Why I Avoid the Obvious Path in Travel and in Business

Last year, I got off a train in Yamagata, Japan, not for cherry blossoms in Kyoto or sushi in Tokyo, but for a hands-on sake-brewing workshop led by a sixth-generation brewer. Most people have never heard of Yamagata. That’s exactly why I went.

I’m not alone in this. A 2026 American Express global travel survey found that 79% of millennials and Gen Z travelers now plan their trips around local workshops and hands-on activities, rather than the landmarks everyone already knows. Call it experience-first travel: choosing the unfamiliar workshop over the famous skyline, because the richer story lives there instead.

In 16 years of traveling to 33 countries and in my work as a CEO, I’ve come to believe the same instinct separates good entrepreneurs from great ones. The founders and leaders I respect most don’t chase the obvious move any more than they chase the obvious destination. They go where the attention isn’t yet — the unproven market, the underpriced opportunity, the strategy nobody has covered.

Here’s what experience-first travel has taught me about leading a company.

1. Look past the obvious opportunity

Travelers who skip Santorini for olive oil tastings in Albania often walk away with a richer story and a far lower bill, because the crowded destinations carry the highest price and the least room to stand out. Trader Joe’s founder Joe Coulombe built his business on the same instinct. Rather than competing with mainstream supermarkets on price or selection, he built his original stores around well-educated, well-traveled customers the big chains were ignoring entirely.

I’ve made some of my better moves as a CEO this way, too, by looking at a market that’s already been written off (much like a sharp traveler looks past Lisbon to Portugal’s countryside). Before chasing the market everyone else is already targeting, look for the one nobody’s bothered to study yet. That instinct cuts both ways. The same traveler who can spot a tourist trap from a mile away should feel the same suspicion toward a business deal that looks too easy.

2. Plan around value, not status

Klook’s 2026 Travel Pulse survey found that 88% of millennials and Gen Zers plan to maintain or increase travel spending this year, even as they cut back on shopping and material purchases. Their spending has gotten more deliberate. They’re tracking exchange rates and off-season pricing the way I track market timing and cost structure. They’re also choosing the trip that delivers the most value over the one that simply looks impressive.

I see the same discipline pay off in business. Status spending — the trophy market, the flashy hire, the headline acquisition — rarely outperforms a decision made on the fundamentals, and the gap between the two usually shows up in the numbers within a year or two. Before signing off on a big expense, ask whether it builds something durable or just looks good in a press release.

3. Hire local expertise over an imported playbook

A traveler hiking in Guatemala with a local Mayan guide gets a richer, more cost-effective and more useful experience than one who books an international package tour. I think about this every time I expand into a new market or hire for a role I don’t fully understand myself. The specialist who already knows the terrain outperforms the imported playbook nearly every time, whether that’s a guide in the highlands or an operator who has already built a business in a market I’m entering for the first time.

When I’m weighing whether to bring in outside expertise, I look for someone who has already made the mistakes I’m about to make, not someone repeating a generic framework. A guide who already knows where the trail washes out saves a trip; an advisor who already knows where a market stalls saves a quarter.

4. Replace guesswork with research

According to Skyscanner’s 2026 Travel Trends report, 72% of Gen Z travelers say they feel confident using AI tools to plan and research a trip in 2026, and they’re pairing that with firsthand blogs and forums rather than outdated guidebooks. That’s also the difference between leaders who adapt fast and the ones who get blindsided.

I try to apply the same standard before making a decision. Would this hold up against the most current information available, or am I working from an assumption that’s a year or two stale? Curiosity, applied consistently, functions as a business strategy as much as a travel habit, and the leaders who keep re-checking their assumptions tend to spot a shift before it costs them anything.

The famous destinations will still be there. So will the obvious moves in your industry. The real advantage tends to show up somewhere else, in the workshop nobody’s heard of, the market nobody’s covered and the hire nobody else considered. Before the next big decision, it’s worth asking whether the plan chases the landmark everyone already knows or the opportunity still off the map.

Last year, I got off a train in Yamagata, Japan, not for cherry blossoms in Kyoto or sushi in Tokyo, but for a hands-on sake-brewing workshop led by a sixth-generation brewer. Most people have never heard of Yamagata. That’s exactly why I went.

I’m not alone in this. A 2026 American Express global travel survey found that 79% of millennials and Gen Z travelers now plan their trips around local workshops and hands-on activities, rather than the landmarks everyone already knows. Call it experience-first travel: choosing the unfamiliar workshop over the famous skyline, because the richer story lives there instead.

In 16 years of traveling to 33 countries and in my work as a CEO, I’ve come to believe the same instinct separates good entrepreneurs from great ones. The founders and leaders I respect most don’t chase the obvious move any more than they chase the obvious destination. They go where the attention isn’t yet — the unproven market, the underpriced opportunity, the strategy nobody has covered.