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3 Questions with Rosie Drumgoole of Deborah's Place

Posted on November 10, 2025   |   Updated on November 12, 2025
Emily Mack

Emily Mack

Deborah's Place event

Deborah's Place is hosting events during Homelessness Awareness Month. (Courtesy of Deborah's Place)

This "3 Questions With" is a sponsored interview in partnership with Deborah's Place

Deborah's Place has been helping women in Chicago find housing and stability for 40 years. Board President Rosie Drumgoole caught up with City Cast Chicago to share what makes their approach unique — and how her own story inspires her work.

The following has been edited for length and clarity.

What is Deborah's place and how does it support women experiencing homelessness here in Chicago?

“We are Chicago's largest and longest running provider of permanent supportive housing for single unaccompanied women experiencing homelessness. …We empower women to achieve housing stability, independence, and healing through housing supportive services, education community. That's why 90% of the residents remain housed after they are placed.”

At Deborah's place, you say that housing is the beginning, not the end, of the journey. What does that mean in practice for the women that Deborah's Place serves?

“I think a lot of times people say, ‘Oh, if you get cleaned up … then you can be housed,’ … But the way that Deborah's Place approaches this is, ‘Hey, you should get housing no matter what.’ Everybody deserves a home. It's a trauma-informed approach. It's a harm-reduction approach, and at the end of the day, it leads to long-term stability.”

How does your lived experience shape the way you lead and connect with the women that you serve?

“I know what it's like to not have a place to put your head at night … I know what it's like to have all your belongings in a garbage bag. I know what it's like to feel isolated. When my family was experiencing homelessness, I wasn't in school so I was isolated from my friends. I didn't have the typical high school experience.

[Now] I sit and I can talk to some of these young women … just having that conversation and being able to draw their personalities out, I see how they light up. That motivates me to continue advocating for this organization … I identify with them, I can see myself in them.”

On Nov. 12, Deborah’s Place is hosting a community conversation at Slant of Light Books in Old Town.

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