I’m watching the Winter Olympics.

 

Figure skating, speed skating, bobsledding, you name it.

 

I don’t usually watch Olympic sports, but this time my eyes were glued to the TV. I was yelling at the screen like I had trained for years.

 

“Next up: curling!”

 

Their stares are so intense. The sweeping. The strategy. The drama.

 

But after two straight hours of Olympic glory, it hit me.

 

I’m not watching for the love of sport.

 

I’m using the Olympics to procrastinate on writing this newsletter.

 

Touché, Subconscious Andrew. 😉


ChatGPT is a great tool. I use it all the time.

 

But it can get you in trouble if you're not careful.

 

A Spanish TikTok content creator with close to a million followers learned this the hard way. She was planning a trip to Puerto Rico with her boyfriend to see Bad Bunny in concert. Before the trip, she asked ChatGPT whether or not she needed a visa to enter the country.

 

ChatGPT told her she didn't.

 

And technically, that was correct. European citizens don't need a visa to travel to the U.S. for tourism under 90 days. But what ChatGPT left out was that she still needed ESTA approval. That's the Electronic System for Travel Authorization, and without it, you're not getting on the plane.

 

So when she showed up at the airport, she was denied boarding.

 

oh no

 

 

She posted a video in tears, walking through the terminal after being turned away. Eventually, she and her boyfriend got the ESTA sorted out and made it to Puerto Rico in time for the concert.

 

But here's the thing. 

 

We already deal with enough inconveniences when we travel. Delays, cancellations, lost bags, long lines. 

 

The last thing you need is a preventable problem caused by trusting AI without double checking.


So here's how I use AI for travel without getting burned.

 

  1. Always ask AI to cite its sources.
    If AI tells you something that could have a major impact on your trip, financially or logistically, ask it one simple question: "Where did you get that information from?" Then visit the original source yourself and verify it. For travel requirements, that means going directly to the government website for the country you're visiting.
     
  2. Understand that AI lies differently than people do.
    When a person lies to you, it's usually easy to spot. Something feels off. But when AI gets it wrong, it sounds completely confident. They call it "hallucinating." AI will give you a wrong answer with the same tone and certainty as a right one. That's what makes it tricky. You have to stay skeptical even when the answer sounds perfect.

    liar

     
  3. Use AI to skim, not to decide.
    I use AI to quickly get the lay of the land. What documents might I need. What the weather looks like. What neighborhoods to stay in. But I always do further research on my own. AI models change constantly. The algorithms get updated. So the responses you get today might be completely different from what you'd get next week. So use it as a starting point, not the final word.
     
  4. AI should complement your trip planning, not replace it.
    Think of AI as a research assistant. It can save you hours of digging. But the final decisions, especially anything involving visas, entry requirements, or money, should always go through an official source. Government websites, embassy pages, airline requirements. That's where the truth lives.

The truth is, AI is only as useful as the person using it. 

 

If you hand over all your decision making to a chatbot, you're rolling the dice. But if you use it as one tool in your toolkit and verify what matters, it can genuinely make your travel planning faster and easier.

 

Keep traveling, 

Andrew


Have you ever gotten bad advice from AI? What happened?

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