?

A pre-writing checklist can help you break bad writing habits like wordiness or strained transitions. It can also remind you of writing advice you forget when you’re caught up in the writing process—like applying proper citation formatting, using parallel structure, and choosing dynamic verbs. A checklist will help you keep these issues front of mind as you write. Just looking at the list can help you achieve clearer focus.

How to Make a Pre-Writing Checklist

Your pre-writing checklist should be achievable, but the items you’ve listed should also feel somewhat uncomfortable. If it feels easy or overly familiar, then it won’t help you much. If you need help stepping out of your comfort zone, consider the critique you have received from instructors or senior colleagues. If it comes up frequently, include it in your checklist.

Next, review writing rules for guidance on what to include in your checklist. Write your checklist using affirmative statements; avoid listing don’ts. Using positive language makes it easier to visualize accomplishing your tasks.

Remember these tips:

  • Rank your to-do’s by importance so you stick to your priorities
  • Group tasks into 1st, 2nd, and 3rd pass; each pass is more granular
  • Include easy-to-miss yet critical tasks
  • Specify essential elements from court- or firm-mandated style guides
  • Limit yourself to one or two pages of easy-to-read font

Reverse Outlines: Flip the Process to Reveal Structure

Outlining helps writers organize ideas, clarify thoughts, and create logical arguments that build on each other. That’s why writers are often told to create an outline before they write. But outlining before writing can feel limiting and overly restrictive—it can even cause people to avoid starting!

Did you know you can get the benefits of outlining without restricting your initial creative flow? Create an outline after you’ve written. A reverse outline can help you reveal and improve structure. It also gives you the flexibility to add to your work when you get new information and reinforces that the first draft isn’t the only draft you’ll write. As long as your finished product creates a linear, logical structure for your reader, it doesn’t matter what the process looked like while you were writing.

What Is a Reverse Outline?

A reverse outline is exactly what it sounds like: an outline based on a draft you’ve already written. By waiting to create an outline, you’re free to write your first draft as it comes to you, then search for patterns later. When you reverse outline, you review your work and pull out the main ideas and supporting points. Then ask yourself: Are these the points I want to make? How can I make these points even stronger or clearer?

Why Use a Reverse Outline?

A reverse outline will yield a condensed version of your argument so you can evaluate it more easily. It will show you whether your logic, support, and flow deliver your intended message.

A reverse outline can help you identify and address potential problems in your writing:

  • Weak organization
  • Unnecessary repetition
  • Vague thesis statements
  • Unclear or unsupported claims
  • Disjointed or disconnected analysis
  • Awkward flow and stilted transitions

It’s tough to spot these issues as you’re writing. If you organize while you write, you might end up overthinking and creating a draft that sounds choppy or disjointed.

How to Make a Reverse Outline

Start with reading your document from the beginning. As you read, summarize the main point of each paragraph. Remember, this is a reverse outline. You’re not making an outline for what you plan to write; you’re analyzing what you actually wrote and using that information to reveal structure and flow. Resist the temptation to generously interpret or mentally revise what’s on the page. If you’re not faithful to what you’ve written, your reverse outline won’t be as helpful.

Here are a few tips to make reverse outlining easier:

  • Number the paragraphs of your document
  • Review your document paragraph by paragraph
  • Identify the main topic of each paragraph
  • Write the main idea in the margin or on a blank page
  • List the supporting points for the main idea

Once you’re done, you’ll have a detailed outline summarizing what you wrote. The next step is to use your reverse outline to revise your writing.

How to Use a Reverse Outline

A reverse outline will help you see the big picture of what you’ve written, and help you evaluate structure and flow. It’s hard to do this while you’re reviewing—it’s even harder to do while you’re writing.

Use your reverse outline to help you recognize if your writing wanders off-course or includes unsupported conclusions and leaps of logic. When you spot weaknesses, use your outline to revise and restructure until your draft and your goals align.

When reviewing your outline, ask yourself these questions:

  • Do your ideas flow logically from one to the next?
  • Can your readers easily follow your main argument?
  • Do your supporting ideas relate back to your main point?
  • Do your paragraphs repeat the same idea?
  • Are your paragraphs too long or too short?

Check that your ideas and arguments support your main thesis and that you clearly guide the reader to your conclusion. Don’t be afraid to move paragraphs and trim sections that have drifted off-topic. You may even want to rework your thesis to incorporate the new insights you’ve uncovered while writing.

Write Better by Working in Reverse

If you’ve been struggling to apply old-fashioned writing advice, this article is your permission to try something different. There’s nothing wrong with a non-linear approach; you can adapt classic writing tools like checklists and outlines to match how you think and write. If you would prefer to let your creative flow run free in your first draft, rather than strangling it with structure, set yourself up for success by laying out the big picture before and after the initial draft.

  • Reverse planning: First, set out your goals, steps, and timeline.
  • Pre-writing checklist: Before you write, list writing tips you want to remember while writing.
  • Reverse outline: After your first draft, make a detailed outline summarizing what you wrote to provide clarity during review and help you identify areas to improve.

Refresh your writing process by working in reverse—it may be just what you need to propel your writing to a higher level.

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About the Author

Ivy B. Grey is the Vice President of Strategy and Business Development for WordRake. Prior to joining the team, she practiced bankruptcy law for ten years. In 2020, Ivy was recognized as an Influential Woman in Legal Tech by ILTA. She has also been recognized as a Fastcase 50 Honoree and included in the Women of Legal Tech list by the ABA Legal Technology Resource Center. Follow Ivy on Twitter @IvyBGrey or connect with her on LinkedIn.

Our Story

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WordRake founder Gary Kinder has taught over 1,000 writing programs for AMLAW 100 firms, Fortune 500 companies, and government agencies. He’s also a New York Times bestselling author. As a writing expert and coach, Gary was inspired to create WordRake when he noticed a pattern in writing errors that he thought he could address with technology.

In 2012, Gary and his team of engineers created WordRake editing software to help writers produce clear, concise, and effective prose. It runs in Microsoft Word and Outlook, and its suggested changes appear in the familiar track-changes style. It saves time and gives confidence. Writing and editing has never been easier.