Working From Italy for a Week Before Doing Absolutely Nothing for Two

Alexandra Ruffa

September 15, 2026

I turned 30 on August 5th. Four days later I got on a plane to Italy for three weeks, with zero real plan besides "work the first week, then disappear." That's very on-brand for me. I'm not a plan-it-all-out person, more of a figure-it-out-when-I-land person. Bouncing between different cousins' houses, deciding day-of where I'm working from? Chaotic in the best way.

Honestly, it might be one of the coolest work perks I've ever taken advantage of.

The heatwave here is no joke, so working 1-4pm, when it's too hot to do anything else anyway, turned out to be perfect. Ice cream became a daily non-negotiable, same as checking Slack. And hopping between English and Italian all day, with my cousins, with their kids, mid-sentence sometimes, has been one of my favorite parts.

I also can't turn the creative part of my brain off, no matter where I am. Between meetings I've been putting together a half live-scrapbook, half-drawing thing, texture hunting around whatever town I'm in that day, grabbing scraps and colors and whatever catches my eye, then sticking it all together later. Not for anything in particular. Just what happens when you give me downtime and a new place at once.

#WorkFreely in action

This is #workfreely in action. Easy to nod along to that value in a meeting. Harder, and better, to actually live it: picking my hours around the heat and my family's schedule instead of the other way around, letting the day unfold instead of scheduling it to death. Nobody needed me at a desk at 9am. I just needed the work done well, and I got to decide what that looked like, which meant turning a normal vacation into three weeks, one working and two off, and making the most of a long flight I was already taking anyway.

I turned 30 right before this trip, and it feels like the right way to kick off the decade. Work bending around my life instead of the other way around. Three weeks in Italy, one working exactly how I wanted, two off completely. Extended, chaotic, and worth it.

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