By Dennis Shiao published June 27, 2022 Est Read Time: 6 min

Need Content Freelancers? Try This Agency’s Accidental (But Successful!) Model

A few years ago, after a company layoff, I tried a career as a freelancer. Since my new path wasn’t completely by design, I called myself The Accidental Freelancer.

In the early days, most of the work was writing, and I had regular and one-off gigs. Since then, I established a marketing agency (Attention Retention LLC) and offer services around consulting, content marketing strategy, social media, and product marketing.

Though I’m focused on consulting and still write occasionally, I more often assign writing projects received through inbound requests or my consulting clients to freelancers. Though I’m the only full-time employee, my network of freelancers serves as the agency’s virtual team to satisfy client requests.

Like my freelancing career, I discovered this network by accident. It all started with a tweet:

A Twitter inquiry about hiring freelancers

An unexpected Twitter comment about hiring content freelancers.

After a guest appearance on the Rockstar CMO podcast, someone replied to a tweet promoting the episode: “Hey, are you by any chance hiring marketing professionals?”

I replied, “I’m looking for a freelance writer or two to help with blog posts on marketing-related topics.” Others replied to that with comments like:

  • “I’d love to send you a few samples for this position!”
  • “Hello, I would love to extend my interest in this. May I know if this requirement is still open?”
  • “I’m a content marketer with six years of freelance writing experience. Are you still looking for a freelancer? Would love to be considered!”

At first, I wasn’t quite sure what to do. I hadn’t anticipated so much interest. Truth be told, I didn’t have enough active client projects to distribute to the interested writers; but the opportunity seemed too valuable to overlook. Here’s what I did to create a solid network of freelance writers ready for assignments.

A tweet asking if he was hiring led @dshiao to create a network of #freelancers via @CMIContent. Click To Tweet

Give every writer a paid gig

I know what it’s like to earn a living from writing. It’s as hard as it seems – you’re not making money unless you’re writing, and all the while, you need to be pitching and hustling for your next assignment.

I didn’t want to ask people for their writing samples or lowball them on a “let’s get to know each other” project. Even though I didn’t know them, I took a leap of faith and hired them for a paid gig.

Every person who asked about a writing gig was given a paid assignment from @dshiao. All of which were good enough to appear on his agency website via @CMIContent. #freelance #writing Click To Tweet

I needed to decide what they would write and thought of two opportunities at my disposal – my agency’s newly launched blog and a Bay Area Content Marketing Meetup of which I was a co-organizer.

I gave a paid assignment to every writer who contacted me on Twitter: Craft a summary of a presentation chosen from the meetup’s playlist. Based on the length and subject of the recording, I gave a target word count, typically in the range of 800 to 1,200 words. 

Here was one of the outcomes from Nicole Pyles, who summarized the presentation by marketing executive David Rodnitzky and his new book, Unfair Marketing. It began:

“Online marketing used to be as easy as panning for gold during the California Gold Rush. You didn’t need to put in a whole lot of effort to earn a decent income. However, much like the gold rush, the competition heated up and made it harder to earn a living.”

Content freelancer test post example

An example of one freelancer’s paid test post.

The full-length article appeared on my agency blog. (If writers requested, I added a link to their websites or LinkedIn profiles.)

This first paid assignment was essential to helping me build a network of outsourced writing talent. Let’s explore the resulting benefits.

Assess freelance writers’ styles and strengths

All the recap submissions were copy-edited by me and published on the company blog. Editing the writers’ work helped me assess their abilities.

By “ability,” I don’t mean classifying them as an average writer or excellent writer. Instead, I got a feel for the types of assignments where each writer could excel. It was based on my clients’ industries, subject matter, and expectations. When a new writing request comes in from a client, I can pair it with a best-fit writer. These paid gigs were worth their weight in gold.

Don’t assess a #freelance writer as average or excellent. Get specific enough to know what type of assignments they’ll excel at, says @dshiao via @CMIContent. Click To Tweet

Develop an engaged network

Having a network of freelance writers is a win-win scenario: The writers win because the work I send them helps pay the bills. I win because I can fulfill more client requests and assignments. When the writers buy into the process, they’re engaged and are eager to take on more work – as you can see from this (paraphrased) email I received:

“Hi Dennis, I enjoyed working with you in the past. Just checking in to see if you have any new assignments coming up.”

Writers in an engaged network usually respond to new requests quickly and are incentivized to continue delivering quality work.

Always have a freelance team

I recommend having a go-to freelance network, whether you’re at an agency or in a full-time role at a company.

While I’m on the agency side now, I once was a director of content marketing at a B2B software company and didn’t have any direct reports. The network of freelancers I built then was essential to the completion of my projects. Even if you have a full-time team of writers and designers, keep some freelancers on standby in case of employee turnover, illness, or other unexpected events.

I also recommend adopting an always-be-looking mentality – like the always-be-recruiting mindset software engineer managers have, since they commonly face hiring challenges. From time to time, freelance writers in my network take on full-time roles and are no longer available for assignments. So I’m always looking to add to my network.

Take advantage of accidents

I’m probably the happiest I’ve been in my career. I have the independence of running my own business and the excitement of working across different clients and industries. I didn’t have a grand plan for getting here, but I’m thrilled with where I’ve landed.

I fell into freelancing by accident. Next, I discovered a network of freelance writers by accident. In other words: Accidents happen, make the most of them.

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Cover image by Joseph Kalinowski/Content Marketing Institute

Author: Dennis Shiao

Dennis is an independent marketing consultant who works with brands on content marketing, product messaging, and social media marketing. Formerly, Dennis led the content marketing function at DNN Software. Dennis curates an email newsletter called Content Corner and publishes marketing-related content on Medium. Feel free to reach out to Dennis on Twitter @dshiao

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