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The Case for Outlines (and How to Draft Ones that Work)

Writing a piece of content without outlining first is like skipping breakfast. It dooms you to a drafting process filled with lethargy, bad eating habits and a general “woe is me” outlook on life.

Unfortunately, outlining is not something we’re naturally inclined to do. It’s a habit drilled into us by history professors whose lives depend on their students’ ability to produce well-structured essays on the Lincoln-Douglas debates, and countless other educators with similar missions.

If you suffered through these or similar experiences, maybe one of the mental vows you made upon exiting academia was “Never will I ever waste time on outlines.” Maybe you, like me, fell victim to the delusion that by putting fingertip to keyboard, the right words would flow automatically, that the only barrier between you and the Next Great American Novel was a senseless outline.

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Today, I’m ready to go where few Millennials have gone before and admit that I was wrong. Whether you’re embarking on a ninth attempt at a New York Times “Modern Love” submission or a white paper on the merits of SEO, outlining is one of the faster ways to ensure a stronger finished product. Here are a few tips to reintroduce the habit and develop outlines that work for you.

1. Stop thinking you’re too good for outlines. The first step to creating a useful outline is swallowing your ego. I promise, despite whatever secondary school flashbacks haunt you still, this will not be a waste of time. If anything, it will save you from having to self-medicate incessant bouts of writer’s block with Manny the Frenchie’s Instagram feed and mindless snacking.

2. Set your own rules. Outlines are your personal Westeros. You’re King of the Andals and Lord of the Eight Parts of Speech; lead as you wish. If you can’t fathom Roman numeral formatting, use bullet points instead. Try numbered lists. Don’t confine yourself to any particular medium either. I draft most content in Word, but my outlines typically live in Google Docs or just-legible handwriting in a notebook. Outlines don’t need to be visually or even grammatically beautiful; they need to give structure to the ideas floating around your head (or your client’s).

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3. Work like an interior designer. Regardless of the type of content you’re drafting, most outlines should account for an introduction, conclusion and core sections in between. Think of these as rooms in the centrally air-conditioned apartment of your dreams and start filling them with statement pieces. Every living room needs a great sofa, and every introduction needs a compelling lede. Fill in the middle with high-level supporting points you already know should be included (these are your beds, dressers and other staples). Fine details like statistics and transition sentences are accent pillows and bar carts. Budget time to scour the Internet for the perfect ones later.

4. Fall halfway down the rabbit hole. Outlining is a humbling process; it makes you realize how little you understand about the topic you’ve been assigned. Unless you have inherent knowledge of tax accounting, PCI compliance or whatever the issue may be, you’ll need to research. Thanks to the Internet, finding information to plug gaps in your outline is easy. The problem is there’s too much of it. Rather than spend days link hopping from Wikipedia to Google Scholar excerpts to trade publications, set a research time limit. Reference primary sources (e.g., quantitative studies, industry associations, government agency websites) to collect objective information and helpful data. Dig up recent news articles to give your outline more timely context. Better yet, interview an expert who has the knowledge you lack (especially if you’re ghostwriting the content for them.)

If Plath and Faulkner weren’t above outlining, we shouldn’t be either. Especially when tasked with drafting multiple pieces of content for multiple clients in tandem, we don’t have the time or energy to waste on (to paraphrase another writing phenom) lousy first drafts. Strong outlines provide the momentum necessary to write smarter the first time around.

Do you have any tips for drafting the perfect outline? Tweet us at @WalkerSands!