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Content Strategy: A Vital 6-Point Quiz from a Six-Figure Freelancer


The Content Strategy Quiz for Freelancers. Makealivingwriting.com.Are you staying up into the wee hours of the morning trying to finish projects? Or wide awake worrying about money, content strategy, deadlines, or your empty client calendar?

That was me. And I realized pretty quickly that focusing on finding the perfect number of clients (Is six the perfect number? Or is it eight?) wasn’t the answer.

Maybe you know the feeling. Or maybe you struggle with getting even one good-paying client.

I’ve been there. I know what it’s like. But five years ago, I broke the six-figure mark for the first time by landing some better anchor clients. And I’ve earned over $100K every year since then.

But it was still a hustle. I was working too much, and I wasn’t sure how to change that. And then out of the blue one of my clients asked me a question:

“Jennifer, can you help us with content strategy?” What happened next changed everything…my income…my work hours…and my happiness with being a full-time freelancer.

What’s content strategy, and can you do this type of freelance work? Take the quiz to find out.

Curious about content strategy?

When my client asked me to help out with content strategy, I figured…what the heck! And instead of just writing content, I started making decisions like:

  • What content the client needs to produce to build trust with their customers
  • Where that content should live online
  • What tone/brand voice to use to connect with customers
  • How to promote content

So instead of just writing a blog post, I wrote a content marketing strategy document that included details about current content, a competitive analysis, a channel plan, and a social media plan.

And if you don’t know what all of that means mean…no worries. I didn’t either when I started, and I can help you with that. But more on that later.

Cashing in on content strategy work

I absolutely loved the project. And I was very good at it.

After the content strategy document was approved, I was assigned most of the writing work – plus a number of hours per week on retainer to continue working on content strategy.

My income not only went up, but my income was much more stable.

How’s that possible?

Work smarter, not harder

I moved away from earning my income by only creating deliverables, and began adding value for my client. Not only could I charge more money, but I was also truly part of the team.

And that’s a good place to be in the middle of coronavirus concerns. You’re likely not going to be the first freelancer let go in a budget crunch.


Could adding content strategy to your services be the secret to solving your feast or famine issues?


Maybe. It’s a great fit for some writers, but not a good one for others.

If content strategy fits your strengths, personality, and goals, it’s a fabulous way to grow your income and finally find that perfect feast or famine balance.

  • Are you cut out for content strategy work? Take this six-question quiz to find out.

1. Do you often yearn for variety, doing something other than writing?

Yes or No?

Content strategy does involve writing, but that’s just a small part of the job. Content strategy involves lots of other tasks:

  • Brainstorming
  • Scheduling
  • Working with people, and
  • Problem solving.
  • Plus, you have to get deep in the weeds with both social media and SEO (more on both of those later).

Yes = If you are happiest when you get to do all kinds of different tasks, including writing, keep reading.

No = If your favorite writing projects are those where the client hands you everything you need so all you need to do is some research and then go back to your computer to write the story by yourself, then becoming a content strategy pro is probably not the right move for you.

2. Is brainstorming interesting topics to write about one of your superpowers?

Yes or No?

Yes = If you love coming up with ideas, and think it’s fun and easy, you’re a good fit for content strategy work.

Years ago, I realized that clients who loved working with me the most were those who wanted me to come up with topic ideas for my projects. I had no idea other people didn’t think of this task as one of their favorite parts of their day. Then a few editors confided in me that they liked to hire me because it meant that I would fill up their editorial calendar for them.

One of the roles of a content strategy expert is coming up with the actual topics for each piece of content -not just telling their client to write a whitepaper. Instead, you’re providing a plan to go with the white paper like:

  • How a company can use the freemium-to-premium model to increase sales
  • Why a potential customer would care about that topic.
  • Creating an editorial calendar AND identifying topics that potential customers care about that help demonstrate the company’s knowledge and build trust

No = If you roll around on the floor, procrastinate, cry, or talk bad about yourself trying to come up with ideas to pitch editors and marketing directors, content strategy work may not be for you.

3. Are you secretly a marketing nerd?

Yes or No?

As content marketing writer, you often wade into the shallow end of content strategy.

Here’s a couple of examples:

  • You create the CTA (Call the Action) for a blog post.
  • Perhaps you’re on a conference call when your client is talking about whether a piece of content should be gated or ungated.
  • Your client tells you that you’re working on top of the funnel content.
  • Maybe the metrics for your writing. project are included in an email that you accidentally open.

When the marketing strategy comes up in your writing projects, do you want to run back to your computer, shut the door, and write for the next four hours?

Or do you head for Google to look up the terms and then look them up again an hour later after getting lost in learning more about marketing?

And then become obsessed with understanding how to improve your writing to increase your page views through SEO and social?

Yes or No = Either answer is more than fine

But if you aren’t super excited about the marketing part of content marketing, then you should stick to writing.

Even the most hardcore journalists can stomach the amount of marketing needed to be a writer on a content marketing project. But as a strategist, marketing isn’t a tiny percentage of your role anymore, it’s your whole job.

4. Do you find SEO intriguing – and even fun?

Yes or No?

Yes = If you geek out over SEO, optimizing blog posts, reverse engineering content that gets a ton of traffic(like Smart Blogger Jon Morrow recommends), and trying to get a post to rank well, you’re a good fit for content strategy.

  • As a content strategy expert, you’re often the person coming up with the keyword – or at least working with the SEO expert (if your team has one) to determine which keywords to target for each deliverable.
  • You will use keyword tools, track Google algorithm changes, and become obsessed over search metrics for the site.

It’s okay if you aren’t a super expert yet, but be prepared to learn quickly. Even better, look for projects with an SEO expert on the team for you to learn from.

No = You might have experience using a keyword that the client gives you to write an article, blog post, or content for a web page (usually the title, first paragraph, and meta description). If you’re mystified by where those keywords come from, and don’t have an interest in learning, you may not be ready for content strategy work.

5. Do you enjoy brainstorming and collaborating with others?

Yes or No?

As a freelancer writer, you are mostly on an island. Sure, you may do an interview with an expert or talk to your contact on the phone. But by and large, you are a one-person team.

Once you venture into strategy, the game changes completely.

Yes = If you’re OK with getting on the phone, asking questions, collaborating with a team, and even working with other freelance writers, you’ve probably got the chops for content strategy work.

You’ll have to get buy-in from lots of different people (called stakeholders), including the:

  • Project manager
  • Marketing manager
  • Tech expert
  • SEO expert
  • Social media manager, and
  • Probably a bunch of other people
  • And that doesn’t even include all the people who you have to work with to gather the information to do your job. You will also probably find your calendar quickly filing up with conference calls.

You must not only talk on the phone, but you must actively work together with other people – and often, it’s lots of other people.

Unlike just negotiating with your dog when it’s time to stop playing ball, you will likely find yourself dealing with at least low-level office politics.

The good news is that because you are working remotely, you can go back to your quiet office with just you and the dog after the video conference brainstorm session.

No = If you’re the kind of freelancer who tries to avoid the phone or video conference calls as much as possible, and working with a team makes you nauseous, you may want to reconsider looking for a content strategy gig.

6. Are you willing to use your client’s project management tools and conferencing software?

Once you are a part of a team as a content strategist, you will likely be asked to use their project management tools like:

  • Asana (used to plan projects, assign tasks, follow-up, and measure progress)
  • Slack (an easy way to text-type chat with colleagues, clients and project stakeholders. Even the Freelance Writers Den 2X members use this.)
  • Trello (another project management tool. Think to-do lists on steroids)
  • Zoom (voice or video conference call software)
  • Or one of a seemingly million other options.

Yes = You’re already familiar with some of these tools, because that’s how you’ve been given writing assignments, even if you didn’t use them much. But you’re willing to learn how to use these tools to manage content strategy and communicate. And yes, if you have three content strategy clients, that means you could end up using three different systems.

No = While this aspect is less of a deal-breaker than the others, I know many writers who really balk at using these tools. And if that’s you, then you should either pass on content strategy or actively look for clients that use the tools you are comfortable with. But honestly, that really limits your opportunities. Project management tools really are just part of a content strategy job.

Move up and earn more with content strategy work

If you’ve made it this far, I’m going to assume you answered YES to most of the questions. And now, you’re wondering how you can actually start getting gigs as a strategist. It’s not something you jump into overnight. But you can learn the skills you need to become a content strategist.

Want to learn more about content strategy? Let’s discuss in the comments below.

Jennifer Goforth Gregory is a freelance writer, content strategy expert, and author of the book: The Freelance Content Marketing Writer: Find your perfect clients, Make tons of money and build a business you love.

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