Two and half years ago we were travelling and living with Grete in South-East Asia as backpackers. We had tight daily budgets, and my head was constantly working as a calculator. Without the budget, we couldn’t have stretched it to 10 months. But it meant difficult decisions every single day. Should I buy this cake? Is this attraction worth it? Can we find it somewhere cheaper?

At the same time, we met many travellers who didn’t have this problem. They worked for some company in Europe, were working as freelancers or leading businesses. Somehow they had found the opportunity to earn money location independently. I was so envious for them.

Remote work conference in Bali confirmed us that remote work was already a reality for many, and many companies had gone fully remote.

I started to wonder if there ever could be a remote job in the logistics industry…

First remote work experience

After our travels, I was happy to get accepted to a Product Manager role in Post11. Among other factors to chose Post11 were: work looks to be flexible, and there should be a lot of travelling. Later, in my reflecting article, I also doubted: “Although, I probably won’t learn many skills that could help me become “digital nomad”, “remote worker” or “entrepreneur” one day.”

Fast forward to the beginning of 2020, I had been promoted to Head of Product Management and a year full of visiting partners and conferences all over the world was planned.

And then Covid-19 arrived, first to our mother company in China and soon to Estonia. Not long after I had to pack my stuff and escape to the home office. The home office life brought new challenges, but for our surprise, productivity in the home office didn’t drop significantly. Although we were at the mandatory home office only for 9 weeks, I even had an opportunity to hire remotely a new team member to my team.

Decision and preparation

After spring lockdown, we understood with Grete that the successful remote work experience might give us a unique opportunity. What if we could return to the home office for a longer period? And then just move our “home” to somewhere else? It could give us the life we have dreamed of – we could become location independent remote workers!

Followed months of doubts, and endless discussions between our dreams, fear of Covid, and negative financial impact. Finally, we asked ourselves what would make us proud many years later. Should we play it safe or take the risk? It was good to discuss our idea with older and more experienced relatives and workmates, who all confirmed that if they could go back in time, they would travel more when they didn’t have kids yet.

After we decided to take the risk, we started delicately asking permissions from our employers. I heavyheartedly gave up my coaching jobs in Spin-programme and Keila JK. And made some small renovation in our apartment and rented it out to a friend, who was luckily looking for a place.

First destination

We were dreaming of moving to Lisbon. Probably, because we spent our first small vacation there as young love-birds, and have very warm memories in our hearts. But since Covid cases in mainland Portugal grow rapidly during autumn, we started to look for an alternative destination.

We found Madeira island, a small island 1000 km from Portugal coast. The climate is warm, Covid is under control, interesting culture, wine is cheap, and nature is breathtaking. Also, infrastructure is developed, wifi is reliable, and only 2 hours of time zone difference with Estonia. What else could we need?

Not too much time later, we were saying good-byes to friends, family, and workmates, packed our bags, and stepped on the plane first time as remote workers.

Proud moment

We have now lived in Madeira for one month and don’t regret our decision for one bit. It’s been challenging to find a balance between work and adventure-time. We are not used to working and travelling at the same time, so we keep reminding ourselves that it’s not a holiday. We are here for many months, and we need to find some routine that is more sustainable than drinking wine on Tuesday afternoon because the Sun is shining.

There’s a quote: “Fortune favors the prepared mind”.

We acknowledge that we are extremely lucky to have jobs during the pandemic. And even more lucky to have jobs that allow us to work remotely.

On the other hand, many life decisions we have made in past years were done to support the location independent lifestyle one day. We have highly valued flexibility when deciding between jobs. Neither have we taken many responsibilities, like a bigger apartment, new car, pets or any small humans.

We have been patiently preparing for this life change. And when we understood there’s an opportunity, we decided to seize it.