How We Got Started as Digital Nomads

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It’s Travel Money Week on Never Ending Voyage to celebrate
the launch of our travel budget app Trail Wallet.

We’ve been travelling the world and working online for nearly three years now, yet three years and nine months ago we had no idea what a digital nomad even was.

How did we go from office jobs in rainy Manchester to working for ourselves by the Caribbean Sea in Mexico? We want to share our journey to show you that it is possible to escape a conventional life, if you want it enough.

Our Travel Background

I’ve always been obsessed with travel. I remember writing detailed reports on Fiji and Iceland in primary school, and devouring books like Work Your Way Around the World in my teens. Simon was less passionate about it but he was up for adventure and took me on our first snowboarding trip in the French Alps as a Christmas present when I was 18.

Our first big trip was interrailing around Europe when we were 19 during our university summer holiday. We were hooked on the freedom and excitement of a backpacking lifestyle and returned the following summer to explore more of Eastern Europe.

After university when everyone was struggling with knowing what to do with their lives I never doubted that I wanted to travel. Simon still hadn’t finished his degree though (he was taking his time) and although I was reluctant to travel without him I didn’t want to dive straight into a career. Instead I spent a month studying Italian in Florence and three months volunteering as an English teacher and working with elephants in Sri Lanka.

Erin volunteering at an elephant orphanage in Sri Lanka
Erin volunteering at an elephant orphanage in Sri Lanka

It was the best decision I could have made as without the volunteering experience I wouldn’t have landed a job doing community development work with refugee communities—perfect for someone fascinated by different cultures. A year later I moved into an even more interesting role—organising art projects and events that showcased the cultural contribution refugees make to the country, including a huge festival attended by 10,000 people.

Our RTW Trip

In 2005 Simon finally graduated with a popular music degree and that summer played at the Glastonbury Festival—one of the biggest festivals in the UK. It was an amazing experience but ultimately he decided the music industry wasn’t for him. In a sudden change of direction he ended up working at a legal aid law centre, trying to help asylum seekers with their asylum claims—a stressful but rewarding job. He also got to practice law wearing flared cords, paisley shirts and with hair down to his waist!

Us at Glastonbury Festival in 2005
Us at Glastonbury Festival in 2005. Look at that hair!
The Deadbeats band
Simon’s band The Deadbeats

In the same year we bought a house, but we didn’t see it as a tie and we began saving almost straight away for a year long trip around the world.

A big trip was something I’d always wanted to do. It took two years of saving hard before we finally left—I took a sabbatical from my job, Simon quit his, and we rented out our house.

We spent a year experiencing more than we had in all the 25 previous put together—washing elephants in Sri Lanka, drifting through the backwaters on a houseboat in India, hiking in the Himalayas, learning to scuba dive, road tripping through the Australian outback, throwing ourselves out of a plane, snowboarding in New Zealand, staying in a tree house accessed by a zipline in the Laos jungle, volunteering on the Obama campaign in New York, and countless other adventures.

Us in Hampi, India on our RTW trip
Us in Hampi, India on our RTW trip

And then it was over…

We returned to the UK in November 2008. It was dark, cold and dreary. We immediately booked a flight to Seville.

Our week in Spain was only a temporary fix and we had to face the reality of life back in England. We missed the excitement, the sun, being outside, and no two days ever being the same. We were frustrated with the monotony of routine, the tediousness of bills and car repairs, and the culture of negativity.

I returned to my job which I’d previously loved, but I struggled with the lack of freedom and being stuck inside an office for an arbitrary number of hours, regardless of what was achieved. I was doing the same job and it was no longer a challenge.

When you’ve experienced the vastness of the globe, it’s hard to go back to the same small world you inhabited before.

Getting Started as Digital Nomads

Simon didn’t rush back into the job market. Instead, he became involved in the music industry again—this time as a solo performer—recording in our home studio and doing gigs around Manchester.

Simon playing a gig
Simon playing a gig in 2009. Less hair now.

This wasn’t likely to make much money any time soon so he also worked on developing his skills as a web designer and developer. He’d been dabbling with computers and creating his own sites since he was a teenager and was entirely self taught (breaking his Dad’s computer and having to frantically fix it before Dad got home was a powerful motivator). He was so passionate about it that I encouraged him to actually get paid to do it.

We’d been back around six months, I was still dreaming of future trips and browsing travel websites when I discovered the world of digital nomads. There were a whole group of people who were travelling permanently, working online as they went. A lightbulb went off. With Simon’s web design skills there was no reason we couldn’t do that too!

Once we realised the possibilities we started working towards this goal straight away and it all came together in nine months of hard work, learning and excitement.

Saving and Planning

Simon got his first (and only) job as a web designer in a small agency to develop some experience and help towards our travel fund. He also began developing his portfolio as a freelance web designer by doing a few jobs for friends and family.

We became ultra frugal with the aim of saving as much money as possible to keep us going while we travelled and built up the business. We were experts at this after saving for our previous trip and managed to save 75% of our income which gave us a £23,000 travel fund—enough to keep us going for a year.

We knew we wanted to start in South America so I began planning our travels and learning Spanish. I researched destinations but we didn’t have a fixed itinerary—all we knew was that we’d fly to Brazil, go down to Argentina and then just keep heading north.

I looked into teaching English around the world—our backup plan in case the business couldn’t support our travels and we ran out of money. I also discovered many ways that long term travel can be affordablecouchsurfing, volunteering in exchange for accommodation and housesitting were all possibilities we considered (and did later try).

Simon with snowman
Fun activities don’t have to cost money

Learning About Running an Internet Business

Simon’s job involved some internet marketing and that’s when we first learnt about it—a useful skill for a digital nomad. At that point I didn’t know what Twitter was, I’d refused to get a Facebook account, and had no experience blogging or anything entrepreneurial. To get started I took a free 30 day crash course which aimed for you to make your first dollar online.

Travel was my passion and after following the steps in the course I set up a site called Kerala India Travel about one of our favourite places in the world. In a month, working on it after I finished my day job, I had set up the site, written lots of content, was on social media and was improving the site’s rank in Google. I didn’t make my first dollar (that came a few months later) but I was inspired to keep going and had learnt an incredible amount in a short time.

We decided to start a travel blog to document our travels and our journey to becoming fully fledged digital nomads. We chose the name Never Ending Voyage on Simon’s birthday in a pub in the Yorkshire Dales after a wintery hike, and Simon began the design while I worked on the content. We finally launched it ten days before we left the UK. We didn’t plan on monetising the site for at least a year as we wanted to focus on creating interesting and useful content and growing our audience.

Selling Our Stuff

We were fully committed to leaving the UK permanently so the other major part of our preparation was selling all of our stuff. We realised after returning from our first trip how much unnecessary stuff we had so it wasn’t a difficult decision—although some things were harder to let go of than others.

We’ve written before about the benefits of selling your stuff and the techniques we used to sell everything—it was a long and tiring process but we’ve never regretted it and love living out of a carry-on size backpack each. In fact, I still complain that we have too much stuff!

The one thing we couldn’t sell was our house. The market had crashed and house prices were so low that we didn’t want to go through the hassle of selling it just to break even on what we’d bought it for. We found friends of friends to rent it instead.

Hitting the Road

Before we left the UK on 1st March 2010 we had bought a one way ticket to Rio de Janeiro, booked a guesthouse for the first few nights, sold all of our stuff, rented out our house, saved up enough money for a year, set up a travel blog, learnt about blogging and internet marketing, and developed web design and development skills.

But there was one thing we didn’t have—a business.

Simon had the skills, we had the Line In Web Design name and portfolio site, and Simon had registered as self employed with the Inland Revenue, but it wasn’t a business. We didn’t have clients, a marketing strategy or business plan. We were going to figure all that out on the road.

The first few weeks were…strange. We were jetlagged, had to adjust to budget accommodation and the stress of travel days again, and had the bizarre realisation that “This is our life now. This isn’t a holiday, we won’t be going back.”

Simon actually dealt with the weird feeling better than me. We were supposed to start our trip with a holiday on Ilha Grande but in between beach time and hiking around the island he threw himself into his work. He had moments of wild happiness and was intoxicated by the freedom he had over his own life and the ability to work on a terrace with a view of the sea and birds singing in the jungle behind him.

Simon working in Ilha Grande, Brazil
Our first digital nomad office in Ilha Grande, Brazil

I felt lost. I’d only been a travel blogger for ten days and I wasn’t quite yet at the point where I considered it a “real thing”. I wasn’t sure what I’d do with myself in this new life of infinite freedom. I don’t think it helped that we were sharing a laptop and I couldn’t work at the same time as Simon (what were we thinking?!).

Every major life change takes adjustment and it didn’t take us long to get into the swing of things. We embraced the neverendingness of our voyage, I began to write and take photos, and we immersed ourselves in exploring the world.

The First Few Months

After a few weeks travelling in Brazil we settled in Buenos Aires for two months, renting an apartment and taking Spanish and tango lessons. Simon got his first client—his previous employer hired him back as a freelancer for a major project.

It was his first proper client job and we learnt a lot from it—about the importance of contracts, the art of accurate quoting, and balancing work with travel. For more about the ups and downs of our first few months see The Life of A Digital Nomad.

So that’s how we got started as digital nomads.

We had a passion for travel, an eagerness to learn about running an online business, the willpower to be frugal, and an overwhelming desire to make it happen—to live life on our terms. Nothing much more than that. If we managed it then you can too—but only if you want it enough. We’ve made many mistakes along the way and it isn’t an easy lifestyle but we’re still going three years later and there’s no other life that we want to lead.

Also see our posts about how we fund our travels including the common question of how we find clients when we’re travelling, and the practicalities of being a digital nomad—tax, insurance, vaccinations and all that other rather dull but important stuff.

On our Getting Started page there are more articles you might find useful on your journey to becoming a digital nomad.


  1. Cool story of real determination, and still going, your life style beats the traditional one of being an employee. Found your blog while searching things to do in Japan.
    Keep going!

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  2. No one has commented for almost five years?! How are people not reading this??

    Wonderful information. My partner and I started travelling out of backpacks about a month ago with plans (and money saved up) to do it for around 2 years. We are hoping to build digital nomad businesses in the process but I’m still nervous! I’ll check out your resources to make sure I’m marketing my skills properly. I also need to figure out SEO for my blog but ooph, it’s overwhelming!

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  3. Such an amazing journey <3. I found your blog when looking for a year trip in South America. I traveled in South east Asia for a year and now have to back to work (it is not easy :)) Now I am saving and learning to become a digital nomad. Your blog is so inspiring. Enjoy your great journey :)

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  4. I am so inspired by your blog (that i only found today after a quick search on Cuba). My wife and I did a similar thing, but we moved from the sunny Australia to live in the UK for under 2-years, scouring our way through different European cities. Now we are on the homeward bound stretch, leaving London in July, with 4-month trip across central/south America and Asia. I really admire your courage and strength and just “whatsapp’d” my wife saying I wish I had the cahoonas to do what you two are doing. It’s awesome to know that there are people living my dream for me :).

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  5. What an incredible story you two have had. This article has really given me and my partner hope. He is currently considering web development courses and as I continue to write for our blog, I am exploring avenues for advertising and sponsorship. Do you have any recommendations for reaching out to advertisers? I greatly look forward to devouring every one of your articles ;) Oh and our goal: To become digital nomads in a year – meaning we have a year to gather skills, save up funds and prepare to live one this life as infinite adventurers!

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    • We found that advertisers contacted us once we’d reached a big enough size. The other thing to do is find blogs of a similar size and exchange contacts with them. Good luck with it!

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  6. glad to see people out there living. I so want to escape “merica” but dont have the balls to do it.
    Be well on your journeys

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  7. very great team you are! Doing freelancing instead of getting a steady job at a big firm surely takes a lot of guts. I officially started as digital nomad a few months ago and this nomadic life experience brought out the potential in me that I didn’t know I had.

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  8. What amazing adventures you’ve had together! Erin, what was the 30 day crash course you did? I often wonder what I’d do as a digital nomad… web skills are certainly helpful for you both! :-)

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    • It was called the 30 day Challenge:

      You probably have lots of skills or knowledge that you could use for an online business. Web design is an obvious one but there are lots of other options too. Good luck if you decide to go that route!

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  9. An awesome story so far! I have been on the road (slowly) traveling for about 5 years now and am so happy with life despite the ups and downs. I’ve been doing some graphic design work and blogging to stay afloat but only just decided to start writing about travel. I’d love to make some cash doing it eventually but of course I think passion and genuine will to help others comes first. You seem to have proved both aspects can be done.

    Thanks and I look forward to reading more.

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  10. Hi guys, Can I ask a really boring question. We’ve just finished our first year of travel and getting insurances etc for the second year FROM abroad seems to be very unpopular with insurance companies and much more expensive than if you do from home. Luckily we managed to extend our previous general travel insurance in the end but finding laptop insurance hard to find. Do you still use separate laptop insurance and if so, who have you used that is reasonable/good.
    We’ve managed to find one for my other half’s mac because it’s less than 6 months old but mine being 9 months only is proving tricky. Any help much appreciated.
    Insurance business is definitely missing a trick for digital nomading!!

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  11. Great post. We’ll be venturing out on our own digital nomad experience in a bit more than a year. Looking forward to more tricks of the trade!

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  12. Nice to see Work Your Way Around the World was an influence. I doubt any of our sites would exist if, like you, as a teenager I hadn’t had my eyes opened to a whole world of possibilities by WYW. When earning a living was still a distant possibility, getting recommended in Susan Griffith’s wonderful book was my first reward for all the work put into one of our early sites.

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    • I never actually ended up working abroad (doing a job in the country) but it definitely did open my eyes to the possibilities. That’s very cool that you were recommended in the book, and a great testament to the book that it’s still around.

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  13. I really enjoyed reading your journey to becoming a digital nomad. We’re 13 months from launch, and until then, my husband and I both have full time corporate jobs. We’re working hard to try to build the digital nomad business/lifestyle before launching. It’s really tough with two full time jobs and two full time kids! I appreciate your transparency in how you felt that first week. I feel so ready, but know I will also feel pretty lost. I look forward to reading the next installments!

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    • That transition time is exhausting but exciting isn’t it? Must be even harder with kids :) Good luck with it all and keep your eye on the prize -it’ll be worth it in the end.

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  14. Fascinating lifestyle. You certainly make it sound easy. I am looking forward to reading your future posts about the more practical sides of it. I always wondered how digital nomads sort out tax for example. Always thought that if you are not living in your home country permanently you count as non domicile and then don’t have to pay tax as such. I am sure you can shed some light on this in your future posts. :-)

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    • Well basically it seems we have to pay tax somewhere and as we never stay anywhere else for long enough it’s easier for us to pay it in the UK. We could try setting up a business in Panama or somewhere but to be honest we don’t earn enough money yet to be bothered with the hassle.

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  15. I recently stumbled upon the term digital nomad and have been doing a ton of research. When I decided to freelance full time a year ago (I’m a graphic designer), I wanted the freedom to be able to travel AND work. Finding out that there is a whole community of people successfully doing that has been a gold mine. I plan to start off slowly with the goal of being a full time nomad. Thanks for this post, it’s good to see the beginnings for someone in a similar line of work.

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  16. What a great story – supremely inspiring. It gives me faith that my life will be same once I take that step soon. Hard, but ultimately wonderfully fulfilling.

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    • Good luck on your journey Marco. The first step is the biggest and once you commit to the idea it all falls in place. It’s hard work of course, but it doesn’t feel like it when you know you’re on the right path.

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