Creative Strategies For Scoring More Freelance Work

Getting started and developing a steady line of work as a freelancer requires persistence and a careful approach. Here’s how to do it.

Creative Strategies For Scoring More Freelance Work
[Photo: Shutterstock; App Photo: LucasFilms]

“How do you make a living?” one recent writing coaching client asked me at the end of our call. He was paying me an hourly fee to help him work on his writing, but surely that couldn’t be enough for me to make a living, he said. What else was there?


As any freelancer will tell you, there’s a lot more. There are regular gigs, gigs in the pipeline, gigs that seem promising, only to trickle into nothing, opportunities you haven’t yet learned about, ones that come to you by way of your network, and others that feel like they come straight out of the blue.

This isn’t just the case for freelance writers, either. There are 53 million Americans working as freelancers in the U.S.–that’s 34% of the population–according to a 2014 study commissioned by the Freelancers Union.

Regardless of what industry you find yourself in as a freelancer, be it technical, creative, business, or finance, learning how to generate more work, elevate your career, build your skills, and develop meaningful relationships along the way are all critical. According to a July 2015 survey of more than 1,000 tech freelance developers by Upwork, contract history and feedback from previous clients was the number one most important factor in winning a work project.

But what if you’re just getting started, trying to build out your client base, or feeling stuck working on the same kinds of projects? I spoke with successful freelancers across industries for their insights on how to not just make it, but more importantly, thrive in the freelance economy.

Persistence Pays

Nancy Borowick
New York City

Nancy Borowick’s photos have been featured in the New York Times, Newsday, International Herald Tribune, CNN, Time magazine, and the Washington Post to name a few. But when she started freelancing in 2010, she’d never photographed for a newspaper or media outlet. Besides shooting a few bands and small jobs for friends, she hadn’t had much in the way of freelance work. But that didn’t stop her. Borowick was determined to break into news photography. She’d met an editor from Newsday at a career fair and followed up. She left a voice mail and didn’t hear back. She emailed and didn’t get a response. A few weeks later, when the editor called to ask if she was free that Saturday to shoot an assignment, Borowick cancelled her weekend plans and jumped on the opportunity.


For many freelancers just getting started, that first gig can sometimes seem like the only one. What if more work doesn’t come along? Borowick knew if she wanted more assignments, she would have to be persistent. She found out what time the morning desk editor at Newsday arrived at work, and she set her alarm every day for 6 a.m. to call and ask if there were any outstanding assignments. She did this every morning for a week and a half before she got a bite.

And later, once she’d built up a portfolio, she did the same with the New York Times. After a personal photo project she did was featured in the Times, Borowick met the morning desk editor on a visit to the newsroom. She started her same morning call routine, calling the editor each day at 7 a.m., until she was finally given her first assignment. “I learned very quickly that if I could get the job right and I was available, I would get work,” she says.

Always Keep Yourself In The Conversation

Ryan Dewhurst
Ethical hacking security consultant
Southwestern France

Eighteen months ago, Ryan Dewhurst told his boss at the security consulting firm where he was working that he wanted to go solo. He worried he might be calling back again in three months, begging for his job. Like most freelancers getting started, the path ahead was uncertain. But it was Dewhurst’s (now former) boss who ended up calling back a few days later, asking if he’d be willing to work on a consulting basis.

Dewhurst also prioritized making the most of the connections he’d developed in the industry over the years. On his first day as a freelancer, he gathered all the business cards he’d amassed from conferences over the past five years and reached out individually to the people he’d met, letting them know he was going freelance. “That’s how I got most of my clients,” he says.

From the start of his career, Dewhurst has understood the importance of staying connected to the people in his industry. Even while working a full-time job, he was writing regular blog posts, sharing his open source coding online and building a Twitter following that today numbers more than 15,000. Having an active Twitter presence helps maintain those connections he’s made over the years. “You tend to forget people you met at a conference, but if you interact on Twitter, it’s an ongoing conversation,” he says.


Curate Your Image For Clients

Adhemas Batista
Graphic designer and illustrator
Los Angeles

One of the biggest challenges of freelancing full-time is juggling multiple clients and projects while making them each feel like they’re your top priority. Adhemas Batista knows this predicament well. On any given day, Batista is working on three or four design or illustration projects at a time, clocking 10- to 12-hour days. He’s worked with major clients like Microsoft, Nike, PepsiCo, and Proctor & Gamble. But the glamour of big-name clients doesn’t make the job any easier. Often Batista will work 50 hours on a drawing, only to have it torn apart within an hour of turning it in.

He’s learned to be acutely aware of how he interacts with the people who’ve hired him. “I have to be able to filter myself,” he says. “The biggest problem with people working freelance is they have this difficulty talking with clients. Sometimes you need to take your ego away and just understand what clients are trying to say.”

With multiple projects in the mix, that means getting as much clarity about what’s expected of you from the get-go. Batista always invests time upfront learning as much as he can about the brands and companies he’s approached by before agreeing to take on a new job with one: figuring out whether his approach will match theirs, how demanding they might be, and what the brand is about.

That also means that curating your own portfolio and image online becomes particularly important as a freelancer. Batista makes sure his portfolio gives potential new clients a clear and easy way to understand the type of work he does. As a result, he leaves a lot of projects he’s done out in order to maintain a clear aesthetic and focus. “I only put in work that has consistency of style and quality,” he says. “I put in only the projects that captivate more clients.”

Be Willing To Step Into Unfamiliar Terrain

Takaaki Okada
Creative director, consultant, photographer, and film editor
Brooklyn, New York


It’s hard to pin down what type of work Takaaki Okada does as a freelancer. He’s worked on film projects, photography projects, and interactive design projects, with clients ranging from media organizations to architects and film production companies. Okada’s impulse is to always continue to pick up and build new skills.

It’s incredibly easy for freelancers to become stagnant in the assignments and work they take on, getting comfortable working on the same types of projects time after time, with little opportunity to grow. That means it’s really up to you to push yourself into new territory and pick up new skills. For example, a few years ago, Okada did a 10-day workshop on documentary film and technology–an area he’d had little experience in before, but which opened opportunities for him to meet people in the industry and take on new projects.

As a freelancer, you’ll often have the best luck convincing clients to hire you for projects you don’t have prior experience in when you’ve done previous work for those clients. According to Upwork’s latest survey, nearly 48% of freelancers said that having previously worked with a client was the most important factor in getting assignments in areas they didn’t have prior experience in. But it’s up to you as a freelancer to find ways to build on your skills. “I relish that–when I can learn something new and do something different,” says Okada. “I just want to be a little bit in that zone where you’re always learning.”


About the author

Jane Porter writes about creativity, business, technology, health, education and literature. She's a 2013 Emerging Writing Fellow with the Center For Fiction