12 Tips for Gaining a Foothold in the Freelance Writing World

Freelance writing as a full-time profession is a rewarding but often punishing gig. Between the flashes of personal fulfillment and expressed creativity are crummy pay, work draughts, and pitches that can feel like they’re subject to the law of diminishing returns. Follow these 12 tips, however, and you’ll soon be producing great content in a way that doesn’t have you pulling out your hair.

1. Position yourself as an industry expert

Whether you’re two decades into a career in the automotive industry, or simply like to tinker with your car’s suspension, it is imperative that you position yourself as an expert in your field when writing an article.

Quite simply, there are too many niche publications out there to label yourself a generalist; they just aren’t as valuable as an industry specialist, in the eyes of an editor. I landed my first financial writing gig simply because I had a mutual funds license that was collecting dust.

2. Focus on producing strong organic content

Google’s ongoing algorithm improvements are making SEO copy less and less viable, so stick to writing articles that people actually want to read. Think about incorporating the following things into your next piece:

  • A strong headline and an engaging lead. Is the topic unique? Is your central idea clearly demonstrated within the first paragraph you’ve written?
  • Clearly structured body copy. Is your central idea laid out in a way that makes sense? Consider the chronology of your facts or arguments and remember to acknowledge any counterpoints that may arise
  • A strong conclusion. Good writing is rhetorical, and ideally, the reader will feel like you’ve sold them on your idea by the end of the piece
  • Complementary visuals. While writing purists might balk at this, remember that your audience consumes content in different ways and at different speeds. An infographic or short video may aid the reader in digesting particularly technical information

3. Write for free-once or twice

Everyone has to start somewhere, but don’t let pro bono writing become a habit, unless it’s a passion project. You’ll burn out quickly. Instead, focus on producing a few polished articles for recognized publications and shop those around.

4. Don’t be afraid to self-publish

Twice in my career, I have gained a foothold in different industries by pitching unpaid spec work to either an editor or creative director: once as a music journalist, and again as an advertising copywriter. Websites like WordPress, Tumblr and Behance are great ways to showcase your work.

The great thing about self-publishing is that you’re not beholden to an audience, publication or brand, so feel free to get as creative with your voice as you want. That being said, remember my previous tip, and be wary of the amount of time you spend writing for free.

5. Remember the KYP/KYC rule

This is an old finance rule that stands for “know your product; know your client.” In the context of freelance writing, your word is your product and your audience is the client. Think hard about how the former will resonate with the latter.

When putting together a pitch or article, it is imperative that you consider your audience’s age, education, subject aptitude and interest levels, as well as your tone of voice. This is especially true if you plan on moving into the realms of branded content or copywriting, where you’ll need to think about how to position a product or service’s benefits, as well as other strategic objectives.

6. Romance the gatekeeper

Remember in Wall Street when Charlie Sheen called Michael Douglas’ receptionist every day for a year, just to get a face-to-face meeting? That really works.

Whether you’re dealing with a senior editor, creative director or executive assistant, make the time to get to know them on a personal level; be that a coffee invitation or a quick phone call.

7. Set attainable goals and stay persistent

Nobody falls caboose-backwards into a columnist role at The New York Times-and you’re probably not going to earn a livable wage writing record reviews for a music blog.

Scale your writing career by thinking critically about your return on investment. Do you want to earn more money? Work for a high visibility publication? Gain a following on social media? Consider laying out these goals in the form of an OKR. You can also use this style of project management to determine the number of pitches you wish to send, each month. Speaking of pitches…

8. Learn how to properly pitch an idea

An editor’s inbox is a nightmare on the best of days. Make the most of the split-second they’ll spend reviewing your pitch by including the following:

  • A clearly developed story topic or idea-a unique perspective will gain you extra points
  • A brief synopsis of why that topic is newsworthy (timely, unusual, proximal)
  • A bullet point breakdown of how you’ll convey your idea
  • A summary of yourself-including a link to your writing examples-if possible
  • Your freelance rate

For deeper insights into writing a pitch, check out this resource. 

9. Consider writing for a brand

Let’s clear this up right now: it’s not “selling out.” We don’t live in Aaron Sorkin’s “The Newsroom” universe, where every approved story is a rent cheque. Realistically, the editorial industry is a volatile place, and it can be hard to make ends meet.

Think about trying your hand at brand journalism; it can pay well and, over a period of time, teach you a whole new skill set: from salesmanship to copywriting and content strategy. Try hunting down a contact email address on the website of your favourite brand, and ask if they’re looking for bloggers.

10. Target publications with big social presence

Even if you don’t use social media, you should make a habit of pitching to publications that have a big Twitter or Facebook following. Why, you ask? Imagine your story idea is your own voice, and you’re talking to a group of people that aren’t really paying attention. Social media acts as the megaphone that amplifies your story. Everyone’s listening now, right?

As an added benefit, a social share increases the chances that your website will be given a valuable backlink. 

11. Use your voice

Once you land a freelance gig, remember what helped get you there in the first place: your voice. It’s easy to get caught up in the technical aspects of a story assignment. I’ve seen veteran writers turn around pieces that read like Ikea instruction manuals, because they fixated on the technical content and failed to offer a unique perspective on the topic at hand. Remember to inject your own tone or personal experiences, whenever acceptable.

12. Find a healthy “out”

Professional writers live a life of duality: for every uplifting, published byline they experience, there will be at least one crushing declination letter. So, next time your pitch gets turned down (and it will happen, again and again) try going for a run, doing yoga or spending some time at the gym. The restorative properties of endorphins are a great thing.

If physical activity isn’t really your style, try a breathing exercise or take a moment to reflect on how far you’ve come as a writer. You’re going to need to think about those experiences when you’re accepting your next literary award.

What are your techniques for finding freelance writing Nirvana? Sound off in the comments.

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