The Trip Planning Platform Paradox

The more planned the trip, the less people tend to enjoy it. The less planned it is, the less likely they are to pay for it.

I’ve tried to crack this nut since we started Nanook in 2015. Now it seems Google, the god of data and predictive algorithms, couldn’t crack it. AirBnB gives it a shot once a year, like clockwork. Trip planning platforms don’t succeed. They never do. Because trip planning isn’t about data. It’s about serendipity, and that’s a code no algorithm can crack.

People can like a planned trip. It can be ok. Comfortable. Predictable. But the magic? The magic happens in the unexpected. It’s the stumble-upon café, the unplanned sunset hike, the local who tells you a story that changes your whole perspective.

Trips are not problems to be solved. They are moments to be lived, and those moments thrive on imperfection. Trying to plan the perfect trip is like trying to write the perfect love story before you meet your partner. It never works. You have to let the unexpected find you.

The real holy grail of travel isn’t about planning at all. It’s about creating the conditions for magic to happen, then stepping back and letting the journey unfold.

And that’s why I believe trip planner platforms will always fail to scale, because magic can’t be scripted.