Tyler Havener
Learning to Lean Into the Adventure
By: Chase Muro
In 2013, Tyler Havener found himself on the back of a motorcycle in Colombia, wearing shorts, a white T-shirt, and flip-flops.
He had no helmet.
The driver was a teenager, and the road ahead curved through unfamiliar surroundings. As the motorcycle passed cars and rounded blind corners, Tyler was well aware of how far he was from the safety precautions he had learned while earning his own motorcycle endorsement the previous summer.
This wasn't how the day was supposed to go.
He and two companions had simply wanted to get to a beach. Instead, a missed turn had led to two taxi rides, a barge crossing, and a motorcycle ride that none of them had planned.
But somewhere along the way, with the sun overhead and the wind in his face, Tyler had a thought that stayed with him.
“This is adventure.”
When I recently talked with Tyler, I expected to hear about the places he had visited and what kept drawing him back to South America for months at a time.
What I heard was a story about someone who hadn't always felt comfortable traveling, and who decided that discomfort didn't have to make the decision for him.
An Invitation, Not a Grand Plan
Tyler's first extended trip to South America didn't begin with a lifelong dream of seeing the world.
It began with friends.
Before that, his international travel had been limited. He had visited Canada and parts of Mexico, but living abroad for months wasn't something he felt compelled to do.
Then a friend he was doing work for offered him an opportunity: come along to South America and continue working together while they were there.
There was work available. There were familiar people. And there were experienced travelers who could help him feel comfortable in a place he didn't know.
For Tyler, that combination made a difference.
“I couldn't pass it up,” he told me.
The group left shortly after Christmas in 2012, beginning a trip that would stretch into 2013 and last approximately five months.
They spent time living in Medellín, Colombia. What had started as an invitation gave Tyler an introduction to a different way of experiencing the world.
He didn't yet know how much he would want to return.
The Long Way to the Beach
During that first stay, one of Tyler's friends met another American through a language exchange or expatriate gathering.
The new acquaintance was planning a weekend in Cartagena, on Colombia's Caribbean coast, and invited them along.
Tyler and his friend were happy to join a trip someone else had organized.
They would fly out, explore the city, visit a beach, and return on Sunday.
Tyler packed light. So light, in fact, that his companions laughed at how little he brought.
Within minutes of reaching the airport, he spilled ketchup on his white shirt.
After arriving in Cartagena, he left his phone in the taxi that brought them to their hostel. Fortunately, the driver noticed it and returned.
The weekend was already giving him stories to tell.
The next morning, the three men set out for a beach they understood they could reach by boat. The directions seemed simple: walk through an opening in the city's old wall, turn right, and find the boats.
They missed the immediate right turn.
Seeing taxis waiting nearby, they assumed they needed a ride to the dock.
Before long, they were driving farther than expected. With limited Spanish between them, they struggled to understand where they were going. They asked to get out near a fishing boat launch, only to discover that it wasn't the tourist departure point they needed.
Another taxi followed.
That ride carried them through small towns and eventually to a channel where the car could go no farther. From there, the travelers were handed off to young motorcycle drivers.
They boarded a barge, crossed the channel, and continued on the backs of motorcycles.
For Tyler, it was a mixture of fear, uncertainty, and excitement.
He knew the ride was dangerous. He also remembered feeling intensely alive.
Then one of his friends disappeared from view.
When Tyler and the other traveler reached the beach, they had to wait, wondering what had happened. About fifteen minutes later, their friend arrived with an explanation involving a motorcycle breakdown, a replacement ride, and another switch along the way.
Finally, all three were together.
They walked onto a beautiful white sand beach and rented simple huts for the night. From their beds, they could look out at the ocean.
On Sunday, they took a small boat out to a larger one and returned to Cartagena.
After getting off, they walked back toward the same opening in the wall where their adventure had begun.
That's when they realized how close the original boat dock had been.
Had they turned right, they could have avoided the entire roundabout journey.
“It felt like we were on that whole trip for a week,” Tyler said. “And it was literally 48 hours.”
The experience became one he would later share in a storytelling class. More importantly, it helped him recognize how much those unfamiliar experiences meant to him.
He wanted more of them.
Choosing Experience
Back home, Tyler built a career in software product development and experience design.
He had run businesses of his own before taking a job that offered a comfortable life, steady resources, and vacation time.
In 2015, he attended Burning Man. Around that period, he also met people who placed a high value on having experiences.
Something about that connected with him.
Experience was already part of his professional vocabulary. Now he was beginning to think more deliberately about its place in his own life.
He wanted to grow. He wanted to see more. And he wanted to find out whether he could do things that felt intimidating.
That didn't mean the fear disappeared.
“Each time I do it, it's a lot of mental effort for me,” he explained.
Traveling alone, navigating a country where he didn't speak the language fluently, and stepping away from familiar surroundings all required him to work through doubts about his own ability.
The willingness to go came alongside those doubts.
Making Room to Leave
For several years, returning abroad for an extended stay remained something Tyler wanted to do but couldn't easily arrange.
His job required working in a fixed location. Then the pandemic changed how his team worked, and remote work made the idea feel more possible.
He eventually left that job before returning to South America in 2021.
With that obstacle removed, he began working through the practical questions.
Where could he store his car? Could someone rent his room while he was gone? How could he keep a base in the Portland area?
At first, he arranged his life at home so he could leave it largely on pause.
But after that first return trip, he knew he wanted to keep going.
Maintaining the same setup became less practical, and he started getting rid of things and reducing the responsibilities that kept him tied to one place.
Packing wasn't the biggest challenge.
Making room in his life was.
Since 2021, extended stays in South America have become a recurring part of Tyler's winters. Many of his longer trips have lasted at least four or five months.
What once required a major leap has gradually become more familiar, even if it still takes effort.
More Than Warm Weather
When I asked what keeps bringing him back to South America, Tyler gave a practical answer first.
Affordability matters.
So does the opportunity to leave the Pacific Northwest winter for warmer weather.
Colombia also offered familiarity. When he returned in 2021, he was choosing a place he had already experienced with friends, but this time making the decision for himself.
There was another reason, too: Spanish.
Tyler had studied the language in high school without leaving those classes feeling fluent. Spending time in Spanish-speaking countries gave him a reason to keep learning and opportunities to practice.
He also spoke warmly about the people he has met, particularly in Colombia, while acknowledging that personalities and cultures vary throughout Latin America.
The appeal goes beyond finding somewhere pleasant to stay.
It's an opportunity to keep learning.
Understanding the People Behind the Product
Today, Tyler describes his work as being more on the product strategy side of software development.
That work still draws on experience design: understanding what people need, what they are trying to accomplish, and how a product can help them.
When I asked whether travel had helped his career, he pointed to empathy.
Seeing how people live in other places has broadened his perspective. It has reminded him that the experiences and assumptions he brings from home aren't shared by everyone.
Behind a business opportunity or a product decision is a person making choices within their own circumstances.
Understanding those circumstances matters.
Tyler believes exposure to different ideas and ways of living has made him more open to differences and better at his work.
The experiences he sought for personal growth have become part of how he approaches professional problems, too.
Starting Small
For someone who wants to travel but feels intimidated, Tyler's advice is straightforward.
“Start small.”
He doesn't pretend to have a single answer that will remove every fear. Instead, he suggests beginning with something close, accessible, or familiar.
That might mean visiting a city in Canada or choosing a destination with established tourism services. He also spoke fondly of Costa Rica as a place where he appreciated the people, nature, and opportunities to explore.
His point was to give yourself somewhere to begin.
For Tyler, the first step came with friends and a sense of familiarity. Later steps required more independence.
He didn't have to make the entire journey at once.
Everyone Has a Story
Near the end of our conversation, I asked Tyler the question I ask everyone:
What does “Everyone Has a Story” mean to you?
His answer brought us back to the storytelling class where he eventually shared his Colombian beach adventure.
He had entered that class hoping to improve his presentations, become more comfortable speaking, and understand how stories work.
But he also carried a doubt.
“I don't feel like I have any stories to tell,” he remembered thinking.
Then the instructor gave the group a simple exercise. Write down a few words naming an event or experience that might contain a story. They didn't have to know how to tell it yet.
Within fifteen or twenty minutes, Tyler had roughly fifteen possibilities on his list.
He chose one, developed it, and told it in front of other people.
The experience changed how he thought about himself.
“The truth is that I do,” he said of having stories. “I may not know how to tell them, but I've got lots of stories.”
As I listened to Tyler, that felt like a fitting reflection on the journey he had described.
He hadn't started out certain that he was an adventurous traveler. He hadn't entered that class certain that he was a storyteller.
In both cases, he gave himself an opportunity to discover something.
A friend's invitation.
A weekend that went off course.
A decision to return alone.
A few words on a page that revealed how much he already had to share.
For Tyler Havener, the journey has been about seeing new places, but also learning what happens when he gives himself room to try.
And somewhere along the way, he found more than experiences worth remembering.
He found stories worth telling.
Everyone has a story. This is Tyler's.
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Tyler,
Thank you so much for sharing your story!
You’ve got me ready to grab my backpack and head to San Pedro de Atacama. I already texted Alexa, so this has officially moved from “someday” to “please talk me out of buying a plane ticket.”
I’ll try to pack more than one white T-shirt and take the correct turn on the way to the beach. No promises on that second part.
Thanks for the inspiration, my friend. Safe travels, and keep collecting those stories!
Chase