4x Jamaica

A vibrant Caribbean Island nation known for its lush landscapes, rich culture, and warm, tropical climate. Surrounded by turquoise waters, it boasts white-sand beaches, majestic mountains, cascading waterfalls, and dense rainforests. Top that off with an all-inclusive resort offering endless food and drink—and at 18 years old, that all sounded pretty damn good.

1)

In May 2006, I graduated from Beaverhead County High School (BCHS) in Dillon, Montana. My friends Tobin, Josh, and Bigs (from the Homies) and I got the green light from our parents to take a post-graduation trip with Eric as chaperone.

The group settled on Jamaica, more specifically Ocho Rios. The vibe, travel time, and cost all made sense. We left the morning after the BCHS-sponsored all-night graduation party, making the long trek from Montana to the Caribbean.

For the next ten days, we soaked in the beaches, indulged in resort food and drink, danced in the clubs, and lived carefree. It became a core memory, the final celebration of adolescence before stepping into adulthood.

That trip sparked an idea—maybe even a dream: open a restaurant/club on the island. I envisioned a vibrant life of business and blending joy with purpose.

2)

In 2009, I graduated from North Idaho College with an Associate’s of Science Degree in Business Administration. My brother Kyle graduated from BCHS that same year. Together, we returned to Jamaica—this time to Montego Bay—with Eric once again serving as consigliere.

A lot had happened in the three years since my first trip. I needed a break, a reset, and some space to simply be 21 again. While Kyle celebrated his own coming-of-age moment, I used the time to decompress.

3)

The restaurant/club idea from 2006 continued to take shape. And with the birth of my daughter in 2008, I decided the establishment was going to be named Kiwis. It was also the foundation of my final project for my bachelor’s degree at Lewis-Clark State College, Coeur d’Alene. But once I dug into the logistics, the dream felt overwhelming. I pivoted toward a career in higher education instead. The disheartening exercise helped me come up with with my mantra of this era: “I love business, it’s just too hard.”

After completing this project in 2011, I graduated with my bachelor’s of arts degree in Business Administration and a minor in Marketing from Lewis-Clark State College, Cd’A and received a promotion at work, so another celebration trip was in order. Eric, his partner Jake, Bigs, Kyle, and I, along with Kiwi, headed to Montego Bay for 10 days.

The trip was full of good food, great people, and memorable nights—but it also marked a turning point. I realized I’d had my fill of Jamaica. I was grateful for the memories, but I was ready to explore new corners of the world.

Three life milestones, all celebrated in Jamaica. The chapter felt closed, in a good way.

4)

In 2015, I began working as a recruiter at Management Recruiters of Coeur d’Alene (MR Cd’A), an independent franchise of the MRINetwork. Each year, the network awards top performers with an all-expenses-paid “Pacesetter” trip to a tropical destination. The 2016 trip was to Aruba—a place I’d never dreamed of going. I also wasn't able to qualify that year as I was still learning the business.

In 2017 though, I hit Pacesetter for the first time.

And the destination? Montego Bay, Jamaica.

It felt like a bit of a letdown to return to a place I thought I’d closed the book on. But I chose to make the most of it. Since the trip would be in March 2018, I extended the vacation and added Ocho Rios for a final lap—twelve years after my first visit.

I went with my then-fiancée and returned to the old stomping grounds. It was a time to reminisce, celebrate my achievement, and let what I had accomplished sink in. But it was also the final straw in a long, drawn-out relationship that officially ended just two months later.

So, in multiple ways, that final Jamaica trip was truly final.

Just like I left higher education behind, I faced a choice: let the sour moments stain the whole experience, or be grateful for what those endings made space for.

I’m choosing gratitude. I’m choosing to remember the celebrations, the milestones, the joy of four different eras of life marked in one colorful place.

What a run.

P.S. Kiwi graduates from High School in spring 2026. One of her dream destinations?

You guessed it—Jamaica.

So maybe... this is actually a to be continued?