Digital Nomad Interviews: How to Work and Travel as a Freelance Developer

So, you want to travel forever and make money on the road? It is possible!

After giving you ideas on how to travel for free and how to make money while traveling now I’m talking to people who are doing just that to get their tips on how you could also make your dreams of a digital nomad lifestyle a reality!

Digital Nomad Interviews: Lewis and Jenny – Freelance Developers and Copywriters

Jenny and Lewis Smith began their digital nomad journey in 2012 after an adventurous honeymoon inspired them to quit their jobs and take their copywriting and programming skills on the road. Although they’re back in their hometown in the UK for a 6-month work contract, they’re determined to bring the digital nomad ethos into their short stint at home, and have no plans to settle down long-term just yet.

The lifestyle of a digital nomad is a dream for so many people. So can you explain briefly how you make money online?

Lewis: I’m a developer doing freelance and contract work. I also have a few iPhone apps which make us a nice bit of pocket money on the side.

Jenny: I’m a freelance copywriter and blogger. My blog, The AdventureSmith has just been a hobby so far, but I’m hoping to monetise and grow it this year.

Lewis and Jenny - a freelance developer and copy writer digital nomad couple

And what made you decide to work remotely as a freelance developer and how did you make it happen?

We went to Thailand on honeymoon in 2012 and it was a totally life changing experience for us. Rather than go for the usual luxury honeymoon, we basically ‘flashpacked’ around the country for three weeks, trekking, taking tours and exploring as much as we could. It really fired up our wanderlust and led us straight to reading the 4 Hour Work Week. Although we’ve never really used any of the advice from that book, it was just the push we needed to realise that there were others out there living, working and travelling at the same time.

Within three months of arriving home we’d handed in our notices, and three months after that were on our way back to Thailand on a 9-month round the world trip. It was a trial run – we knew almost straight away that we didn’t want to go back to our office jobs afterwards, so after just three months of backpacking we slowed right down and started working in anger.


What do you like the best about life as a freelance developer and digital nomad?

Visiting different countries and exploring somewhere completely new – culture-wise, food-wise, history-wise – never gets old. We love noticing all the little details, like how different grocery stores are, how people shop and eat, and the small cultural quirks that make each country stand out. And, without a doubt, street art and street food are the two things that keep us happy anywhere in the world. You get to meet some great people too!

But nothings perfect right? Are there any downsides?

Of course! Don’t let anyone tell you otherwise! It can be very lonely outside the popular digital nomad hubs, particularly when there’s an added language barrier. We have a pretty good system for meeting new people now though – we use (which Lewis did the vast majority of development for), and also #nomads and, all of which have helped us to connect with people from all over the world, both locals and nomads.

There’s also the niggles of long term travel – the disruption of uprooting and settling in to a new location every few months, only taking what you can carry, having transient friendships, getting burned out. And then there’s the “feast and famine” cycle of freelance work to contend with.

But it’s all worth it, of course, and great thing is that you have the freedom to deal with the downsides on your own terms.


Do you have one standout highlight from your time as digital nomads?

Lewis: I really loved New Zealand, I could go on about it all day! We house-sat for a couple while they went off to be on a reality TV show (which is a story in itself) and then we got to camper-van around the islands for 6 weeks. The scenery there is incredible and the people are so friendly. I really enjoyed having a mobile home, and it’s actually a pleasure to drive when there are such fantastic views around every corner.

Jen: I loved New Zealand too, but one of the biggest highlights for me has to be experiencing Day of the Dead in Mexico last year. It was such a full-on, sensory experience, and everything about it, from the parades, to the food, to the atmosphere, the people, the reverence – and the fact it went on for five days, not just one – really encapsulated everything that I loved about Mexico.

And what has been the greatest challenge for being a digital nomad?

A few years ago, the breaks failed on our scooter as we were travelling back down a VERY steep mountain just outside Chiang Mai. We were very lucky – no major injuries, but we left enough skin on the road to make it very painful and uncomfortable for a few days. So take our advice: Don’t just go for the cheapest rental place you can find!

What do you wish you had known before you started working remotely as a freelance developer?

Lewis: I wish I’d put more effort into building a platform early on: having a blog, or podcast or something to build connections with people. It makes finding work and meeting people so much easier. I only started my blog, ItinerantDev, last year, but it’s already grown into a weekly newsletter for nomads and opened up a whole network of contacts.


So, what are your plans and ambitions for the future?

Lewis: We had big plans to meet friends in Thailand in January and then explore Europe in Spring and Summer, but I’ve just been offered a great 6-month contract in the UK, so we’re unexpectedly back in our hometown for a while! We’re treating it like anywhere we’ve stayed as digital nomads – we’re looking at the local area with fresh eyes, researching what tours and day trips we can do, trying all the food places that have sprung up whilst we’ve been away, and trying to live an uncluttered lifestyle… which may be easier said than done!

Jenny: We don’t tend to plan too far in advance, precisely because of things like this contract – stuff that crops up out of the blue. But in terms of general plans and ambitions, we definitely want to explore more of the world – Berlin, Eastern Europe, Japan and South Korea are all high on the list – as well as creating more passive income streams and experimenting with the balance between work and travel.


Finally, and perhaps most importantly, what tips would you give for people wanting to follow in your footsteps and become freelance developers and digital nomads?

I would certainly recommend having enough savings to cover you for at least 6-12 months before you go. Be clear on how you’re going to make money as a digital nomad, and start building your business or your portfolio BEFORE you leave so that you’re ready to hit the ground running.

In terms of location, I would highly recommend Chiang Mai. It’s super cheap but very comfortable and there are entrepreneurs and digital nomads everywhere – it’s the best place to learn from people, get inspired, enjoy a different culture and get some serious work done.

If you want more advice don’t hesitate to look us up!

ItinerantDev –
Digital Nomad Weekly –
The Adventure Smith –

Thanks so much Jenny and Lewis for sharing your adventures and tips with us! Best of luck with your future travels and work! If you are working abroad and want to be featured here contact me. 

Do you Live to Travel, or Travel to Live?

  the greatest risk of all quote 

Sign up to the FREE newsletter and learn how you can make travel your lifestyle too!

Related posts

The Downside to Living in Goa


How to Travel the World and get Paid by Teaching English


How to busk your way around the world!



Lewis February 2, 2016 at 9:30 pm

Hi Anna, thanks so much for sharing this. Keep up the great work 🙂

Anna February 3, 2016 at 11:50 am

Thanks so much Lewis for getting involved and sharing your tips! Best of luck with everything 🙂

Jenny February 3, 2016 at 7:02 pm

Ah fab – thanks for sharing our story! Have fun on your travels, I hope our paths cross at some point 🙂

Anna February 5, 2016 at 7:44 am

Thanks so much Jenny! Loved hearing about your lifestyle. Happy Travels and let me know if you come to India! 🙂


Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.

This website uses cookies to improve your experience. We'll assume you're ok with this, but you can opt-out if you wish. Accept Read More

You cannot copy content of this page