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Life's Voices: A New Calling Leads to a Second Career

Ann-Elise Henzl
City on a Hill Executive Director Diane De La Santos visits one of the organization's afterschool programs

During this holiday season, WUWM reporters are sharing stories of local people who give back to the community. In this installment of our year-end series Life's Voices, we meet Diane De La Santos.

She works in urban ministry as executive director of City on a Hill, a non-profit on Milwaukee's west side. It provides a number of services, including a free health clinic and afterschool programs for central city youth, making the job a natural tie-in with passions De La Santos has had her whole life.

"I grew up, actually, in the civil rights era, watching Dr. King work for justice, then majored in ethnic and intergroup relations in college and worked cross-culturally and in communities of color for a period of time as a young woman," De La Santos says.

Yet De La Santos says it took years to get a job that so closely matches her interests. She says she took a "career detour" that lasted two decades before she felt the need to make a change.

"I had pursued a career in business and organizational administration, you might say, as a single mom trying to climb out of poverty. And in about the year 2003-2004, determined that I really wanted to do something with the rest of my career. And I was just sensing a call to respond to the problems in the central city of Milwaukee, and just wanted to do something about it," De La Santos says.

At that time, De La Santos was serving as vice president of public affairs for Aurora Health Care, and her new career opportunity presented itself. The nonprofit City on a Hill had formed, to reuse Good Samaritan Medical Center, a hospital Aurora had shuttered. De La Santos first served as a loaned executive to help the struggling organization get on its feet. After a year, she took over full-time.

"Our challenge here was really to do two things. One, to repurpose the hospital facility and help a neighborhood that was deteriorating around it and to bring life back to the neighborhood, and the second challenge was to impact lives of children and families struggling in this neighborhood," De La Santos says.

De La Santos says the large, shuttered hospital itself had become part of the problem.

"When you have a major facility that is essentially boarded up and dark, that draws crime to a neighborhood. And so I think within the first couple of weeks of my being here, there was a drug-related double homicide on the corner of the property. I remember looking out my window one day and watching my car being broken into," De La Santos says.

De La Santos says it was a huge undertaking to breathe new life into the property. And she admits she didn't always know what she was doing.

"I knew I was supposed to be here and I just believed that if I stepped into the challenge the answers would come, which they have," De La Santos says.

As the answers have come, they've allowed De La Santos to help repurpose nearly the entire old hospital building. It's been transformed into City on a Hill's health clinic and afterschool center, plus space for job training, housing for families and seniors and programs run by other non-profits. In helping to orchestrate the renaissance, De La Santos says she's learned a thing or two about herself.

"I have a bit of stubbornness to me, that I'm not a quitter, and that my whole life really has prepared me for this work. And I think that's true of all of us, that we are given talents, gifts, opportunities, experiences all along the way in our life that prepare us for the next thing, and that if we just take a look at our own lives it'll often help to direct us to a calling that is perhaps surprising, perhaps doesn’t look like the next thing that we should do, but is exactly what we are equipped to do."

Ann-Elise Henzl became News Director in September 2017.
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