The grey has arrived in Belgium. The mornings are darker, the air already smells like rain, and sunshine feels like something that happens to other people. Which is probably why, when I realised the Herfstvakantie was coming, I booked flights south.
Next week, I’ll spend five days in Lisbon — my first official workation since I started this blog. Not my first ever (those who know me know I’ve worked from many places before), but the first one I’ll share here, in real time.
A familiar city, a new story
Lisbon is an old friend. I spent several weeks there years ago on a project, and later we went back for a family trip when my son — who now towers over me — was three. He doesn’t remember it. I do. The seafood, the miradouros, the yellow trams that squeal up impossible hills. More than ten years later, we’re going back.
This time, it’s just the two of us. One week, one laptop, and a teenager who promised he’d treat it like his own little workation. (He’ll read and study while I work in the mornings. We’ll see.)
I wanted sunshine and good food. He wanted a week of videogames at home. In the end, polvo à lagareiro and a promised Benfica kit did the convincing.
Half work, half wonder
I’ll work half days — mostly analysis and testing, no client calls — from the hotel room while he studies. Then we’ll close our laptops, shake off the work energy (maybe literally), and go exploring. There’s a day trip to Fátima, Nazaré, and Óbidos, a visit to Quinta da Regaleira, and maybe — if he can stay awake — a Fado night.
I know myself: I’ll probably check emails on a tram or two. He’ll probably roll his eyes. But that’s the challenge of a real workation — the balance between the pull of work and the promise of a new place.
This trip feels like both an experiment and a homecoming. A chance to test what I write about here: that workations can make space for life, not steal from it.
Stay tuned on the blog
Very soon I’ll share how we planned it — the flights, the hotel, the activities, and a few lessons from organising a mum-and-teen workation without breaking the family budget. For now, I’m just counting down the days — and the grey Belgian mornings — before we trade clouds for sunlight.
💬 Have you ever taken a workation with your kids? Or thought about it? Tell me in the comments — I’d love to know how you make it work.
💻 About the Workation Diva
I’m Caro, an early pioneer of remote work, studying IT in the ’90s when “the Internet” still made dial-up noises. I’ve been blending work and travel since before it was fashionable, from spa weekends during business trips to half-vacations at my family’s place in Buenos Aires. These days, I live the part-time laptop lifestyle — balancing motherhood, projects, and plane tickets, proving that freedom can come in Wi-Fi and family-size portions.
Workation Diva 