The 5th December 2018 marked 2 years of travelling with my best friend and partner in crime James.

Our journey so far has comprised of 1 year in South East Asia, 5 months in Australia and New Zealand, 2 months in Berlin, 2 months in the UK, and 1 month in Eastern Europe. Now we’re working our way through South America, having explored Argentina, Chile, and Bolivia. At the time of writing we’re actually on a bus to Peru, trying to type while bouncing around on the terrible roads out here!

A little history

James and I are both web developers originally from the UK. We studied Computer Science at University and became friends whilst working for the UK Government. James was a graduate and I was completing a year of work experience that was part of my degree. We bonded over our love of craft beer, good food, and both had a little rebellious streak.

When my year was up I went back to university to complete my studies, and in the meantime James ditched the secure 9-5 and excellent pension to take a job at a startup data science company. When I graduated, I was lucky to land a job back at the Government with an excellent starting salary and great benefits - boy were my parents proud. Though it turned out that was short lived, as I managed precisely 51 weeks before ditching the corporate life and seeking more adventure!

We moved to Bristol together, a fantastic city we both really loved. I landed a job at a startup making dynamic ads for the sports betting industry. Joining the company meant that front-end team doubled in size - to two! I really enjoyed my time there. I was the first female developer and despite my concerns about lack of diversity and fitting in, I wasn’t treated any differently. Everyone was super friendly, inclusive, and good at their jobs. I learned quickly, and before long became an integral part of the team.

Both the startups we worked for were growing rapidly. With that growth came more bureaucracy and structure, which was great for them, and not so great for us. We had itchy feet.

We already knew we wanted to travel more. We’d fallen in love with it during a 3 week winter backpacking trip exploring Europe by train - despite freezing our butts off! All we knew is that we wanted our next trip to be somewhere warm and cheap. South East Asia was calling us!

We had no idea how much this would cost. Research dictated that we’d need anything between €1.50 and €150 a day. We plucked €18,000 as our budget as a happy compromise, which would give us €1,500 a month (€50 a day) for a year. I’m the spreadsheet lover and spending tracker out of the two of us, so naturally I documented all of our incomings and outgoings and worked out that we should easily be able to save €1,500 a month. If we hit that goal we could leave at the end of the year!

Closing down sale

Saving went well. Before we had time to change our minds, December crept up and we needed to start selling all of our belongings. We didn’t want to pay for expensive storage and most of our furniture was second hand anyway so everything would be sold or given away. We only kept a few winter clothes and sentimental items which we were able to store with family.

- My mum thought she was only keeping our junk for a year but now I’m sure she’s wondering if we’ll ever collect our stuff… thanks Mum!

We raised some extra travel cash by selling a lot of things, but we also ended up giving a lot of stuff away. It’s incredible what people think they need just because it’s free. One lady turned up in a brand new Mercedes to collect all of our kitchen crockery and pans that didn’t sell. The boxes filled her car and when we asked what she would do with them, she said they’d go in the garage with “all of the other stuff to be sorted”. We were grateful to have them off our hands, but it would have been better if they went somewhere they were needed rather than to an old hoarder!

Handing in my notice was something I was dreading. Just before the deed I found out that my team lead was also leaving to go travelling - a week before me! I felt awful for leaving them at a busy time, but thankfully I’d just hired an excellent developer to join the team and now he could be my replacement. My CEO took it really well, in fact he was more interested in where I was going to visit than the problems I was causing by leaving.

In what seemed like no time at all, the 4th December 2016 was upon us. We were homeless, unemployed, exceptionally excited, and a little scared. Everything we owned and would need for the next year was on our backs. We were ready to leave our old lives behind and catch our flight to Bangkok!

2 years ago and looking about 5 years younger!

One giant leap

From the moment we landed in Bangkok we fell in love with South East Asia. Everything about it was so completely different from anything we’d experienced before. The people, the weather, the culture, and of course the food. Two hours after the aircraft touched the tarmac we were in the heart of a loud, dirty, crazy city. We wasted no time drinking our first Chang and kicking off our love of street food with a Pad Thai cooked right before our eyes.

- Nowadays, whenever taking flights around Asia we try to stop in Bangkok to spend a few days sat on plastic chairs sharing a large Chang with ice and watching the world go by. Despite how hectic the place is we both feel incredibly calm and at home there. Maybe it’s because we started our journey there, maybe it’s the price of the beer! Whatever the reason, strange as it sounds, I leave that place feeling refreshed and relaxed, and sometimes a bit hungover.

Food and drink are two of the main reasons we travel. We love to explore countries with our taste buds. We often start each country by taking a cooking class to learn about the cuisine and what the local foods were to order and eat in the restaurants. I’ve actually written about our favourite classes we took in Laos and Cambodia. If we had to decide our all time favourite cuisine it would be a tough call but Vietnamese would win - we could both happily eat Pho noodle soup for breakfast every day for the rest of our lives!

Day 1 in Bangkok

Our first launch

In the run up to leaving we started working on a side project called ReleasePage with the intention of continuing and launching once we were by the beach. Both our startup employers in the UK expressed a need to share new releases with their customers easily and we thought we’d found the perfect solution to this.

The project was sidelined as we spent the first few months drinking too much cheap beer and recklessly eating street food that yes, did come back to bite us! After a while we started to miss coding. We both missed making things, solving problems, and worried slightly about losing all of our brain cells to one too many Changs.

So, we began working from little coffee shops and managed to finally finish ReleasePage. Shortly after, we launched on Product Hunt from a kebab shop in Phnom Penh at midnight. Perhaps a strange choice of location but they had incredible hummus and great wifi. We’re not ashamed to admit that we’d eaten there three nights in a row!

At this time we were not very active on Twitter and we had built the product without much user feedback. This turned out to be a mistake. We also didn’t know about the best time to launch or how to build up pre-launch hype, but it still went ok.

We stayed up until the early hours responding to comments, sharing on social media, and staring at the analytics - watching the “people live right now” number creep up was very exciting! We finished the day with a couple of hundred upvotes, a modest traffic spike, and a few Release Pages created, but sadly no paid subscriptions.

After the launch we continued to work on ReleasePage part time for the next 6 months and tried our hand at marketing on Reddit, Hacker News, Twitter, and Facebook. When this didn’t work I compiled a list of startup companies that might benefit from ReleasePage in a big spreadsheet (remember I like spreadsheets!) and started emailing every one of them. I spent hours crafting emails for each company that would sound personal and genuine but my efforts yielded no results.

Our final attempt at getting ReleasePage noticed was via press coverage. Noting our prior failings in marketing, we decided to pay a startup PR agency to help us. We used Promotehour who guarantee press coverage and also had a promotion reducing their price - though we still paid about €250. In hindsight this was completely crazy but we after months of work were desperate to see this product succeed.

Unfortunately, after weeks of answering questions and filling out profiles about our startup they couldn’t find anyone who wanted to cover us. The worst part was that they suggested we go for the “women in tech sells” angle and make me the subject rather than the product.

I’m a huge advocate for encouraging more women to get started in tech and having more products built by women, but I felt disappointed by them suggesting that if I shared the hardships of my journey it might sell my product. But I digress, this is perhaps a topic for another article.

Coco is always working with us!

Lessons learned

James and I are both developers, not marketers. We thought this might help as we wouldn’t be full of marketing talk, but obviously this meant we suck at selling ourselves and our products. Marketing is hard and it remains our biggest hurdle when we make products today.

We implemented far too many features and spent too long polishing unimportant aspects of ReleasePage before launching. There is a chunk of complicated logic which manages what happens if a customer downgrades their subscription when they’d be over the new plan limit - completely pointless without any paying customers! We spent 6 months building it and didn’t have any users before we launched so we lacked vital feedback and validation. This lesson was the biggest one, and is why we’re now big supporters of building in the open and the open startup movement.

Despite the failure of ReleasePage we still keep it running on a cheap server. We like using it and all of our products have Release Pages. Though if we’re being honest, then the real reason it’s still live, is that we hope the idea still might take off. It would also be heartbreaking to pull the plug on our first ever side project

Founding a company on the road

By July we were 6 months in and still loving the nomad lifestyle. We knew already that we wanted to travel for longer. To make our dreams become reality we would need to earn some money.

By pure chance we found a work opportunity in Chiang Mai, well he found us. We were working in a cafe and a guy approached us asking if we were developers and if we’d like to do some work for him in the future. We exchanged emails and promptly forgot all about it (more on this later).

If we wanted to take on freelance work we decided it would be a good idea to start an agency officially. This is when the idea for our company Squarecat was born.

- The name and logo were inspired by a big yellow square cat plushie that I won in an arcade in Japan. His name is Colin and he is very dear to us. You may even have seen him at the bottom of our websites!

The moment Colin was born

- He was too big to come travelling with us so he currently lives with James’ mum in the Isle of Man. Before we left James knew how sad I was to leave Colin and had a miniature version made. We named him Coco and he is our travel mascot. He always rides shotgun in my daypack with me.

Coco with Colin and always in our backpack on the road

To start a company while travelling was not going to be an easy task. We knew we’d need a way to start and run our company fully remotely. We no longer had a permanent address which is the first thing you need to do almost anything business related.

Estonian e-Residency Program

James had been following something called the Estonian e-residency program for a while and it seemed perfect. We wanted to keep ties to Europe and if approved, the digital identification would provide a way for us to run an Estonian company despite not living in Estonia. The identity card would allow us to digitally sign important documents - such as those required to incorporate, conduct our banking, do our taxes, and everything else we would need to do from wherever we may be in the world, assuming there is internet of course.

We also discovered LeapIN, a company partnered with the Estonian e-residency which would help us start our business and manage all of our accounting and compliance. We’d just need to upload invoices and expenses, and they would calculate our taxes on a monthly basis. They charge us nearly €100 a month but we absolutely could not live without them.

Anyone can apply to the e-residency program for the cost of €100, and pick up their ID card from any Estonian embassy in the world! Unfortunately in our case, the only nearby embassy we could collect ours from was Singapore, which happened to also be the only one that needed three months for delivery. This didn’t fit with our schedule, and the only other option on this side of the world was Canberra, Australia. I guess we’d be heading down under!

This part of the story ends here as we wouldn’t collect our cards for 5 more months. We prayed they would still be there when we finally got round to it and promptly forgot about them.

Give us your money

Squarecat Web Development became more than just an idea and shortly after launching our website we landed our first freelance gig - from the random guy we met in Thailand!

We estimated the project would take 3 months and committed to working 4 days a week - we didn’t want to shock our systems too hard! Client work presented a new set of challenges; balancing work with travel, ensuring we would have stable internet, and locating suitable work environments. We also wanted to ensure we would have time to work on our own side projects while still remembering to take care of our own health and avoiding burnout.

We started the project when we were in the Philippines. Surprisingly, the internet was pretty good. We even managed to work from a remote beach town which only had electricity for 5 hours a day using mobile data on local SIM cards!

Working from one of our favourite places - Sabang, Palawan

Most of the challenges turned out to be very easy to manage. Internet in South East Asia is very good so we were able to work anywhere there was wifi and coffee.

- We don’t usually feel the need to spend money on co-working spaces or specific working environments as we’re productive enough using cafes. We always prefer to stay in Airbnb’s so that we have a work space if required and it usually costs us less than 2 beds in a hostel.

Our travel plans didn’t change because we needed to work - our travel style was already quite slow. We felt absolutely no need to keep up with the other (much younger) backpackers who hopped around all the tourist attractions in one day! We liked to spend a week or so in each place, get a feel for the culture, and eat everywhere we could. This gave us time to still enjoy travelling, see the sights, and crack out some code.

Work smart, not hard

On work days we developed a routine of having breakfast in one cafe and working there until lunch, changing location for lunch and working until late afternoon, and then finishing a few loose ends off with a beer. The only difficulty for us was that James and I have different work schedules. He works best in the morning and loses focus by the afternoon, whereas I have trouble being productive before midday and some of my best work is done late in the evening.

I started trying to match his schedule by rising early together but it was silly. I would poke around the internet for a few hours until my brain switched on after lunch. I’d get in a few good hours but James would want to finish and go home when I was right in the productive zone. It was pointless to be sitting in a cafe trying to work when I knew I wasn’t going to get anything done, but it took a long time of this pattern before I listened to my body.

Everyone knows the motto “work smart, not hard”. Eventually I gave in and was much happier and more productive for it. My routine changed; I stayed in bed two extra hours when James got up to work, we’d share a few hours working in a cafe for lunch, and when James finished I’d continue for a few more hours in the evening.

It seems obvious now, but at the time I had this idea that we had to work at the same time and I felt guilty for staying asleep if James was working! I was beating myself up for not getting enough done, and if I hadn’t changed my mindset it definitely would have ended badly. This was affecting my physical and mental health and it’s important to remember that this can easily happen, regardless of lifestyle and location.

Travel highlights

We had an incredible year exploring so many stunning countries whilst also earning some money to continue for another year. Some of the highlights include:

I started to fall behind writing articles about our travels so the last couple of highlights don’t have an article yet, sorry. I have a lot of drafts and travel stories I want to write about. I’ll get round to finishing them all one day!

Avoiding travel fatigue

It’s important that we don’t paint a picture of non-stop travel because that’s not how we did things. Constant travel is tiring. Forever unpacking and repacking our bags, finding accommodation, booking transport, haggling prices, and fending off street traders is hard work. We travelled slowly and stayed in several places for a week or two to recover our energy. Our focus for a place was rarely the main tourist attraction and if we didn’t manage to visit everything we were happy so long as we did manage to eat everything!

When we finished motorbiking Vietnam we decided to take a little break. We loved Chiang Mai so we flew there, rented a nice apartment with a rooftop pool, and planned to stay for 3 months. This was where we did most of our work on ReleasePage. Chiang Mai has become a huge digital nomad hub in the last few years and although there’s some stigma attached to the place we loved it. However, we did stay away from the people trying to sell us courses on how to become digital nomads!

After spending 2 months zooming around the Philippines near the end of the year, we fell victim to another bout of fatigue and decided to relax and work in Hanoi for a while. We ended up staying for two months (and ate Pho almost every day). There’s also some great craft beer and western style places to eat which we took full advantage of after so long eating just chicken and rice. We finished our first freelance project but winter was coming and it started to get cold. The air quality was terrible, too, so even a sunny day looked overcast.

It was time to go back to the warmth. Next stop, Australia!

This article is the first in a three-part series. Read the next post here.

Originally published at makermag.com on January 13, 2019.