hire freelancers
Creativity Marketing Transformation

Yes, You Should Hire Freelancers (and Treat Them Like Gold)

7 Minute Read

Someone hold me back. I’ve seen enough “best places to work” lists to last me a lifetime, but I have yet to see a single award for “best places to freelance.” In fact, when I search for the former, I’m presented with shining examples of enterprises that really value their people (and “check out all the creative perks that prove it”). Tech startups and financial services brands are especially keen on making the list. It’s great exposure, and landing a spot can highlight a company’s commitment to hiring and retaining the best and brightest—but why wouldn’t they hire freelancers?

When I type “best places to freelance,” I’m given a staggeringly long list of places that might hook you up with a gig. That is, if you play your freelance cards just right.

So far, I haven’t found a list of companies highlighted for their ability to attract the sharpest, most creative freelancers.

Why, exactly, does that fire me up? Do I need a ping-pong table nearby to do good work? No. Am I about to go on strike because no one is matching my 401(k) contribution or paying my gym membership? Of course not. I’m frustrated because enterprises are missing out.

A Culture of Entrepreneurs

These days, it’s hip to tell employees they’re joining a team of fellow entrepreneurs. Brands do their best to foster a culture of innovation, encouraging risk-takers to “do their thing,” even going so far as to reward failure. Before starting my own writing business, I interviewed at a place that proudly told me to bring my dog to work, if that’s what would help my creative juices, or to pick up a tennis racket and lob a soft one at the exposed brick wall while brainstorming, if that encouraged my muse. I’ve even heard managers tell employees to treat their corporate role like their own small business, nurturing every aspect and willing it to flourish. Emphasis is often on imaginative ideation, and smart brands compensate handsomely for zany creativity.

Many financial services brands place a high priority on employee creativity, but fail to hire more freelancers, the most creative group of all.

Image attribution: Paul Simpson

I can’t help but wonder: why all the effort, when freelancers are, by nature, the real deal? If you want an honest-to-goodness culture of honest-to-goodness entrepreneurial spirit, why not put a group of real-life entrepreneurs on a project and watch the thing soar? Why task uninspired workers with something as important as your brand’s digital storytelling, when you have the real deal sending you saucy proposals?

About 10 years ago, I worked at a music downloading startup that was constantly looking for a creative “disruptor.” You know, the disruptor. The one employee we would hire who would produce the most outlandish, brilliantly innovative ideas. We would find him, yes, and hire him, yes, and he would do all our prolific ideation, yes, and if all went according to plan, we would adapt his ideas and disrupt the industry. Business as we knew it would never be the same. It was a great plan, and as I observed other startups, I saw they were all seeking the same person. Everyone wanted to hire the disruptor. And you know what? It appears that, since then, everything else in the business world has changed, but the desire to disrupt has held steady. According to the human resources consultants at Berkshire Associates, brands that lack that creative spark are less agile, less competitive, and less likely to keep up with the market. And I would argue that they know this.

Today, the contingent talent pool is growing larger and larger—35 percent of the total US workforce, as reported by Upwork and Freelancers Union, and I can’t help but think: the disruptors have arrived. And it’s true that business will never be the same. The only problem? Enterprises that need that dose of disruption are still focused on crafting the ultimate W2 bene package for the old disruptor character who will probably never show up.

Many financial services brands want an enthused, inspired team, but fail to hire more freelancers - the most inspired (and inspiring) group of all.

Image attribution: Steve

I’m Calling It

Imagine, instead, what it would look like to pivot your recruiting efforts toward attracting the most in-demand freelancers. Which company will start the trend? Who will be the first to label themselves as the “best place to freelance?” What brand will jump in front of this wave and enjoy the benefits of hiring the best, most creative entrepreneurial players? And what publication will start the contest? My prediction is that whichever brilliant leader begins the movement will also win the digital storytelling game. As with all disruptions, this one would be a furiously paced competition with only one or two stand-out winners. And then, of course, thousands of predictable, feeble copycats.

Only a few will look back at this brave new marketing transformation and say, “We saw that coming when no one else did.”

Risks Versus Benefits (Package)

Since I’ve never been in charge of a behemoth financial services enterprise or a slow-moving legal operation, I can only hypothesize why some brands choose to hire creatives on a full-time basis only, instead of relying on a combination of in-house and freelance work. Is it because of the risk of a high turnover that could accompany the decision to hire freelancers?

Most hiring managers are, understandably, a little worried that the stereotypical freelancer may turn out to be a transient. Someone who claims to be committed, then flakes. Or worse, someone who is trained up, only to land a sweeter gig a few months into your content strategy’s execution. That’s a legitimate concern, sure, but what might it cost employers to play it safe?

Many brands in the financial services industry are frustrated by their lack of in-house creativity.

Image attribution: Matthew Rutledge

Today’s millennial professional is expected to hold 20 jobs throughout life, a fact pointed out by the Education Advisory Board. I don’t need to tell you how costly that could be for traditional employers. And remember, the oldest millennials are already 35 years old. We’re not talking about a subset of youngsters we should consider preparing for someday. Job hoppers are immediately expensive. Much more so than the short-term designer or brand storyteller that doesn’t inspire you to take the partnership long-term.

Those are the risks. Now, consider potential benefits you can offer to attract the best of the best freelancers.


When you applaud a freelance contributor publicly, you’re giving her the one thing most respondents cite as why their company won “best place to work,” according to Forbes. This benefit is just good business. It would make sense to see kudos for a job well done transfer straight from your in-house employees to your favorite hustling freelancer.


Show freelancers examples of what you’ve admired in your competitors’ ad campaigns. Discuss consumer trends that have led to marketing transformation in other industries. Brainstorm aloud together and affirm your creative when she’s on the right track. Send your freelancer to industry conferences to get inspired and be encouraged. Give her an Audible membership, so she can consume the smartest new industry books (and a few fiction thrillers, too).


Just because your freelancer is independent doesn’t mean you can’t still hook her up the old-fashioned way. Offer incentives for her to stick around. There’s no need to reinvent the wheel here, since a yearly bonus or two can cover each one. Think paid vacation, mental health days, and a subscription to Spotify. When you find a freelancer you really love (and you will, if you stick with it), offer free samples of the products or services that you sell to consumers. Send her swag and a birthday card and consider padding her pay with enough to cover about the amount she’d likely be stashing for retirement or her health savings account.

Tell me I’m not the only one who sees this next development coming. There has to be someone out there who can agree: the first brand to jump in the race to attract the smartest, hottest minds will be rewarded with much, much more than new teammates. I, for one, cannot wait to see who it will be. Which industry? And what incentives will be used? And who will be left bewildered, saying they wish they had had a crystal ball?

Interested in working with top creatives to bring your brand’s story to life? Check out Skyword’s community of influential writers, videographers, photographers, and graphic designers.

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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 bethanyjohnson.com.

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