What does homelessness look like in an affluent suburb like Westport—and who truly gets to call it home?

In this deeply human episode, we go beyond the stereotypes to explore the hidden faces of housing insecurity in one of America’s wealthiest towns. At the heart of this story is Homes with Hope, a local nonprofit quietly rewriting the narrative on homelessness since 1984. From emergency shelter to affordable housing and wraparound services, they’ve been helping people not just survive—but rebuild their lives with dignity.

Featuring three thoughtful and inspiring guests, one of which lives in affordable housing in Westport.

💡 Inside the Episode:

• You’ll hear from three powerful voices, including Olena, a courageous mother who fled war-torn Ukraine and now lives in affordable housing at 122 Wilton Road. She shares her journey from refugee to rooted Westport resident—and how Homes with Hope helped her family plant new seeds of hope and independence.
• We also take you inside the Gillespie Center, a homeless shelter just steps from downtown, where residents talk candidly about the paths that brought them here and what it takes to move forward. Along the way, we unpack big questions: Who benefits from the invisible “safety nets” that cushion life’s blows? What happens when those nets aren’t there?

🌱 Communities vs. Castles:
We close with a heartfelt reflection on what makes a town feel like a true community. Why should the people who care for our children, serve our meals, and heal our wounds be able to live where they work? And how can we build towns that don’t just welcome—but truly include?

💬 Why This Episode Matters:
This episode is a powerful reminder: a stronger, kinder community is one that makes room for everyone. Westport is setting a high bar leading by example.

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