Diana Kelly Levey

Why I Started Freelancing While Working Full-Time

woman drinking coffee freelance writing laptop

October 1, 2020

Last week my freelance friend Yuwanda Black invited me to write a Q&A on her blog about why I became a freelance writer and the reason I decided to create my freelance writing e-course “Get Paid to Write” on Teachable. Here, I’ll expand on one aspect of that freelance blog post.

How I Started a Freelance Side Hustle While Working Full Time

I started freelance writing to make extra money on the side while working full-time at a magazine job, particularly right after college while living in NYC. I graduated from Rutgers University with a B.A. in Journalism and Media Studies and Anthropology majors.

  1. I used writing samples I had. I had a few published writing clips (samples) I would leverage to get freelance writing jobs—and my first editorial job at WeightWatchers.com—from our Daily Targum newspaper, print magazine stories from internships South Jersey magazine and Redbook magazine.
  2. I  used my free time to work on freelance assignments. I landed my first freelance writing assignments while working full-time in an administrative sales position at the now-defunct Child magazine (Gruner & Jahr) and wrote for my college alumni magazine. I’d do interviews on work breaks, nights, and write up articles on weekends.
  3. I searched for freelance writing  jobs online. Once I started working full-time at WeightWatchers.com, I was excited to be in an editorial role, but wanted to expand my freelance writing skills and learn how to work with different brands and clients. I sought out gigs on Craiglist and through some writing e-newsletters I received. Now, I peruse a variety of websites for freelance writing jobs and use LinkedIn to find  freelance work, but I’m more likely to find clients through referrals and cold email pitches.
  4. I spent money on learning freelance skills. I also took a few in-person and online Mediabistro.com courses and paid to attend some Ed2010.com events. I stayed in touch with one of those course instructors who went on to give me assignments as a contributing freelance editor for ESPN’s RISE magazine for teen female athletes. Now that editor is an Editor-in-Chief at a major consumer sports magazine. This is just one example of why you should stay in touch with people over the years. Let previous employers, colleagues and new friends know that you’re a freelancer. (Ready to launch your freelance writing side hustle? Enroll in my freelance writing weekend course and send out your first pitch in a few hours!)
  5. I set goals for why I wanted to earn money freelance writing. I initially spent my free time freelance writing as a side hustle so I’d have extra money for vacations and all the friends’ and family weddings I attended during my 20s. But, there’s also a thrill a freelancer experiences when you secure an assignment for a story you pitched. (See article pitch examples that sold!) I didn’t consider myself a “salesperson” at that time in my freelance career but selling story ideas and helpful advice in the form of articles was something I could get behind.
  6. I created a fall-back plan for my full-time job. While freelance writing on the side was fun and earned me extra cash, I liked it gave me some financial security in the tumultuous media industry. I worried less about being laid off from an on-staff magazine job. As I moved from WeightWatchers.com to Prevention magazine, I had first-hand experience watching management changes and staff layoffs happen every few months. Eventually, I was let go, and while it was upsetting and an ego blow, I felt more confident knowing I had freelance writing skills and experiences that could provide a full-time salary. The rest, as they say, is history.
  7. I let everyone know I was a freelancer. When I lost that full-time job in 2013, I reached out to many of the editors and staffers I worked with in my nine years in the industry, letting them know I was available for writing work and editing assignments. I sent over 300 personal emails! This is an important piece of advice I share with freelance students: Exhaust your network first when you’re looking for freelance writing work. When you have a solid reputation, your former colleagues will want to work with you again. I’m still working with many of those former colleagues from WeightWatchers.com and Prevention.com and probably have about 60 percent of my assignment from referrals within networks. Also, I heard from some of those contacts months later about freelance assignments. You never know when editors will need freelancers so make sure you’re always following up on emails.

In just 10 lessons on my freelance writing course, I’ll teach you how to find freelance assignments and steady work. (Stuck in an idea rut? In this freelance blog I tell you how to find ideas.)

If  you liked this blog, check out a guest post by freelancer Jenn Sinrich on how she turned her freelance side hustle into a full-time freelance career.

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Diana can help with:

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Email Diana about opportunities: Diana(at)DianaKelly.com.

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