Today we’re going to be talking about creating a quarterly content marketing plan—in other words, a content calendar to guide your business over the next three months.

What I’m about to tell you might sound like a lot of work. But I encourage you to stick with me. Because as we head into one of the busier times of the year, taking the time to plan out your content will keep you on track during the holidays.

And maybe even get ahead, so that you can sail through the holidays knowing that your content is taken care of.

Hashtag life goals. ;)

In this email, I’ll talk you through the system I use, which gives me the guidance to stay on track and meet my own deadlines, while also allowing me to pivot as I go along.

It’s an extremely flexible system, perfect for someone like me who tends to rebel when I feel too trapped by obligations—even those of my own making.

Let’s talk about what this looks like in practice.

Step 1: Understand your overall strategy

Start by brainstorming your goals for the rest of the year. What launches do you have planned? What are your sales goals?

Write down any important dates (launches, holidays, sales) so you can work backwards from there.

Then, revisit your core content pillars to remind yourself about the 3-4 broad categories your content falls into.

For example, my Q4 goal is to get consistent in providing value in my newsletter, and to grow my audience with the goal of signing people up for 1:1 coaching. I also want to gauge demand for a new course.

My core content pillars are content marketing, book writing, storytelling.

Step 2: Decide what 1-2 problem(s) you’ll solve for people in the next 3 months

What’s the most pressing thing you can help your audience with over the next three months? What wins (related to your goals) can you help them achieve?

One of the best ways to find these problems is by mining conversations with your target audience. What issues keep coming up again and again?

Pick 1-2 problems that are linked to your offers/launches.

For example, I kept hearing in coaching conversations that people were struggling to know what to write, and having trouble staying consistent with their content. Hence my decision to do a series on content marketing.

Step 3: Brainstorm content ideas

Start jotting down different topics that hit that sweet spot in the Venn diagram:

Core content pillars
Problem you want to solve
Sales goals

For this step, I like to bust out the sticky notes. Jot down single post ideas on a small sticky notes, and sketch out larger series ideas on a bigger note.

If you’re fancy, you can even color code your notes by content pillar, or by where it is in your marketing funnel. (TOFU, MOFU, or BOFU—and don’t worry, we’ll be talking about that more next week.)

For example, if I want to teach entrepreneurs to be better content marketers in a way that generates interest in a potential course about creating a personalized story messaging blueprint, I could do a series about:

—> mapping your customer’s journey through your sales funnel.

—> the types of stories you need to tell at each stage of the sales funnel.

—> why storytelling helps you sell without feeling salesy

Step 4: Sketch out your calendar

Now, start giving all this brainstorming a shape.

I like using a whiteboard—I got a 2’ by 3’ whiteboard panel at a hardware store for a few bucks, and I prop it up on my table whenever I need it. You could also use a big sheet of paper, or a spreadsheet if you want to go digital.

Write the dates in a column down the left hand side.
Add any launch dates or holidays you need to consider
Start organizing your brainstormed topics based on flow

I find it helpful to think in terms of having a large monthly topic, then break that into sub-themes by week.

For example: Because I’ve decided to focus on the overall problem of helping people get better at content marketing, I broke that into three big themes by month: Top of funnel (TOFU) in October, Middle of funnel (MOFU) in November, Bottom of funnel (BOFU) in December.

Each week of October will go deeper on a sub-category of TOFU content—social media posts, reach vs nurture content, market research, lead magnets, etc.

Step 5: Work 1-2 weeks out

Now that you have the broad strokes of your plan, dial in on the specific topics you’ll write about each week.

But here’s the trick. I don’t want you to plan every newsletter, Instagram reel, or LinkedIn post for the next three months.

Instead, just focus on the next week or two.

Break that week’s theme into the content you want to post. And, along with topic, consider your distribution plan. Where will these pieces live, and how will you repurpose them? How does every piece act like a web, drawing readers further into your world?

If your typical week looks like:

One newsletter
Three LinkedIn posts
Five Instagram posts

You probably want to go deepest in your topic in your newsletter, then explore different aspects of that topic in your social media posts.

For example, when I launched this new series, I put the first post up on Substack and LinkedIn with an invitation for people to subscribe to this list if they want to read the rest of the posts. I’m also posting breakdowns of these ideas on Instagram with the goal of driving people to my list if they want to go deeper.

Step 6: Track what’s working and revise your plan

You don’t have to go wild with metrics, but if you want to escape the content hamster wheel you need to be gathering intel on what works and what’s a waste of time.

We'll go deeper later into what metrics are useful and what are just vanity metrics. But for now, pay attention to the things that invite engagement.

What pieces of content sparked conversation? What got people to sign up for your newsletter? What got people to DM you?

Then use that information to shape your plan as you go forward. If people really resonated with one topic, it's fine to rearrange your content calendar and stay there longer. If you wrote a post that brought up a question that shoots you off in a different direction, feel free to follow it.

This is where having a whiteboard and sticky notes really is helpful. It’s super easy to move things around as you get going on your plan for the quarter and decide you need to shift focus, jump ahead, go deeper, etc.

Now you have a content calendar!

I know this looks like a lot more work than what you might be currently doing, but imagine how much energy you’re wasting on that hamster wheel. Divert a bit of that energy to strategy this coming week, and I guarantee you’ll become more efficient in creation.

I’m living proof. After weeks of dragging my feet because I didn’t know what to post, I finally sat down and created my own content calendar for the rest of the year. Because of that, I was able to crank out three 1000-word+ emails and a bunch of social posts in a few hours.

Not only did I know what I wanted to say, I was excited about it, too!

I hope you’re also excited about the glimpse I gave you into what my content calendar looks like—because if you're an entrepreneur who's been spinning your wheels trying to make content that actually feels like it's making a difference, then the topics we're going to cover over the next quarter will transform your business.

What I’m going to teach you is that important.

So I hope you’ll stick around!

Talk soon,

Jessie

P.S. Do you know someone who could use this info?

Please forward it and invite them to subscribe! I want to help as many people as possible tell their stories, and I could use help spreading the word. Thank you!

Story Rebel