Organising a workation might sound like a luxury or a fun team getaway. But now — three editions in — we can confidently say it is much more than that. It started as an experiment in 2023 and has since become a Moneypenny tradition that reinvents itself every year.
In this blog, I’ll take you through how our workation concept has evolved, what we’ve learned along the way and why it turns out just a little different each time.
It started in a year when our business was doing really well. Fueled by excitement and curiosity, we rented a villa in Moraira, Spain, for three weeks. Team members were free to come and go as they pleased, and even our VAs were invited. But we soon realised that such an open format, with a rotating group and people outside the core team, worked better in theory than in practice. It was fun and insightful, but also a bit chaotic.
One year later, we chose to focus: one week, just with the core team. We returned to the same location (mainly because we booked too late), even though the workspace wasn’t ideal. Once again, it was a valuable experience, but we learned that even flexibility in arrival and departure times can unintentionally lead to fragmentation. And one thing became clear: reliable wifi and decent desks are not optional.
This year, we wanted to do it better. A different location, better planning, enough bedrooms (because having people share rooms didn’t sit well with me as an employer). We chose a villa near Lisbon. And although the wifi still wasn’t perfect, we had a house where no one had to move or share rooms. Plus, we had an actual office setup in the basement with large screens.
What stood out most: every edition feels different. The group changes, the conversations shift, and you can see how the workation format evolves alongside the team. The fixed ingredients remain: living together, cooking, working out, playing games, having conversations, and building the company along the way.
We learned that a workation is not a vacation. It’s intense. You work and live together, you sleep less, and you go home exhausted. But you also return with stronger connections. New team members feel part of the whole more quickly. And it creates space for conversations that wouldn’t normally happen. You talk about work, but also about life.
We also learned this kind of time together is no longer optional for us. It has become an essential part of our company culture. Especially in a remote team. What other companies try to achieve through return-to-office policies, we find here — not through obligation, but through connection.
We really need to book earlier
The accommodation must be more suitable for working, ideally with a desk in every bedroom — and of course excellent wifi
We need to make clear agreements in advance about work time versus downtime
And maybe… we need two workations — one in summer, one in winter?
What’s certain: a workation is no longer a nice-to-have for us. It’s a core part of how we collaborate, grow and connect.
Three years ago, it was a spontaneous idea. Now, it’s a tradition we cherish and continuously improve. Every year we learn something new. Every year the concept gets a little bit better. And who knows — maybe one day it will feel as natural as Friday drinks at the office used to be.
Got a tip for an amazing accommodation somewhere sunny in Europe, with at least 10 bedrooms, plenty of bathrooms and fast wifi? Let us know!
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