Home / Digital Nomad Lifestyle / How I Built a Successful Freelance Writing Business So I Could Work from Anywhere and Travel the World
Doing cartwheels on the Salar de Uyuni, Bolivia

How I Built a Successful Freelance Writing Business So I Could Work from Anywhere and Travel the World

I’m a freelance digital nomad travel writer and I love my job and my lifestyle.

You’ll typically find me hunched over my laptop in hammocks, hostel kitchens and coffee shops from Buenos Aires to Bangkok to New Orleans – furiously typing stories about all of the amazing things I have experienced around the world. I have the freedom to work from anywhere in the world and take on many exciting projects that interest me at once. Over the last few years Lee and I have travelled to over 30 countries across North America, Europe, Asia and South America (check out the photos!).

But how in the world did I get this job? It’s not like I applied to a job listing – my job didn’t exist so I had to create it from scratch. I started up my freelance writing career while working 45 hours per week at my “day job”. “How do I become a freelance writer?” is one of the most common questions that people ask me, so read on to hear the story:

It Started When I Was a Broke Backpacker in New Zealand

In 2009 I was 23 years old and on my very first big adventure – a working holiday to New Zealand. This trip changed my life in many ways – it made me more confident, I met my amazing boyfriend and my lust for travel was made even fiercer rather than being satiated. I will remember my six months in New Zealand forever – it was a time of self-discovery that built my confidence and taught me so much.

White Water Rafting in New Zealand - What an awesome adventure!
White Water Rafting in New Zealand – What an awesome adventure!

But of course that trip wasn’t without its mistakes. By the end of the journey I had spent more time enjoying the Holiday part of the visa rather than the Working part. Oops, I was almost out of money!

Lee and I were living in a cheap apartment with a few other young travellers and students in the city of Christchurch, New Zealand. The rent was coming due at the end of the week and the chunk of savings that I had gathered in Canada before I left was slowly dwindling down to zero. I was on a steady diet of spaghetti-in-a-can, ramen noodles and anything from the discount shelf at the supermarket.

I tried desperately to find a job in Christchurch, even offering my time on TradeMe, the local online classifieds, for odd jobs or babysitting. I even tried working as a fundraiser for Greenpeace, but I couldn’t stand more than two weeks of it – I am not cut out for approaching random people and convincing them to donate money to save the polar bears.

It was during this time when I was broke and desperate in New Zealand when I first started to play with the idea of writing online.

My mom had sent me an email about a website she had seen which was looking for writers to provide content. Although I didn’t end up working for that particular website, the seed of an idea had been planted in my mind; that I could actually make money by using my writing skills on the internet.

What I Learned:

I discovered that there is actually a big demand out there for writers, so if you have a talent for putting words together and you are willing to work hard there are a lot of opportunities available. There are thousands of businesses out there that need web copy, blogs, brochures and other content – I just had to figure out how to build up my reputation online as a writer. 

How I Got Started As a Freelance Writer – The First Tiny Gigs

Working on one of my first writing gigs in our cheap apartment in Christchurch, New Zealand.
Working on one of my first writing gigs in our cheap apartment in Christchurch, New Zealand.

I created a profile on ODesk.com, a website that connects freelancers and the people who are looking to hire them. My portfolio was very empty when I started out, but I wrote confident and persuasive cover letters for any writing job I thought I was even remotely qualified for.

The first job I got was writing ten 200 word blog posts for a website about Nudism (a little unusual, but I was happy to take any writing gig!). At first, the blog owner was hesitant to hire me because I had no experience, but he decided to take a chance on me because he liked the sample article I had sent. He said, “you have this ‘youth/backpacker/traveling around the world’ thing which I have found often produces out of the box thinking….which I like.”

With that, I got busy making my first $50 as a freelance writer.

What was even more valuable than the payment was the feedback that he gave after I finished the job. He gave me a five star rating and wrote this:

“Kelly is a great writer, fast efficient, creative and sticks to the brief. She researches very well and comes up with original ideas which are refreshing and vibrant. I will gladly engage Kelly again when the next opportunity comes by.”

Yes! I had been vouched for! I no longer had an empty portfolio and no track record, this positive endorsement was incredibly helpful for getting my next few writing gigs.

With all the time I spent applying for different jobs and writing these articles, I should have been more than $50 up. However, any money was better than no money at this point. I also tried to look at these hours as an investment because if I could actually pull this off and make a real income from writing I could find my way into my dream job.

Over the next few weeks I found a few more small writing jobs here and there and started building up my portfolio even more.

What I Learned:

When I started out I learned that I needed to take any writing job I could get. No job was beneath me. I wrote about carpet cleaning and dog flea medication as passionately as I would write about art or politics. I took every opportunity and the more I impressed my writing clients on each project, no matter how small, the faster I moved up the ranks and was able to write the kind of content I was interested in.

Working Full Time in England While Building a Writing Career

York
Checking out York during my time in the UK

Soon after, Lee’s time in New Zealand was up and he had to return back home to Lancashire. We were both devastated, as we felt that our travel romance had the potential to be so much more. So he said, “You can come with me if you want?” and I thought, “why the hell not?”

Within three weeks of landing in Accrington, Lee’s small hometown in Northern England, I had gotten myself a job. Strangely enough, at 23 years old this was my first full time job. I had been a high achieving middle class Canadian honour student who had studied Fine Arts at University. I had only ever worked full time for three month stints in temporary summer jobs or part time side gigs while going to school. I was about to learn what a real full time work week was actually like.

I had to borrow some cash from my parents to get from New Zealand to England, as I was pretty broke at this point… but after only a few months of living in the UK I had paid them back in full and had begun building up my savings again.

My job was at a nursery and it consisted of 45 hours per week of non-stop running around changing dirty nappies, calming down crying babies, entertaining restless toddlers, blowing runny noses and wiping up never ending spills. I enjoyed it because I loved the kids and I was glad to have money again.

In the meantime, I had picked up a Saturday job working in the shop at the Accrington Stanley football club and the little bit of writing work I had done in New Zealand was beginning to grow into the odd article here and there. I fit my writing work around my two jobs, sitting down with a cup of tea and hammering out articles on evenings and weekends.

What I Learned:

I really learned a lot about the value of a strong work ethic. It was a crazy time in my life when I worked more than I ever had before. Between my two jobs and my writing projects on the side, I sometimes worked around 50-60 hours per week. It was hard work, but I was happy because I was working toward an exciting goal. 

I Worked My Ass Off – And Things Started to Happen

Working on a big goal is like climbing a mountain, it’s hard work but the reward at the top is so worth it!

Hiking in the Lake District, England
Hiking in the Lake District, England

The more writing work I did, the more positive feedback I received. As my portfolio and feedback grew, I could apply for higher standards of jobs. I started to get a few regular clients who were impressed by my writing enough to send me ongoing work.

The amount of money I was earning in the hours that I was writing soon became more than double per hour what I was earning at the nursery. There came a point when I calculated that working at the nursery actually meant that I was potentially holding myself back from making more money, because I had less time to dedicate to my writing. The only thing stopping me from “quitting my day job” at the nursery was that it was a guaranteed income while my writing work was still somewhat irregular. I didn’t feel like I had enough consistent writing work to rely on so that I could justify leaving my steady paycheque.

This is not to say that I didn’t enjoy working at the nursery. I loved it and the wonderful moments of playing and laughing with the children were incredibly rewarding. However, it was never going to be a long term career path for me. My lust for travel and the fact that I was only on a short term Working Visa in England meant that my writing had more future potential.  I had to make the decision to commit to the writing and turn it from more than a side gig and into a serious source of income.

“Just talk to your boss,” Lee said, “Tell her about how you enjoy working at the nursery but you need to commit more time to your writing work.”

He suggested that I ask my boss to cut down my schedule to 20 hours per week. This way, it wouldn’t be an all or nothing proposition. I could make a smooth transition from nursery nurse who writes on the side to freelance writer who looks after kids in the mornings.

My boss agreed to let me go part time, which I suppose meant that I had half quit my day job. Now I needed to focus on the writing and make this decision work for my career.

I believe that if you have one source of income, such as a high paying job, your cash flow is like a river. There might be a lot of water flowing through the river, but if something happens and the river dries up you have absolutely nothing left.

However, if your income is made up of several diverse sources this is like several different creeks, streams and other tributaries flowing together. They add up to the same amount of cash flow, but they are very unlikely to all dry up at the same moment. If you have 10 streams of income and one disappears, you can still live on 90% of your income until you find something to replace it.

Therefore, the more diverse your income is the more financial stability you can have. This concept has been very important to me as a freelancer and I have always tried to have as many different clients on the go at any one time as possible. Keeping this in mind, I set up and maintained profiles on several different freelance websites including Elance.com, PeoplePerHour.com, Problogger.net and Odesk.com as well as contacting SEO writing agencies to see if they needed a writer.

What I Learned:

Building up my freelance career while still working at my “day job” was a great idea because it means that I still had a reliable source of income while I experimented with freelancing. I was able to make mistakes and learn from trial and error without taking a huge risk. I waited to switch over to full time freelancing when I was confident and had a steady income and a solid base of clients. 

Transitioning to a Digital Nomad Lifestyle

This is me waiting for a bus on the side of the road in Borneo with everything I own.
This is me waiting for a bus on the side of the road in Borneo with everything I own.

Lee made an estimate that with a safety net of savings and some budget backpacker techniques we could travel the world indefinitely if we could make a minimum of £1600 per month online. At the time, that seemed like a bit of a crazy dream although it turns out that he was right.

At the time I was already making around this amount, except 400-500 pounds of it per month was coming from my part time job at the nursery. Our next goal was to grow the freelance writing more so that it would replace the money coming from the nursery so that I could go full time.

It was March 2011 by the time I finally quit my job at the nursery. Although, back when I said I loved the job I wasn’t kidding. I agreed to carry on coming in for a few hours per week so that I could continue to see the kids and carry on some of the creative projects I had already started with them.

I had made it! I was finally a full time writer. I had dreamt about making a living as a writer for years and I had tried to figure out how to get started, but it had never made much sense to me. I had read books, taken courses and even listened to successful writers, but the steps from where I was to where they were never appeared that clearly. They were always talking about working with publishers, selling your book and other things that you need to know when you are already an established writer. I had never heard anyone talk about the grunt work of starting from the very bottom with no credibility, no portfolio and no experience.

During this year I realised that there is no set formula for making a living as a writer. The only mistake is expecting it to be something simple that happens overnight. It took me 14 months to go from my first assignment to writing full time.

You don’t have to have a lot of experience to get started as long as you can write well, you are willing to work hard and you can listen to what the client wants. It is a long and difficult process that is sometimes unfulfilling and can be tempting to give up on at points.

It’s also an ongoing learning process that never ends. Even now that I have been a full time freelance writer for three years I am still learning and improving myself. I am always discovering new ways to make my writing better or to make myself more efficient and get more done. I’m excited for what the future will bring.

About Kelly Dunning

A Canadian freelance writer with a love of art, culture, literature and adventure, Kelly loves exploring foreign lands and expressing her experiences through the power of the written word.

11 comments

  1. Great post, Kelly, and well-timed for me. I’m slowly working through my goals in life. I recently became an expat, which was one of my goals, so the next on my list is to become a full-time freelancer. That will give me the freedom I need. I’ve been looking at some jobs on one of the freelance sites. Now is the time to just go for it, as you did. 😉

  2. A truly inspiring story! I love to see fellow travelers make it doing something they are truly passionate about. Keep up the great work!

  3. Thanks for an honest and inspiring post, Kelly. I’m in the transition of becoming a fulltime freelance writer and I have a job on the side too. I absolutely agree with you that it’s better to have several incomes instead of just one so that’s what I’m working on at the moment. Your article gave me hope!

  4. Very honest post Kelly. It was the right blend of inspiring and realistic. I feel better going into the unknown.

  5. It was wonderful reading about your origin story. Very inspirational and the lessons were nicely emphasized. Thanks for sharing this

  6. Great post. Such a lovely story!

  7. hello Kelly, your story is very inspiring I also like traveling and I am a wordpress developer and their are some points which are common in my and your story.
    thanks for sharing your story

  8. Digital Nomad- Every one wants to be one but only few people make it. Kudos to you for being one of the few success stories and inspiration

  9. Hi Kelly, I have a new profile up on Upwork and found your application for a freelancer job which I would have loved to apply for. However like you a few years ago I have no freelance experience (yet) no rating (yet), no previous writing jobs (yet). I then had a look at your blog and I just had to send you a BIG thank you for explaining the process of becoming a freelance writer. Loved your article on the Digital Nomad and will definitely take your advice. Happy travels and Happy writing. !!!

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