I used to pack shoes by outfit.
Now I pack around priorities — and the quiet hope that my mobile internet will hold.
Packing for a workation is not about clothes. It’s about identity management.
You’re not just deciding how many T-shirts to bring — you’re deciding who you plan to be.
Because the moment you combine “work” and “vacation,” you also combine selves.
One self is structured, spreadsheet fluent, and fond of ergonomic chairs.
The other one believes mornings are for coconut milk matcha, sea air, and staring at tiled rooftops.
They don’t always get along.
The working self wants strong signal, predictable hours, and maybe a power outlet that isn’t doing its best impression of a fire hazard.
The vacation self wants to wander, eat questionable street food, and pretend deadlines are a myth invented by management.
So when I pack, it’s not “laptop or no laptop.” It’s which self will win today?
The Mental Packing List
No one warns you that the heaviest item you’ll carry isn’t your gear — it’s your expectations.
Remote work promises freedom, but freedom comes with choices, and choices come with guilt.
If you’re working, you feel bad for not exploring.
If you’re exploring, you feel bad for not working.
It’s a suitcase of contradictions.
Then there’s the performative side: that inner voice that whispers, “If you’re not posting a photo of your workspace with a view, did you even work remotely?”
Meanwhile, you’re crouched next to an outlet in the hallway because your charger cable is 10 cm too short.
I sometimes think workations should come with disclaimers:
“Results may vary. Side effects include existential confusion, inconsistent tan lines, and long internal debates about whether ‘living the dream’ should feel this stressful.”
The Two Worlds Problem
Work-life balance sounds noble until you realize both sides have customs officers.
Work demands deliverables. Life demands experiences. Both stamp your passport and charge you emotional baggage fees.
The working world tells you to optimize.
The living world tells you to romanticize.
And somehow, you’re supposed to do both — ideally before checkout time.
I’ve learned to pack less — not because I’ve become minimalist, but because I’ve made peace with the fact that you can’t bring everything.
Some days, productivity makes it into the bag. Other days, presence does.
And when I inevitably forget something — a cable, a shirt, a sense of balance — I remind myself that travel isn’t about perfection. It’s about improvisation.
What Always Makes the Cut
Three things always earn their space:
- My laptop, because pretending to be “off-grid” doesn’t pay the bills.
- My phone with mobile data, because I trust my own signal more than any “free Wi-Fi” that comes with malware and regret.
- My sense of humor, because without it, remote work would feel suspiciously like regular work, just with better scenery.
I’ll never truly travel light.
The mental load weighs more than any gadget.
But I’ve learned to carry it differently — like a seasoned traveler who knows the weight will always be there, but chooses what’s worth the lift.
At least my laptop and my hopes both still fit under 7 kg.
💬 Curious — what’s the one thing you can’t travel (or think) without? Drop it in the comments. Bonus points if it’s not an adapter.
💻 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 