Here's a list of why freelancers fail, according to both clients and creatives.
Creativity Marketing Transformation

Why Your Freelancer Failed: A Postmortem Analysis and Correction Kit

7 Minute Read

In hindsight, maybe you feel like you should have sensed it coming. But the optimist in you kept trusting, investing, and hoping, right?

Well, whether you’re blindsided or saw the storm brewing, at least now it’s out in the open: You’re cutting ties with a freelancer.

The scenario is more common than you’d expect. The only reason you don’t hear more about why freelancers fail on occasion is because the topic doesn’t promise readers instant business growth. It’s not as clickable as the exciting prospect of recruiting freelancers.

Plus, it’s always a little trickier than the fun stories brands want to tackle. In other words, when managers part ways with an outside expert, they’re not exactly motivated to publish every lesson learned, because they can’t know the other side’s story. So most community management teams simply move on and don’t stop to educate the rest of us.

But if you’re dealing with content gone bad, you’re likely hungry for help. And while the failure of a business relationship isn’t the sexiest marketing topic, what you do next is just as important to your bottom line. So today, we’re going there.

Let’s give the situation a quick toxicologic once-over. Sure, it’ll seem indelicate, and you may feel a little queasy, but the wisdom you could gain is worth the blue-light exam.


Think back to when you first outsourced brainstorming and content creation. One of the main draws to hiring freelancers is the flippant belief that brands risk very little. After all, according to your team lead, if things don’t work out, there are thousands of other fish swimming in the talent pool. Plus, it’s not like you completely onboarded this writer. So whatever. No biggie.

But now that it’s happening, you sense a certain gravity. You’re moving a person off the project, not a mere widget. Like it or not, you have a history, and parting ways is more complicated than you’d expected.

Why Your Freelancer Failed: A Post-Mortem Analysis and Correction Kit

Image attribution: Damian Gadal

First, just realize it happens. Denying dismissals (or worse, spinning removals to try to make light of them) is a symptom of a culture-wide insecurity. That type of negaphobia can and does backfire. Acknowledging you’re not the only reasonable client who’s had to pull the plug helps ease feelings of both guilt and blame. A simple declaration, “Hey, this sometimes happens,” is like a neutralizing blanket that smothers drama before it can sabotage anyone else’s creative energy. That means with a simple statement, you can hush rumors, quiet inner critics, and soothe doubts on every side.

Next, learn the main reasons why freelancers fail so you can empathize. Paychex’s SEO and content marketing manager, Erica Bizzari, says there’s more than one good reason to suspend a contributor’s involvement in content creation. “We’ve parted ways with writers because they weren’t abiding by our guidelines or taking the time to submit quality work,” she says. “I’ve also lost writers to competitors.”

Why Your Freelancer Failed: A Post-Mortem Analysis and Correction Kit

Image attribution: chriscom

Inadvertently, I hit a raw nerve in one of the web’s largest, most vibrant business writing communities by inquiring the same. “What’s the number one reason you think we freelance writers and clients occasionally ‘break up’?” I asked. Of the thousands of participants, the overarching sentiment was the same: Overlooking guideline requirements caused brands to view writers as a mismatch for the program. To my surprise, the other most-voted answers had a similar, disenchanted tone:

  • Improper time management leading to missed deadlines
  • Inability to take (informed) action consistently
  • Juggling too many lower-paying clients to produce quality work
  • Incapability to handle criticism with resilience
  • Obsessing over learning more, consuming information instead of execution
  • Getting stuck on marketing, sales, and professional development instead of creative work
  • Writing for clients for pay, not fulfilling work
  • Realizing projects are more difficult than anticipated, and giving up
  • Difficulty organizing points regularly
  • Expecting successful writing to come easily
  • Resenting low pay and letting the disappointment show
  • Being afraid to ask clarifying questions for fear of appearing incompetent
  • Finding better clients and letting work suffer as a result

There’s a common misconception that the market is supersaturated with writers. But ask anyone who’s had to vet, hire, manage, and develop a team of writers, and you’ll quickly hear the truth: Most of those applying aren’t the writers they claim to be.

“With the emergence of content marketing and brand publishing in the last few years, the business for freelance writers has really taken off,” says Bizzari. “Paychex actually did a study to analyze job titles that were featured in freelancers’ resumes and found that writers dominated in 14 states and that writing/editing was one of the most common job fields among freelance workers.” And that, she says, can make it seem like good relationships with writers are easy to come by. “I think a lot of brand publishers operate in industries that have complex and dynamic audiences, which can be challenging for writers if they aren’t familiar with the business or industry at the onset,” she says. “From my perspective, it doesn’t say anything about the writer, but puts more pressure on the brands to adjust how they work with freelancers.”

In other words, expect a learning curve on both sides. One where you’ll both be investing in one another. And yes, there may be the occasional freelancer who continues to fall behind. That’s the bad news. The great news is that for every misfit, there’s a capable creative writer who gets it. One who knows your industry, appreciates your brand’s back story, can read your guidelines, understand your purpose, feel your excitement, and contribute to your brand’s voice.

Here’s how to find, nab, empower, and retain them.

First, ditch the job boards, bidding sites, and classifieds. Find a writer you love by analyzing the stories that engage you regularly. The ones that demonstrate both curiosity and authority all at once. Writers who provoke thought without being cynical. Support them by commenting on and sharing their work. Then, reach out to assess their interest in contributing to your digital publication.

Why Your Freelancer Failed: A Post-Mortem Analysis and Correction Kit

Image attribution: Shaylor

Or, find talent pools of creatives by reaching out to trusted conduits like Skyword, a platform that builds trust on your behalf as well as on behalf of creative writers. As a freelance writer, I’ve seen my Skyword team diplomatically maneuver tricky misunderstandings so both I and my clients can keep working happily together.

Bizzari agrees. “I am lucky to have the Skyword team help recruit good writers in our program, so thankfully we don’t have a lot of turnover,” she says.

Why Your Freelancer Failed: A Post-Mortem Analysis and Correction Kit

Image attribution: kwinkunks

Forget “Best Place to Work”—Become Best Place to Freelance

Next, learn to become a good client. “If you find freelance writers you enjoy working with, treat them well,” says Bizzari. “It is important to coach them, to provide feedback, and pay them in a timely manner.”

Bizzari’s advice comes from a place of appreciation. After all, you’re not the only party interviewing here. “Writers get to choose what companies they want to work for just as much as we get to choose what writers we want to work with,” Bizzari says. “It is important to test the relationship out in the beginning to make sure it’s a good fit for both sides.”

Why Your Freelancer Failed: A Post-Mortem Analysis and Correction Kit

Image attribution: kwinkunks

And finally, offer continuing support and feedback. “As a brand, it is important to make sure the writer has ample information so they can write about a subject accurately and successfully,” says Bizzari. “It is also imperative to keep lines of communication open and to provide continuous feedback and coaching.”

Eventually, Learn to Expect the Best

In the same writers’ forum where I asked my question about why freelancers fail, the group’s community management leader posed another fascinating question: “What do you enjoy most, hunting and landing the client, or doing the actual work?” I was dismayed as I saw hundreds of answers pour in voting for one or the other. All the while, I wondered, “Aren’t the two one and the same?” Your freelance gems—the one you grow to love—should continue to dazzle you. I’ve heard clients wonder aloud how writers can start out so incredibly strong and slowly morph into a lackluster version of the same. Here’s an opportunity to build a relationship that’ll last a lifetime. Offer to meet up with your freelancer at a content marketing event or send him a pair of tickets to his favorite sports team. As with compounding interest, it’s not the initial investment that’ll really pay off someday, it’s your continuing involvement that’ll pay you both the most in the end.

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Bethany Johnson is a multiple award-winning content marketing writer and speaker. Her work empowers marketers to ditch interrupt advertising in favor of original content that converts passive readers into active followers. Thriving brands like Tom's of Maine, MasterCard, ADP, Fidelity and the Content Marketing Institute currently rely on Bethany's fresh style to connect with audiences daily. As a consultant, she combines simple change management principles with her insider knowledge of freelancing to show traditional marketing teams how to flourish in today's gig economy. For more, visit

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