Sheboygan Stories: Unhoused and Unheard

In this heartfelt conversation, Jenna shares her journey of struggle, survival, and resilience. From setbacks to new beginnings, she opens up about what it truly means to start over and why everyone deserves another chance. Her story is honest, powerful, and a reminder that hope can be found even in the hardest places.

Chapters

• (00:00:24) - Second Chance
• (00:00:48) - Rock Bot...

In this special episode, Scott and Kathleen share the difficult decision to dissolve Sheboygan Area Pay It Forward. They reflect on the challenges, lessons, and impact of their work, while reaffirming that the podcast will continue as a space to share voices and stories from our unhoused neighbors. Honest, heartfelt, and deeply human — this is a chapter you won’t want to miss.

Chapte...

In this episode, Scott sits down with Pastor Ruth from St. Luke United Methodist Church in Sheboygan to explore the role of faith in serving people experiencing homelessness. Pastor Ruth brings powerful insight into how compassion and boundaries can work hand in hand, and why faith communities often find themselves on the frontlines of service.

From offering safe spaces to addressing spi...

In this episode, I sit down with Jackie from Elevate Yoga, a downtown business owner located in the heart of “unhoused central.” Jackie shares her firsthand experience navigating the complex realities of homelessness, loitering, safety, and humanity in shared public spaces. She opens up about balancing compassion and understanding with the everyday challenges of keeping her doors open. W...

In this powerful episode, we sit down with someone who’s been fighting a war on two fronts—navigating life without stable housing while also facing the grip of addiction. This honest, raw conversation highlights how deeply connected these two struggles often are, and the strength it takes to push forward through both.

We talk about the barriers to recovery, the stigma people face, and th...

What do people think they know about homelessness — and what’s actually true?

In this episode, Scott sits down with his wife and co-founder, Kathleen, for a no-fluff conversation about the most common myths surrounding homelessness: the belief that people choose this life, that all unhoused individuals are addicts, and that help is always accessible. Together, they reflect on what they'v...

Hidden homelessness through the eyes of a youth or single adult.

In this episode, Shana shares what it’s like to live without a place of her own — moving between couches, temporary spaces, and uncertain nights. Her story highlights a side of homelessness that often goes unseen but affects so many.

With honesty and resilience, she re...

Interview with someone who recently found housing after living unhoused.

Amanda opens up about her journey from in-patient rehab to shelters to finally finding a place of her own. It's a raw and honest look at what the path to housing can really look like — one step at a time, and not always in a straight line.

Chapters

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A caseworker talks about their role, what keeps them going, and the barriers they see

In this episode, we go behind the scenes with a caseworker from Lakeshore CAP, a local organization working directly with individuals and families facing housing instability. This conversation shines a light on the human side of social work — the long hours, the hard conversations, and the heart it take...

A personal story of survival and resilience from someone with lived experience.

In this powerful episode, we meet Jimmy — a man who's lived on and off the streets of Sheboygan for a couple years. Recorded outside Mead Public Library in Sheboygan, this conversation doesn’t take place in a studio. It takes place where Jimmy lives his truth: on the sidewalk, with nothing to hide.

Jimmy open...

A conversation with Scott and his wife about why they started Pay It Forward.

This podcast gives a voice to the people we so often walk past but rarely hear from—those experiencing homelessness here in Sheboygan, Wisconsin. But before we dive into other people’s stories, we thought ...