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There is a particular flavor of unpleasant discovery that happens to new digital nomads about three months into their first extended trip abroad

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Let's be honest about the economics. Travel insurance for a two-week vacation is easy — a $40–$80 policy covers the dates, you barely think about it

Working remotely from another country sounds like a dream — and often it is. But the moment your laptop gets stolen from a café in Lisbon or you end up in a Bangkok emergency room with food poisoning, the reality of being uninsured abroad hits fast

Most people think of travel insurance as the thing that reimburses you if your flight gets canceled or your luggage goes missing. And it does that

Most travel insurance is designed with a two-week vacation in mind. You book a trip, you buy a policy, you go, you come home. The whole industry was built around this model, and for decades, it worked fine. Then remote work happened

When a remote worker in rural Colombia fractured her spine in a motorcycle accident last year, the nearest neurosurgeon capable of performing the required surgery was 1,400 kilometers away — in Bogotá. The air ambulance to get her there cost $38,000

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Most travel insurance is designed with a two-week vacation in mind. You book a trip, you buy a policy, you go, you come home. The whole industry was built around this model, and for decades, it worked fine. Then remote work happened

When I quit my job in Toronto to work remotely and travel full-time, I had a detailed spreadsheet for everything. Monthly budget by category. Gear list with weights. Backup internet setup. List of coworking spaces in my first four cities