The Procrastinator’s Guide to a Better Content Calendar

William Goldman, arguably the greatest screenwriter of all time, once said, “The easiest thing to do on Earth is not write.” Goldman had a knack for coming up with perfect quips. Out of all his famous lines, this one resonates with me most.

What Goldman captures here is simple: Creativity doesn’t always happen on a schedule. For anyone who’s ever put off a college essay, stumbled over a cover letter, or even struggled with an email, you can relate. It’s also true for any creative endeavor, not just writing.

But for people who write (or design, record, illustrate, etc.) professionally, timelines matter. As a writer, I’ve been known to let the occasional deadline pass if I felt like the quality wasn’t right. As Contently’s editor-in-chief, I also want to keep things moving. Those two perspectives will always clash. The key is to figure out how to maintain high standards while staying accountable. Be flexible but disciplined. And the best way to do that is by building a content calendar.

Over the years, I’ve developed a system that helps me stay on top of so many moving parts. So if you’re a writer or editor trying to stay on task, here are a few rules that will help.

Sketch 3 months out

The biggest mistake people make when setting up a content calendar is treating it as just a daily tracker. The calendar is more than a to-do list. Whatever your creative trade, you need a long-term lens first.

Every publication—branded or editorial—has pillars. Let those pillars guide you here. For The Content Strategist, I start my planning by mapping out the calendar on a quarterly basis. Members of our marketing team meet every Monday to brainstorm story ideas, so the pillars offer helpful boundaries. I pick three core topics and match one to each month in a given quarter. Then I create a spreadsheet where each person can fill in their pitches before we discuss.

The calendar is more than a to-do list.

Here’s a rough idea of what the themes will look like next quarter:

April: Financial services

May: Storytelling

June: Video

Since I set these at the beginning of the quarter, the team has a pretty good notion of where we’re headed short- and long-term. Also, because the calendar themes are monthly and the editorial meeting is weekly, topics can build off each other. We have space to riff on stories from different angles and put a fresh spin on the news cycle. Last January, for example, Emily Gaudette turned a pitch about content marketing ROI into a timely reflection on the impact of fake traffic.

I put the system in place three years ago because people were bringing undercooked ideas to our edit meetings. I realized we all needed more structure and visibility into the content calendar. Now that we sketch three months out, those issues have largely disappeared.

Plan 1 month out

Growing up, I wasn’t much of a planner. In high school, the school-issued agenda was usually buried in my locker by November. Today, though, the number of moving parts in my life has increased while my capacity to remember things has decreased. To clear that hurdle at work, I plan TCS stories one month out.

Here’s a snapshot of our current calendar:

One month isn’t a long amount of time, but for this exercise, I think it’s the right amount of time. Most people aren’t going to write a draft or mock up an infographic months in advance, so scheduling assignments that far ahead won’t give you any benefit. The only exception worth noting is if your company has a lengthy approval process. (But if it takes 90 days to publish a blog post, you should probably focus on fixing that before you get to the calendar anyway.)

When companies start creating content, many of them have a common misconception that they need to fill the calendar with every asset they expect to produce for the next year. Don’t do that. I understand where the impulse comes from, but it can be paralyzing. You’ll end up slotting stories that become stale or irrelevant.

Just think about how fast the media moves. Remember that weird Area 51 raid story? That was six months ago. Avengers Endgame came out 10 months ago. And Amazon cancelled its plans to put its HQ2 in Queens over a year ago. Keep that perspective in mind as you prepare for the future so you can stay nimble.

Use the 75/25 rule

Speaking of nimble, the last rule for planning your content schedule is to leave some days blank. Specifically, leave 25 percent of your days blank.

In the screenshot of the TCS calendar, you’ll notice roughly one day per week is empty. This might seem unorthodox, but it’s by design. When something gets in the way of the schedule, I adjust the calendar on the fly. I bake those days in at the start of the month to buy everyone on the team (including me) some time.

In my years managing the site, I’m certain of one thing: shit happens. People miss deadlines. Sources don’t respond in time. The design team can’t find the right image. I can’t edit a draft. A flexible content calendar is about more than just coming up with ideas for the current news cycle. It’s also about realistic expectations. Any other approach—to borrow another word from Mr. Goldman—would be inconceivable.