August 14, 2026 | Read Online​

Ask a Better Question

We were standing outside Pena Palace in Sintra, Portugal, trying to decide where to go next. Our guides, Margarida and her understudy Miguel, asked if we wanted to see the Initiation Well. An infinitely Instagrammable spiral stone staircase winding into the earth.

By that point in the trip, Wendy and I had watched people travel thousands of miles to stand in front of the exact thing they'd already seen on their scroll. And we’d been guilty of the same thing. The algorithm wasn’t just dictating what we saw on our phones, it was driving our real-life experience.

We were done with the tourist hordes holding phones aloft to capture the perfect reel. So we asked a different question. “What’s a place you enjoy that no one ever asks to see?”

Margarida thought about it. “There's the Convent of the Capuchos. It's hidden in the forest. Most people skip it.”

Sold.

We spent almost half a day there with maybe two other tourists. Eight Franciscan friars settled that spot in 1560 and built a monastery into the native rock formations, designed to refuse comfort. The cells are carved into granite boulders. The doorways are so low you have to bow to walk through them. Every surface they could reach is lined with cork stripped from the trees around them, because cork was free and plaster was not. They even fashioned cork blankets to keep warm in winter.

We learned the legend of Friar Honório. Seeking a more pious path, he withdrew from the comfortless monastery to choose an even rougher existence. He spent decades in a tiny grotto in the nearby woods and, as the story goes, lived to be 100. Lord Byron immortalized him in a poem. “Deep in yon cave Honorius long did dwell, In hope to merit Heaven by making earth a Hell.” I looked into the tiny, moss-lined cave he called home and did the math. My back wouldn’t last ten minutes curled inside, much less decades.

That afternoon almost didn't happen.

If we'd asked the common question, “What should we see next?”, we'd have gotten the common answer. Algorithms love the top of the bell curve. They don't serve up off-the-beaten-path grottos. They are designed to deliver what most people like most of the time.

That’s what dominates in your feed. It's what I get when I ask an AI what's best. Good answers. Answers that belong to everybody. But delivered in a highly personalized way that makes them feel unique.

I got into this with Simone Stolzoff, author of How to Not Know on the podcast this week. Simone spent years as an international correspondent, so he's asked a lot of strangers where to eat. He noticed that if you ask the guy at the front desk for a dinner recommendation, he sends you somewhere safe. Ask where he eats on his night off, and a completely different menu becomes possible.

Same person. Different question.

We wrote in The ONE Thing that the quality of any answer is determined by the quality of the question. Asking better questions is the ultimate life hack. Better questions don't just get better answers. It isn't just about making travel more delightful. Better questions get you answers that are actually yours instead of the crowd's.

The Initiation Well is probably beautiful. I don’t know.

I do know about Honório’s cave.

One question to ponder in your thinking time: Where am I settling for the most popular answer instead of the right one?

Make an Impact!
Jay Papasan
Author | CEO | Coach

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