The other day I met an American gentleman about my age. Before long we were doing what travellers so often do—comparing notes about airlines, hotels, favourite destinations, and the little routines we’ve developed after decades on the road.
Then he said something that genuinely surprised me. When he travels, he pays for almost everything with cash.
At first I thought I’d misunderstood him. Surely he meant markets, taxis, or the occasional café that doesn’t accept cards. No. Before every trip he obtains enough local currency for the entire journey and simply pays cash almost everywhere. Restaurants, transportation, museums, shopping. . . it was just the way he travelled. His credit card stayed in his wallet unless he absolutely needed it.
Naturally, I asked if he collected airline miles or hotel points. He smiled and said he never had. That answer intrigued me even more than the cash.
This wasn’t someone trying to stretch every dollar. He had been a successful businessman, travelled regularly, and clearly wasn’t making decisions because he couldn’t afford the alternatives. He simply wasn’t interested in optimizing everything. No points strategy. No comparing credit cards. No wondering whether one airline program was better than another.
It made me realize how much my own travel habits have changed.
These days I enjoy the puzzle of it all. Before I book a hotel or a flight, I’m comparing whether I should use points, cash, a travel credit, or some combination of the three. AI has become another tool in that process, helping me sort through choices that would have taken hours only a few years ago.
I also caught myself wondering how many decisions I make today simply because the technology exists. Twenty years ago, I wasn’t comparing loyalty programs, checking exchange rates in real time, or asking AI whether I should pay with points or cash. I couldn’t. Somewhere along the way, what began as useful tools quietly became part of the travel experience itself. There’s nothing wrong with that. I genuinely enjoy it, but meeting someone who had chosen a much simpler path made me realize that not every improvement has to become a habit.
Neither of us was wrong. We were simply spending our mental energy on different things. His approach was beautifully straightforward. Mine has gradually become more analytical, not because I have to save every dollar, but because I genuinely enjoy figuring out the best way to pay for a trip.
As I walked away, I realized our conversation had very little to do with cash. It was really about philosophy.
Some travellers enjoy researching every detail. Others would rather spend that same time planning where they’ll have dinner. Some carefully maximize points. Others happily ignore them. Some travel with a detailed spreadsheet, while others book the first hotel that feels right.
Over time, I have become less convinced that there’s a single right way to do it. Travel has a remarkable way of reminding us that our own habits aren’t universal. Every so often, someone comes along who approaches the world completely differently, and instead of wondering why they’re doing it wrong, perhaps it’s worth asking what they’ve figured out that we haven’t.
The older I get, the more I realize that travel isn’t just about discovering new places. It’s also about discovering that perfectly intelligent people solve the same problems in completely different ways. Whether it’s paying with cash, collecting points, packing light, booking every hotel months in advance, or simply showing up and seeing what happens, there are countless ways to have a wonderful trip. Every conversation with another traveller reminds me that I haven’t found the right way to travel. I’ve simply found the way that works for me—at least until the next interesting person comes along and makes me question it.
So now I’m curious....
When you travel, do you enjoy optimizing every part of the experience, or do you prefer to keep it simple and just get on with the adventure?
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