Nicole Clark ’16, Sara Deeter ’16, Aaron Reiss ’10, and moderator Chloe Tsang ’17

In a livestream career workshop moderated by Chloe Tsang ’17, co-chair of the Yale Alumni Journalism Association (YAJA), a shared interest group that connects more than 1,000 alumni working in journalism and media, three alumni journalists shared their professional experiences and offered their advice on how others can break into the field and succeed as freelance writers and journalists, whether they are recent graduates or career changers:

  • Nicole Clark ’16 – Freelance culture writer covering identity, entertainment, and mental health; contributing editor at Catapult
  • Sara Deeter ’16 – Managing editor at Hispanic Executive; board member and communications director for YaleWomen Chicago; vice president, Yale Club of Chicago
  • Aaron Reiss ’10 – Freelance multimedia journalist, researcher, and cartographer

While journalism is a highly competitive field, the good news is that it is possible to break into it without prior experience.

Clark, who studied English at Yale and never engaged in journalism as a student, got her start soon after graduation with a comedy piece she wrote about Burning Man that was pitched to and published by a small San Francisco magazine. She found the magazine through an online search of Bay Area publications and learned how to craft an effective pitch through resources gleaned from the Poynter Institute for Media Studies and the Nieman Foundation for Journalism. 

She recommended that those new to journalism start with smaller local publications to get a foot in the door.

“There’s always a market for you, even if you feel intimidated by those bigger papers,” Clark said, adding that after her first piece was published, she followed up with other story ideas and became a regular contributor, which led to a contract editing role and other opportunities later, including a staff writing position at VICE.

Reiss said he got into journalism by accident. While studying Urban and Environmental Studies at Yale, he made Facebook photo albums and then did photo essays, initially guided purely by interest. After graduation he moved to China for two years under a Yale-China Fellowship and began documenting what was happening around him. Eventually, he began freelancing his work. This led to more projects and assignments, covering topics ranging from education to employment to transportation.

Deeter spent several years working as a freelance writer, researcher, and editor before landing a staff position as a writer and now managing editor for a publication that covers Hispanic leaders.

Succeeding as a Freelancer

While no previous experience is required, those contemplating a career in journalism must be excellent writers and possess certain skills – with pitching being one of the most important.

“I’ve gotten most of my opportunities from cold pitching,” said Clark, adding that freelancers should treat every assignment as an opportunity to build one’s reputation as a reliable writer who can consistently deliver clean copy in a timely manner.

“Once you land that cold pitch, make yourself just ‘love-me-to-work-with,’” she emphasized.

Reiss said he likes to incorporate multimedia in pitches to demonstrate to editors his versatility as someone who can not only write copy but also photograph images and shoot video.

“What’s nice about a visual pitch is you can communicate both ‘here’s what I have to offer, here’s the talent that I have,’ and also, ‘here’s what it could look like,’” he said.

There was strong consensus that the ability to cultivate and sustain good relationships with others in the industry, especially editors, is a critical skill for a freelancer.

“The key is to maintain a positive sense of communication and a positive attitude at all times,” said Deeter, adding that freelancers with whom her company no longer works include those who are extremely argumentative or push back too hard and too insistently over editorial changes to their copy, especially changes that are relatively minor.

Where’s the Money?

When discussing the downsides of being a freelancer, compensation stood out as the most prominent.

“The economic side of freelancing is one of the few bad sides of freelancing,” said Reiss, who noted that the life of a freelancer can frequently involve compromises between income and choice of assignments, enduring lean times and unpredictable pay, and side jobs outside journalism to make ends meet or subsidize a freelance career.

“Either you’re a machine and you’re constantly pumping things out, and you’re really good at that,” he said. “Or you find creative ways to make money in the margins.”

All agreed that freelancing rates can be highly variable and that it is incumbent upon freelancers to negotiate not only higher rates but also ownership rights for their work, if they wish to maximize their financial stability.

Clark recommended that freelancers diversify their income streams; build up a roster of “anchor clients” who can be relied upon for regular assignments, stipend, or income; and apply a methodical time-and-effort-versus-reward approach in assessing every assignment.

“Evaluate whether the money that they offer you is worth the hours that you’re putting in,” she said, adding that freelancers also must take into account self-employment taxes and the turnaround time between invoicing a client and getting paid.

Deeter, who in her current role has discretion to hire freelance writers, recommended that even in cases where rates are set, there are always exceptions – and writers who have something unique or particularly valuable to offer should not hesitate to negotiate rates.

“Always feel free to ask,” she said. “If you have something to leverage, please do ask.”

An Amazing Gig

Despite the challenges of a freelance career in journalism, there are upsides and advantages that can make it worthwhile, including the autonomy to pick and choose assignments and configure one’s own career path.

“When you are a freelancer, you have a little more freedom to try different things out,” said Clark, who has worked on assignments ranging from celebrity profiles to product descriptions to stories about marginalized communities.

And there are plenty of opportunities for those who have the drive, talent, and gumption.

“If you have ability, there are so many places that need new content every single day,” said Reiss. “It’s an amazing gig.”

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