The Awkward, Early Years of Freelance Writing

My first “job” as a writer was signing up to write for a site called Examiner.com, which paid literally pennies at the time. I wrote over fifty short pieces for them on keeping exotic animals as pets, and earned $30 for two months of work. I would have starved or been evicted in these early months if I didn’t have a partner who was earning income and parents who lived nearby.

I broke every rule about pitching editors, sending emails along the lines of, “Hello, My name is Amanda, I’m a freelance writer with a BA from Drury University. I would be delighted to write for your publication. I’ve attached my resume for your reference.”

I joined job platforms that make you pay to use them, some of which never yielded any work at all.
Essentially, I had only a handful of arrows in my quiver, and I was shooting them in every direction with my eyes closed.

Then, in 2010, an arrow stuck: I discovered something called Demand Media Studios (DMS). With my limited experience and obliviousness to how the editorial world actually works, DMS was perfect for me. It worked like this: I submitted a resume, cover letter, and writing sample. I checked a few boxes indicating which subjects I wanted to write about. Someone evaluated it, and (apparently) deemed me worthy, and I was accepted onto their global team of freelancers. I claimed up to ten articles a week from a list of titles and got paid twice a week for writing them.

The titles were often obscure and sometimes completely un-writeable. How to Cure Melanoma in Ducks. The History of Gossamer. How to Skin a Beetle for a Festival. Still, I claimed articles and wrote them.

Writing for DMS wasn’t all bad, and money for approved articles would be in my account within a couple of days. Admittedly the pay for DMS wasn’t great—only $15 per article at the time I was writing for them—but it was like, a one-million percent raise from what I had been earning, so of course I was going to gobble it up like a dumpster turkey on an empty belly.

Once I was in a rhythm, I thought DMS was the bee’s fucking knees. However, there was no upward mobility with it: my income was limited to how many articles I could “crank out” in a day. I would spend an entire day writing three articles, then I’d have no energy to pursue anything else. It was starting to feel similar to the purgatory of waiting tables, but lonelier and more sedentary.

I figured it was time to actually educate myself. I picked up one of the most helpful books I’ve ever read on freelance writing, a book by Mediabistro called “Get a Freelance Life.” This book was no-nonsense. Here’s how you write a pitch letter. Here’s how you get good ideas for articles that will sell. Finally!

With the advice from the pitching chapter in hand, I pitched Mommyish.com, a blog I’d been reading for some time. I sent my story idea to the editor – a pitch for a serious essay on being the only atheist parent in my immediate community.

Despite some tone-deafness in my pitch, I will never forget the moment I heard back. I was at the grocery store in the canned foods aisle with my baby daughter when my phone pinged the email alert noise. The email was from K, the editor. It was a very truncated acceptance message, with a contract attached stating that she’d pay $50 for the piece.

Fifty dollars to write about something I care about. It wasn’t much, and if I’d lived somewhere a little more upscale, fifty might have only afforded me a stick of organic, gluten free, non-GMO gum. But in Springfield, Missouri, fifty bucks was half the utility bill. I took my time with that piece, writing and rewriting, having friends proofread it for me. K was happy with it, and she invited me to pitch more ideas.

I kept writing for Mommyish. Months later, my name was on the masthead as a contributing writer, alongside people who had written for “real” publications. Best of all, my writing was no longer rote and voiceless. I infused each piece with my own personality; in fact, because it was a blog, I was encouraged to do so.

'Months later, I was on the masthead with people who'd written for 'real' publications.' #FreelanceWriting Click To Tweet

I was elated at the ease of creating these stories. All it took was observing my life in terms of how my struggles or epiphanies might benefit other people. However, after a few months, it started to feel an awful lot like exploitation. On the day of the Sandy Hook shooting, all of the bloggers on the team were implored to pitch stories about gun violence and mental health, when work was the farthest thing from my mind, and it was all I could do to keep from bursting into tears every time I looked at my baby daughter, safe in my home, in my arms.

And speaking of mental health, the other price I paid was my own. The Mommyish readership, like many blogs, was notoriously tight-knit and opinionated – and some readers openly ridiculed me when I anonymously published some very sensitive pieces. I made a bad judgment call one morning on the angle of a post and the backlash was immediate: hundreds of comments within hours, all of them piling on, making assumptions about my character and even swearing off my column and my writing altogether, deciding in that single moment that they hated me.

I took my daughter for a walk in her stroller that day, smoking in the springtime humidity, tears rolling down my cheeks. Cyberbullying was all over the news at the time and I wondered how teenagers survived this phenomenon when I, a twenty-five year old woman, was very close to suicidal over a series of heated blog comments.

Despite this, I didn’t get out right away. I needed the money, and I had just started to feel like a “real” income-earning freelancer. I started thinking of other types of writing I could do, and I recalled that Mediabistro book I loved. I perused Mediabistro.com. There was information in the book about pitching them, and I figured it wouldn’t hurt, so I pitched an essay about my weird experience writing for DMS. This time, I was offered $80 for an essay. Shortly after that, a new editor named V came aboard. V needed more articles, too, and now I had a guaranteed few hundred dollars a month from Mediabistro alone.

I sold several one-off essays to other publications over the next few months and took on editing clients who found me through my Craigslist ads. It was then, in 2013, after three years of floundering, that I stepped into my first legitimate B2B writing job — but it turned out to be far more demanding than I was ready for…

Want to read more on my freelance journey, and some essential tips for avoiding the mistakes I made? Enter your email below to be notified when my upcoming book becomes available online — and to receive a special discount for your early interest:

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