Some news stops you mid-scroll, thumb hovering, tea going cold.
Sad news reached me from the Dominican Republic — an Italian tourist lost her life in a fire that tore through a beach resort. The kind of story that quietly punctures the illusion every glossy brochure sells us: that a holiday is a place where nothing can go wrong. My heart genuinely goes out to her family.
We’ll leave the grief exactly where it belongs. But I do want to talk, gently and usefully, about the unglamorous financial scaffolding built for precisely these moments — the safety net almost all of us underestimate right up until the day we can’t.
Yes, I mean travel insurance. Stay with me. I promise to make the dullest product on earth at least mildly interesting.
Be honest — you do this too
When you book a trip, travel insurance is the box you tick at the very end, in a hurry, faintly irritated by the extra cost, silently certain you’ll never need it.
I know this because I’ve done it. Cursor hovering over “add cover,” half-asleep, thinking, do I really need this? — as though I’m far too sensible for anything to go wrong on my watch. There’s a name for that little delusion, and it’s rather flattering to none of us: optimism bias. The deep, cheerfully irrational conviction that misfortune happens to other people’s holidays. It’s the very same instinct that lets us scroll past forty pages of terms and conditions and click “agree” as if we’ve read a single word. Mostly harmless. Occasionally, spectacularly expensive.
What a proper policy actually does (it’s not the flight refund)
Here’s where most of us have it wrong. We picture travel insurance as a glorified refund for a cancelled flight — a bit of pocket money if the airline lets us down.
The serious cover is doing something far heavier. It handles emergency medical treatment abroad — which, in a fair few countries, arrives with a bill that could make your eyes water and your knees buckle. It covers emergency evacuation. And in the very grimmest scenarios, repatriation. These are costs that can climb into the tens of thousands, and no ordinary holiday budget on earth is built to swallow them.
Which brings us to the beautiful, backwards logic of the whole thing. Insurance is the one purchase you hope to waste your money on. You are, in effect, paying good money and quietly praying it turns out to be pointless. And if it does? That’s not a loss. That’s the happiest ending the policy could have.
The quietly elegant idea underneath it all
Peel back every insurance policy ever written, and you’ll find one rather lovely principle holding it up: risk pooling.
Thousands of us each pay a small, survivable amount — the sting you resent at checkout — so that the unlucky few who meet genuine catastrophe aren’t financially flattened by it. You’re not really buying a product at all. You’re buying your way into a great invisible crowd of strangers, all agreeing to catch one another if any of us falls. Rather, move when you sit with it. This is a community, dressed up as an administrative fee.
So here’s the one small thing I do now that I didn’t always bother with in my younger, breezier days: I actually read what my policy covers before I travel, not after. The fine print is staggeringly boring — right up until the single moment it becomes the most important document you own.
Travel insurance is a bet you sincerely, desperately hope to lose. Place the bet anyway.
And this time — read the slip.
The Jacqueline Brand — knowledge builds confidence, confidence builds wealth. This is editorial commentary for inspiration, not financial or professional advice. Always do your own research.
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