How I decided to jump in and work remotely from Italy

Modern technology allows us to discover the past

By Preston Ciere

We have a “mountain” where I live in Hamilton, Ontario.

And yes, it’s of the quote unquote variety. Us locals know it’s not a mountain (even before that fact is being pointed out by visitors, thank you), but its precocious 300ft height casts enough of a shadow over my city to merit its facetious title. I’ve lived my whole life next to, or on top of this mountain. I’ve never lived beside a real mountain.

This is the story of how I found myself living and working surrounded by mountains. Real mountains — no quotes. And the sea. In an ancient town founded 2,500 years before my town started calling our little escarpment a mountain. But now I do, at least temporarily.

— at Castello Della Rocca

How did I get here?

Like many people, I have spent a lifetime dreaming of travel. So much so, that sometimes it can even be a bit distracting. I’m at the laptop working away in my apartment, some history or travel doc is playing in the background.

Eventually I came to realize something: I could be doing this anywhere. I can work at the desk, or work on the couch, or even out there on the balcony. I can work at a coffee shop, or at a friend’s house, or at the cottage to extend a trip up north — anywhere, really — as long as there’s electricity and some internet.

There, right there in the TV — where those people are walking through ancient cities, with all the cool old buildings, where they speak a language I want to learn and prepare some food I want to try — I could even work there. Imagine taking a morning walk over steps in the same place that inspired the renaissance before settling down for your workday, or popping out quickly for some never before experienced street food, or relaxing after the workday to some now local wine.

If one of the reasons you’re not able to travel is that you have to work, what if your work was where you travelled?

For a while, that was all I could talk about, because it seemed so within reach. We are lucky to live with today’s technologies that while sometimes makes us feel way too connected to work and stress, on the flip side also allows us to change how, where and when we can work. I’m especially lucky when it comes to that, because my job allows me this kind of flexibility. And working for a digital company, we’ve found ourselves wanting to experiment with all kinds of digital culture. Further, the pandemic certainly has taught us all that way more people can adjust to working from home than we thought before all this started. And obviously some of us started thinking, well maybe home is wherever you lay your hat, or open your laptop.

Then one day, as I was no doubt droning on about it again, my friend, boss and walks-the-walk-er of empowering a company with a great work/life balance, said to me “I think you should do it.” Yeah, maybe some day. Funny thing about some day though, it’s always there, and you always expect it to be, so you kind of forget about it. Some day, a pandemic happens. Another some day, some health issues happen. This, that and the other all happen, unscheduled, unexpectedly, beyond your control, on some day.

So on some other day, with the ability to work remotely, and the motivation to not miss an opportunity, I sat down and figured out what was possible, planned it out, and after a whirlwind of excitement, I had plane tickets in my inbox, a delightful welcome from an Airbnb host and was showing pictures to friends of the balcony I’d be working on. That day sure was some day!

There are plenty of places where I could have gone, but I decided on Europe, so I could take a relatively long (3 month) stay and really immerse myself in a different culture. I painstakingly narrowed my search down to the Netherlands and France, where I have family connections and could definitely experience a rich culture and history different from my own. But just as I was finalizing my decision, some travel doc I had on in the background about Sicily, where they described various cultures taking over the little island over the centuries, each contributing to a unique lifestyle, history, architecture and food. I saw those arches in the palace cathedral and I had one of those rare decision-making eureka moments. Actually, that might have been after I found out they eat gelato for breakfast, I can’t remember exactly. Either way, Italy was where I was going.

— at Leaning Tower of Pisa

Staying connected and productive

But this is no vacation. I can’t imagine I’d be so lucky to just get paid to be a tourist. In order for this to work, I need to, well, work. So a few considerations needed to be made before all those travel plans were finalized: Will I have everything I need to do my work — internet, a workspace, phone. Then I needed to make sure that I am available to both colleagues and clients.

Next time, I’ll talk a bit more about how I planned a remote working experience in more detail, but there was one last detail I had to work out at home first. Actually two.

Most importantly, I needed to make sure everyone felt comfortable that there would be very little difference between Canadian Preston and Italian Preston.

For example, I set a schedule that would work for the 6 hour time difference. Perhaps Italian Preston won’t be so available late in the evening, but the trade-off is that he’s much less grumpy getting up early in the morning (because that’s his afternoon and would already be filled with a couple of espressos by then). I might not be able to attend a meeting in person, but we’re living in the times of Covid, and I can share an exotic Sicilian background in a Zoom call. Of course, we already have team members all over the globe, so it shouldn’t be that unusual.

So we talked as a team, and it turns out not only did we all figure out how best to work with me in some far-off city hours in the future, but everyone was pretty excited for me. If I’m being honest, I’m hoping I’m both the guinea pig and the trailblazer for my colleagues.

Maybe we’ll get to see the view from a ski villa on a future zoom team meeting, or some palm trees and fruity drinks at the desk, trying to stay on mute because the kids are playing in the sand outside, or just maybe an ever so subtle but purposeful wide shot from the webcam to show the rest of us how the fireplace is keeping the old brick cottage warm, you know, like it did in that movie. No biggie.

at Chiesa di Santa Caterina

Translating the travel experience into a refreshed approach

The great thing about travel is that it gives us a wider range of experiences and perspectives — both of which help in our digital industry, and the more of it the better.

The end result in exercising broadening our horizons will be seen in our work, and how we see things, how we create. Adding to that the opportunity to do what you love doing, you become recharged and motivated for whatever comes next. And obviously, we all become better from a rich work/life balance, which we here at Rain have always truly believed in because it keeps us engaged, rested, strong and full of excitement.

Add that all up, and you’ve got me here typing this under mountains, in an ancient city, a little tired from walking the stone alleyways to pick up fresh food from the market for lunch, ready to dive back into the project I’ve been working on, excited to find out what’s to come next — in this project and my travels.

Stay tuned for part 2, where I talk about how I planned a remote work experience and with the help of my team made it possible.

Alla prossima volta amici!

And yes, breakfast gelato (on brioche!) was procured.

Follow more of Preston’s dolce vita on Instagram or Facebook.


As an aside, I should mention this remote work trip was all planned and paid for during that lovely stage when Covid was in decline and all the countries were asking tourists to start travelling again, and well before Omicron hit. We all watched the situation closely, and I took every precaution and followed every procedure, including several tests, diligently wearing masks, and continuing to follow protocols while I’m away.



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Rain Digital

Rain Digital

Digital Done Properly. Rain is a boutique digital agency based in Hamilton, Ontario 🍁, with team members in Toronto, Niagara, Chicago and Timisoara.