Leading With Humility: A Youthlinc Journey to Cuba

By: Nathan Anderson

Over the holiday season, Youthlinc sent out two  Friends and Family trips rooted in connection, curiosity, and shared reflection. This journey brought together people of different ages, backgrounds, and relationships, united by a desire to learn, listen, and experience life beyond our usual routines. Over the course of the trip, we engaged with Cuban communities in meaningful ways through cultural exchange, conversations with local partners, moments of service, and nightly reflection. What emerged was an experience that challenged assumptions, deepened empathy, and reminded us of the power of showing up with openness, humility, and care.

Music and Art

Many of our experiences centered around music, dance, and other cultural expressions that highlighted Cuban resilience in the face of trauma and hardship. We had the opportunity to visit a vinyl master who guided us through the history of Cuban music and how it has been distinctly shaped by the country’s evolving relationship with the United States across different eras. We also learned about Cuba’s deep African heritage and the essential role it plays in shaping the nation’s identity. Throughout the trip, we attended a cabaret performance, a ballet, and a jazz club, immersing ourselves in the rich, vibrant diversity of Cuban art and culture.

Entrepreneur Program

We were also privileged to pilot a new entrepreneurship program during this trip, an opportunity that felt both timely and meaningful. Historically, entrepreneurship in Cuba has been extremely challenging due to the country’s socialist economic structure. In recent years, however, there has been a gradual push to open the private sector, creating new, though still complex, pathways for small business owners. In partnership with our Cuban counterparts, Youthlinc sought to explore how we might support this emerging entrepreneurial landscape. Our partners in Cuba identified five entrepreneurs across a wide range of sectors, including a perfumist, a construction company, a media and music enterprise, a 3D printing business, and a cleaning products entrepreneur. Engaging with these individuals offered a fascinating window into how Cuban entrepreneurs navigate a dynamic and often restrictive environment and adapt creatively to limited resources.

Mosquito-Borne Illness and Supplement Drive

During our pre-trip preparations, we stayed in close contact with our partners in Cuba to coordinate logistics, ensure smooth execution, and thoughtfully plan the experience as a whole. In October, we were notified that the island was facing a severe wave of mosquito-borne illnesses that were rapidly spreading and deeply affecting communities.

The situation had become dire due to multiple factors. Hurricane Melissa, the strongest tropical cyclone of 2025, struck the eastern side of the island just months before our trip, leaving widespread damage in its wake. At the same time, Cuba’s rainy season running from May through October created wet conditions for mosquito populations to surge. Fuel shortages further compounded the problem by limiting trash collection, leaving waste in the streets that became additional breeding grounds for mosquitoes. Together, these conditions formed a perfect storm for the rapid spread of mosquito-borne illnesses.

Making the crisis even more severe, access to over-the-counter medications in Cuba is extremely limited. As a result, many people who fell ill were unable to receive proper care, causing thousands to suffer gravely from illnesses that are often preventable and treatable elsewhere.

Immediately after hearing this heartbreaking news, Youthlinc initiated a community drive for supplements and over-the-counter medications, based directly on requests from our Cuban partners. We felt it was essential to rally our generous Youthlinc community to respond in a tangible way and provide support to those most affected. The response was overwhelming. Our community donated hundreds of bottles of acetaminophen, magnesium, zinc, electrolytes, and other essential medications. Seeing people step up so quickly and generously was deeply moving and reaffirmed the power of our Youthlinc community.

Once the supplies were gathered, our teams worked closely with our Cuban partners to create a thoughtful and sustainable distribution plan. Team leaders organized the donated items into household kits to ensure the medications could be shared in meaningful and practical ways. This process was guided by local insight, ensuring that distribution efforts aligned with real needs on the ground.

Throughout our time in Cuba, we carried these supplies with us and distributed them to the many people we met along the way. Medications were shared with professors who hosted lectures, neighbors near our accommodations, our hosts, guides, local partners, and entrepreneurs. The gratitude we received was profound. We were repeatedly told how difficult these medications were to obtain and how vital they would be to families’ recovery and well-being, making the impact of this effort both immediate and deeply felt.

This experience served as a powerful reminder that our time in Cuba was not only about learning and exchange, but also about showing up in moments of real need. By listening closely to our partners and responding together as a community, we were able to offer support that was both practical and rooted in relationship. The supplement drive reinforced the deeper purpose of our trip: to lead with humility, act in solidarity, and walk alongside our Cuban partners as they navigate complex and ongoing challenges. It was a beautiful reminder that when you lead with service, only beautiful things will happen. 

Community and Humanitarianism

One of the most resonant parts of the trip was our nightly team meetings. Each evening, we gathered together at our accommodations and made space to thoughtfully digest everything we had observed, learned, and experienced throughout the day. These moments of reflection became an essential part of our time together.

Cuba has a fascinating, interwoven, and complicated relationship with the United States, which made it all the more important to intentionally create space for collective processing. Coming together as a community allowed us to navigate the complexities of this experience with care and openness. As a group, we felt it was vital to reach beyond political and historical complications and instead connect to the shared humanness of the people we encountered, rather than allowing differences to create distance.

As a team leader, one way I encouraged this reflection was through a challenge. During our first team meeting, I shared with the group: Youthlinc believes that although this trip is not focused on direct, hands-on service, it still deeply aligns with our mission of creating lifetime humanitarians. I want you to think about why we believe this as you move through the trip. You don’t have to agree with me. There are no right or wrong answers. But on our final night together, I’m going to ask what you think, and whether this experience has informed you as a lifetime humanitarian.

Throughout the remainder of the trip, we encountered countless moments filled with warmth, understanding, new perspectives, and opportunities to confront challenging biases and preconceived notions. In a remarkably short amount of time, we were changed in meaningful and lasting ways.

On our final night in Cuba, we gathered together one last time, and I asked the team to reflect on the original challenge. Their responses were deeply moving. We spoke about how learning firsthand about a country so often framed as an adversary allowed us to move beyond black-and-white narratives and instead meet one another as allies. We discussed how gaining a deeper understanding of the systems and structures shaping Cuban communities helped us better grasp the real-world challenges people face, leaving us with a more nuanced and compassionate perspective. We reflected on how responding to a moment of need by bringing medical supplies strengthened our understanding of what it means to act as humanitarians. And ultimately, we talked about the importance of setting aside differences and choosing to love one another as neighbors, no matter where in the world we are.