March 07, 2013 149 Reactions

Diving In: Surviving Your First Year as a Freelancer

By , under Content Watch, Make it Work. Kylie Jane Wakefield is a Los Angeles based freelance writer and publicist.

The first year of freelancing isn’t easy. For writers, it’s all about trial and error, figuring out exactly what they want to accomplish in their careers, and making changes to their everyday life to survive.

The Freelance Strategist spoke to freelance writers about their first year experiences, including their biggest challenges, early accomplishments, and mistakes. From low pay, to contractual misunderstandings, side jobs, gaining self esteem, and learning how to balance work and life, these freelancers have gone through the early stages to come out on the other side.

This is how they survived.

Rhiannon Fionn-Bowman

“I ended up working and worrying too much, but I never considered quitting.”

Before Rhiannon Fionn-Bowman became a freelancer, she prepared herself for the lifestyle. The writer, who has been published in The Huffington Post, the Carolina Weekly Newspapers, and Charlotte magazine, spent all of her spare time in college writing, interning at an alt-weekly in Charlotte, North Carolina, and working in insurance.

Once she established herself in her local press scene and got gigs regularly, she quit the insurance job and focused solely on writing. She graduated from college, wrote an average of eight to 10 articles per work and was “working way, way too much,” she says. “But, I learned a lot and accomplished a lot, too.” During that first year, her biggest accomplishments included piling up decent clips, establishing connections, and gaining confidence in herself.

It took a while in that first year for Fionn-Bowman to get a hang of the freelancing schedule, which resulted in, at times, work overload. “I didn’t know the flow of the business yet — like when times would be slow, and when they would be busy,” she says. “I wasn’t sure when to shore up my savings and when it would be okay to take a vacation. So, I ended up working and worrying too much, but I never considered quitting — and I remain determined to succeed.”

Cara Cannella

“It takes a while to develop discipline and manage time/workload.”

Like Fionn-Bowman, Cara Cannella, editor at Biographile and former research chief at Every Day with Rachael Ray, started her freelancing career while she was still in grad school.

While she was working towards a degree in creative writing at the New School, she fact checked part-time for different magazines. During her first year as a full time freelancer, she waited tables and supplemented her income with other work. “I have experienced some very learn times financially,” she says.

In the beginning, her mistakes included not paying taxes quarterly, taking on assignments she wasn’t interested in, and struggling to balance the amount of work she had. “It takes a while to develop discipline and manage time/workload,” she says. “But that challenge is worth the flexibility and freedom offered by freelancing.”

Beverly Akerman

“It was great to see my name regularly in print. But I also spent a lot of time wondering what the heck I was doing.”

Beverly Akerman, freelancer and author of The Meaning of Children, says that transitioning into a freelance career wasn’t exactly her decision. “I didn’t exactly choose to change  it’s more like change chose me.”

Akerman had worked for over two decades in science, particularly molecular genetics research, but with the death of her father-in-law, she realized that life was too short. She decided to start writing fiction and took workshops at the Quebec Writers’ Federation. Then, she joined the Professional Writers Association of Canada, networked, and took on some paid non-fiction assignments at university administration newspapers and medical publications.

She also found work with a communications firm, and it was there that she made the mistake of low-balling her hourly rate: “I thought they were hiring me to do photocopying and that sort of thing,” she says.”Before I knew it, I was writing summary documents for their online training programs. But I had to realize what was happening, and then get up the gumption to do something about it.”

During Akerman’s first year, she says that she was mainly trying to strategize what to do. “It was great to see my name regularly in print. But I also spent a lot of time wondering what the heck I was doing. Not that that’s changed all that much.”

Jennifer Nagy

“I think that only over time do we really understand the effect that our writing has on other people and on people’s perceptions of us.”

Jennifer Nagy, founder of marketing firm jlnpr and a writer for The Huffington Post, became a freelancer following her divorce in 2011. She pitched a story to the HuffPo divorce section about her particular experience, and the published article received a lot of attention.

“The best part for me was the fact that I had quite a few people emailing or tweeting me saying that I really helped them because they realized that they weren’t alone in a similar divorce situation,” she says.

From there, she branched out to writing public relations and marketing articles for the small business section of the website.

Nagy says that her first year as a freelancer was typical. She had a few great opportunities, but still had to continue working at her PR business full time. This means that her progress is slower since she writes during off hours or on weekends. The biggest challenge, for her, was figuring out her to translate her true self through her writing while still connecting with readers.

“I think that only over time do we really understand the effect that our writing has on other people and on people’s perceptions of us. Especially when you’re writing about something as personal and private as divorce, it’s always tough to balance sharing enough to help people and protecting yourself (and your ex).”

Top image courtesy of shinealight/flickr

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