Our First Freelance Writing Gig: 11 Experts Share Their Stories

For freelance writers just starting out, sending your first pitch and landing your first freelance writing gig can be a little intimidating. Believe it or not, we’ve all been there! Even the most successful freelance writers started right where you are today.

Freelance Writing Gig

In order to inspire you to keep on keepin’ on, I asked a few experts in the freelance writing world to chime in about their very first freelance writing gig – how they got them and what they involved. Every one of these amazing people would be happy for you to reach out to them for advice. And one or two of them even have courses available to kickstart your career or take you to the next level!

Let’s see what they have to say!

Bamidele Onibalusi | Writers in Charge

Bamidele Onibalusi Writers In ChargeI got my first freelance writing gig through my blog. It was for a telecommunications website; I was actively involved in guest blogging then, and I had no idea how freelance writing worked, when I got an email from a telecommunications website that wanted to hire me to guest blog on their behalf. The pay was good (at the time), and that job kick-started my freelance writing career.

Bamidele Onibalusi is a young freelance writer from Nigeria who has been writing for a living since 2010. You can get some great advice and resources from him over at www.writersincharge.com!

Andréa Jones | Andréa Jones

Andrea Jones Social Media SimplifiedWhen I first started freelancing, I had no idea what I wanted to focus on. So in the beginning, I submitted proposals to tons of different types of jobs on Freelancer, Elance, and oDesk. My first freelance writing gig was creating a video advertisement for a school’s online writing program. It was a super fun gig and since then, I’ve incorporated video wherever I can in my business.

Andréa is a Social Media Manager & Community Builder who creates engaging and beautiful content for lifestyle brands, startups, and small businesses in the fashion, wellness, and eCommerce industries.

Carrie Smith | Careful Cents

Carrie Smith Nicholson Careful CentsI tried using traditional job boards in the beginning of my freelance career but they just weren’t for me. Instead, I reached out to the content director of an online bank I did business with. Since I didn’t have any other samples in my portfolio, I offered to become a freelance contributor for free for 90 days in exchange for a testimonial and using the articles as samples in my portfolio. The opportunity didn’t pay money but I was able to leverage these first samples and a good testimonial to land my first paying freelance writing gig with a financial startup, worth $50 for each blog post. I feel like working for free for a couple months was worth being able to secure a decent paying gig without much experience.

Carrie Smith is a financial writer, business consultant and freelance coach. After paying off $14,000 of debt she quit her accounting day job and launched carefulcents.com. In the past 5 years it’s grown into a blog and community aimed at helping freelancers overcome financial mountains and build successful client-based businesses. When she’s not writing about finance, and geeking out over numbers, she enjoys painting, sketching and making food with her chef husband. You can connect with her in real time on Twitter or Instagram: @carefulcents.

Gina Horkey | Horkey Handbook

Gina Horkey HorkeyHandbookI found my first paying freelance writing gig through a paid job board that I had just subscribed to – it was actually the owner of the service that had listed his own ad looking for a subcontractor to write WordPress theme descriptions of all things! If you know me, you’ll laugh, because I’m not the most “tech savvy,” but I was confident I could figure it out and exceed his expectations. It paid $7.50 per theme description of 150-200 words. I would click on a theme link, peruse the copy for a bit and then write up my blurb – I really had no idea what I was doing, but in hindsight it was great experience. It also helped me to break $800 in income for my first month!

Gina Horkey is a married, millennial mama to two precocious toddlers from Minnesota. Additionally, she’s a professional writer and online business marketing consultant with a decade of experience in the financial services industry. Gina enjoys helping other freelancers gear up to quit their day jobs and take their side hustles full-time via her website, Horkey HandBook.

Kayla Sloan | Shoeholic No More

Kayla Sloan Shoeaholic No MoreWhen I decided I try being a freelance writer for my side hustle, I emailed all of the bloggers I already “knew” and asked them for tips on how to get my first gig. Many of them said they’d keep me in mind if they heard of any job openings. But one blogger I emailed said she had an opening on her team, thus I landed my first job. It was only $15 per 500 word post, but it was a good way to get my foot in the door (so to speak) with a pretty popular blogger. I’ve built my business and raised my rates off of her referrals, and referrals from their referrals, ever since then. I rarely have to “pitch” anymore and I’ve never used job boards to get new gigs.

Kayla is a mid-20s single girl living in the Midwest, USA. She is focused on paying off her consumer and student loans, while simplifying her life and closet. You can join her on her journey at ShoeaholicNoMore.com or follow her on Twitter @shoeaholicnomor.


Brent Jones | Brent Jones Online

Brent-Jones-BrentJonesOnlineI won my first freelance writing gig on Elance back in 2014. At the time, I hadn’t really narrowed down the services I intended to offer just yet — so at the time, I was actively pitching clients on writing and editing jobs. The first job I won involved editing a 400+ page manuscript for a book… and I earned a meager $300 to do it. At the time, it seemed like a lot of money to me. But most importantly, it was a huge boost to my confidence. If I could win that job, I knew I could win others. Plus, I got great public feedback from that client which allowed me to more successfully apply to new jobs on Elance, now Upwork.

Brent Jones is a freelancer and blogger living in Fort Erie, Canada with his beautiful wife and two dogs. Since 2014, he has earned his full-time income as a freelance social media manager.


Ashley Gainer | Ashley Gainer

Ashley Gainer_ Freelance writerMy first freelance writing gig came from a friend. He ran a web design agency, and he hired me to write a bunch of content for one of his client sites. The gig was mostly writing product descriptions and category pages, and I think I made $20/hr, which wasn’t a terrible hourly rate for a first-timer in 2010. It was a great introduction to freelance writing, and it really drove home the significance of tapping your personal network.

Ashley Gainer is a freelance writer specializing in money and entrepreneurship. When she’s not writing for her awesome clients, she’s teaching other at-home freelancers how be successful. Sign up here to get her FREE report on the best resources for freelance writers.

Lorraine Reguly | Wording Well

Lorraine Reguly WordingWellMy first client was Greg Narayan from Dear Blogger. When I first started blogging, I wanted to learn how to be a better blogger. I began following Greg’s posts. I commented on every one I read. Eventually, we built up a relationship, even though WordPress tried to keep us apart.

After allowing me to be the first person to guest post on his site and promote my blogging ebook, Greg was impressed my knowledge, my ability to write and edit, and he hired me for three different job positions: writing, editing, and social media Tweeting.

I learned many things from Greg during the 8+ months I worked for him. When I asked for an increase in my pay rates, I got it.

When I resigned from the Social Media Manager position, Greg understood.

Although he does not blog regularly anymore, I will be forever indebted to him for the boost he gave me when I was first starting out, and will always remember him as both my worst and best client. He taught me many valuable lessons as a freelancer… and I won’t ever make the mistakes I made with Greg with my other clients… EVER!

Lorraine is a freelance writer/blogger and editor. Find her on Wording Well, where she gives away a free blogging ebook, 20 Blog Post Must-Haves. She also runs The Blind Writer, where she provides writers (and bloggers) with direction on how to move their writing forward.

Friend her on Facebook and get an inside peek into her life! Mention you found her here!

Diana Marinova | Diana Marinova

Diana Marinova Freelance WriterI landed my first freelance writing gig on oDesk (now re-branded as Upwork). It was one of the first projects I applied to. It was a miniature English-Bulgarian translation job in the SEO niche, that took me about 10 minutes to do but it got me my first $10 and a five-star review.

I think I landed that project and many others thereafter, because of my positioning. I didn’t bid to as many projects as I could. Instead I took time to complete my profile, pass some skill tests and position myself as a marketer. I was choosing my prospective clients wisely and offering them proposals they couldn’t resist – in this case, I was a native Bulgarian speaker with experience in the SEO niche, which instantly differentiated me from the other applicants.

Diana Marinova helps aspiring freelancers break free from the rat race and regain control of their time &life. Through her blog, books and coaching sessions she provides guidance and support to everyone who wants to start working at home to achieve their goals and live their dream lives. Stay in touch with her at www.DianaMarinova.com.


Yusuff Busayo | StartTiny

My first freelance writing client was referred to me by a friend. Prior to that time, I had always told people (including publishing on my blog) that I was a freelance writer.

But soon as this client requested an email copywriting service, I took it up…and have been in the email copywriting field ever since.

I earned my first five figure online with this project…and I’m now close to earning my first six figure offering THE SAME service.

The key to my getting this job and being able to pull it off was that I had a track record of daily writing habits and reading lots of email marketing strategies from leading email copywriters.

Yusuff Busayo is an Email Copywriter who shares no-watered-down strategies to help new entrepreneurs get real building businesses that truly earn…ALL VIA DAILY EMAILING. He offers 7 PDF downloads of expert interviews for FREE to newbies (and veterans) who want to build viable online businesses. Click here to get yours http://starttiny.com

Cheri_Read_Freelanc_writerI found my first freelance writing gig on the Problogger job board. I had sent out dozens of pitches and finally landed a job writing wedding photo descriptions for a photographer. The job lasted a little over a month, and paid $25 per description. I think the key to my getting hired for this job was that I had a template letter ready and replied immediately, probably making me one of the first applicants!
Cheri is a single mom and professional writer who quit her day job to work from home after only 6 months. Visit her at www.cheriread.com to find out how she did it, and how she can help you do the same!

I hope this inspired you to keep pitching and keep writing. If you have any questions about landing a gig, ask it below and we’ll do our best to help you out!

Please note: I reserve the right to delete comments that are offensive or off-topic.

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18 thoughts on “Our First Freelance Writing Gig: 11 Experts Share Their Stories

  1. Hi there Cheri!

    What a fun idea for a roundup post. 🙂

    I can reflect back on my first gig like it just happened yesterday…

    And I loved reading through the answers since I’m familiar with all but one of the contributors. (Going to go follow Kayla on Twitter right now!)

    Thanks so much for inviting me to contribute.

    One thing I hope your readers take away from this post is that sometimes successful freelance careers can blossom from rather humble beginnings. The early days are the hardest days.

    Have a great weekend,


  2. Hey Brent!

    You’re right…the early days can be rough! Not only is it a challenge to land freelance gigs, it can also be insanely nerve-wracking!

    I’m so glad you contributed. I know my readers will get some great information from this post!

    And Kayla’s awesome! You’ll be glad you did. 🙂

  3. I really enjoyed reading the variety of ways these blogging colleagues got their first writing jobs as freelancers. I find it helpful to learn from others’ experiences. Thanks for putting this together!

    • Hi!

      Thanks for taking the time to read and comment! I agree…the best way to learn is from others’ experiences…good or bad.

    • Hi Gina!

      Thanks so much for contributing! I love seeing how successful writers like you got their start. Hopefully our readers will enjoy it as well!

  4. Thank you for these inspiring tips! I have been building up my nerves and confidence to just START; this post has really encouraged me.

    • Hi Katherine!

      I’m so glad this inspired you. It DOES take a lot of courage to just start. It can be really scary, but once you do, you’ll be so glad you did!

  5. Hi. Cheri,

    I’m sorry I joined the party a bit late.

    Great compilation here. And of course, I’m glad to be featured alongside great experts; most of whom are very, very good friends of mine.

    I’m certain this here is a very good material for Newbie freelancers. If I had me ALL these hacks long ago, I’ll be even richer.

    Thanks a lot for featuring my friends…and me…on your blog.

    Wonderful week, Cheri.

    Off to share.

    • Hey Yusuff!

      Thanks so much for contributing. I think it’s great for new writers to see that everyone starts in the same place! Have a great weekend!

  6. Cheri, I was sure I left a comment here from my phone… but now that I’m on my laptop, I don’t see it.

    At any rate, thanks for including me in this round-up!

    It’s interesting to see that we have all had many different experiences… and have come a long way since we began freelancing.

    It’s important to show new freelancers that each of us is unique and no two people will follow the same path.

    • Hi Lorraine!

      I’m so glad you contributed. I agree…as a new writer, what helped me the most was seeing how other writers started out. Hope we inspired some people with our stories!

  7. Hey Cheri! Thanks so much for inviting me to participate in this roundup! There’s tons of great experiences shared here. Love it! I hope this has encouraged a few others to get out there and start freelancing! 🙂

    • Hey Andrea!

      Thank you so much for agreeing to contribute. I agree…I hope it encourages my readers to get started!

    • Hey Lawrence! Glad to “see” you here! This is an impressive group of people, and I’m honored that they took the time to contribute!