“You have to eat like a local when you go there.”

It sounds wonderfully adventurous. Skip the tourist restaurants. Find the tiny place with no English menu. Order whatever everyone else is having. If you really want to understand a country, the argument goes, start with its food.

There’s certainly some truth to that, but there’s also a dirty little secret that almost nobody talks about: after a few weeks traveling through remote parts of the world, sometimes you’re not searching for authenticity.

You’re just hoping to find something that won’t spend the next three days trying to kill you and make you regret your life choices.

Anyone who’s spent even a little time on the road knows exactly what I’m talking about. Somewhere between your second questionable street meat and your first frantic search for a pharmacy in a language you don’t speak, your definition of a “good restaurant” changes dramatically.

Suddenly, pizza starts looking like one of humanity’s greatest inventions.

The funny thing is that the more I’ve traveled, the more I’ve realized “local food” isn’t nearly as straightforward as self-proclaimed travel gurus make it seem.

Walk around almost any city in the world today and you’ll find pizza. And burgers. And sushi. And fried chicken.

…and if you’re really lucky (at least in my books) coffee shops with hipsters that wouldn’t look out of place back home.

One of the biggest surprises for me has been Africa. (Let’s be honest: one of the best parts about Africa in general is all the wonderful surprises.) Thanks in part to decades of Chinese investment, I’ve lost count of the number of surprisingly good Chinese restaurants I’ve found in places where I never expected them. Not because they’re catering to tourists...there usually aren’t any...but because that’s simply part of modern life there.

Authenticity isn’t frozen in time, and neither are the people who live there.

We sometimes forget that locals don’t wake up every morning asking themselves “hey, how am I going to eat more authentically today?”

They’re just...you know…people.

Sometimes they cook family recipes that have been passed down for generations, and sometimes they order pizza because it’s Friday night.

Sometimes they grab burgers after work, and sometimes they celebrate birthdays at the local Chinese restaurant.

Think about your own hometown and how often you eat the cuisine your region or country is famous for?

If someone visited Australia, would I insist they eat meat pies, barramundi, and kangaroo and wash it down with a flat white every day? Of course not.

I’d probably suggest Thai one night, Chinese the next, and tell them where to find the best little hole in the wall wine bar.

So why do we expect everyone else in the world to live inside the pages of a guidebook?

That realization has changed the way I think about food while traveling. I still love trying regional specialties whenever I can, but I’ve stopped treating every meal as some kind of authenticity exam that I either pass or fail.

Sometimes the most local thing you can do is simply eat what everyone else around you happens to be enjoying.

Recently I watched a friend use AI repeatedly on a trip to translate a menu. Then he asked it to recommend “something really local.” Then he asked which dish it thought he’d enjoy most. Objectively, it was brilliant.

AI knew his preferences. It understood the menu. It could probably recommend something he might never have picked on his own.

But I realized I wouldn’t want it to do that for me. Not because I think it’s wrong, but because, for me, it removes the best part:

I’ve ordered things I couldn’t identify. I’ve accidentally eaten dishes I still can’t name.

I’ve loved meals I never would have chosen based on my preferences.

I’ve also had more than a few spectacular failures, and those failures usually make the best stories.

Travel has always been a little messy, and for me that’s exactly the point.

Which brings me back to that original advice:

Yes...eat like a local.

But maybe we should spend less time trying to define what that actually means.

Sometimes it means the family recipe that’s been served for generations, sometimes it means the Chinese restaurant that’s become part of everyday life, sometimes it means pizza after work because nobody felt like cooking.

Food, like travel itself, refuses to fit into neat little categories.

And maybe that’s exactly why I love it so much.

Because whether it’s king crab in Murmansk, lemon chicken in Cabinda, pizza in Cameroon, or the world’s most famous hot dog in Reykjavík, the meal is rarely the thing I remember most.

It’s the conversation, the people around the table, the laughter after ordering something completely unexpected.

Years later, I can barely remember what half of these dishes tasted like, but I can easily remember exactly who I shared them with.

“You should write a book.”

It usually comes a few minutes after someone discovers I’ve visited every country in the world...or 196, if you’re using my admittedly obsessive way of counting. They assume that’s the obvious next step. Visit the world. Write the book. It almost feels like part of the contract.

The funny thing is, I never really wanted to.

It wasn’t because I don’t enjoy writing. Quite the opposite. I genuinely look forward to sitting down and trying to make sense of something I’ve experienced. The problem was that I never felt I had a book that needed to be written. There are already wonderful travel memoirs. There are guidebooks, coffee table books, books about visiting every country, books about finding yourself on the road. I wasn’t sure I had anything unique to add to the shelf.

Then, a few weeks ago, it hit me…I’d already named the book years earlier.

I just hadn’t realized it.

When I started traveling internationally, I thought the destinations were the story. I was fascinated by airports, passports, unfamiliar languages and countries I’d only ever seen in an atlas. Every border crossing felt like unlocking another piece of the world, and for a long time I measured my travels the same way most people do: by where I’d been.

Somewhere along the way, though, I realized I almost never tell people about the destinations.

I tell them about the taxi driver.

Or the border guard.

Or the woman who invited me into her home along with a dozen strangers to show me her doll collection from travelling around the world.

Or the tiny plane that landed on a dirt runway because there wasn’t another way to reach the village.

The countries simply became the settings. The stories were always about the people, the moments, and the unexpected turns that happened once I got there.

I think part of the reason it took me so long to see this is because of the people I’ve been lucky enough to spend my life and career around.

For twenty-five years I worked at the World Bank alongside people whose jobs routinely took them to places most travelers never visit. I started spending more and more time with people who thought nothing of spending a weekend in Central Asia or a vacation in West Africa. Visiting fifty countries wasn’t unusual in that crowd. Neither was one hundred…but even they often found my travels unusual and “exotic.”

When you surround yourself with people whose stories sound just as extraordinary as your own, it’s surprisingly easy to convince yourself that yours aren’t particularly special.

Then something funny happens.

You mention your trip to North Korea at a random dinner with the Director of one of DC’s “Alphabet agencies” and they drop their fork.

Or tell someone about hiring a boat to cross from Colombia into Peru.

Or explain why you voluntarily flew three different airplanes just to visit one tiny region that almost nobody has heard of.

Suddenly you’re reminded that what has become normal to you is anything but normal to most people.

That’s when I finally understood what people had been trying to tell me all along.

They weren’t asking for another book about visiting every country.

They were asking for the stories.

Not because everyone dreams of standing on the North Korean border or finding themselves on a beach in Kiribati, but because stories have a remarkable way of making distant places feel human. We remember stories far longer than statistics. We remember awkward moments, unexpected kindnesses, ridiculous travel mishaps and the people who quietly changed our perspective without ever realizing they’d done it.

Those are the memories that have stayed with me too. Years later, I rarely remember what a plane ticket cost or what “must see” thing I saw in a museum. I remember the taxi ride that became a philosophy lesson, the stranger who insisted I join his family for dinner, the airport that looked more like a garden shed than a terminal, and the border crossing that taught me patience better than any self-help book ever could.

That’s also why I think these essays have grown into something I never expected.

When I started writing 196 Stories, I assumed the audience would mostly be other travelers. People chasing new countries, obscure flights or impossible itineraries.

Instead, many of the messages I treasure most come from people who have never been to any of the places I’m writing about. They aren’t reading because they want to copy my itinerary.

They’re reading because the stories remind them of something they’ve felt in their own lives: curiosity, uncertainty, excitement, fear, wonder or the simple joy of trying something new. The destination almost becomes incidental.

And honestly, that’s incredibly freeing to me.

Because maybe the goal was never to convince someone to visit Kiribati or Abiye or North Korea.

Maybe it’s simply to convince someone to finally apply for a passport.

Or book the trip they’ve been putting off.

Or say yes to an opportunity that feels just a little outside their comfort zone.

Some people will discover they love traveling.

Others won’t.

Both are perfectly okay.

What matters is giving yourself the chance to find out.

So yes...maybe there will be a book someday soon. I certainly hope so. Not because I visited every country, but because every country gave me another story to share.

Looking back, I can’t believe it took me this long to realize it, because the answer had been staring me in the face from the very beginning.

It’s the name at the top of this page: 196 Stories.

Not a travel checklist. Not a guidebook.

Just a collection of stories from a very curious life that I hope encourages someone else to become a little more curious about their own.

Not just the places, but the details that probably shouldn’t matter after all these years. The Delta L-1011 from Cincinnati to London Gatwick. At the time, flying Delta across the Atlantic felt impossibly exotic. From London we connected onto British Airways for Leningrad (yes, it was still called Leningrad then) and somewhere during that journey I realized the world was so much bigger than I’d ever imagined.

Everything about that trip seemed extraordinary. The airports felt exotic. The food was unusual. Street signs were in different languages. Even simple errands like boarding a tram carried a sense of adventure because I had no idea how they were supposed to work. Finding money meant searching for a bank or exchange office to exchange travelers checks. Nobody had smartphones, translation apps, or GPS. Getting a little lost wasn’t poor planning; it was simply part of traveling…and a real risk…which for a first-time international traveler was slightly terrifying.

What I remember most isn’t any single landmark I saw. It’s the feeling that every hour held the possibility of something I’d never experienced before.

Today, almost all of those things have become second nature.

Landing in another country rarely raises my pulse. If I need cash, there’s usually an ATM a few steps away. If I can’t read a sign or a menu, my phone can translate it in seconds. Hotels, train schedules, restaurant recommendations, even obscure visa rules now live in my pocket. Increasingly, people are asking AI to build detailed itineraries before they’ve even booked their plane tickets.

Travel has never been easier. Wonder, however, still takes work.

It’s tempting to conclude that technology has somehow stolen the magic. Certainly, some of the uncertainty has disappeared. But the more I think about it, the less I believe technology is the real story…the bigger change has been me.

The first passport stamp is unforgettable because you’ve never had one before. The first overnight flight feels magical because you’ve never watched the sun rise over the Atlantic. The first country where nobody speaks your language leaves an impression that stays with you for decades.

Eventually, if you’re fortunate enough to keep traveling like I’ve been able to, those experiences stop being firsts. They don’t become less remarkable, they simply become familiar. Somewhere along the way, bucket-list moments quietly turn into Tuesdays.

That realization hit me recently while looking back through photos from my recent trip to South America. In the span of about twenty-four hours, I flew into Brazil, crossed by taxi into Colombia, hired a private boat into Peru, then wandered back into Brazil that evening for a caipirinha before flying onwards into Colombia the next morning.

Objectively, that’s a ridiculous sentence. Yet while I was living it, it felt completely normal to me. Not because those places had become ordinary, but because I'd slowly become accustomed to living experiences that once would have sounded impossible to me.

Maybe that’s why I’ve found myself gravitating toward strange little milk-run flights lately. Tiny airplanes hopping between airports that almost nobody has heard of. Remote regions that will never appear on a “Top 10 Places to Visit” list. Places I probably wouldn’t have considered twenty years ago because I was too busy chasing first the thrill of an international trip…then new countries…then every country.

I wondered whether I was simply moving the goalposts. Had I become so spoiled by travel that I needed increasingly obscure experiences just to feel excited again?

I’m not so sure.

The more I’ve reflected on it, the more I think what I’ve been chasing isn’t obscure aircraft or forgotten airports at all.

I’m chasing the ability to see the world the way I once did. Not because I knew less, but because everything was new.

That feeling I had stepping onto that L-1011 all those years ago. The sense that I didn’t know exactly what the day would bring. That almost every experience had the potential to surprise me.

Children don’t stand in front of a waterfall wondering whether it’s one of the ten best in the world. They don’t compare today’s sunset to the last fifty sunsets they’ve seen.

They simply look.

Somewhere along the way, many of us stop looking quite that way. Experience gives us perspective. The challenge is not letting it cost us our sense of wonder.

Sometimes that means choosing the tiny airport over the major hub. Sometimes it means wandering down the street that wasn't in the guidebook instead of following the crowds. Sometimes it simply means asking one more question instead of checking one more attraction off the list. None of those things are guaranteed to create a memorable story. But they all make it more likely that I'll actually notice the one that's unfolding around me.

The destination always changes…the feeling doesn’t have to.

I can’t recreate my first international trip. I can’t recreate the first flight that I remember. None of us can. Once you’ve seen the world (or even just a small part of it) you can’t unknow what you know. Experience changes us, and that’s a gift.

But perhaps experience also comes with a quiet responsibility to ourselves. To remember that the things we’ve become accustomed to are still extraordinary. To remember that what has become common through “our eyes” is still magical to someone experiencing it for the first time.

To occasionally put the phone away instead of searching for the perfect experience.

To notice the little things, because those are usually the stories we end up telling years later anyway.

Because the goal was never simply to collect countries…or flights…or passport stamps.

The goal was to become the kind of person who still notices them...who can still look at the world with just enough of a child's eyes to be surprised by it.

Not finding somewhere more exotic. Just remembering to look at the world with the same curiosity that made us fall in love with it in the first place.

It wasn’t some principled stand against tours. I simply liked having control over my own time. I could stay somewhere longer if I liked it, leave early if I didn’t, change my plans halfway through the day, or pursue some obscure regional border that no normal person would find remotely interesting.

For most of my journey to every country in the world, I think I took exactly one proper group trip: North Korea. And that was mostly because, well, there wasn’t exactly another option.

Over the past few years, though, I’ve found myself traveling with groups more often, particularly as the places I want to reach have become more remote and complicated. Along the way, I’ve realized I was thinking about “group travel” completely wrong.

There really is no single thing called group travel. There are just groups.

And the people in them can matter every bit as much as the destination.

One of my first lessons came in Greenland, where I signed up for what was technically a group excursion and discovered the “group” consisted of exactly two people.

By complete coincidence, the other traveler turned out to be one of the most traveled people in the world. We spent hours talking about obscure countries, remote regions and a community of extreme travelers that I had mostly watched from the sidelines. That encounter eventually helped convince me to become much more involved in that world myself.

Had there been forty people on the boat, we might never have spoken.

That’s the first thing I’ve learned: not all groups are remotely the same. A group can mean two strangers in Greenland or twenty people on a bus. And when you sign up, you usually have no idea who those people will be.

That’s probably the biggest gamble.

I’ve joined inexpensive trips where I barely connected with another person, and more expensive ones where a higher price definitely did not guarantee more compatible personalities. Age doesn’t guarantee compatibility. Nationality doesn’t. Income certainly doesn’t. Even being extremely well traveled doesn’t necessarily make someone pleasant to travel with.

Sometimes you click. Sometimes you don’t. The opposite is true when you already know the group.

Years ago, a friend convinced me to join an all-inclusive resort trip in the Dominican Republic, which may be one of the least “me” travel sentences I’ve ever written.

And I had an incredible time.

It wasn’t because I suddenly discovered a passion for wristbands and all-you-can-eat buffets. It was because I was with people I genuinely enjoyed, we met more great people, and the destination almost became secondary.

The right people can magnify even a trip you might never have chosen yourself.

Unfortunately, the reverse is also true.

Put ten strangers together somewhere remote and you’ve basically created a small social experiment. Different personalities, different expectations, different travel styles and very different ideas about what constitutes an emergency.

Usually it works out at least reasonably well.

Sometimes one personality dominates everything.

Maybe someone complains constantly. Maybe they’re loud as a foghorn. Maybe they have an opinion about absolutely everything and feel a civic responsibility to share it.

You have two choices: spend the trip focused on that person, or refuse to give them control of your experience.

That may be the most useful thing group travel has taught me, and it has very little to do with travel.

We give other people an astonishing amount of power over whether we enjoy our lives. One rude stranger ruins dinner. One annoying coworker ruins the day. One difficult person becomes the story we tell ourselves about an entire trip.

You can’t always control who ends up beside you. You can control how much of your experience you surrender to them.

Of course, surrendering some control is the basic bargain of group travel. You eat when the group eats. You leave when the group leaves. You can’t always linger because the light is perfect or skip something because you’ve discovered a café where you’d rather spend three hours.

For someone like me, those compromises matter. But so does what you get in return.

Groups can make difficult logistics possible and expensive journeys affordable. They can arrange permits, charter transportation and get you into places that would be extraordinarily difficult to reach independently.

Most importantly, they can introduce you to people you never would have met otherwise.

Some of my closest travel friendships today began on group trips. I’ve traveled again with people I met that way, learned about destinations I’d never considered and become part of communities I probably never would have found entirely on my own.

So I’ve stopped asking whether I like group travel. The better question is: what kind of group travel works for me?

Maybe it’s friends at an all-inclusive. Maybe it’s ten experienced travelers heading somewhere logistically absurd. Maybe it’s two strangers on a boat in Greenland.

And sometimes you’ll get unlucky. The chemistry won’t work. Someone will drive you absolutely insane. That’s the gamble.

I still prefer independent travel most of the time. Give me my own itinerary and the freedom to make questionable logistical decisions without putting them to a committee vote.

But some of my best travel experiences (and some of the friendships I value most) would never have happened if I’d insisted on doing everything alone.

Or at least to the place where my laundry machine lives.

That’s become my working definition these days. It’s where my own pillows are. My prescription refills. Many of my friends. Doctors who know my medical history. Clothes that haven’t been stuffed into a carry-on for two months. Home isn’t really a place anymore. It’s wherever my life pauses long enough to reset before the next trip.

But before I board that flight, I have one last decision to make, and I’ve spent an embarrassing amount of time thinking about it.

One option gets me home earlier, costs a couple hundred dollars less, and has much more civilized flight times. It also gives me a day in Costa Rica, a country I’ve already visited extensively. The other option is objectively worse. More expensive. Worse connections. Less sleep.

The reward? One new Colombian region.

Here’s the ridiculous part: there isn’t even anything in that region that I’ve always dreamed of seeing. No attraction I’ve been saving for years. No hidden gem that everyone’s been telling me about It’s just...

...new.

Apparently that’s enough to send my brain into overdrive.

The funny thing is, I’ve already done Costa Rica properly.

My first trip lasted almost an entire week. I visited every province. I never left thinking, I wish I’d had more time. Honestly, it was one of those rare trips I feel like I wasn’t checking boxes at all…I really saw a lot. Going back wouldn’t be filling in unfinished business. It would simply be revisiting a country I genuinely enjoyed. (…and yes, I’m unofficially working on visiting every country a second time and this would be #108…so there’s that.)

So why is my brain still fixated on the region in Colombia? Because it’s new.

I mentioned this dilemma to a few friends I’ve traveled with before. They listened patiently and asked really good questions. But then one of them hit the nail on the head:

“If you fly through Costa Rica, would you have to come back a third time because you missed something? Do you have regions left to visit there?”

“No,” I answered. “I’ve already done all the regions.”

“So...what’s the problem?”

It was such an obvious question that it completely stopped me in my tracks. I wasn’t really deciding between two flights….

…I was trying to decide what counts.

Travelers have very strong opinions about what counts.

Spend one day somewhere and someone will tell you that’s not enough. Spend two weeks somewhere and someone else will insist you still “missed the real place.” Visit every region in a country and you’ll be accused of checking boxes. Skip a famous attraction because it doesn’t interest you and someone will wonder why you bothered going at all.

We’ve all heard these conversations. Some of us have probably participated in them.

The irony is that every traveler is constantly making compromises.

Some people have more money than time. Others have all the time in the world but need to stretch every dollar. Some travel for food. Others for wildlife. Some want to hike every mountain they can find. Others are perfectly happy sitting in cafés talking to locals.

None of those approaches is more “correct” than another. Yet travel has an odd habit of attracting people who are convinced they’ve discovered the One True Way.

The backpacker who insists hostels are the only authentic experience.

The luxury traveler who can’t imagine taking a bus.

The foodie who thinks you haven’t experienced a country unless you’ve eaten at that restaurant.

The anti-list traveler who spends an astonishing amount of energy criticizing people with lists. Honestly…it can be super exhausting.

Years ago I asked a good friend whether they ever felt the desire to travel more.

Their answer has stayed with me ever since. “Nah,” they said. “My life is good enough.”

I knew exactly what they meant, but I remember physically recoiling from those words. Not because I think everyone should travel like I do. Quite the opposite. Some people genuinely have no interest in seeing the world, and that’s perfectly fine.

What bothered me was the phrase itself.

Good enough.

It sounded like curiosity had quietly packed its bags and gone home. And yet here I am, asking myself whether a two-hour visit to a Colombian region would be...

...good enough.

Funny how perspective has a way of humbling us.

The truth is, none of us gets everything. Not in one city. Not in one country.

Not in one lifetime.

Every trip involves trade-offs. Every itinerary leaves something on the table. Every traveler decides what’s important to them, whether they realize they’re making that decision or not.

The only real question is whether you’re making your choices or someone else’s.

That’s why I think we’ve become far too comfortable telling other people how they should travel.

“You need at least a week.”

“You have to go in the dry season.”

“You can’t miss...”

“That’s not real travel.”

Maybe.

Or maybe those are simply your priorities.

One of the best things about getting older is becoming comfortable with the idea that my travel doesn’t need to impress anyone else. I don’t need strangers on the internet validating how long I stayed, how I got there, or whether I checked the “right” boxes.

What matters is whether, years from now, I’m happy with the choice I made.

That’s why I value friends who know how I travel. The ones who understand that I genuinely enjoy collecting regions. The ones who know I’m perfectly happy taking a three-hour bus ride to see something obscure if it scratches an itch that’s important to me. The ones who also know when I’ll enjoy slowing down and spending another day somewhere I’ve already been.

Good travel advice isn’t universal.

It’s personal.

So...

Will I visit that extra Colombian region?

As I write this, I honestly haven’t decided…but I need to do so tonight.

But I think I’ve finally figured out the right question.

Not...

“Does it count?”

Not...

“Will other travelers approve?”

Not even...

“Is it enough?”

Instead, I’m asking something much simpler: “What choice will make me happiest a year from now?”

Because that’s really all any of us are doing when we travel.

Making the best decisions we can with the time, money, curiosity, and priorities we have. The rest?

That’s just someone else’s definition of enough.

Given the choice, I’d rather wander a city by myself or in a very small group than follow someone holding a flag. I’d rather spend an afternoon talking to the owner of a neighborhood café than listen to a microphone describing the history of the building across the street. I like making my own mistakes. Taking the wrong street. Changing my plans because something or someone unexpected caught my attention.

Group tours have never been my favorite way to travel. That doesn’t mean they’re bad. Sometimes they’re the only realistic option. The Amazon is a good example.

Manaus isn’t somewhere you simply rent a bicycle and explore.

If you want to see pink river dolphins, visit an Indigenous community, go searching for caiman after dark, or spend time on the river, chances are you’re joining a tour. Unless you have unlimited time (or a budget for a private guide) you’ll probably find yourself climbing aboard the same boat as twenty or more strangers.

That’s exactly what I did…and, as usual, I came away with mixed feelings.

Language was part of it.

I’d spent the previous five weeks making a real effort to improve my Portuguese, and I really did make great progress. It helped. I could order meals, joke with waiters, ask questions, and have simple conversations. But a boat full of Brazilians chatting naturally with one another reminded me how much further I still have to go. I could follow pieces of conversations, but not really join them. That’s frustrating, especially because talking to people is one of my favorite parts of travel.

That’s on me. I could have tried harder. But honestly, for five weeks, I did the best I could. Brazil is great this way, btw, English is so uncommon that you’re forced to practice Portuguese, so it’s a great place to learn.

The bigger challenge for me, though, wasn’t the language. It was authenticity.

One stop brought us to an Indigenous community where we watched dances, demonstrations, music, and ceremonies before browsing a souvenir market. The people we met were welcoming, and there’s no question tourism provides income that matters. I don’t want to dismiss that.

But I also couldn’t shake the feeling that I was watching people perform their culture for an audience of tourists. That’s uncomfortable for me. Not because I think culture should be hidden, but because I kept wondering where the line is between sharing traditions and staging them.

Then again, what’s the alternative?

Without tourism, I almost certainly wouldn’t have met anyone from an Amazonian Indigenous community at all. At least not in this kind of setting.

The same questions followed me onto the water.

Pink river dolphins appeared because fish were dangled just out of reach. Caiman had their mouths taped shut while visitors held them for photographs before they were released. Giant arapaima (the largest scaled freshwater fish in the world) gathered around platforms where tourists could feed them using bait tied to strings instead of hooks.

None of it struck me as overtly cruel. The fish still got the meal. The caiman were released. The dolphins seemed eager to return because they associated boats with food.

But none of it felt entirely wild, either.

That’s the uncomfortable middle ground travel often occupies. We all say we want authentic experiences.

What we usually mean is that we want authentic experiences that fit into one afternoon, cost less than a nice dinner, are easy to photograph, and don’t require weeks of building trust with local communities.

Real authenticity doesn’t work that way. It takes time. It takes language.

It takes relationships.

And sometimes, it takes money that most of us simply don’t have.

My favorite tour of the week, oddly enough, was also the smallest.

It was just me and one other traveler. A Colombian undergrad going to University in France but studying in China, on a night caiman excursion. Ironically, the tour itself wasn’t very good. But having only one other person meant we actually talked. We exchanged travel stories. Compared notes. Laughed at how different our experiences had been.

Sometimes the people make the tour. Sometimes the itinerary barely matters.

Did these tours make me fall in love with Manaus? Honestly...not really.

But am I glad I went?

Absolutely.

Because travel isn’t about waiting for perfect circumstances that may never come. If your options are the ideal experience or no experience at all, then yes, wait for the ideal. Most of the time, though, that’s not the choice. Most of the time the choice is between something imperfect...and nothing.

I’ll choose something almost every time.

As long as people are treated with dignity, animals aren’t harmed, and I’m willing to leave with more questions than answers, I think that’s a trade-off worth making. Now, make no mistake, I don’t want to come across as one of those holier-than-thou backpackers who preaches about their respect for indiginous people, is often a vegan for animal rights reasons, and pretends to have the ethical secret of the universe. Nope, plenty to learn here.

Travel isn’t always about certainty. Sometimes it’s about becoming just a little less certain than you were before.

…but no, not like “normal” people love planning trips. Not just booking flights and hotels, but really planning them. Comparing airlines and potential routes. Reading about neighborhoods. Deciding whether three nights is enough or if I should make it four. My spreadsheets often have spreadsheets. I genuinely enjoy the process, and after traveling to every country in the world, I’d like to think I’ve gotten reasonably good at it.

And to be fair, planning matters. You should probably know how you’re getting there. Having somewhere to stay that first night is usually a wise move. A little research can keep you from missing something you’ve always dreamed of seeing. Logistics reduce stress, and less stress usually means a better trip.

But here’s the thing…once you’ve landed, made it through immigration, dropped your bags at the hotel, and stepped outside for that first moment of exploration, most of that planning is over. The flights have been flown. The hotel has been chosen. The itinerary has done its job.

That’s when the trip actually begins.

From that moment on, your experience is shaped less by the decisions you made months ago and more by variables you never could have controlled in the first place.

The weather. Your mood. The people you meet. The waiter who insists they no longer have that dish you’d heard so much about. The musician playing in the square you hadn’t intended to walk through and asking for change. The museum that’s unexpectedly closed. The conversation that starts because someone overhears you trying to order in their language and offers help. The wrong turn that ends up being exactly the right one.

Those variables are impossible to plan for.

They’re also the reason I travel.

I was reminded of this on my run this morning.

It was raining, so the sidewalks were full of umbrellas. What surprised me wasn’t the weather (it’s winter in Brazil after all) but how many people seemed completely disconnected from where they were. Heads down. Eyes fixed on their phones. Umbrellas tilted so low they couldn’t see more than a few feet ahead. Several times I had to dodge people who never once looked up. Had I been doing the same thing, we almost certainly would have collided.

As I was thinking about what I wanted to write today, it struck me that travel can be exactly like that.

We spend weeks planning a trip to somewhere extraordinary, then experience it while looking down at a screen. We worry about getting to the next attraction before we’ve really experienced the one we’re standing in. We obsess over checking things off a list while missing the life happening all around us.

Ferris Bueller understood this long before social media was ever a thing.

“Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.”

It’s a great line because it isn’t really about life. It’s about paying attention and being present.

Some things are impossible to miss. A giant crab overlooking the beach in Aracaju. An enormous iguana in the middle of a park in Macapá. A caterpillar the size of a bus. A tree in Lençóis that seems to have decided growing sideways was a perfectly reasonable life choice.

Those things don’t require much effort to notice…however, the moments that matter most usually do.

They’re the old men arguing over a game of chess in the park outside a bakery. The woman who hears you struggling through a few words of Portuguese and gently teaches you a better way to say it. The tiny neighborhood bar you duck into because it started raining. The family celebrating a birthday at the next table who somehow ends up inviting you for one too many rounds of celebratory cachaca.

None of those experiences appear on anyone’s “Top 10 Things to Do.”

Yet years later, after most of the trip is a distant memory, they’re always the stories I remember best.

I sometimes wonder if we’ve convinced ourselves that a perfectly planned trip is automatically a better trip. Maybe this is why some people are so enthralled by AI: the more you can plan and schedule (their reasoning goes) the “better” your trip is ultimately going to be.

A well-planned trip gets you to the right place. It makes the logistics smoother. It gives you confidence that you won’t miss something that’s genuinely important to you.

But after a certain point, more planning doesn’t improve the experience. More presence almost always does.

Looking up instead of down. Leaving room in the schedule to wander. Sitting in a park for half an hour without feeling guilty that you’re “wasting” time. Talking to the person next to you instead of checking what strangers on the internet think you should do next.

Travel isn’t a project to complete.

It’s an experience to notice.

So yes, keep planning. Book the flights. Reserve the hotel. Read enough that you understand where you’re going and why it matters. Then, when you get there, let go a little. Leave room for the variables.

Because the flights only get you to the destination.

The real trip begins after you arrive.

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There’s a line from U2’s City of Blinding Lights that has stuck with me for years:

“The more you see, the less you know
The less you find out as you go
I knew much more then than I do now.”

When you first start traveling, it feels like you’ve unlocked something. That first country, that first stamp, that first moment where you realize the world is bigger than your day-to-day life. It’s easy, in those early trips, to think you’ve figured something out. Discovered the Meaning of Life. You’re the “expert” traveler in your group of friends. That you understand how the world works just a little bit better.

But then you keep going. And something changes.

The more places you see, the more people you meet, and the more perspectives you’re exposed to, the less certain everything becomes. Not in a negative way, but in a way that forces you to recognize just how much exists outside your own frame of reference.

The world does not get smaller with travel. It expands. Exponentially. And if you’re paying attention, so does your awareness of how little you actually know.

There’s another U2 line that fits just as well, from Beautiful Day:

“What you don’t have, you don’t need it now
What you don’t know, you can feel it somehow.”

Travel rarely gives you clean answers. More often, it leaves you with questions, impressions, and a sense that there’s far more going on than you can fully grasp in a single visit, or even a lifetime. This fits nicely with my recent discussion of lists and counting countries and places. What’s “enough” to “count” as a visit? After all, you’ll never see every square meter of a place. Every city. Every person. You won’t see it at every point in time as it changes.

And that’s where the value is. Not in “knowing” a place, but in realizing you don’t.

That said, I’ve also come to realize that not everyone travels this way.

There are plenty of people moving quickly from place to place, collecting destinations, collecting photos, collecting moments for the algorithm. They see a lot, but they don’t always process much. And that’s fine. Everyone has their own reasons for being out there. It’s just not what I’ve been thinking about lately.

But if you never stop to reflect, to think about what you’re seeing and how it’s changing you, then a lot of what travel has to offer just passes you by.

Places I recently visited in Brazil like Lençóis and Jericoacoara have been that reminder for me recently. Not just visually stunning, but the kind of places that force you to slow down, sit still, and actually think. I don’t “sit still” well, but this trip and these expeditions “forced” me to…and once I actually slowed down, there it was.

Thinking about where you’ve been. About what you’ve learned. And about how much you haven’t.

Because if there’s one thing travel has taught me over time, it’s this:

The goal isn’t to know everything. The goal is to understand that you never will, and to stay curious anyway.

The Bottom Line

Travel doesn’t make you an expert on the world. If anything, it does the opposite. It shows you how vast it is, how layered it is, and how much of it exists beyond your current understanding.

And if you let it, it makes you more open, more curious, and a little more self-aware along the way.

Over to You

Do you reflect on your travels?

Was there a moment where you stopped and thought, “wow… I really had no idea”?

The short version of that idea was simple. Lists should not be about bragging rights or ticking boxes. They are about inspiration. They push you toward places that were not on your radar, and more often than not, those are the places where some of the best experiences happen.

Over the past year or so, I have leaned into that idea hard. Regions, countries, obscure corners of maps that most people scroll right past. Now that I have finished every region in western continental Europe, I have been thinking less about the accomplishment itself and more about what the process actually taught me.

Not in a scoreboard sense, but in terms of how I travel and what I take away from it.

1) Lists are incredible idea generators. Full stop.

This one played out exactly as expected, but probably more strongly than I imagined.

There are dozens of places I visited this past year that I never would have gone to without a list pointing me in that direction. Small towns, overlooked regions, places that do not make anyone’s highlight reel but quietly deliver something much more interesting.

What I found is that once you show up, the label of the place matters a lot less than the experience you create there. The list simply gets you in the door. What happens after that is entirely up to you.

2) Ticking boxes is easy. Filling your story bucket is not.

This is where lists can either help you or completely miss the point.

Yes, you can move quickly and cover a lot of ground. You can check the box, take the photo, and move on. But if that is all you are doing, you are leaving almost everything on the table.

Every “box” is really just an entry point into something deeper. A conversation, a shared moment, an unexpected detour that ends up being the part you remember.

The difference is not how long you stay. It is how present you are while you are there. And yes, it’s pretty hard to have much of an experience if you just hop off the train and get right back on, but I’ve found that if you give a place a chance and at least stay the night…well, chances are much higher.

3) Running became my way of understanding a place

This was not something I set out to prove, nor was it something I saw coming, but it turned into one of the most valuable things I learned.

At some point, I built a lengthy running streak. Minimum 2 km every single day, no exceptions. What started as a simple “let’s see if I can do this for a year” turned into a completely different way of experiencing new places.

Landing somewhere, dropping your bags, and heading out for a run forces you into the real version of a city. Not the curated highlights and tourist hotspots, but the neighborhoods, the side streets, the everyday rhythm of how people actually live.

It strips away the layers quickly and gives you a sense of place in a way that very few other things do.

4) You will never see it all, and that is exactly the point

Finishing every region in western continental Europe does not feel like an ending. If anything, it makes it more obvious how much is still out there.

Even in places I have technically “done,” there is depth I have barely scratched. And when you zoom out further, it becomes almost absurd to think in terms of completion.

Those who know me know I have a giant underwater scene/octopus tattoo sleeve on my arm. I often get asked what the meaning is. Roughly 71 percent of the planet is covered by water. That alone puts everything into perspective. No matter that I’ve seen all 193 countries and hundreds of regions…71% of the planet still remains just below the surface.

The takeaway is not that you should try to see everything. It is that you cannot, and that is what makes the whole thing interesting. There is always another angle, another layer, another place that was not on your radar yesterday.

The Bottom Line

Lists are tools. They can open doors, create structure, and push you into new experiences. But they are only as valuable as what you do with them.

If you use them to chase completion, you will always feel like something is missing. If you use them as a starting point and stay curious once you arrive, they become something much more powerful.

The goal is not to complete the list. The goal is to make the experience count.

Over to You

Do you travel with a list, or do you let curiosity lead the way? And when you think back on your trips, what stands out more: the places you went, or the stories you came back with?

There are three words that I’ve come to notice over time (both in travel and in life) that tend to quietly hold people back: try, can’t, and wrong. They’re words we all use all the time without thinking, but they shape how we approach things more than we realize, and all too often we let them run our lives.

Let’s start with try, because it’s probably the least controversial.

There’s a reason that line from Yoda has stuck around for decades: “Do or do not. There is no try.” It sounds a bit dramatic, but it’s accurate. “Try” sounds like effort. It sounds like you’re doing something. But in reality, it often builds in an escape hatch before you’ve even begun. I’ll try to go to Europe. I’ll try to make it happen. It leaves room for things not working out, and more importantly, for you to accept that outcome a little too easily.

For example, when I went to North Korea, I had only been to maybe 40 or 50 countries. In my mind, it was the most difficult place in the world to visit. I didn’t think I was every likely to get there. Then the opportunity arose out of the blue, and instead of questioning if I COULD go, I called the tour company, and before I knew it I was on a plane. But, here’s the key: I didn’t tell myself I would try to go. I told myself I would go. And once that decision was made, everything else became a problem to solve. Sure, roadblocks came up along the way, but I found ways of solving them…because I’d told myself I could do this.

That same idea carries over into life. You can try to get the job, try to move to your dream city, try to change direction in your career, but when you decide you will, the mindset shifts. You will still fail at times, but you don’t stop at the first obstacle. You adjust and keep moving.

That brings us to the second word: can’t.

This is usually where things stop before they even start.

In travel, I hear it all the time: I could never go there. I could never afford it. And yes, there are things that genuinely aren’t for everyone. But a lot of “can’t” is just fear that’s been given a more acceptable set of clothes

I’ve had those moments myself. White water rafting is not exactly where I’m most comfortable, and there were stretches of that trip where I was very aware of that fact. But the difference between doing it and not doing it wasn’t ability…it was simply deciding that I could, even if I wasn’t entirely convinced at the start.

In life, “can’t” often becomes a default conclusion before we’ve really tested it. Maybe something takes longer than expected. Maybe it’s harder than we’d like. But if it’s within the realm of reality, it’s usually within the realm of possibility. The people who do unusual things aren’t necessarily more capable…they’re just less willing to accept “can’t” at face value.

And then there’s wrong, which is definitely going to come across as a bit more controversial.

I’m not talking about obvious wrongs. I’m talking about the kind that comes from expectations…the idea that there’s a “correct” way to live your life, and anything outside of it needs to be justified. Stable job, predictable path, a life that makes sense to everyone else.

A while back, my friend Johnny Ward gave a talk where he shared one of his harder-earned travel lessons: ego is not your enemy. That stuck with me. We’re constantly told to suppress ego, not to chase things for ourselves, not to do things that might look indulgent or unnecessary from the outside. But if your “ego” is pushing you to explore, to challenge yourself, to see the world…why is that something to feel guilty about?

Travel has a way of exposing this. You don’t end up in unusual places or build unconventional experiences by following a script. At some point, you have to be comfortable doing something that might look “wrong” to someone else. And more often than not, those are exactly the choices that end up defining your life in the best way.

More often than not, those are the choices that end up mattering most.

When you step back, all three of these words are doing something similar.

“Try” softens commitment.
“Can’t” shuts things down early.
“Wrong” adds doubt where it doesn’t belong.

Individually, they don’t seem like much. But over time, they shape what you’re willing to pursue, and what you quietly decide not to.

The Bottom Line

Be careful how you frame things before you even begin. Decide when it matters. Question “can’t” when it shows up. And don’t let someone else’s definition of “right” limit what you’re willing to experience.

Over to You

What’s something you’ve been telling yourself you’ll “try” to do…that you know you either need to commit to—or let go of?

A few weeks ago, we talked about the idea of the “perfect trip” and how it doesn’t really exist. Perfect isn’t something you plan. Perfect is the trip you actually take, with all its imperfections, delays, surprises, and randomness. And sometimes, the best trips are the ones that barely resemble a plan at all.

As I posted earlier, I had a gap of about a month between trips recently. Not long enough to settle down and get “boring”, but long enough to get restless. So I did what any rational person would do… I booked 10 days bouncing around the Caribbean on small planes, mostly just to avgeek and see places I hadn’t been before.

Do I like heat and humidity? Not in the least. Still don’t. But you know what? I had a great time.

That trip reminded me of something simple that we all too often overlook in life: you don’t need the perfect conditions to have a great experience. You just need a reason to go…or at least a reason to get the gears in motion…

So, let me illustrate just a bit more what I mean. A few months back, I committed to a couple of events. Each one spaced out just enough that they could have easily been separate trips. But then the thought crept in: what if I just…connect them? And that’s how the next two months turned into one long, slightly ridiculous, very unplanned adventure.

So, this upcoming trip. It starts in Portugal, where more than 100 of the roughly 500 people who’ve been to every country are meeting for lunch. The largest gathering of “every country people” ever. But can I really go all the way to Portugal without finishing the regions of Spain and Portugal I still have left?

Of course not. So I’ll head over a couple of weeks early.

A week later, I’ve got a travel conference in Brazil. Conveniently, Portugal and Brazil are very well connected thanks to historical ties, so that part basically planned itself.

Then some friends mention they’re doing a 10-day trip after the conference. Easy decision. Then I start thinking…while I’m already in Brazil…why not hit a few more regions?

And that thought snowballed into this:

Eventually, that idea stretched all the way to the Amazon. Then Colombia. And beyond that…we’ll see. Did I “plan” any of this?

Not really. Am I excited for it?

Absolutely.

Will it be chaotic? Without a doubt.

Will things go wrong?

Most likely….But that’s kind of the point.

Because the trips you remember aren’t the ones that went exactly according to plan. They’re the ones where something unexpected happened. A place you almost didn’t go. A conversation you didn’t see coming. A detour that made no sense at the time but somehow became the highlight.

Like Abyei.

If you had asked me ahead of time whether I wanted to go there, I would have asked you where it was. And why I’d want to go there. Maybe overthought it. Maybe talked myself out of it.

Instead, I went…And it ended up being one of the most memorable experiences I’ve had.

Then…there’s St. Pierre and Miquelon.

A Europe trip fell through. Plans changed. Instead of forcing something else, I looked at a map and thought, “Why not here? Why not now?”

So I went….And then ended up doing Europe anyway.

You see, that’s the thing that happens when you stop “planning” and start “living.”

You can follow the standard script. Hit the same top 10 cities everyone else goes to. Optimize everything. Plan it perfectly. Or you can pay attention to the random ideas, the offhand suggestions, the places that weren’t even on your radar five minutes ago… and see where they lead.

Sometimes the best trips don’t come from a plan. They come from curiosity. From restlessness. From saying yes before you’ve had time to talk yourself out of it.

The Bottom Line

You don’t always need a perfect plan. Sometimes, throwing a few ideas at the wall and seeing what sticks creates something far more interesting than anything you could have designed in advance.

The trips you take on a whim, the ones that don’t quite make sense, the ones that feel a little chaotic…those are often the ones that stick with you the longest.

Over to You

What’s a trip you took that made absolutely no sense at the time… but ended up being unforgettable? And if something like that popped up tomorrow…would you say yes?

It comes down to a question most of us avoid asking ourselves honestly:

What are you waiting for?

It’s human nature to procrastinate or put things off, however, “tomorrow” has a funny way of never quite arriving. There is always a reason to push something off. Work gets busy. Money could be better. Timing isn’t ideal. The kids are too young, or too old, or in school, or about to leave. There is always a version of life that feels like it would make travel easier, cleaner, more justified.

But that version almost never shows up.

Instead, what happens is that time moves on without us. Quietly, steadily, without asking permission. And the trip you meant to take “someday” just keeps slipping further and further from your grasp.

There is, of course, something to be said for patience. For planning. For waiting until the time is right. But travel, especially the kind that stretches you a bit, is not just a financial decision. It is also a physical and mental one.

Long flights, unfamiliar places, moving through cities, adapting to “the different”…these things are easier when you have the energy for them. That doesn’t disappear overnight, but it does change over time. The version of the trip you can take today is not necessarily the same one you will take ten or twenty years from now.

And that matters.

One of the more interesting things I’ve seen on social media lately involved a family with two young kids, both under ten. Instead of waiting for the “right time,” they sold their house, sold their car, bought a sailboat, and set off to see the world.

On paper, it sounds chaotic. Risky. Completely impractical.

In reality, they made a decision about what they valued. They chose experience over stability, education through exposure over structure, and time together creating memories as a family over the idea that there would be a better moment later.

That’s not a choice everyone needs to make. But it does highlight something important: there is always a reason not to go.

And yet, when you actually do go, the experience is almost never as intimidating as you imagined.

We tend to build up the unknown into something larger than it is. The “what ifs” stack up quickly. What if something goes wrong? What if it’s not safe? What if I don’t know what I’m doing?

But in practice, the world is a lot more balanced than that.

Yes, things can go wrong. But just as often, if not more often, things go right in ways you couldn’t have planned.

A stranger gives you directions. Someone helps you when you’re stuck. A small moment turns into something memorable because you were there to experience it.

The risk is real. But so is the upside.

This idea played out for me recently in a much smaller way.

I had a few weeks in between trips, and found myself looking at flights to the Caribbean. It’s not typically my go-to region. I don’t like beaches or resorts. I loathe heat and humidity. People often say there’s “nothing to do” on “those” islands. But I realized there was an opportunity to visit as many islands, territories, and overseas “states” as I could reasonably fit into a single trip…and avgeek out in the best way and fly a bunch of new plane types.

The airfare was reasonable. I had the time. I could plan it without too much friction.

So I went.

And it turned into one of those trips that quietly reminds you why you do this in the first place. Not because it was perfect. Not because it checked every box. But because it existed. Because it happened. Because I didn’t wait for a better version of the same opportunity that may or may not have come later.

There is also a practical side to all of this that people don’t always like to talk about.

Money doesn’t sit still. It loses value over time. Points and miles get devalued. Award charts change. Hotels get more expensive. The idea that things will simply become more affordable later is, more often than not, wishful thinking. And then there’s the other uncomfortable truth: none of us are getting any younger. We can do more, and for longer, than ever before, but our bodies will eventually start to set limits. I’m a big believer in using every bit of runway we’re given, but that also means recognizing those limits and making the most of our present abilities while we can.

Waiting can cost you more than going.

Which brings us back to the original question.

What are you waiting for?

If the answer is something real, something specific, something that genuinely needs to happen first, that’s one thing. But if the answer is vague…more time, more money, better timing, fewer unknowns…then it might be worth asking whether you’re waiting for something that doesn’t actually exist.

Because the truth is, most trips don’t happen because everything lines up perfectly.

They happen because you decide to go anyway.

The Bottom Line

There will always be a reason to wait.

There will always be a version of the future that looks slightly better, slightly easier, slightly more convenient.

But travel doesn’t reward perfect timing.

It rewards action.

Over to You

What’s the trip you’ve been putting off? And if you’re honest with yourself…why?

For me, travel is one of the clearest places it shows up.

We tend to overthink our trips before they even begin. The itinerary becomes something to optimize rather than something to experience. More cities, more countries, more “must-sees,” all packed into a fixed amount of time. On paper, it feels efficient. In practice, it often just means moving faster than the experience can keep up. A good itinerary leaves room. The “perfect” almost never does.

The same instinct shows up in how we get there. We wait for the ideal routing, the perfect departure time, the exact aircraft, the connection we like instead of the one we don’t. None of that is unreasonable on its own, but taken together it creates friction. There is almost always something slightly off. The perfect flight rarely exists. A good one gets you where you need to go at a price you can stomach, which is the whole point.

Accommodation follows the same pattern. Every hotel is a tradeoff between price, location, and comfort. You can optimize for one, maybe two, but rarely all three. And yet it’s easy to spend hours trying to find the option that somehow does. Eventually you book something that’s good enough, and once you arrive, it usually is. Not perfect, but entirely sufficient and pleasant for what you actually need it to do.

All of this builds toward a bigger realization: the “perfect trip” itself is mostly a myth. You can plan structure: where you go, how you get there, where you stay, but you cannot plan the parts that actually make a trip memorable. Those tend to be the unplanned moments: a conversation with a local, a detour where you got lost, something that happens because the plan wasn’t airtight. The same way life at home isn’t defined by perfectly executed days, travel isn’t either.

That’s why the idea of not letting perfect get in the way matters more than it seems. Waiting for ideal conditions like more time, better timing, a cleaner plan, often just delays the experience or might even prevent it from happening altogether. A good trip taken now is almost always better than a perfect trip that never happens. And once you’re on the road, holding too tightly to perfection can make the experience more rigid than it needs to be.

None of this means planning doesn’t matter. It does. But there’s a difference between planning to enable a trip and planning to control it. The former gets you moving. The latter often keeps you stuck.

The Bottom Line

There is no perfect itinerary, no perfect flight, no perfect hotel, and no perfectly executed trip. There is only the one you take. And more often than not, it’s the imperfections…the small deviations from the plan…that end up defining it.

Over to You

What’s a trip you almost didn’t take because it wasn’t “perfect”? And aren’t you glad you went anyway? What made it memorable?

It sounds like a simple question, but I’ve spent a few hours thinking about it over the last week and I really can’t come up with a succinct summary.

I went back to Ireland last week for my second trip, but it was my first trip in about fifteen years. Last time I was there I visited Dublin and Belfast. Two cities, two very different identities, two very different experiences… and technically, depending on how you count, two separate countries. At the time, I was all about going to every country, and I felt I’d seen “enough” of Ireland to count it. This trip made it clear how while it made sense at the time, I still had unfinished business.

This trip, after going to Italy and Spain, I headed to Ireland where I started in the west, spending a few days in Galway and Cork. On paper, these pretty common stops for visitors to Ireland, the kind of places people associate with “real Ireland” at least from a city perspective. And in many ways, they delivered. Lively streets, people music spilling out of pubs, that unmistakable Irish energy.

What surprised me, though, was something that in retrospect should have been expected, but I hadn’t given it any thought

The crowds.

Not just crowds, but severely intoxicated crowds. Weekend energy dialed up to a level that felt closer to a major festival than a cultural experience. And layered on top of that, a heavy presence of American tourists. Familiar accents, familiar patterns, a version of Ireland that felt almost like St. Patrick’s Day on steroids, almost exported, almost a caricature of the place.

Then I went north.

When I got to Derry, it felt different immediately. Still busy, still alive, still social… but the composition of the people I encountered had changed. There were visitors, certainly, but no Americans. More local movement, more regional travel, a different rhythm entirely. Sadly, also, this is where the intoxicated crowds in Galway and Cork gave way to socioeconomic realities…twice I witnessed medical emergencies as a result of drug/alcohol overdoses. That’s not to say that’s what Derry “is,” but it was the Derry I experienced…and at the core of it, that’s what this post is about: depending when you go, where you go within a city/country, you can have vastly different experiences.

Places like this force you to slow down, even if you don’t intend to. They ask different questions. They tell different stories depending on the parameters of your visit. And they make it very obvious that what you experience in one city…or even two…is only a fragment of country.

I finished the trip in Dublin.

And Dublin, in its own way, brought everything full circle and provided the common link between my two trips to Ireland. Not because it was representative of the entire country, but because it showed yet another version of it.

Crowds again, but this time truly global. Americans, Europeans, travelers from everywhere. A capital city energy that felt both local and international at the same time. Familiar, but still distinct from everything that came before.

So, after this long ramble, what do I think it means to “see” a country?

Because I’ve now spent time in multiple parts of Ireland, across different trips, in different contexts. And I still wouldn’t claim to fully understand it.

This is the illusion of travel at scale.

You can visit 193 countries and still only scratch the surface of each one. You can hit the highlights, the capitals, the major cities…and miss everything in between that actually defines the place.

Or you can do the opposite. Travel slowly. Move overland. Spend time in smaller towns, different regions, less obvious stops. Build a more layered understanding of a single country.

Neither approach is right or wrong.

They are just different ways of engaging with the world.

And this is exactly why I’ve come back, at least in part, to travel “lists.”

Not as a finish line, not as a scoreboard, but as a prompt, because lists force you to go beyond the obvious. They push you to see France as more than Paris. Spain as more than Madrid and Barcelona.

And even within a single trip, they remind you that diversity exists within borders, not just between them.

And then there’s places like this:

The United States alone proves the point I’m trying to get at. New York is not Chicago. Chicago is not Alabama. Alabama is not Alaska. Each one could be its own story, its own lens, its own version of what that country is…and depending when you go to each…very different experiences. New York City in July is not New York City at Christmastime.

And yet, we often reduce places to a single experience.

One city. One trip. One impression.

The reality is more complicated, and far more interesting. Because “seeing” a country is not a box you check. It’s a process. One that evolves over time, across trips, across different moments in your life. You don’t finish it.

You build it.

The Balance (Yes, Again)

This brings me back to where we’ve been over the past few weeks. You don’t need to see everything. You can’t see everything.

But at the same time, if you move too quickly, you risk seeing almost nothing at all.

The balance is in how you engage.

Not just how much ground you cover, but how deeply you experience the ground you’re standing on.

Now…Over to You

When you think about a country you’ve visited…how much of it have you really seen?

And what’s a place that completely changed your perception of a country you thought you already understood?

Over the past few weeks, I’ve been writing a lot about risk. Not eliminating it, because that’s not possible, but understanding it, managing it, and deciding which risks are actually worth taking, both in life and in travel. Travel has a way of forcing those decisions on you, often in moments where you don’t have the luxury of time or perfect information. But there’s another tension that sits just beneath that conversation, one that’s less obvious but just as important: not whether to take risks, but how fast to move once you do.

Because in travel, as in life, there is always the pull to do more. Especially in our 24/7 always plugged-in and online lifestyle of 2026.

We are living in an era that rewards acceleration and “likes”. Scroll through social media and it feels like everyone is in motion, racing toward something: the youngest to visit every country, the fastest to visit every country in Europe, the most efficient itinerary imaginable. There is an unspoken assumption that if you are not maximizing your time, you are somehow wasting it. And if you are someone who is naturally curious, ambitious, or driven, it is very easy to internalize that message without even realizing it.

It’s an instinct I’ve certainly lived, and I know it’s one many of my friends experience as well. But over time, I’ve also come to recognize the tradeoff that comes with it. Because when everything becomes about the next place, the next milestone, the next achievement, you begin to lose something along the way. You stop fully experiencing where you are, because part of your mind is already somewhere else. Planning the next trip instead of enjoying the one you’re on. Looking for the next race instead of enjoying the process of training for your current one. You get the drift….

I learned this lesson long before I finished visiting every country. Before I did my first Ironman triathlon in 1996, I asked a veteran of the race what it would feel like to cross the finish line. I expected something dramatic, something transformative, the kind of moment that changes how you see everything that comes after it.

His answer was much simpler, and at the time, a bit surprising. He said you would feel incredible…for a moment. And then, almost immediately, you would start to wonder what comes next when the goal that’s consumed so much of your life for so long is finally accomplished.

It took me years to fully understand what he meant. When you invest so much time and energy chasing a goal, the achievement itself can feel fleeting. The finish line, which you imagined as an endpoint, turns out to be just another transition. And if you are not careful, you move on too quickly, without ever really sitting in what you just accomplished.

Travel can fall into that exact same pattern.

Looking at something like this, it is easy to feel a sense of scale. Nearly 3,000 flights, hundreds of airports, millions of miles traveled across the world. It represents years of movement, planning, and experience. But it also makes something else very clear, something that is easy to overlook when you are caught up in momentum.

You cannot see it all.

No matter how fast you go, no matter how efficiently you plan, no matter how many places you check off, there will always be more. Entire regions, cultures, and experiences that remain just out of reach. That realization can feel overwhelming at first, but over time, it becomes something else entirely. It becomes freeing.

Because once you accept that you won’t see everything, you can finally stop trying to.

There is a line in Billy Joel’s Vienna that captures this tension perfectly: “You can get what you want or you can just get old.” And the story behind the song adds another layer to it. Billy Joel once described visiting his father in Vienna and noticing an elderly woman, well into her later years, sweeping the street. When he asked why she was still working, his father explained that she had a job, she felt useful, she was part of something. She wasn’t finished.

That moment became the metaphor behind the song. Not everything in life is meant to be rushed toward an endpoint. There is no single moment where you are “done.” The meaning comes from the act of doing, of participating, of being engaged in the world over time.

That idea runs directly against the urgency we often bring into travel.

There is always more you could be doing. Another viewpoint to chase, another restaurant to try, another town just an hour away that everyone insists you have to see. The list is endless, and if you let it, it will define your experience.

But sometimes the right choice is the opposite. To stay where you are. To watch the light change. To let a place reveal itself slowly instead of trying to extract everything from it as quickly as possible. Those quieter moments rarely feel urgent at the time, but they are often the ones that stay with you long after the trip is over.

Places like this reinforce that idea in a different way. You can spend hours, days, even weeks in a landscape like this and still feel like you have only scratched the surface. And yet, the value is not in how much ground you cover, but in how present you are while you are there.

Because even in the most visually striking places, it is rarely just the scenery that defines the experience. It is the conversations, the unexpected moments, the subtle interactions that were never part of the plan. Those are the things that give travel its depth, and they are also the things you miss when you move too quickly.

For all the miles, all the flights, and all the places, something like this still stands out more than almost anything else. Not something acquired along the way, but something given. A reminder that behind all the movement and ambition, there are people who support you, encourage you, and make those journeys possible in the first place.

Travel, at its core, is not about accumulation. It is about connection. And the moments that carry the most weight are rarely the ones you can plan or optimize. They are the ones that happen when you slow down enough to actually experience them.

This is the balance.

There is nothing wrong with wanting to see more, to go further, to push yourself beyond what feels comfortable. That curiosity is what drives travel in the first place. But if you move too fast, you risk turning the experience into something transactional, a series of boxes checked rather than moments lived.

Because whether you have two weeks, two years, or fifty years ahead of you, the goal is not to fill that time as efficiently as possible. It is to fill it with things that bring meaning, joy, and connection. And those things do not come from rushing.

They come from being present.

Over to You

Have you ever felt this tension while traveling…the pull between doing more and actually experiencing what is right in front of you?

And when have you gotten that balance right?

For me, one of those moments came recently in Potenza, Italy. It’s a place that feels remote even by Italian standards, perched high in the mountains as the country’s highest regional capital. Getting there requires more than a little bit of time and planning. There’s currently no train service, so you take a bus from Naples or Foggia, and even then you’re not quite finished. From the bus stop, you can take a taxi (which I couldn’t find) or a small shuttle train that climbs toward the town. And once you arrive there, there are still several hundred steps and staircases to reach the old town itself. It’s not that difficult, but it’s enough to remind you that you are not in a place built for convenience or mass tourism.

The more interesting part of the story, though, was not the journey in. It was trying to escape the next morning.

I had an early start…one of those oh-dark-thirty departures that feels closer to the middle of the night than the beginning of the day. I made my way down to the shuttle train station, which, in fairness, was considerably easier going downhill than it had been the day before. The station was quiet. I checked the schedule I had photographed the previous day and waited.

And waited.

Ten minutes passed beyond the scheduled time, then fifteen. I started to worry about my connecting bus which was leaving soon. At first, it felt like a minor delay, the kind that happens everywhere. But as the minutes ticket on by mild panic started to settle in. Connections depend on timing, and timing, in this case, was not on my side .

At that point, a man approached me and asked, in Italian, what I was doing there. Now, I don’t speak Italian beyond maybe 100 words, but Potenza is one of those places where you still don’t find much English, but with my 100 words and google translate I managed to explain that I was waiting for the overdue train. I showed him the schedule on my phone.

He looked at it, confused…paused, and then pointed to a sign on the wall nearby.

The schedule I had taken a pic of and which was prominently posted on the wall was from 2024. The current one…the one that mattered…was different and posted on another wall I never saw. The train I was waiting for was not coming.

With only a few minutes left before my onward connection, the situation had moved from inconvenient to missing my bus and the next region I planned to visit. I explained as best I could that I needed to be at the bus stop quickly. There may have been some wild Italian-style gesturing…there was no hesitation in his response. He simply gave me that “come with me” gesture and started speed walking.

This is the point in the story where instinct takes over.

We are taught, quite reasonably, not to trust strangers. That instinct serves an important purpose, and ignoring it entirely would be naïve. But travel also introduces moments where rigidly applying that rule doesn’t quite fit the reality in front of you. The decision becomes less about rules and more about reading the situation: tone of voice, body language, urgency, context.

There was nothing theatrical about the moment (well, nothing more than is that “passion” that Italy does so well. No attempt to persuade, no ambiguity in intent. It was direct, practical, and immediate. It felt like help.

So I followed.

He led me to his car, parked a short distance away, and we set off. What followed was a drive that can best be described as efficient in the way that only Italian driving can be: fast, controlled, and entirely focused on the task at hand. Within minutes, we arrived at the bus stop, just as my connection was about to depart.

There was no ceremony to the end of it. A brief exchange, a quick and heartfelt grazie mille, a nod of acknowledgment, and he was gone.

The entire interaction lasted perhaps six or seven minutes. Its impact on me will last much longer. He made a difference.

“Look for the Helpers”

The phrase “look for the helpers” comes from Fred Rogers, who shared a piece of advice his mother gave him when he was a child. Whenever he saw something frightening in the news, she would tell him to look for the people who were helping. The idea was simple: even in difficult or uncertain situations, there are always individuals who step forward to make things better.

It is an idea that can feel almost overly saccharine and sentimental in the abstract. But in practice, it is something most experienced travelers recognize immediately.

Because if you have traveled enough, you have your own version of this story. The stranger who offered directions when you were lost. The driver who went out of their way to make sure you arrived safely. The person who noticed something was wrong and intervened without being asked. These moments are rarely dramatic, but they are often decisive.

At the same time, travel also teaches the opposite lesson. There are moments when trust is misplaced, when someone takes advantage of uncertainty or inexperience. Those stories exist as well, and they are part of the same reality. The challenge, then, is not to choose between trust and skepticism, but to find a balance between the two.

There is no precise formula for doing this. Experience helps. Awareness helps. Over time, you become better at interpreting the signals that surround a situation. You learn to recognize when something feels off, and just as importantly, when it doesn’t. Instinct, in this sense, is not blind; it is informed by everything you have seen and learned along the way.

The goal is not to move through the world assuming the best of everyone, nor is it to assume the worst. It is to remain open enough to accept help when it is genuinely offered, while staying aware enough to recognize when it is not.

That morning in Potenza was not extraordinary in the grand scheme of life or travel. It did not involve danger or dramatic stakes. Missing a region to visit wouldn’t be the end of the world. But it served as a reminder of something easy to overlook, particularly in this day and age when it often feels as though division and distrust dominate the narrative.

On the ground, in real places, among real people, the story is almost always more nuanced. There are risks, certainly. There are those who wish to divide us, absolutely. But there are also many people who, without hesitation, choose to help.

And if you pay attention, you will find them.

Over to You

What is your “helper” story? When has a stranger stepped in and changed the course of your trip?

And just as importantly, when have you trusted your instincts and decided not to?

These are the moments that shape how we travel and how we understand the world around us.

Hotels feel like somewhere you should feel safe and secure. You check in, drop your bags, exhale a little. But they also concentrate risk in ways most travelers don’t always think about. At the low end, maybe it’s something minor: an item that goes missing, a room that doesn’t feel quite secure. And at the far end there’s the rare, but very real risks: you have fires, natural disasters, or even targeted attacks. Hotels, especially international chains and high-traffic properties, can be visible, predictable gathering points.

As I said in the last couple of posts, and it’s worth repeating here: you can’t erase all risk. But you can understand which risks are worth taking and which ones are simply careless.

The good news is that hotel safety doesn’t require paranoia or a checklist that takes an hour to complete. It’s about small, deliberate habits that might take a minute or two, but meaningfully change your exposure. The kind of things that, once you start doing them, become second nature.

1. Location, Location, Location

The moment you arrive in your room, before you unpack or even sit down, take a minute to understand your surroundings. Most people walk straight in, drop their bags, and never look up. That’s a missed opportunity.

Start with the basics: where are the nearest emergency exits? Not the one you used to get there, but the closest alternative. If there’s a fire or blockage in the hallway, your primary route may not be available, and in those moments, familiarity matters more than speed.

Floor selection also plays a significant role, even if it’s something you decide in advance. Ground floors are more accessible to opportunistic intruders, while very high floors can complicate evacuation or emergency response. A general rule of thumb is to stay somewhere between the third and sixth floors which is high enough to reduce casual access, but still within reach for most emergency services.

Even the orientation of your room is worth considering. Rooms facing busy streets or main entrances tend to be more visible and, by extension, more exposed. Quieter sides of the building, while less exciting, often provide a bit more privacy and distance from potential threats.

None of this guarantees anything. But it subtly shifts the odds, and over time, that’s what matters.

2. Stay Safe Inside the Room

Once you’re inside your room, the next step is straightforward: use the security features that are already there. Deadbolts, chains, locking bars, these are not there to look pretty, and like seatbelts they don’t help if you don’t use them. They are simple, effective layers of protection, and it’s worth using all of them consistently.

The idea here isn’t to create an impenetrable space. It’s to introduce friction. Most unwanted situations are opportunistic rather than highly planned, and even small barriers can be enough to deter someone from trying.

There are also a few low-effort habits that can add an extra layer of security. Many travelers are familiar with the “hanger trick,” where a hanger is looped through the latch mechanism to make the door harder to open from the outside. It’s not foolproof, but it adds resistance and noise, and resistance is often enough.

The point is not perfection. It’s making your room a less appealing option than the one next door should someone be on a mission.

3. Don’t Broadcast Your Room Number

One of the most overlooked aspects of hotel safety is information…specifically, how casually it’s shared.

At check-in, a well-trained front desk should never say your room number out loud. If they do, it’s a small but telling signal that attention to detail may be lacking. You don’t know who is within earshot, and neither do they.

The same principle applies to your own behavior. It’s easy to mention your room number in passing: at the bar, in the spa, or while coordinating plans. But those small disclosures can add up, especially in environments where people are constantly moving in and out.

When you’re outside the hotel, a bit of discretion goes even further. There’s rarely a need to tell someone exactly where you’re staying, particularly if you’ve just met them. If an address is required for a practical reason, it’s far safer to write it down than to say it out loud.

You don’t need to assume the worst about everyone. But you also don’t need to make yourself easy to track.

4. Know Your Room (and What Might Already Be in It)

The first few minutes in your room set the tone for your stay, and they’re also the right time to do a quick, practical check.

Before fully entering, it’s a good habit to prop the door open with your luggage and take a brief look around. Check the bathroom, glance inside the closet, and pull back the curtains. You’re highly unlikely to find anything or anyone, but you’re confirming that everything is as it should be.

After that, turn your attention to the bed. Bed bugs are an equal-opportunity problem; they show up in budget properties and 5 star luxury hotels alike. A quick inspection of the sheets and mattress seams for small dark spots, reddish stains, or visible insects can save you from a much bigger issue later.

Luggage placement also matters more than most people realize. Setting your bag directly on the floor (especially on carpet) creates an easy path for pests to find their way in. Using a luggage rack or keeping your bag elevated is a small adjustment that significantly reduces that risk.

These steps take less than a minute. But if you skip them, you’re leaving things entirely to chance and potentially opening yourself up to months of pain down the road.

5. ICE: In Case of Emergency

Finally, there’s the question of what happens if something actually goes wrong. In those moments, clarity and speed matter, and that starts with knowing your options in advance.

Take a moment when you arrive to check a few basics. What is the local emergency number? It’s different in every country, and assuming it is going to be 911 or another common option can waste valuable time. Does the room phone work? It’s easy to ignore, but it provides a reliable backup if your mobile phone is out of battery, has no signal, or isn’t connected to a local network.

It’s also worth noting the location of fire alarms, extinguishers, and any emergency call points on your floor. These details are often posted, but rarely noticed until they’re needed. Most hotels will have a diagram of the emergency escape route on the back of the door…take a quick glance before you need it.

Your smartphone is an incredible tool…until it isn’t. Having a simple, low-tech backup plan is part of traveling responsibly.

The Bottom Line

Taken together, this might seem like a lot of small and paranoid precautions. In reality, it’s a couple of minutes max of awareness at the start of your stay.

You’re not trying to predict every possible scenario. You’re simply reducing your exposure to the most common and most avoidable risks. That distinction matters.

Because the goal, as always, isn’t to eliminate risk entirely. It’s to make sure that the risks you do take are the ones that lead to meaningful experiences, not preventable problems.

Over to You

What are your go-to hotel safety habits? Anything you’ve learned the hard way that others should know?

Drop them below, because the best travel advice is almost always written in hindsight.

So let’s make this practical.

Here are five things you can do right now to meaningfully reduce your travel risk, without turning your trip into a hyper-controlled, joyless operation.

1. Don’t Put All Your Money in One Place

If your wallet or purse disappears…whether you lost it or someone helped it disappear…you don’t want your entire trip disappearing with it.

The fix is simple, and it’s amazing how many people don’t do it: split your resources. Carry your primary wallet as usual, but keep a backup credit card and some emergency cash somewhere separate. That might be your luggage, your hotel safe, or even a different bag.

This isn’t about paranoia, it’s about basic resilience. I’ve seen travelers go from completely stuck to completely fine just because they had a backup card tucked away. Same problem, totally different outcome. One person is canceling their trip. The other is ordering an umbrella drink and figuring out next steps.

Don’t let a single point of failure end your trip. I admit I’ve failed to follow my own advice here multiple times thinking “it won’t happen to me” but travel enough and it eventually will.

2. Back Up What Actually Matters (Not Your Whole Life)

Travel comes with friction. It’s as inevitable as the sun rising and setting each day. Bags get delayed. Things get misplaced. Occasionally, stuff just vanishes into the void.

So the question isn’t “how do I prevent that entirely?”…you won’t. The question is: what can I absolutely not function without?

For most people, that list is pretty short:

• Prescription medication

• Glasses, contact lenses, or other assistive devices

• Essential documents such as your passport

Those are the things worth duplicating or planning around.

What’s not on that list? Your third backup phone. Your second laptop. Your “just in case” tablet. I know people who travel like they’re opening a Best Buy pop-up, and it’s completely unnecessary. If your laptop dies, you log into the cloud on a new one. If your phone breaks, you replace it.

Be thoughtful about redundancy where it matters, but don’t confuse preparation with overpacking. Pro-tip for your passport and other critical docs: always store a PDF copy in the cloud…that way, if it decides to wander off you at least have something to show the police or other officials in the meantime.

3. Tell Someone Where You Are (But Don’t Tell the Internet)

There’s a sweet spot between being completely off-grid and broadcasting your every move to the world.

When you’re doing something even slightly higher risk…remote hiking, long solo drives, unfamiliar areas at night…tell someone you trust where you’re going and when you expect to be back. Build in a little buffer so they don’t panic if things run late, but make sure someone has a general sense of your plan.

At the same time, resist the urge to post everything in real time, especially in places where security is less predictable. Not everyone following you has good intentions, and you don’t need to make it easy for anyone to track your movements.

Share the story later. Experience it fully in the moment. A little bit of discretion goes a long way.

4. Safety in Numbers…But Not a Traveling Circus

There’s truth to the idea that two heads are better than one. Traveling with a companion can make decision-making sharper, provide a second set of eyes, and generally reduce risk.

But there’s a tipping point.

As groups get larger, they become more visible, less flexible, and frankly more chaotic. You’re more likely to stand out, more likely to attract attention, and almost guaranteed to have at least one person making questionable decisions that affect everyone else.

Large groups can also become easier targets. They’re predictable, they move slower, and they often signal “tourist” from a mile away.

Smaller groups, or even pairs, tend to move more intentionally. They blend in better, adapt faster, and keep a tighter awareness of their surroundings.

Travel like a team, not an entire traveling circus.

5. Go Where the Locals Go (With Eyes Open)

There’s a reason certain places show up in every guidebook. They’re famous, accessible, and designed to handle large volumes of visitors.

They’re also predictable.

And anything predictable (big chain hotels, major tourist restaurants, packed festivals, iconic attractions) can become a natural focal point not just for travelers, but for people looking to take advantage of them.

That doesn’t mean you should avoid these places entirely. Some are absolutely worth seeing. But it does mean you should approach them with awareness.

Balance them out by spending time where locals actually live their lives. Stay in neighborhoods that aren’t built exclusively for visitors. Eat at places that aren’t optimized for tourists. Explore beyond the obvious.

You’ll often find that not only do you feel more grounded and less targeted, you also have a far richer experience.

One small reality check: your immune system is not local. That incredible street food spot might be perfectly normal for residents and a full-blown adventure for you. Ease into it. Your stomach will thank you.

The Bottom Line

Derisking your travel isn’t about wrapping yourself in bubble wrap or eliminating every unknown.

It’s about making a series of small, smart decisions that compound in your favor. So when something inevitably goes wrong, it’s not catastrophic…it’s just an inconvenience.

You’re still moving. Still exploring. Still saying yes.

And that’s the whole point.

You can stay home, sit on the couch, watch TV, avoid difficult places, avoid difficult people, avoid uncertainty, and build a routine where almost nothing truly unexpected ever happens. You can convince yourself that this is wisdom. After all, if you never go anywhere, never try anything, and never expose yourself to unfamiliar situations, the odds of something going sideways drop dramatically. Unless, of course, the house burns down. Or your health fails. Or life finds some other way to remind you that total safety is mostly an illusion.

That is the problem with a fully “derisked” life. It may feel safer in the short term, but it is definitely not more rewarding. And at some point, whether we admit it or not, most of us are not really asking how to avoid all risk. We are asking a deeper question: what makes life worth living in the first place?

There is a quote often associated with Thoreau that hits me hard:

"I went to the woods because I wished to live deliberately, to front only the essential facts of life, and see if I could not learn what it had to teach, and not, when I came to die, discover that I had not lived"

That, to me, gets to the core of travel and of risk. The goal is not to eliminate uncertainty from your life. The goal is to avoid waking up one day realizing that you spent decades trying so hard to protect yourself from the essence of life that you forgot to actually live it.

Of course, there is another extreme. Some people do not merely tolerate risk. They actively seek it seemingly 24/7. They bungee jump off bridges, throw themselves into violent rapids, and treat fear as if it were a hobby. I am not wired quite that way, even if I have occasionally found myself brushing right up against that world.

That is where this gets interesting, because there are risks, and then there are reckless decisions. Those are not the same thing, even if they can look similar from the outside. Recklessness is blind. It ignores context, dismisses consequences, and often has very little payoff beyond the adrenaline hit or the story afterward. Risk, by contrast, can be informed. It can be measured. It can be chosen with your eyes open. One is chaos for chaos’s sake. The other is an intentional bet that the reward outweighs the downside.

That distinction matters enormously in travel.

People who work in the area of risk management view risk analysis as a matrix: on one axis, risk. On the other, reward. Low risk and low reward is the easy default. Staying home. Doing what you have always done. Nothing wrong with it in moderation, but no one is writing epic memoirs about the week they stayed in and reorganized the pantry. High risk and low reward is where recklessness lives. That is where bad judgment disguises itself as bravery. There is very little romance in making dumb choices with terrible upside.

Then you get to the more interesting quadrants. Low risk and high reward is where many of us should be living more often than we do. Take the trip. Book the ticket. Speak to the stranger. Wander the neighborhood. Try the thing that scares you just a little. Most of the time, these are not reckless moves. They just feel scary because comfort is addictive. And then there is high risk and high reward, which can absolutely be worth it, but only when you are honest with yourself about the tradeoffs and your own appetite for uncertainty.

The sweet spot is personal. But if I had to guess, for most people it is probably further out than they think.

That is where travel becomes such a useful teacher. Travel exposes how many of our “safe” decisions are really just habits. It shows us that what we often call prudence is sometimes just fear wearing sensible shoes. It also forces us to sort out what we really mean by risk. Is the danger physical? Emotional? Financial? Logistical? Social? Is the reward fleeting, or does it change you in some lasting way?

Take something like sledging in New Zealand, for example. If you have never heard of it, imagine whitewater rafting, except instead of being inside the raft, you are in the river itself clinging to a board and attempting to look like this was all a very reasonable life choice. It sounds absurd because it is. But it is also structured, guided, and managed. It is not random chaos. It is informed risk wrapped in a ridiculous package.

And because of that, it becomes the kind of experience that stays with you. Not just because it was intense, but because you chose to do something that demanded presence. The river did not care about your to-do list, your inbox, your insecurities, or your plans for next week. It forced you fully into the moment. That kind of reward is hard to get from safe, padded, predictable living.

Lately, these thoughts have collided with something much more real and much less theoretical: having a seriously ill parent. This is not the main point of the piece, but it is part of how I have been thinking about informed risk lately. There are times in life when the question is not just whether something sounds exciting or meaningful, but whether it is responsible given the circumstances around you.

That was part of the reason Yemen no longer made sense for me recently. It is not that Yemen is not worth seeing. It absolutely is. But it is also not a place where you can just hop on the next hourly flight home if something goes wrong. If someone passes away while you are somewhere like that, there is a real chance you simply do not make it back in time. That is not drama. That is logistics.

That, to me, is where informed risk-taking becomes less abstract and more personal. It is not about becoming timid. It is about recognizing that context matters. This is also one reason I have spent more time in Europe lately. Worst case, if something happens at home, I can generally be back in the United States from Europe in under 24 hours. As it happens, that exact logic mattered this week. And I did make it back in time. That does not mean Europe is “safe” and Yemen is “bad.” It means that in one season of life, one risk/reward calculation made sense and another did not.

That is what maturity in travel looks like. Not staying home forever. Not pretending all destinations carry the same consequences. Just knowing your own matrix.

The funny thing is that most of us do not need encouragement to be more cautious. The world gives us that constantly. Family gives us that. News gives us that. Algorithms especially give us that. We are endlessly reminded of what can go wrong, what might happen, what could fall apart. Very few voices are out there saying, yes, but what might happen if you go anyway? What if the upside is bigger than your fear? What if the thing that feels risky is actually the thing that makes your life more vivid, more textured, more worth remembering?

I suspect that for most people, the real growth is not in becoming more reckless. It is in becoming more honest. Honest about what actually matters. Honest about what is merely comfortable. Honest about the fact that many of the best experiences in life begin with some version of I am not totally sure about this.

That does not mean everyone needs to jump off bridges, raft through rapids, or throw themselves into whatever adrenaline circus is nearest. It means knowing your personal sweet spot and admitting that, for most of us, it probably involves taking more risks and trying more things than we currently do.

Because there is a huge difference between derisking your life and shrinking it.

Travel is one of the clearest ways I know to test that idea. Not because every trip has to be extreme, but because every trip asks some version of the same question: are you here to protect your routine, or are you here to expand your life? Sometimes the answer is rest. Sometimes the answer is caution. Sometimes the answer is staying closer to home because that is what your life demands in that moment. But sometimes, maybe more often than we admit, the answer is to go. To try. To say yes. To accept that life cannot be fully optimized against pain without also being optimized against joy.

So I will leave you with this:

When did you take a risk and it really paid off?
And when did you realize you had gone just a little too far?

Because most of us do not need a push toward recklessness.

We need permission to live a little more fully.

That is Valencia for me right now.

I booked this trip without realizing I’d be landing in the middle of Las Fallas, the city’s most famous festival and one of the wildest cultural events in Spain. Fortunately, prices were still reasonable, logistics held together, and instead of getting punished for my lack of planning, I somehow got rewarded for it. I walked into a city that had effectively turned itself into an open-air fantasy world of giant sculptures, street celebrations, firecrackers, music, and collective sleep deprivation.

And honestly, it slaps.

If you have never been, the simplest explanation is that Las Fallas is a festival built around art, satire, neighborhood pride, noise, and fire. Throughout the year, different neighborhoods commission and construct enormous sculptural installations called fallas. These are not casual decorations. They are elaborate, expensive, technically impressive works of art, often playful or surreal, sometimes political, sometimes absurd, and always designed to be noticed. During the festival, they are displayed throughout the city, admired by locals and visitors alike, and then, at the end, all of them (except one which is “pardoned”) are burned. That is part of the tradition. The beauty is temporary on purpose so it can happen again next year.

The city lives differently while Fallas is happening. During the day, you wander from one installation to another, turning street corners and suddenly finding yourself face to face with some giant, hyper-detailed creation that looks like it came from a fever dream. At night, the energy shifts. The crowds get thicker, the lights get brighter, and the whole place feels like it is operating on pure adrenaline and communal momentum. Valencia stops being just a city and starts behaving like a living event.

What struck me almost immediately was that the festival itself is not just about spectacle. It is also about participation. The city is outside. People are moving, talking, laughing, drinking, lingering, and sharing the experience. That matters, especially when you are traveling alone.

Because here is the truth about solo travel: your experience is mostly on you.

Yes, some places are more open than others. Yes, some people are warmer than others. Yes, luck matters. But if you are alone in a city and want more than photos and observations, at some point you have to participate. You have to put yourself out there, speak to someone, ask a question, accept a little awkwardness, and see what happens. Travel is not just about where you go. It is also about whether you are willing to step toward other people once you get there.

That thought hit harder yesterday because I had one of those conversations that lingers, though not for the best reason. I met someone working at a restaurant, an immigrant from Asia who has lived in Spain for more than twenty-five years. Their partner is from another European country, so the two of them have also built their lives here from the outside. And for what felt like a very long time, all I heard from them was how unwelcoming the Spanish are, how impossible it has been to connect, and how even after all these years they still do not feel accepted in Valencia.

Now, to be clear, I am not saying their experience is invalid. It is their experience, and I am sure it is real to them. But there is a difference between acknowledging that connection can be difficult and deciding that connection is impossible. The whole conversation felt so relentlessly negative that I eventually found myself looking for an exit. People who have settled too comfortably into resentment can drain the oxygen out of a room.

And the thing is, my own experience here has been almost the exact opposite.

Not because I am somehow magical. Not because every Valencian I meet is trying to become my best friend. But because I speak at least some Spanish, I make an effort, I ask questions, I smile first, and I am willing to accept that not every interaction needs to become some deep, life-changing bond to still be worthwhile. Especially during a festival like Fallas, when half the city seems to be operating with a little extra courage courtesy of whatever is in their cup, it is not that hard to meet people if you are open to it.

That is the philosophy piece here, and honestly it applies far beyond Valencia.

A lot of travelers say they want “authentic connection,” but what they really want is for connection to arrive effortlessly, on their terms, without discomfort, rejection, effort, language barriers, or vulnerability. That is not how it works. Not in Spain. Not anywhere. Real human connection, even the casual kind, requires initiative. You do not need to leave a place with lifelong friends. You do not need a dramatic story about how you were adopted into a local family and now return every Christmas. Sometimes the win is much smaller, and still meaningful: a shared laugh, a recommendation, a drink, a conversation that lasts twenty minutes longer than expected, a sense that for one evening you were not just observing the city, but participating in it.

Fallas is actually a perfect setting for this lesson because the festival itself is communal. These sculptures are not just dropped in by some anonymous event company. They come from neighborhood organizations, local traditions, local pride, local energy. You can admire them as an outsider, sure. But the experience gets richer the moment you remember that these are not props for your content. They are part of a city’s identity, created by people who live here, celebrate here, and understand layers of meaning you probably do not.

That is one reason I love being surprised by events like this. They break the tidy version of travel. You think you are arriving in one kind of place and instead you land in something louder, stranger, and much more alive. They also force you to decide what kind of traveler you want to be. You can stay detached and consume the event visually, moving from sculpture to sculpture like you are scanning museum exhibits. Or you can lean in, ask questions, talk to people, and let the city become social rather than scenic.

And then there is the deeper travel lesson underneath all of this. So much of travel is not about whether a place is welcoming in some abstract, universal sense. It is about whether you are willing to give the place something to work with. That does not mean ignoring real barriers. Some communities are more closed. Some societies are harder to crack. Some conversations go nowhere. Some people simply do not want to talk, and that is fine. But if you bring curiosity, humility, and a little linguistic effort, you are dramatically increasing your odds.

That matters because negativity can become self-fulfilling. If you walk into a place already convinced that nobody wants you there, you will notice every cool interaction as an exception and every cold interaction as proof. But if you arrive open, observant, and willing to engage, you start giving reality a chance to surprise you. Not perfectly. Not every time. But often enough that a city begins to feel less like a backdrop and more like a relationship.

That is what I keep thinking about as I walk through Valencia this week. The sculptures are amazing. The festival is ridiculous in the best possible way. The whole city feels enhanced. But the real story is not just the art in the streets. It is the chance to step into the mood of a place and decide whether you are going to remain separate from it or become, even briefly, part of it.

Traveling alone does not mean being alone the whole time. It means that connection is less likely to happen by accident and more likely to happen because you chose it. That is not a burden. It is a gift. It means your trip is not just something that happens to you. It is something you actively shape.

And that is probably the bigger lesson here.

Valencia gave me Fallas by accident. What I do with that accident is up to me.

So I will leave you with this: what is a time you put yourself out there while traveling, connected with someone, and your trip was richer because of it?

Because places matter, of course.

But more often than not, it is the people who make them unforgettable.