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The face of freelance

Independent writers discover that freedom comes with the price of persistence, passion and adaptability.

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freelancefacesxpenYou may think you know the profile of the freelance life: struggling to get published, always selling a story, always looking for opportunity, short on vacation time. And all of that can be true. Mostly. Also true is that the market is loaded with opportunity and obstacles, making the task of defining “the freelance life” rather difficult.

Let’s say that a freelance writer is anybody creating original work, solicited or unsolicited, for pay or not, for an established outlet, be it print or digital. While writing for friends and family in your blog may lead to your discovery down the road, it’s hardly the surest path.

Of course, that assumes there is an accepted way to become a freelance writer. But if that was ever the case, it isn’t anymore, with outlets for writing appearing and disappearing daily.

These profiles of freelance writers show the range of those presently toiling in the professional marketplace. Those spotlighted also offer some suggestions for others hoping to make their own impact as writers.

Finding a home

Philadelphia journalist and novelist Solomon Jones started his freelance writing career as a means to an end. He sold his first freelance piece for $35 to the Philadelphia Tribune in 1993, while he was living in a homeless shelter.

“I needed that $35, so I took the assignment very seriously,” Jones, 45, said.


In the end, Jones found his calling with that assignment.

He graduated cum laude in journalism from Temple University in 1997, and his writings have appeared in Essence, Newsday, The Philadelphia Inquirer, Philadelphia Magazineand The Philadelphia Weekly. He is also a published novelist, with his eighth book, The Dead Man’s Wife, having been published in 2012. He has been featured on NPR’s Morning Edition, CNN Headline News, and Essence and in a Verizon advertising campaign titled Realize that spotlighted entrepreneurs who overcame adversity to succeed.

Jones has continued to evolve his work and is now a multimedia producer for while he continues writing freelance for the Philadelphia Daily News and He juggles a full-time job with freelancing and writing novels by carefully budgeting his time and working a little more than he did in the past.

Active in his local community, Jones has worked on campaigns to bolster literacy and empower the homeless. Being a community activist has helped him as a writer.


“There’s nothing more important than your reputation,” he said. “Your reputation is currency. Helping others builds up a trust in the community where people will come to you with their stories and trust you to handle them sensitively.”

Jones is energized by the ever-changing creative marketplace.

“It’s an exciting time for those who are willing to put in the work,” he said. “There are a lot of entities where you can get published. The downside is that you’re not going to get paid as much as you used to. But if you build a brand, people will come to you and offer work if your work is of a certain quality.”

Whatever the format, Jones seeks to be a storyteller.


“I love to be a voice, to write about things that matter and to affect some kind of change,” he said. “I’m moving in the direction of becoming a content creator. Writers are needed to create material for online and video entities, and we need to equip ourselves for different media. I want to write for every medium and see those stories come to fruition.”

Digital design

One way freelance writers can increase opportunity is to embrace what new technology offers.


Take the route chosen by Scarborough, Maine-based writer Kathryn Hawkins.

With her husband Jeff, a website developer, Hawkins, 31, runs a content marketing agency, Eucalypt Media. “Content marketing” refers to producing content on behalf of corporate clients, such as blogs, articles, e-books and white papers. The Hawkins contract with freelance writers and designers for projects as needed.

One such Eucalypt project is a website the couple owns and operates,, which focuses on positive news stories and self-improvement. They also work with many large clients on sponsored content and digital marketing initiatives.

“For us, this is a way to diversify our income streams and an opportunity to build a self-sustaining business that lets us keep making income while taking vacations now and then,” Hawkins said.


Also, over the past decade, Hawkins has written freelance pieces for magazines, web publications and corporate clients, covering such topics as business, philanthropy, personal finance, lifestyle, environment, technology and parenting (the Hawkins have a 2-year-old daughter, Leah).

Hawkins got her start while studying for an MFA in creative writing at Chatham University in Pittsburgh in 2006. One day, she attended a panel on freelance writing, and one of the panelists was freelance writer Rebecca Skloot, later the author of The Immortal Life of Henrietta Lacks.

“I was intrigued by the stories she was sharing of her life as a freelance writer and the prospect of having the opportunity to explore and write about anything that interested me,” Hawkins said.

Skloot explained that she began writing for the University of Pittsburgh alumni magazine. The editors of that publication were at that conference, and Hawkins soon wrangled some assignments from them, gaining clips to show other publications.


“I’d originally planned to pursue a teaching career with my MFA, but decided that writing was much more fun,” Hawkins said.

And yet, she has seen the digital revolution create a tumultuous marketplace for freelance writers.

“I’ve seen the rise in content farms, and now, thanks to changes in Google’s search results, it looks like they’re falling again, which I’m thrilled about,” she said. “I’ve seen a lot of great media outlets shut down, and pay rates drop for many of the ones that are still around. At the same time, though, there has been a huge boom in content marketing for companies. Instead of sinking their marketing dollars into advertising on media publications, a lot of brands are creating their own content outlets and are willing to pay good money for writers with journalistic skills.”

Musical journey

Music and writing have always been Geoffrey Himes’ twin passions.


Himes wrote poetry and articles for his high-school paper and was a music fan, but he came out of college determined to be a teacher. He taught English, first in high school and then at community colleges. Then he began writing music and theater reviews on the side. By age 25, he made the move from teaching to full-time freelancing.

That was 35 years ago, and Himes has become one of the premier music writers in the country.

He has written about music on a regular basis in the Washington Post and No Depressionmagazine. He has also written for Rolling Stone, the Oxford American, Musician Magazine, National Public Radio, Crawdaddy, Fi Magazine, Request Magazine, Downbeat Magazine, Country Music Magazine, JazzTimes, Bluegrass Unlimited, New Country Magazine and others. He has been honored for music feature writing by the Deems Taylor/ASCAP Awards and by the Music Journalism Awards.


Himes wrote two chapters of the book The Blackwell Guide to Recorded Country Music and contributed entries to The Encyclopedia of Country Music, The Music Hound Folk Album Guide and The Rolling Stone Jazz & Blues Album Guide.

On one recent day, he was working on a feature about Willie Nelson for Texas Music Magazine, one on Emmylou Harris and Rodney Crowell for Paste Magazine, an article on Maria Schneider for Jazz Times and a review of African music for the Washington Post.

Himes’ secret? “Following my own curiosity, my own passion and writing something that I was excited about, something that I had something to say about.”

About the current freelance market, Himes, who is teaching again, tells his students: “It’s easier to get published today, but harder to get paid.”


Himes has managed to navigate these shifting currents because he continues “developing new relationships along the way.” “If an editor you’ve been working with gets fired or retires, it’s good to have other connections you can expand upon,” he said.

To that end, Himes, who lives in Baltimore, travels to music-industry conferences to make those oh-so-important connections, a move that he urges any specialized writer to do. Still, Himes warns that it’s possible to get caught up in chasing assignments to the detriment of the writing.

“Don’t concentrate on the hustle to the point that your writing isn’t getting any better,” he said. “Make time for the craft. The best way to get better as a writer is to write a lot, and to write stuff that you want to show other people.”

Even after more than three decades, writing is something Himes has to do.


“If I don’t write for several days, I get antsy,” he said. “I have a lot to say, and I feel better when I get that down into words.”

A new wild life

Andrea Kitay’s concern for animals started her freelance journey.

She had earned an undergraduate degree in French, but had no formal training in writing at that point.

“During graduate school, I worked at a wildlife rehabilitation center and helped form their board of directors,” she said. “A local newspaper got wind of this event and, the editor came out to interview me. I was very passionate about educating the public about the wildlife we as humans increasingly live with – urban wildlife – and he picked up on that. Somehow we came up with the idea that a weekly column addressing his readers’ issues with urban wildlife conflicts might be of interest. And so the beginnings of Living With Wildlife were born.”


That column led first to feature writing and now travel writing for the Southern California resident.

“For me, every move has felt equally rewarding, whether it was the move to writing my column in The Los Angeles Times after a cold-call to the editor, or writing feature stories for a local glossy magazine,” said Kitay, 50. “Opportunities can be created as you go if you keep your eyes open. The joy in being a wordsmith is in the final product, whether it’s read by millions or just a zinger of an email.”

Kitay suggests formal training for potential freelancers. “If I were starting out again and knew instinctively that writing is where I wanted to ultimately be, I would probably get a degree in journalism,” she said. “That discipline not only provides writers a formal skill set, but it also allows them time to work out the kinks and hone their craft.”

But she knows it can be a tough world out there for freelancers.


“My career in writing has paralleled almost perfectly the advent of the Internet and the demise of newspapers – as we who held that fine, crinkly paper in our hands every morning knew them,” she said. “Obviously there is more information available to weed through today, and more people vying for fewer slots. Despite what writers say – or don’t say – it’s very difficult to make a viable living as a freelancer these days.”

Still, Kitay loves the flexibility her career choice has allowed her.

“Every phase of my writing has been different, so they’ve all served different personal needs,” she said. “I’m fascinated by the complexity of interplay between human society and wildlife, and can get almost distraught over ignorance around the subject. Writing my column channeled that curiosity and frustration into something useful. Feature writing keeps me in touch with my community. Travel writing began as a means to provide an educational opportunity for my three kids. What’s not to love?”


An American freelancer in Paris

As with many creative types, Ethan Gilsdorf spent about a decade post-college casting about for a profitable avenue for his efforts.

While at Hampshire College in Amherst, Mass., Gilsdorf wrote short stories and poems, which he continued while studying for an MFA at Louisiana State University from 1990 to 1992. He got his start then as a freelancer, writing book reviews for the Baton Rouge Morning Advocate.

But his a-ha moment came in December 1999, when he and the woman he was living with quit their day jobs and moved to the City of Lights.

Like the Joni Mitchell song says, he was a free man in Paris.


“We were going to try out life as artists,” said Gilsdorf, a Somerville, Mass., native. “It gave us permission to leave that safety net behind.”

Gilsdorf, 46, soon discovered that English-language publications in Europe needed writers and began getting assignments. This led to freelance assignments in Europe for stateside papers.

“I would get names, pitch ideas and hope that the editor would take a chance on me,” he said. “Between that, and a part-time marketing job, I stayed in Paris for five years.”

That was the beginning of Gilsdorf’s full-time freelance career. He has written travel, arts and pop culture stories, essays and reviews that have appeared regularly in The New York Times, Boston Globe, and, and has published hundreds of articles in dozens of other magazines, newspapers, websites and guidebooks worldwide. He blogs at, and the Cognescenti blog for WBUR radio. He is a book and film critic for The Boston Globe and is the film columnist for Art New England. He also teaches creative writing on the side about a third of his time. His travel memoir investigationFantasy Freaks and Gaming Geeks grew out of a series of features he wrote.


Aspiring freelancers are coming into a crowded marketplace, Gilsdorf said.

“A lot of full-time journalists have been laid off and are now competing with freelancers for assignments,” he said. “There are a lot more places to get published and a lot more online outlets that are growing, but there’s a large range of payments.”

While others may be entering the freelance workforce with support from other full-time income, Gilsdorf said writing is his only career option.

“At this point, I can’t get employed to do anything else,” he said. “Maybe a full-time writing job would be better and give some security. But I’ve grown accustomed to this lifestyle. The field is big enough that you can move around as your interests change. I’m even thinking about writing fiction again for the first time in 25 years, which is scary.”


The accidental freelancer

From an early age, Sandra Oliver knew she wanted to be a writer. It just took her a while to find her way into the field.

For 16 years, Oliver, now 65, worked at the Mystic Seaport Museum, where she became a food historian. In 1989, she left with the intention of writing a cookbook.

Instead, a former co-worker at Mystic began giving her regular assignments ghostwriting content for a business textbook company. That became her first toe in the pool of freelance writing.

Also in 1989, Oliver, who lives in the Maine island town of Islesboro, began writing, publishing and distributing Food History News, which made a name for her. Her food-historian niche led to assignments from magazine editors seeking “origin” features about various types of food.


At this same time, Oliver was writing Saltwater Foodways, a history of New England seacoast and seafaring food, which was published in 1995. Since then, she has publishedGiving Thanks (co-written with Kathleen Curtin) and Food in Colonial and Federal America, both in 2005, The Saltwater Foodways Companion Cookbook in 2009 and Maine Home Cooking in 2012.

In 2006, Oliver made the next move that helped her career when she agreed to produce a weekly recipe column, Taste Buds, for the Bangor Daily News in Maine.

“It gave me a grounding to what was going on in Maine,” she said. “Also, I was writing about food in the present, not just its history anymore.”


She also writes the Journal of an Island Kitchen column for the Working Waterfrontnewspaper and occasional historical maritime food features for Maine Boats Homes and Harbors.

Oliver shut down Food History News in 2009, because of its aging readership and eroding subscriber base. This thrust her back into actively seeking freelance jobs, a role for which she has always felt ill-equipped.

“I don’t have the disposition for freelance,” she said. “I don’t want to be out there selling myself all the time.”
And she has her doubts about the ascension of food writers in a technological age.

“The Internet has turned food writing on its head,” she said. “Every reasonable home cook with time on her hands can have a blog and is willing to write for free. And what publisher is going to pay when they can have something for free?”


liver illustrated the viability of freelance food writing with a joke that she heard at a food-writers conference: “What do you call an unmarried food writer? Homeless.”

Teaching and speaking gigs have provided supplemental income for Oliver’s writing career, with the split being about three-quarters writing and one-quarter ancillary jobs. She’s looking forward to the cushion of Social Security on the horizon.

“I rely on this stream of income to support me,” she said. “It won’t be nearly as important in a few years, but I’ll keep my regular gigs.”
Advice for aspiring freelancers

• Value quality over quantity: “If you don’t have any clips, look for opportunities to start small ‒ introduce yourself to an editor at a local newspaper or weekly and do some work there,” said Kathryn Hawkins, a Maine freelancer. “It may not pay much, but it gives you clips editors at larger publications will respect. And if you’re not getting the kinds of assignments you want, do them for your own website. Anyone can create a media outlet today.”


• Know your audience. Philadelphia journalist and novelist Solomon Jones suggested following trends in the target publication or website, then pitching three to five story ideas along those lines.

• Keep it fresh: “Look at publications, get a sense of what they like to publish and do some research to make sure the story hasn’t been done before,” said Somerville, Mass., freelancer Ethan Gilsdorf.

• Check out paid online networking groups, such as Freelance Success, which offers a weekly newsletter about writing markets and online message boards where experienced writers share advice and commiseration. “It’s $100 a year but has paid for itself many times over in the leads I’ve received, and it helped me slip away from the $10-an-article markets I’d used to pay the bills when I first started out,” Hawkins said.

• Reach out and touch someone. “Stay in touch with people and let them know what type of writing that you’re doing,” said Jones. He told of a time when Bill Cosby told him to call Essence editor Wendy Wilson. Neither Jones nor Wilson knew why Cosby had them get in touch, but Jones ended up with an assignment for the magazine from that call.

• Develop a thick skin: “You’re going to get rejected,” Gilsdorf said. “Don’t take it personally. It doesn’t mean you’re a bad writer. There’s no substitute for perseverance.”

• Avoid the so-called “content farms” that offer low wages or at least limit the time that you spend on this kind of writing. Content farms are massive online content sites that generate thousands of articles to cover every keyword imaginable, which generally pay writers in the ballpark of $15 for a 500-word article “It does nothing to impress editors at more prestigious publications, and it takes time away from pitching more profitable markets or from developing your own platform with a blog,” Hawkins said.

• There are no small assignments, only small writers. “You need to treat all assignments seriously,” said Jones. “You have to consider each piece you write as building your brand. That way, editors are going to consider everything you write as being of a certain quality.”

• Take the long view: “Understand you’re not going to get the best assignments right out of the gate,” Gilsdorf said. “It will require less glamorous stories for less glamorous publications to improve your writing and to prove yourself to editors.”

• Stop talking, start writing: “Everyone will tell you they want to write, but most don’t have the discipline to start,” Southern California writer Andrea Kitay said. “Avoid the ‘what ifs’ and get a daily discipline going. I’ve always written starting at about 3 in the morning. I can’t produce a coherent sentence after 2 in the afternoon. Know your limits and edit, edit, edit. Then edit again.” Originally Published