The Algorithmic Paradox

Call me old-fashioned, but the more I travel, the less I depend on algorithms. In a world obsessed with efficiency, I find myself adding friction to my travel experience. I’ve shifted away from digital recommendations, and towards human ones.

For all the buzz about landmarks and sightseeing, I find that immersive, local experiences reveal the surprising, culturally-specific ways of living and thinking that make travel educational. We over-rate the importance of visiting the best-places and under-rate the importance of connecting with the best people. If you want to learn about a culture, nothing beats personalized time with a passionate local who can share the magic of their culture with you.

There’s one problem with this strategy: this kind of travel doesn’t scale. It’s inefficient and doesn’t conform to the 80/20 rule. It’s unpredictable and things could go wrong.

Travel — when done right — is challenging. Like all face-to-face interaction, it’s inefficient. The fact that an experience can’t be found in a guidebook is precisely what makes it so special. Sure, a little tip helps — go here, go there; eat here, eat there; stay here, stay there — but at the end of the day, the great pleasures of travel are precisely what you can’t find on Yelp.

Algorithms are great at giving you something you like, but terrible at giving you something you love. Worse, by promoting familiarity, algorithms punish culture.

Here in San Sebastián, the best pintxo bars are the dirtiest ones. They have tons of napkins on the ground. The more napkins, the better the food. Locals depend on this unspoken rule-of-thumb. A floor full of napkins signifies tasty, local food but a terrible Yelp review.

In New York, where I live, the issue is most acute with speakeasies. Traditionally, these once-secret-bars could only be discovered through word-of-mouth. They were hidden in basements and behind secret doors. On the internet, speakeasies receive prime algorithmic real-estate. They are no longer secret. With such prime visibility, they might as well be located in the middle of Times Square. Strikingly, the same traits that would have made a place obscure in the 1980s make it a popular, line-out-the-door draw in 2018.