There was an article making the rounds a few weeks ago about how Positano was “the most unpleasant place” the author (Rebecca Jennings) had ever been. If you haven’t read it, I’d really encourage you to do so. It’s short and the observations are astute, even if I don’t agree with all of them.

Something in this article hit me on an existential level and I’ve been trying to unpack it for the past several weeks.

I traveled extensively in my 20s and early 30s by gaming credit card points. Frankly, I had enough points to go anywhere and do anything. Time was my rate-limiting factor. It was exhilarating and exhausting.

Looking back, travel was a game to be won rather than anything meaningful. Destinations were chosen based on award availability and efficiency. Why visit three countries when logistically I could visit four? I told myself that I wanted to go everywhere and see everything, so letting award availability dictate my itinerary allowed me to have more points for more trips. Adding a day trip to a nearby country was one more I could check off on my list. More More More

This isn’t a mea culpa. I’m not sure I’d change any of it if I could. But as I’ve started to plan travel for a family rather than for a single guy, I’m realizing the missed opportunities. I’ve got pictures of myself in almost every place you’re “supposed” to go, but my memories are far fewer.

The positive spin is that it was all just a tasting menu— a way to try many places before coming back later for a bigger serving. But “I’ve visited 60 countries” sounds much more impressive than “I’ve visited 30 countries twice”.

Which brings me back to Jennings’ article. She ends with:

Everything about the way the industry works now — booking websites, credit cards, Chase points, Instagram — makes us believe that actually, we can afford to visit a place like Positano, and that it will look just as glorious as the photos taken from the most expensive resorts. Being adjacent to luxury, though, is not the same thing as experiencing it. In fact, it can make us feel bereft of something we never had in the first place, but somehow felt like we deserved.

Booking websites, credit cards, Chase points can allow you to afford to physically locate yourself in a place like Positano. Or Bhutan. Or the Maldives. But making these trips more than Instagram likes and desktop wallpapers requires more than a travel hack: it demands time, patience, and trial and error. Or a ton of money. Preferably all four.

We all want unique and special without the work it takes to make things different and notable. But the very definition of unique and special makes them uncommon. So if we’re going to attain the type of trip that Jennings—and frankly all of us— are looking for, it’s going to require a reframing of expectations, a changing of mindset. Less pilgrimage and more meandering. There should always be room to visit the Eiffel Towers and Big Bens of the world, but spare some time to find your own memories, as well.