3 Major Lessons from Traveling Where Most People Don’t

Matt Wilson
January 16, 2024

San Juan del Sur, Nicaragua August 2012

I’ll be honest, we had no idea where Nicaragua was.

Yes, the story is true, Under30Experiences Co-founder Jared O’Toole was at an event at Thomas Edison’s estate when someone from the microfinance organization Opportunity International told us about a project they had in Nicaragua.

Jared called me in Costa Rica and after a quick consultation with a map, I thought, “That doesn’t seem too far from Costa Rica… why not?”

I told some gringo buddies of mine I needed to get to Nicaragua and they said, “Oh man, you’re in luck - we’re headed in that direction. We’ll drop you off at the bus station.”

Two hours later, I started wondering if my friend’s rusted out Isuzu Trooper was ever going to make it to this alleged bus to Nicaragua...

Sure enough, my friends didn’t have a clue.

We were headed in the complete wrong direction down the Pan-American Highway…towards Panama.

It was my first #gringofail.

So much for an early morning start. I’d be crossing the border into a country I’d never been to at night…no cell phone…not a lot of Spanish…not even the wherewithal to distinguish North from South.

It’d turn out to be a classic start to a trip that would change the way I looked at the world.

Nicaragua was mindblowing.

This might not sound so politically correct, but I’ll be honest. I’d never seen true poverty before.

I’m from New York. I’d been to Harlem. I’ve worked in the rough parts of Poughkeepsie. I'd seen homeless people.

But, I’d never really taken the time to understand what it meant to be poor.

I knew there were people who couldn’t read or write, but I never considered what life for those people was actually like.

Again, I knew dirt floors existed, but I’d never known anyone who grew up like that.

It was a complete perspective change.

Am I saying everyone should go to developing nations and create a spectacle out of people we perceive as less fortunate than ourselves? Absolutely not.

Am I saying, you, and everyone else in the world should go out and see what the world is really like? Absolutely, yes.

Leave your white-guilt at home. Please don’t take off your shoes and give them to kids who actually enjoy playing soccer barefoot.  

And if you want to give, please, do it through the right channels. There is nothing worse for a society than teaching people to associate tourists with handouts.

Now that my disclaimer is out of the way, let’s dig into how incredible this country is and what we can learn.

Lesson #1: Simplicity

My first trip to Nicaragua featured beachfront accommodations for $7/night.  

Did I wake up with a fever, soaked in sweat, only to discover the power was out and the rickety little fan wasn’t working? Yes.

Did I still have the time of my life? Fuck yes.

If you want more on minimalism and simplicity, you can read the past few articles in this series. You can also listen to my podcast with the Co-founder of Hurley and Billabong on why the best days of his life were spent taking bucket-showers and living out of his car in the Baja of Mexico.

I mean come on, where else can you have unadulterated fun like helping a farmer catch his pig on the beach?


Lesson #2: Perspective

One of the most critical components of this trip was getting off the beaten path.

Sure - you can go to Cancun, or sit on an all-inclusive resort in the Dominican Republic...but what will you learn besides how many daiquiris it takes you to wash down your fifth plate of sushi?

My trip was a little different.

Through the microfinance organization we were invited into the homes of people who had received loans to start their businesses so they could earn a living wage to feed their families. 

We heard directly from the loan recipients on the challenges they face and what life was like as a micro-entrepreneur in the developing world.  

We sat in on trust group meetings, where women business owners discussed challenges they faced in a masculine dominated society.  

As a group they received coaching and did role playing exercises on how to explain to their husbands that they were working late and that the men in the household needed to cook dinner and feed the kids…something foreign to men in most of Latin America, especially in the working class.

Later that day, we met a farmer who received a loan to start a small patch of crops which he would sell at the local market. 

He explained that although he was illiterate, with this loan he was able to make enough money to keep his daughter in school. She went on to University and now makes frequent trips home to teach her father how to read and write.  

Microfinance invests in people at the grassroots levels so that they have seed capital to start a business. 

For many people, they are able to grow or create a value-add product to sell and that in turn provides a living wage. Investing in women is key to the process, as 90% of female earnings is invested back into their families and their local communities.

How could I go back to my life in New York where we were so caught up in our own pettiness?

Lesson #3: Tourism and Travel could be a vehicle for change

Did I mention that Nicaragua was a tropical paradise?

Up to this point in the article, I’ve talked about the value in living simply and understanding the challenges an area faces. What I haven’t talked about is why you’d go there on vacation...


Untouched beaches, incredible surfing, volcanoes, cloud forests…Nicaragua has enormous potential to be an eco-tourism stronghold, providing jobs, supporting small business owners, and could become a major part of the economy.

But, back to the story…

I can’t remember how this happened, but somehow I was introduced to Premal Shah, President of the booming microlender Kiva. Premal happened to be in Nicaragua at the same time I was, on an investor relations trip with his wife Ayesha, who also works in microfinance.

Premal was part of the famed “Paypal Mafia” who’s alumni went on to found companies like YouTube, Linkedin, Tesla, and Yelp.  

Needless to say, Premal and Ayesha are inspiring humans.

After a series of deep conversations with Premal and Ayesha about the impact they thought sustainable tourism could have on a developing economy when done the right way, I knew Under30Experiences had proof of concept.  

I spent the rest of my trip riding down dirt roads in the back of pickup trucks to hidden surf spots, speaking my still broken Spanish, and reading books like Small Loans, Big Dreams about Nobel Prize Winner Muhammad Yunus.

Fast Forward...

Five years later and Under30Experiences has built an amazing community of young people who want to see the world but don’t want to settle for big box tourism.  


Have we transformed the world? Not yet.  

Have we began to help transform a few little pieces of it? Definitely.  

While we are incredibly proud of our projects like our rural tourism project with the indigenous people of Peru, we are really just getting started.  

It’s our goal to have U30X run projects everywhere we visit, working with local organizations who understand the challenges their part of the world faces even better than we ever will.  

And yes, the U30X Foundation is coming.

Most importantly - if you want to lead others, you must first lead yourself.  

It’s why we always say at Under30Experiences, 

“It’s not what you do on your trip that matters, it’s what you do after.”

Thank you for listening to my story of self discovery and as always, the Under30Experiences Community is here to support you on your journey.

- Matt

For more inspiration listen to 80+ episodes of the Live Different Podcast, or read my first five articles in this series on crushing your comfort zone, connecting with nature, how to become a digital nomad, or how to become a minimalist.   

Want to join me on a trip? Come with me to Peru for our Yoga and Machu Picchu trip that I'll be co-leading this summer!

Matt Wilson
Matt Wilson is Co-founder of Under30Experiences and Author of The Millennial Travel Guidebook: Escape More, Spend Less, & Make Travel a Priority in Your Life. He is host of the Live Different Podcast, Millennial Travel Podcast, and formerly Co-founder of He is committed to helping people live more adventurous lives.


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