Trading Comfort for Courage
This episode of Oui Talk Raw, we’re talking to Jen Greenberg—a woman who turned her dream of island life into reality. Three years ago, she and her husband packed up their life in Charlotte, North Carolina, and moved to St. Croix in the U.S. Virgin Islands. We’ll dive into what it really takes to walk away from comfort, lean into courage, and start fresh in paradise. From culture shock to community, the magic and the mess, Jen shares what island living is really like—and how following your dream can change everything.Jen Greenberg: The Truth About Island Life
Finding Courage and Paradise: Jen Greenberg’s Journey from Charlotte to St. Croix
On this episode of Oui Talk Raw with Jennifer Busco on rBeatz Radio, we meet the radiant and adventurous Jen Greenberg—a former Charlotte resident who packed up her life, followed her intuition, and started over on the island of St. Croix with her husband Josh.
Jen shares the highs, lows, and real truths about living in “paradise,” from unreliable power to finding purpose in simplicity. Their conversation is inspiring, raw, and a reminder that courage often means just saying yes to that inner nudge.
Moving from Comfort to Courage
Jen spent 10 years in Charlotte before taking the leap to St. Croix. What started as her husband’s long-running joke about selling “coffee and cocktails on the beach” became a life-changing reality.
When asked how she found the courage to move, Jen explained:
“I have always been somebody that I get really uneasy after I get really settled and calm, and I kind of had hit that point, and I’m adventurous.”
For Jen, it wasn’t just about the island lifestyle—it was about starting fresh with her partner and creating a life that truly aligned with her spirit.
Life in Paradise: The Myths and the Truths
While Instagram-worthy sunsets and beach walks are part of her daily life, Jen stresses that paradise comes with its challenges:
- Unreliable power and internet
- Limited shopping and conveniences (yes, she misses Trader Joe’s!)
- Extreme weather and hurricane stress
- Healthcare challenges on the island
Her reminder is clear: “Paradise is a state of mind.” The island forces her to slow down, live with less, and focus on what truly matters.
Relationships and Community in a Transient Place
One unexpected challenge Jen faced was friendships. Many people come and go from St. Croix—seasonal workers, military families, adventurers starting fresh—so community can feel fleeting. But her background in real estate helped her build strong bonds with people who share her values. She admits, though, that island life has made her more cautious about who she lets close Jennifer jokingly points out: “St. Croix, people could be like, I’m running from the law, honey.” The reality? Some truly are.
Healing, Intuition, and Self-Trust
A powerful theme throughout this episode is intuition. Both women emphasize the importance of listening to that inner voice. Jen reflects on how moving to St. Croix gave her the space to heal from past struggles and abusive relationships, while also building trust in her own decision-making.
She says the move has made her:
- Less materialistic
- More courageous over time
- Deeply connected to nature and spirituality
- Intentional in her choices
Everyday Island Living
From Tart Wars (yes, it’s a competition over fruit tarts) to Mango Melee festivals, life in St. Croix is full of unique cultural traditions. Weekends are slower, often spent volunteering, enjoying the Botanical Garden, or just staring at the ocean from her window—a reminder of why she chose this path. Even during hurricane season, Jen stays grounded: “You just got to roll with it…everything’s gonna be fine.”
Key Takeaways from Jen Greenberg’s Story
- 🌴 Paradise is not perfection: moving away won’t fix everything—you still bring yourself wherever you go.
- 💡 Courage grows after the leap: the real challenge isn’t deciding to move, but choosing to stay through the ups and downs.
- 👫 Relationships shift: friends may come and go, but having the right partner makes everything possible.
- ✨ Trust your intuition: when your body, heart, and spirit nudge you—listen.
- 🌊 Less really is more: simplicity can bring freedom, joy, and healing.
Final Words of Wisdom
Jen closes the episode with a powerful reflection:
“I will never regret this decision… it has brought an immense sense of healing to my life that I needed.”
And Jennifer Busco ties it together beautifully, reminding listeners that this isn’t just about moving to the Caribbean—it’s about finding the courage to follow your intuition, wherever it leads.
✈️ Thinking about your own leap? Jen encourages anyone curious to reach out to her directly—or book a direct flight to St. Croix (STX) and see the “real green screen” for yourself.
About Me – Jen Greenberg
Creativity, persistence, and keen problem-solving skills are some of Jen’s greatest attributes and are what make her a well-versed Realtor and Property Manager. She began her real estate career in 2003 in Salt Lake City, Utah where she gathered extensive experience with first time homebuyers and buyers purchasing newly constructed homes. She studied interior design and gained a vast knowledge of the new construction process from start to finish.
After settling in Charlotte, NC Jen spent almost a decade working in one of the top real estate markets in the country. Countless hours of work behind the scenes and in the field managing hundreds of transactions for a top producing team gave Jen the opportunity to hone her skillset. Her background in real estate provided opportunities for her as a property manager adding this to her resume. Jen treats each client with a full-service approach and prides herself on taking the best care possible of everyone she transacts with.
Her knowledge, confidence and fun-loving personality brings much needed levity to any real estate transaction while maintaining attention to all the critical details to ensure the experience is as smooth as possible.
Jen is a proud mother of two young adult children and shares her life on St Croix with her husband and dog Max. She enjoys relaxing in the crystal-clear ocean, working on her green thumb, reading, doing yoga and spending time with friends.
Contact Jen at Jen@ColdwellBankerVI.com or 801-628-3982.
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