How to Start Freelance Writing, Part 1: My Story

that Slide1

Many people dream of a freelance life.

It’s a seductive dream. Imagine you’re sitting on a lounge chair on the beach, typing away on your computer while a tropical breeze wafts by. Beside you on a small wood table sits a frosted glass with a green umbrella. When you sip, it tastes like pineapple and possibilities. Your loved one is surfing or chilling on the beach. You remember the turtles that nipped your toes in the water when you snorkeled yesterday; you plan on diving deeper later.

My Freelance Writing Dream

My Freelance Writing Dream © Darlene Reilley 2017

It’s tempting.

The myth of the freelance life is a nomadic life, traveling on a whim, writing whatever tickles your fancy for clients that magically appear.

I hope you enjoyed the moment in the sun. I’m in the Pacific Northwest and it’s grey and rainy outside – according to one weatherperson, we haven’t had a day of sunshine since November.


Me at my Goddard Graduation in Port Townsend, 2017

While some freelancers do live the myth, my experience is different. I’m going to share my story with you, and then tell you how I started.

I’m Darlene. I’ve been a freelance writer off and on since 2009 while going to school full-time and caregiving. Don’t get me wrong…there are moments when the clients are calling, the money is flowing, and you’re swimming in words. I live for those moments. There’s nothing like the rush of a deadline – I thrive on them.

But there are other moments…the darker moments when the email box is empty besides sending out dozens of pitches…when I wonder where my next paycheck is coming from…and I worry about where my dog’s next bowl of food will come from. In those moments, I just want to play video games – usually Assassin’s Creed or Uncharted. I find treasures and battle enemies to release tension. If you haven’t tried it, you should – it’s a great stress relief. Usually while playing, my mind drifts and I think about going to back to a dead-end cubicle job where I was okay…at least the paycheck was steady. When you’re a freelancer, you often dream about steady schedules and set days off.

I’m not one to knock a steady paycheck. I’ve had all kinds of jobs while I was searching for what made me happy. Here’s my work list:

babysitter, salad girl, video store clerk, assistant sous chef, ice cream server, production associate, video store clerk, entertainment consultant, retention specialist, coaching consultant, house painter/handywoman, wreath maker, customer service representative, house sitter, cookie maker, pet sitter, cleaning houses, taxi dispatcher, secretary, au pair, dispatcher, starter, barista, receptionist, tax preparer, tutor, peer mentor, server, note taker, driver, library technician aide, teacher, freelance writer, author.

A few things to note before you think I’m a vagabond who goes from place to place dropping jobs like flies: I started working as a babysitter when I was eleven. Back in the 90s, it was normal to work between homework and sports. I never had time off to get into trouble and frequently participated in school, basketball, drama, and work. My strong work ethic comes from my mom, who as a single mother, often worked three jobs just to keep a roof overhead. As far as I remember, I always had a job and never shied away from hard work. I often worked more than one job at a time. At one point, I remember working two full-time and two part-time jobs at the same time for years…that was back in my 20s.

I can hear my writer friends in my mind: Darlene, this is good information, but why is it important for me to know this? Can you say TMI?

Sorry if I’m oversharing. I need to lay it out there to be honest – it’s hard to make a living writing. We can’t all be Stephen King or Nora Roberts…not yet, at least. My goal is to write 100 books in my life…and hopefully make people as happy with my work as others are with King’s and Roberts’ creations. But the reality is not all of us are going to be as popular as they are. But we can hope…plan…and try.

I’ve written all my life. I always had a pen in hand and notebook to scribble in. I’m sure you can relate to that (and a few of the jobs above).

Then, in 2009, while working on the drive-thru window at Starbucks, I had a moment of clarity: this was the one life I had and did I want to spend it going from dead-end to dead-end, or did I want to do the one thing in my gut I knew was mine – the thing that I thought about when I first woke…and the last thing I thought about when I fell asleep?

I want to leave a legacy. I wanted to make a difference in the world.

I worked there for five years. I liked the job and loved the perks—not many companies can beat free coffee and beverages. I love Starbucks. But at the time, I needed to dive full-time into this life I wanted to lead. I needed to challenge myself in a way I hadn’t before. So I quit and went back to school full-time in 2010. I tucked my head down, studied hard, worked side jobs, wrote, and learned my craft.

I am not a perfect writer. No one is. As a freelancer and as an author, I’ve made mistakes – sometimes whoppers. Quitting a job I loved cold turkey without a backup plan wasn’t the best way to transition. But every time I make a mistake, I think about what I did, how I did it, and I adapt. I am persistent.

Later that year, I realized I needed to make money. All my life I read craft books on how to write, why to write, and reveled in the delicious words of books. For me, as well as many advisors and peers, reading and writing go hand in hand. It’s how I realized I could make a bit of money by freelancing.

I jumped into freelance writing without a plan. It was a gut impulse I followed and haven’t ever regretted. I started off blogging for myself – teaching other writers what I knew and was learning. Problem was, that didn’t earn money, that was for fun. So I borrowed the two books the library had on freelance writing, bought a book on craft, and started sending out pitches.

The first ones were horrible. I didn’t hear from anyone at first. But I was a new and stubborn. If others could do it, I could too. I adapted. I searched online for pitches that sold. I worked through many websites before finding one that I thought I could adapt – and I mirrored my pitch letter after that one. It worked. I got my first freelance client from a Craigslist ad and made my first $20. I repeated the same pitch several times with success. Then I learned how to craft my own pitches and made more money.

Looking back, I wouldn’t recommend jumping in or quitting your job without a plan (please don’t), market research, and a platform. I tried many different types of freelance writing before I hit on ones that worked for me. What works for me may not work for you, but if you do your own work and are persistent, I bet you can achieve your writing dreams too. I’m not going to say it’s easy – this is a hard job without guarantees – but it’s possible.

I would recommend starting to think about the types of freelance writing. I’ve created a graphic to show you the different types of freelance writing. Check out the ones that sound interesting to you and make a list. Do your research – search for the type of craft online – see samples others have done and check out a few freelance writer websites.


Types of Freelance Writers, © Darlene Reilley 2017


Next week, I’ll discuss making a plan for starting freelance writing and share links I’ve found useful.

These were the books that helped me the most when I started freelancing:

The Writer’s Market Companion by Joe Feirtag, Mary Carmen Cupito and the Editors of Writer’s Market

Start Your Own Freelance Writing Business and More by George Sheldon

The Well-Fed Writer by Peter Bowerman




About Darlene Reilley

I'm Darlene, a Book Author, Associate Editor and Journalist. I am the author of 16 books including Gliese 667, Life, Liberty and the Pursuit of It, and 1,001 Plots to Get You Started. I'm an Associate Editor and Journalist with more than three years of experience creating content. My work has been published in The Vernal Express, The Uintah Basin Standard, The Basin Nickel Ads, the Harbor Light Newspaper, FFPRWA, Hearts Through History RWA, and DarWrites. Before I became a journalist, I was a freelancer creating content for websites and individuals. I now cover a variety of topics including travel, history, anthropology, business, politics, and current affairs. I am a geek turning jargon into plain speech.
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16 Responses to How to Start Freelance Writing, Part 1: My Story

  1. Pingback: How to Start Freelance Writing, Part 1: My Story | Dar Writes | Arrowhead Freelance and Publishing

  2. Rachel says:

    Thank you for sharing your experiences. I’m currently trying to get my foot into the freelance writing world.

  3. Jason Tremere says:

    Really enjoyed this, over the last week I’ve had a career transition forced upon me after 23 years with the same employer. Planning to focus on writing non-fiction books, helping others and leaving a legacy.

    • I’m sorry. Sounds like you’re having a hard time. The good news is that period of your life is now over and you can focus on what is next for you – my sister tells me that things happen for a reason. We don’t always know why, but it will all work out. You’ll see. Keep in contact! I’d love to hear about your journey.

      • Jason Tremere says:

        Thanks Darlene, according to my wife I’m handling things extremely well. The day after she said I was the most relaxed she’d seen me in awhile. I truly believe things will work out. It’s only been a week but my career coach wants my help getting a book published, my lawyer wants my help on his website and I am helping create an acts of kindness book based on the personal contacts I’ve made after blogging this local story:

      • Sometimes the universe conspires to help us. Becca’s story is heartbreaking and inspirational. Thanks for sharing.

  4. Pingback: How to Start Freelance Writing Part 3: The Website | Dar Writes

  5. Pingback: Setting Writing Goals: April 2017 | Dar Writes

  6. Pingback: How I Made My First $1,000 as a Writer | Dar Writes

  7. GeorgieMoon says:

    I’m glad I found your blog! I have dabbled in freelance writing and had several articles published in UK sailing magazines (I live on a yacht and sail round the greek islands for six months every summer). I would like to write more general articles for other magazines but not sure how to start. Your blog has been interesting to read and I’ve picked up some useful info. Good luck on your ambition to write all those books!

  8. Pingback: 2020 Writer Helpers | Dar Writes

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