Freelancer crowd
Storytelling Communications

The Crowded Future of Freelance Writing Jobs (And Why There’s Room for You)

10 Minute Read

Among square dances, rectangular pizza slices, reading circles, and the other geometrically dissonant aspects of childhood that pepper my memories, there’s one thing in particular that stands out from my elementary school career: choosing a hero.

In fourth grade, my teacher asked everyone in class to name a hero and explain why s/he was so significant. While my classmates confidently stood behind presidents and comic book protagonists as heroes, I remember presenting about Robert Frost. It wasn’t just because he, like me, was a poet; rather, it was because he was my introduction to the notion of freelance writing jobs, having sold his first poem, “My Butterfly: An Elegy” for $15 in 1894. I was stunned that someone could make money from a passion like that. Frost knew he had something to say that would add dimension to the human conversation and change the lives of all who listened. And that impressed me to my core.

SupermanToday, as an associate community manager at Skyword, I work with full-time freelancers who inspire me both professionally and creatively. Through our conversations, I’ve learned that freelancers work long, unconventional hours crafting stories from keywords and doing deep dives into research. They’re masters of craft, working and reworking their pieces to fit a wide range of tones and brand voices; digging into the lives of various audiences to learn exactly what they need. Part storyteller and part analyst, these digital strategists combine data and algorithms with their passions and inherent knowledge to help create stories that add dimension to conversations and enhance lives. And they do all this alone, tuning out ambient noise to weave work from the fabric of their minds.

It makes sense, given everything freelancers do, that challenges would arise. From big-picture issues like maintaining a work/life balance to more granular difficulties surrounding writer payment and health insurance, there’s a lot to account for in a freelance career. To better understand the challenges freelancers face, I spoke with New York-based freelance writer Nicole Cammorata, as well as Howard Schwartz, Mark Roth, and Joe Rubin—the founders of, a marketplace for on-demand workers. Here’s what I learned.

1. Freelancers Are Small Businesses

In running what is, essentially, a small business of one, freelancers face many of the same challenges as entrepreneurs. As Schwartz notes, these struggles include “exposure to opportunities, putting yourself out there and scheduling your clients, making sure your equipment is in proper working order, paying for your own materials and figuring that into your bottom line, actually knowing what business expenses you can deduct and then remembering to save your receipts, paying your own taxes, and being diligent in saving enough money to do so […] and of course having insurance to cover your medical bills.”

2. They Work Alone

While freelance writers do get opportunities to interview others or conduct research in their fields, much of the actual storytelling process happens when they’re alone. So instead of being able to turn to a colleague or supervisor for assistance with a question, they’re often left to their networks and pools of resources.

So which resources are most helpful for freelancers? According to Cammorata, there are a few worth noting. “I use Invoiced, which is a free online service that automatically stores all your past invoices,” she says. “UberConference (also free) is really great for doing interviews. It’s a call service that lets you schedule and host conferences and even allows you to record the call directly through the service and then download the recording. […] I also use Google Drive to keep all my stories and assignments organized. This is another super helpful tool for me because since it’s stored in the cloud, I can access it wherever, whenever.” itself is another great resource that meets a huge need for freelancers. “In our conversations with the [on-demand] workers that brought us lunch or delivered packages, we started to see a need for a place that aggregates all of these services into one place for the benefit of the worker,” Rubin says. “Even now as the market is emerging in the major cities, most workers we speak to still have no idea about 99 percent of the other platforms and opportunities out there. Discovery of new on-demand gigs and getting people more consistent work are the two main objectives of”

Freelance Writing Jobs: Working Alone

3. Finding Consistent Work Is a Challenge

Issues with workflow can manifest in different ways for freelancers at all stages. Having transitioned to full-time freelancing in July of 2014, Cammorata experienced the struggle of finding consistent freelance writing jobs firsthand. “[S]ome months I [wouldn’t] have a single story or project to do, which is a challenge when you really need to have that money coming in to pay for bills like rent, health insurance, and student loans,” she says. “So when I was first getting started, it was a constant hustle to make contacts, pitch stories, and look for any and all opportunities that would allow me to work.”

After establishing herself in Boston for nearly 10 years as a journalist for The Boston Globe, Cammorata made the move to New York City and had to reestablish herself as a full-time freelancer in a new place. Today, she finds, the challenge of inconsistency has a different, but equally challenging, spin.

“[N]ow that I’m more established, there are way more opportunities. Sometimes I’ll have months where I almost have too much work, where there will be multiple assignments from many different places, and all with equally important deadlines. It can be a challenge to juggle it all.”

4. Freelance Writers Seek Their Own Educational Opportunities

In traditional work environments, employees often have opportunities to learn and grow both personally and professionally. But for freelancers, continued education is often pursued through online resources.

“I’m always looking for new ways to learn about what I do, but it’s usually just by reading blogs, talking to fellow freelancer friends, or keeping an eye on other publications and writers,” Cammorata says. “I read a lot and I think as a writer that’s the most important thing you can do. Probably even more important than writing. But would I be into something more formal, like classes or online seminars? Absolutely. This business changes so frequently and so quickly I think it’s important to do whatever possible to stay sharp.”

Schwartz agrees that providing education to freelancers and other independent workers is an important service, and strive to provide resources for their network of users. “At, we put together worker meetups and a community where we educate [independent] workers. They learn from experts as well as each other. The worker meetup sessions have proven incredibly valuable for everyone who attends.”

5. Staying Motivated Can Be Difficult

Cammorata echoed the findings from this infographic from, saying that she values the freedom and flexibility freelance writing jobs afford. But it’s easy to understand how staying motivated could be a challenge. How can freelancers maintain their enthusiasm for their work?

“Lots of reading helps,” says Cammorata. “I read a lot of fiction, but I also read a lot of nonfiction about things that interest me: food, cooking, urban farming, social history, and beekeeping are all current topics on rotation. I also find it helps to have some passion projects in the mix—things I’m writing just because they interest me and not necessarily because I’m being paid to do them. For me, that means writing a novel. But for someone else it could be anything: poetry, blogging, travel essays, whatever.”

It’s also important for freelancers to pursue clients and subject matter they’re genuinely curious about. “As a lifestyle writer, I love telling stories, sharing information, giving the inside scoop about a city, or helping a brand bring their mission to life through custom content. I really value the variety; that it allows me to do many different things but that it always comes back to the thing I love most: writing.”

Freelancers Have to Make Their Own Opportunities

6. Getting Started Isn’t Easy

Starting a freelance career is a daunting task. But according to Cammorata and the founders alike, there are a few tips that can help.

“Try to book some jobs that are more consistent so that you know you can plan on that money,” Cammorata suggests. “I’m lucky in that I snagged a regular freelance gig doing digital advertising copy so everything else I take on that has a longer lead time, like magazine stories for instance, can happen around that. That way, if I have to wait a while to get paid for something I’ve written (sometimes it can be months), then I at least have a steady paycheck coming in.”

Cammorata explains that another key to advancing your career is taking on new challenges, even if you fear they’re beyond your capabilities. “I can’t tell you how many times I’ve just jumped into something that I was nervous about and wound up learning so much and using it as a stepping stone to something else down the line. You have to be the one to advance your own career. Because you’ll have many different bosses as a freelancer, you have to constantly prove yourself and what you can do.”

And when it comes to paying your taxes, make sure you do your homework. “Something I wish someone had told me is to pay your taxes quarterly if your gigs are not taking taxes out as you go,” Cammorata says. “I learned that the hard way last year when I wound up owing a lot of money to the IRS. Ouch.”

Roth adds that research is a crucial component to any successful freelance career. “There are plenty of opportunities out there for on-demand workers. Some are better than others, some are a better fit than others, some will be your passion, and some will be just an income stream. Be sure you consider all the other things that go along with being an independent worker—do your taxes, save your receipts, etc. Then, once you start, be the best you can be.”

7. The Future of Freelancing Is Bright

With the continued evolution of collaborative technology that allows for remote work, it’s no surprise that freelancing is so popular today. But if you’re jumping headfirst into freelance writing jobs, you might be wondering what’s on the horizon.

According to Cammorata, the future of freelancing is bright. “Everyone is on the go these days and has the ability to log in from anywhere. As I answer these interview questions, I’m actually on my computer in the car driving from Boston to New York and using my cell phone as a mobile hotspot. Modern technology is awesome and has allowed me the flexibility to work from anywhere. ”

And statistics support her beliefs: “Right now freelancers represent a third of the US workforce, and this number is expected to go up to 40 percent in the next few years,” says Roth. “The on-demand segment of that is expected to double to almost eight million people in the next few years.”

To meet the needs of that growing segment, is continually working to ensure they are meeting their users’ needs. “We use these services every day and have on-demand workers show up to our office six or seven times a day,” Schwartz says. “We hear the good, the bad, the things people love and don’t love about their jobs and the platforms they work for. […] We’ve built around that feedback.”

No matter your level of experience as a freelancer, you’re bound to encounter challenges you can’t face alone. But with the right tips, resources, and the past experiences of others, you’re sure to come much closer to reaching your goals and advancing your career. Want to learn more? Be sure to follow Nicole Cammorata on Twitter (@nicolecammorata), and check out everything that’s available at

To keep up with the latest career advice for content creators, subscribe to the Content Standard Newsletter.

Register for Forward 2019!

Content Standard Editor, Cofounding Editor-in-Chief of Spry Literary Journal. Past lives include: Poetry Editor for Mason's Road, Student Editor for the Bryant Literary Review. Previously written work has appeared in such publications as Now What: The Creative Writer's Guide to Success After the MFA; future work includes Idle Jive, a poetry collection in progress.

Recommended for you