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5 Amazing Personalities You Meet on The Road

Luke Armstrong | May 28, 2024

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Group of friends viewing the mountains from the peak.

Stay around a group of human people for long enough, and personality patterns emerge. At the office, there is often a gossip, a comedian, an optimist, the slacker, the achiever, the sweetheart, and there’s always that guy who makes awkward eye contact in the men's room (shame on him). 

Ten years living on the road, I've jotted a long mental list of personalities that keep appearing—a 21 year old Aussie surfer who has packed nothing but his sunnies, bodies, and thongs—the Peace Corps volunteer who speaks of nothing but the Peace Corps—the alcoholic foreign exchange student—the local merchant hellbent on selling you something—the raving lunatic who might just be a genius—and of course no country would be complete without a Chinese convenience store owner.

This list of international stereotypes goes on, so here's an abridged version of five of my favorite recurring sets of people you run into out here on the road. 

1. On The Road, You'll Meet People Overcoming Adversity to Help their Family Survive 

His name is Edgar, he lives in a rural village in Guatemala, and he is a hero. Just to see him inspires admiration. To know his story and why he endeavors daily is to be awed by such a soul. Edgar puts our "problems" into perspective.

Edgar was born with twisted legs that don't bend at the knees. He has a wife and an eight-year-old daughter. Every day, he wakes up at dawn. With the aid of a crutch, he slowly makes his way to the bus stop. It's only a quarter-mile away, but this takes him an hour. The 15-minute bus ride drops him off for blocks from Antigua, Guatemala's Central Park. 

It takes him an hour to crutch it there. What for most would be a 5-minute walk takes him an hour. When he gets there, he hustles to earn a living asking tourists in the park if they would pay $2 dollars for him to take and print their picture. 

Financially, he used to be much more successful when he had a Polaroid camera. When they stopped selling Polaroid film in the area, he had to resort to a simple digital camera. Instead of being able to give customers an instant Polaroid photo, he has to ask them to come back the next day for their photo. 

He’s at it every day to support his family. His 8-year-old daughter wants to be a doctor and so Edgar works to keep her fed, clothed, and in school. 

If you ever find yourself in Antigua,
Guatemala's Central Park, keep your eye open for Edgar. For just $2 you could have your photo taken by a hero. 

2. An Older Traveler Bailing Out a Younger

Wherever you go in the world, in any culture or country, within any political system, regardless of what clothes are worn or gods worshiped, young people are are getting themselves into sticky situations and being bailed out by slightly older people. 

So it with travelers. The stories of older, financially more stable travelers helping younger, broke ass wanderers, are as common as crew cuts on the USS Kennedy. 

On the road, if you can't access cash money and have an unpaid hotel bill, you usually don't know anyone who will vouch for you or lend you a dime. So you end up feeling utterly doomed.

I heard the story of such doomed traveler in a jungle-bound shuttle bus cranking along crappy roads in backcountry Guatemala.
Will him Cory. The short of Cory's story was that everything that could go wrong was going wrong—he was catching the wrong buses, missing the right ones, losing things, hurting himself, and couldn't shake his Montezuma's revenge. 

His mishaps climaxed when his wallet and passports were stolen—he lost all his money, identification, and access to cash. 
Whoever stole these was pretty bold and enterprising. The thief used the information from his wallet to contact his family back home to say they were holding Cory hostage, demanding dinero for his release. 

That's when we met Cory. Right after his family had somehow gotten ahold of the shuttle driver's phone number. The driver's cell phone rang and it was for Cory. 

"Who was that?" I asked when he hung up. This was the first time in my experience that a gringo had gotten a call on a shuttle driver's cell. 

"My dad," he said in a ghostly voice, "He thought I was kidnapped." 

At the time, I was hearing their story, I was traveling with the editor of The Expeditioner Matt Stabile. Matt seemed mildly amused by the young guy's mishaps. 

"What are you going to do for a hotel tonight if you don't have any money?" Matt asked him. That doomed look appeared in Cory's eyes. He had no plan. 

When our shuttle arrived, Matt gave him $100 to keep him alive until he could figure out how that whole wiring money thing worked.

When you're broke, $100 really can save your life. I still have the image of utter elation on Cory’s face when Matt handed him the cash—he would live to misadventure another day!
(Hopefully next time he’s wiser and gets some travel insurance to cover his mishaps). 

3. The Local Who Stalks his/her Way to a Friendship 

You could be anywhere—walking around Venice, chilling in Cartegena's Central Park, or just trying to find The Sentosa in Singapore—and suddenly—you have a new friend!

Anywhere you go, someone will see that you're not from around there and they will want to chat with you because of it. If you're open to a chat, gab away—what better opportunity is there to see a place from the perspective of one of its outgoing inhabitants.

Your new friend might hang around for a few minutes or hours. In some cases, a real friendship will form. Other times, you might end up drinking mint tea and buying a Moroccan rug and wonder if the connection was fueled by commerce.  

Preschool stranger danger rules apply. Always trust your gut and stay in public when you first meet someone on the road. 

4. The Artistic Eccentric Adding a Touch of Strange Magic to Mundane Life 

When E. A. Bucchianeri said "Weirdism is definitely the cornerstone of many an artist's career," he was talking about characters all too familiar on the road. 

Wherever there are people, there are eccentric artists who live in a world much different than the rest of us—because they inhabit a lifestyle of their own crafting.

There's a street performer in Valparaiso who makes his living by banging two sticks together and shouting gibberish. 

There was the late, "Devil of Prague," a rogue professor who spent the last ten years of his life painting self-portraits of himself wearing devil horns on the St. Charles Bridge. 

There's "The Ambassador to Yemen", who lives in rural Kisii, Kenya. Even though he has never been to Yemen, one day he found a sign that read "Yemen Embassy" and he put it in front of his land and declared himself Kenya's ambassador to Yemen. 

Iceland has film director Hrafn Gudlaugsson, who turned a junkyard of salvaged objects, piles of concrete, old ship parts, glass, and stone into an impressive house and sculpture garden. He leaves the place unlocked and lets people come by, take a look around, and pet his kitties.

On the road, weirdos will always be the most memorable people you meet. So enjoy every moment you have in the presence of a weirdo. 

5. The Possible Lunatic Who Maybe Has the Answers to All Life's Questions?

They call him “The Traveler.” He’s always going but never arrives. His right-hand hangs on to an old leather briefcase filled with books, tied with twine. He’s the most notorious face along the streets of Old Mombasa, Kenya.

“He’s a very educated man,” is what the townies around Fort Jesus, Mombasa have to say about him. 

Dangling from his left shoulder is an ancient green backpack. His tunic is made from recycled canvas with a return address from a time when the fabric protected a crate being shipped overseas.

“He has no home,” the soda pop ladies in front of Fort Jesus say. 

A falafel vendor in front of Fort Jesus says, “He’s a happy, happy man.”

Much of what The Traveler says is a combination of English, French, Arabic and gibberish—most of it makes no sense. But some of it makes a lot of sense and The Traveler walks around the main drags of the old town ranting all day long. 

He cavorts around declaring things like. "And the waters are cold in the villages . . . I can’t, I can’t, I can’t do that!. . . You can go while it is and bring me what is, then you can see the lesson!" 

The soda ladies across the street from Fort Jesus say he used to be a university professor. But one day he went over some cognitive deep end. He filled his briefcase with books, started eating from alms, and began ranting around The Old Town. 

"Where are you going?" people ask him. 

"To the airport!" he answers. 

But he never gets there. He's been going without arriving for years—and there's poetry somewhere in this fact. 

To most tourists who encounter him, he fits the mold of lunatic. The locals speak of him as enlightened. What everyone who has listened to him says is that one thing is clear, he is abundantly happy.

luke armstrong

About the Author

Luke Maguire Armstrong is the author of "The Nomad's Nomad." He has spent the last decade traveling, writing and designing, and funding philanthropic programs around the world.

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