117. The Harsh Reality of Living Overseas: Week 4 - 6 in Uruguay with Boundless Life
In this deeply personal episode of Transform With Travel, Kelly Tolliday shares the emotional rollercoaster of weeks 4 - 6 in La Barra, Uruguay with Boundless Life.
What started as an exciting worldschooling adventure quickly turned into a crash course in the realities of living overseas — navigating injuries, grief, missing major family milestones back home, extreme weather, and the emotional complexity of leaving behind a strong village in Florida.
But through every hard moment, one thing became crystal clear: the power of community.
Kelly opens up about:
- Missing family milestones and family loss
- Multiple surfing and back injuries
- Why having a built-in village through Boundless Life changed everything
- The unexpected transformation that happens when you allow new people into your life overseas
This episode is an honest look at what people don’t always talk about when it comes to worldschooling, family travel, and relocating abroad: life doesn’t pause just because you move somewhere beautiful.
And yet… even through the hard moments, there’s still magic in slowing down, watching the ocean every day, and creating a life that feels deeply aligned.
In This Episode:
- Why Kelly’s family chose Uruguay for their first Boundless Life program
- The emotional reality of leaving a strong support system at home
- Building deep friendships quickly while living abroad
- The “week 4 slump” many families experience during long-term travel
- How the Boundless Life community became a true support network
- Why village and community matter more than location
- Reflections on parenting, identity, and personal growth overseas
- Surfing injuries, SI joint rehab, and navigating healthcare abroad
- Mid-cohort travel to Punta del Diablo & Santa Teresa National Park
- The beauty and difficulty of creating a life outside your comfort zone
Mentioned in This Episode:
- Boundless Life
- La Barra, Uruguay
- Workschooling
- Episode #55: Parenting Across Cultures with Elodie Fourchaud
Boundless Life Discount Code :)
If you’re considering a Boundless Life program and want to ask questions about Kelly’s experience, feel free to reach out.
Use code KELTOL11 for €400 off your first program.
(And yes — Kelly shares transparently that she also receives a future program credit if you use the code.)
Connect & Follow Along :)
- Podcast: Transform With Travel
- Instagram: @kelly.tolliday
- Follow the family’s Uruguay & worldschooling journey for more honest reflections on travel, parenting, surf life, and building community abroad :)
