Reflections on 2000 Days as Digital Nomads

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We had so many backup plans—teaching English in Taiwan, crewing on yachts in the Caribbean, getting a working holiday visa in Australia—as when we set out in March 2010 with a one way ticket to Rio, a 10 day old travel blog, and Simon’s first and only freelance project, it all seemed so unlikely that we’d be able to create a business that would fund our travels. We had savings for a year so that was our deadline to make it work before we’d have to try something new. Despite our lack of business plan, reluctance to do marketing, and refusal to follow much of the online business advice, we somehow made it work.

2000 days later we are still going.

It’s an epic milestone and we feel blessed that we’re able to live this life.

The Good

We’re free to go where we want, when we want; to work on projects we love; to have lazy lie-ins on Tuesday mornings and trips to ancient ruins on Thursday afternoons; to book a flight to Italy because we’re craving melanzana parmigiana; to answer to nobody but ourselves.

We’re free from the constraints of an office—from arbitrary work hours, pointless meetings, office politics, and being stuck inside on sunny days.

We’re free from winter—we follow the sun and only see snow when we choose to.

We travel light so our possessions don’t weigh us down. We can pack up everything we own in 10 minutes and be on the road, off on another adventure. Our travels have taken us to 30 countries—to beaches in Brazil, Thailand and Mexico; mountains in Bolivia, Slovenia and Guatemala; and ancient ruins in Peru, Cambodia and Jordan.

We’ve learnt to sail a yacht in the turquoise seas of Malaysia, studied Spanish and tango in Buenos Aires and salsa in Cuba, discovered yoga in Thailand, and taken cooking classes everywhere from Bolivia to Japan to Turkey.

We’ve experienced so many magical moments: floating in a hot air balloon at sunrise over the otherworldly rock formations of Cappadocia; watching a volcano erupt at sunset on a Sicilian island; hiking in ancient Petra; releasing baby turtles in Mexico; washing giant elephants in Thailand. We’ve been to Disney four times!

Hot air ballooning Cappadocia
Hot air ballooning in Cappadocia, Turkey

We’ve housesat horses on a remote off the grid farm in Andalucia and cats in a quirky Kyoto house; stayed in a luxury beachfront villa on Koh Lanta and a temple in the mountains of Japan; lived in an apartment with panoramic views of the volcanoes of Lake Atitlan and in an open-sided casita overlooking the jungle in San Pancho.

We’ve eaten so much good food.

We’ve built a business—with no idea about what we were doing, no experience making money outside a paycheque, and without a business bone in our bodies. We’ve grown Never Ending Voyage into a site that’s had over 2 million visitors and inspired many to explore the world; and created Trail Wallet, an app that has helped thousands of travellers stay on budget.

We’ve had time to write, draw, read, run, cook. We’ve had time for each other—we’ve spent almost every hour together for the last 2000 days and, after 16 years together, we’re stronger and happier than ever.

Erin and Simon on the beach in Puerto Escondido, Mexico
Us on the beach in Puerto Escondido, Mexico

We’ve met amazing people. People often wonder if nomadic life is lonely but we find that not only can we visit friends and family when we want to (and spend more quality time together than we ever did living in England), but we’ve made new friends, fellow nomads who understand our lifestyle, share our interests, and inspire us with their creativity and passion. Couples like Tom and Jenny, Victoria and Steve, and Warren and Betsy, some of whom we’ve crossed paths with on four continents. Most of the time we’re happy with each other’s company but we know our friends are just a plane ride away.

The Challenges

Everyone says we’re living the dream and we do feel like we’re living our dream, but it’s not everyone’s dream. This isn’t an easy lifestyle. The highs are higher but the lows are lower—self-doubt, travel burnout, work burnout, and money worries have all been challenges along the way.

The Battle with Self-Doubt

The biggest challenge for us has been building a business (and we still feel calling what we do a “business” is rather laughable). We didn’t have any business experience before we left and we had to learn as we went along. When you work for yourself you have to make a constant string of decisions and we are never sure if we’ve made the right one. The self-doubt can be paralysing. It’s gotten much better over the last few years but we still occasionally feel that everything is going to collapse around us—what if the app stops selling or the blog’s traffic plummets?

It helps to realise that everyone feels like this sometimes, to focus on what is going well, and to realise how many backup plans we have before the worst could happen (and we are lucky that our worst is going back to England and getting a job!).

Mostly we realise that if we’ve made this work for 2000 days then there’s no reason it won’t continue.

Balancing Work and Travel

We have struggled to balance work and travel, especially in the early years. We either spent too much time on our laptops and didn’t get to enjoy where we were or we’d be travelling without getting any work done. We’ve discovered that slow travel is essential. Once or twice a year we spend 2-3 months in one place and that allows us time to get into routines that make our work more productive, gives us time to explore, and time to focus on health—cooking for ourselves and exercising. At these times work will be our main focus, and then we’ll hit the road and travel will take over. In “travel mode” we still prefer to spend at least a week in places, sometimes a month, and we work when we can, but it’s less likely to be on big projects that need more focus.

San Pancho, Mexico at sunset
We spent three months living in the tiny Mexican beach town of San Pancho and enjoying sunsets like this every night.

Travel Burnout

Long term travel can be exhausting. You have to make so many decisions every day—where to sleep, where to eat, what to work on, what to do for fun, where to go next. Simple tasks take so much longer as everything is unfamiliar—navigating supermarkets where nothing is in English, finding a SIM card, buying a sketchpad. The act of travel itself is tiring—why sitting on a bus saps my energy so much I don’t know, but it does.

We do get tired but we find travel burnout has a simple solution—stop moving. Slow travel is so important to keep our energy levels up— when we feel ourselves getting exhausted and appreciating places less we rent a place for a few months until we get itchy feet again.

We find planning in advance helps reduce the stress of decision making. We’ve realised that we hate turning up in a place and traipsing around looking for accommodation so we always book at least the first few nights online. It helps to have a list of restaurants to try so we don’t have to walk the streets looking for vegetarian options while getting increasingly hangry.

We conserve our energy in other ways too—by flying or choosing a luxury bus rather than spending 12 hours on a chicken bus; by renting comfortable apartments where we feel at home and can cook for ourselves; by mixing new destinations with old favourites (Chiang Mai, Koh Lanta, San Francisco, Rome) where familiarity makes things easier.

Erin working at our housesit in Umbria, Italy
Erin working at our housesit in Umbria, Italy

Finding a Purpose

I especially have struggled with my purpose. Simon has always had so many projects he wants to do—illustration, development, writing, music—that his problem has just been deciding what to do next. My passion has always been travel and after a few years on the road I felt that as that goal had been achieved shouldn’t I want something else? Shouldn’t I be pursuing a new challenge? Travel was normal now, it was our life. The blog was doing well and although I continued to write regularly it was no longer as time consuming as in the beginning. I struggled with the question of what to do next but I just didn’t know what I wanted to do.

Eventually I realised that it was OK not to know and that I don’t need a huge mission in life. I am living a life I love and I don’t need anything more. I love researching travel, visiting places and writing about them on the blog; I love taking photos and sharing them with our readers; I love having time in my day for running, yoga, and lazy afternoons reading by the pool. New challenges are important but I’ve stopped asking myself that overwhelming question, “what is my purpose in life?” and instead am trying new things, like running a half marathon or writing a book about packing light.

Sharing our Lives with the World

I’m a private person and before we started the blog I didn’t even have a Facebook account. Now we share our lives with the world—how much we spend, what we eat, where we go—and at times I feel vulnerable and exposed. Most of the time running the blog is incredibly rewarding, especially when we hear stories of others who’ve been inspired by our posts, whether it’s to eat at our favourite restaurant in Chiang Mai or to sell everything and give nomadic life a go. But people aren’t always positive and the criticism can be hard to hear—whether it’s a judgment against our travel style or a bad review of the app. We’re trying to develop thick skins but the truth is it still hurts.

Swinging in a vine at an Beng Melea temple in Cambodia
Swinging in a vine at an Angkor temple in Cambodia

What We’ve Learned

Finding Our Own Path

We’re not motivated by money. Sure, we’d like more of it, but we don’t do nearly as much as we could in pursuit of it. We used to do annual reviews and set lofty income goals for the next year that we wouldn’t come close to achieving. It made us feel bad, but it didn’t change our behaviour.

Now we’ve accepted that enjoying the work we do is more important to us than money. We make our work decisions based on how we want our life to be rather than how much money it can make us, and adjust our lifestyle accordingly.

Simon made the risky decision to stop doing freelance web design work, to say no to many clients because it wasn’t making him happy. Freelance work was a great way to get started in our early years but it felt like having lots of bosses rather than just one—we wanted a life without deadlines and to work on projects that interested us. So Simon turned down paying work, taught himself to make iOS apps, and built Trail Wallet. It was a lot of work and many months before it made any money, and for a long time it didn’t make enough to justify the amount of time he spent on it. But it was so satisfying to have created something that people found useful, and working on our own product gave us much more freedom, so he kept going, kept making it better.

We often doubted the decision and felt like the correct business decision would be to fail fast, cut our losses and try something new. But it felt right to carry on, so we did. 33 months, 25 updates, and over 1000 hours of work later and Trail Wallet has had 55,000 downloads, over 300 reviews with an average rating of 4.5 stars, and is now our main source of income. And it finally feels like passive income—Simon has barely worked on it in the last six months but sales keep growing. Giving up freelance work and continuing with Trail Wallet despite its initial low income might not have been the sensible business decision but it was the right decision for us.

We now feel more confident in following our own path. We don’t do anything we don’t enjoy just for the money. We don’t work long hours—in defiance of the workaholism culture that’s prevalent in some digital nomad circles that say that for a business to succeed you have to live and breathe it. That’s not what success looks like for us.

Breaking even after over five years might not be success to some people, and while we would like to contribute more to our savings, it’s not worth changing our lifestyle for. And it’s a good life—we stay in comfortable accommodation (I’m currently writing this with a jungle view from our pool villa in Bali), splurge on fancy meals when we want to, and generally do what we want.

Digital nomad cost of living -Lake Atitlan
Simon jumping off our dock at Lake Atitlan

Persistence is Everything

You have to keep on going. Keep on posting on the blog when it feels like no one is reading and your writing is painfully bad; keep on improving the app when you’re not even earning minimum wage and those one star reviews sting like hell; keep on writing and drawing and developing and taking photos and whatever else it is you love to do.

You have to ignore those negative voices in your head and on the internet and from those around you. You have to stop comparing yourself to others. You have decide what success means to you and not quit until you achieve it.

Accept Change

Accepting and embracing change is vital. Not only of our surroundings but in our business too. We have multiple income streams and they’ve changed dramatically over the years—from freelance web design in the early years to blog advertising to our app and affiliate income. It’s nerve wracking when a source of income dries up but we’ve always found something to take its place. We just have to keep trying new things and keep believing that it’ll all work out.

Privilege is a Thing

Although we do fundamentally believe that persistence has been the one thing that has helped us reach 2000 days, we also have to recognise that we enjoy many privileges that have made this journey easier. We come from relatively well-off backgrounds, we both have university degrees, and we are from a rich country with good diplomatic relations with the rest of the world and decent, free healthcare.

It’s no fun to be reminded that the world is indifferent to the concept of fairness, but one of the most important things we can do is to recognise the advantages we’ve been able to exploit, to remain grateful and humble for the privilege we enjoy, and to recognise and validate other people struggling with challenges we’ll never face and helping out whenever and however we can.

The Importance of Digital Detoxes

When you work online it’s too easy to become inseparable from your laptop or phone, constantly checking emails and tweets and instagrams. We believe that time offline is essential for staying sane—to have time to relax and appreciate your surroundings, and to have a break from the constant external noise of opinions and snark and outrage in order to listen to your, much quieter, inner voice.

We try to limit checking emails and social media to once or twice a day, and turn off notifications on our phone so we’re not tempted to check them when we’re out. When we’re settled down in “work mode” we have at least one day off, completely offline, a week. We have regular digital detoxes where we spend a few days or weeks offline—we always end up feeling much more positive and content.

Us in Trinidad, Cuba
Cuba was perfect for a digital detox – no internet for 2 weeks!

We Don’t Need Things

This has become so natural to us that I almost forgot to include it here, but relinquishing our dependence on possessions has been an important part of nomadic life. We sold almost everything we owned before we left the UK and we don’t miss any of it. We’ve lived out of a carry-on sized backpack each for years and we don’t need anything else.

Owning things is fun—Simon especially likes shiny new technology—but by living with less we find life is easier and we value what we do own more. We choose quality over quantity.

Do We Plan to Stop Travelling?


We don’t want to stop and we can’t imagine choosing just one place to live. After years on the road many of our digital nomad friends are choosing home bases for part of the year and, although I can understand the urge, it’s not something that we feel the need for. When we rent an apartment or house for three months that becomes home to us, but we like the flexibility to change the location each year. I’m sure over the years we’ll end up travelling even more slowly but we have no desire to give up the freedom this lifestyle gives us.

To learn more about our digital nomad journey see our posts on how we got started, how we fund our travels, our year 6 expenses, recommended resources for digital nomads, and the practicalities of nomadic life. We also recently answered your questions about our digital nomad lifestyle


  1. You are a couple. You are a minority. Vast majority of DN are single, bachelors. The older you get, the less friends you make. Loneliness becomes boring then depressive. You cannot count on one another in case anything happens (just a little sickness). Hurdles are everywhere. The laptop becomes the buddy. Then, taking a detox-day from it is like losing Wilson in Cast Away movie. Virtuality does not replace a romantic diner by the beach. Sex life is reserved to the young and cute. For the others, abstinence or paid intercourse; not than glamorous anyway.
    So, you’re lucky to do that as a couple even if I can imagine it is not rosy every day. I have seen some couples shooting at each others on a paradise spot. But loneliness is often worse, as it reminds of what you’re missing, mostly when surrounded with couples on holidays resorts. Reason why, eventually, solo DN resume to the normal, boring, 9-5 office job. To settle and build something.

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  2. We could relate to so many of your reflections! Travel burnout is real. . . but you’re right, slow travel is the solution. We just started our journey earlier this year, but are committed to continuing to travel and help other nomads do the same. Thanks for sharing your journey!

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  3. Funny, I have also had Trail Wallet for two years now, but only now found your blog. Maybe you guys need to sneak in some promo of the blog in there? I am sure a lot of people who use the app would love this blog.

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  4. I’ve been cruising around your blog this evening and really digging it. I found a post on Laos or Malaysia first, as we’re likely heading to both soon(ish). We’re traveling for the year and have run into our first bit of travel fatigue six months in, so we’ve rented a place in Kunming for the month and are laying low and recharging. Lots of your writing has really resonated with me… thanks for sharing, both the helpful information and the fun and more personal insights. And PS — I’ve owned Trail Wallet for a while! I was happy to see it’s Simon’s doing; I really like it.

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