So You Want to be a Freelance Writer

When I first began freelance writing five years ago I never imagined all of the opportunities that would come my way. I was fortunate enough at the time that the nature of my day job required me to write for the Cayman Airways in-flight magazine, Skies. Years later, I moved on to a marketing role at a major offshore law firm and realised how much I missed writing; so I dropped the editor of Skies an email letting her know if she ever needed a freelance writer to reach out to me. It was a long shot, but I figured the worse she could say was: “Thanks, but no thanks.”

A few weeks passed before I received my first assignment, an 800-word article on a local boutique hotel. I was over the moon! I remember the article was printed near the back of the magazine and chopped over several pages, but I was beaming with pride. The editor began regularly sending me assignments and shortly after I had a 1,500-word feature cover article that spanned four pages.

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I wrote exclusively for Skies for three solid years then, last summer, a former (different) editor of Skies reached out to me via LinkedIn with an opportunity to write for a new magazine the Cayman Islands Tourism Association would launch in 2016, Visit Cayman Islands. I was excited to branch out to a new magazine.

This New Year, I resolved to grow my freelance portfolio – I love writing about my home, the Cayman Islands, but I wanted to challenge myself beyond what had become comfortable for me.

I was reading the second issue of Cayman Parent magazine and thought: “Hey, I’m a mom. I’d love to write about what challenges, worries and inspires me as a parent.” So I sent an initial email introducing myself and suggesting the editor have a look at my blog (see tip #6), which featured some work I’d done previously. Before long, I had three assignments under my belt. And, more recently, I was working with the team at REAL LIFE on a work-related matter and mentioned in passing that I freelance in my spare time. That conversation developed into yet another assignment!

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Over the years, my writing has strengthened and I’ve found ways to improve my research, time management and getting my name out there. Editors are always looking for new talent but, in addition to the tips I’ve offered below, one of the most important things I’ve learned over the years is not to second-guess my abilities as a writer. I had to believe in myself before I could ask it of an editor.

  1. Be Yourself

    Having a diverse set of freelance writers allows thriving magazines and blogs to bring to the table differing opinions and writing styles. So be yourself with your writing approach.

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  2. Make Connections

    Start networking with other writers and bloggers on-island to get your name out there. The freelance business in the Cayman Islands is still fairly small and most writers are willing to recommend others who may be interested in work. Start attending writing-specific events, like the monthly Cay Writers meeting at Books & Books, so you can meet and mingle with other freelance writers. Use social media as a tool to help you; join writing groups on Facebook and LinkedIn to stay abreast of upcoming events and potential assignments. Sometimes, editors will use these groups as a way to reach out to writers.

  3. Write About What Excites You

    In my early days of freelancing I was a Yes [wo]Man – I accepted every assignment that came my way. I’ve gotten better over the years at saying no to assignments that don’t excite me or I feel there’s an imbalance between my time and compensation. If you’re freelancing as a primary source of income, you may not have this flexibility but, if you can, learn to hold yourself and your craft at a high standard. It benefits no one if your writing is mediocre because you just weren’t interested in the topic and you should carefully weigh the research and writing time involved against the demands of your personal life.

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  4. Do your Research

    Once you’ve figured out what you’d like to write about, you can narrow down which publications are going to best suit your interests and writing style. Pick up copies of the magazines you’re interested in writing for and familiarise yourself with the types of articles they publish. Read the masthead – the list of editorial team and writers’ names found in the first few pages of a magazine. You may also find that an editor oversees more than one publication on your radar, which potentially allows you access to several opportunities.

  5. Have Examples of your Work

    If you’ve contributed to blogs or magazines in the past, keep copies of your work on file so you can share them with editors. Most local magazines have PDF versions online that can be downloaded and shared electronically or printed on quality paper.

  6. Start a Personal Blog

    In order to be a good writer, you have to keep writing. I highly recommend starting a personal blog, especially if you do not have any previous freelance experience. It’s a great way to showcase your writing style. There are several easy-to-use and free blog platforms out there, like WordPress, Weebly and Blogger. Your blog is a reflection of who you are as a writer, so choose and personalise a template carefully and thoroughly consider your content.

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  7. Pitch your Story

    Do you have a story idea for a local magazine? Share it. Editors are constantly seeking new ideas for content so send an email with a summary of your pitch. They just may love your idea! I once sent 33 pitches to a local magazine I’d never written for and received three assignments from that email.

  8. Cultivate your Skill

    Actively seek out ways you can grow your freelance career and your skills. There are tons of free or inexpensive webinars and podcasts online. Join a writing challenge group, like the annual NaNoWriMo which occurs every November, or attend locally held writing workshops hosted by Cay Writers. Consider stepping out of your comfort zone every so often with a writing prompt that pushes your creative boundaries.

  9. Think Outside of the Box

    While most freelance writers in the Cayman Islands tend to write for local magazines it’s not the only option available to you. Consider offering your services to a small, start-up business that may need copywriting for an advertisement or flyer or social media content.

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Published: CayWriters blog, May 2016

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