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Choosing travel insurance as a remote worker isn't just about finding the cheapest monthly premium

Nobody plans to be the person who skips travel insurance

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Most people understand, on some level, that travel insurance is more important abroad than at home. What they often don't understand is why — and why the policies themselves are structured so differently

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

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Pre-existing conditions are one of the most misunderstood aspects of travel insurance. They're also one of the most consequential

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I used to be the person who skipped travel insurance. Every time I booked a flight, I'd see that little checkbox — add travel protection for $45 — and dismiss it without a second thought. I'd been traveling for years

There's a specific kind of stress that comes with crossing a border and suddenly wondering: am I actually covered right now? For nomads moving between countries on irregular schedules, insurance coverage can feel like a patchwork quilt —