In Prison For a Day

Faith, Forgiveness and Second Chances: What Volunteering Taught Me About ChangeFaith at Why Not Prosper Headquarters, Philadelphia, PA

Volunteering often stirs a complex mix of emotions. We may start with the desire to do good, but the experience can profoundly change us, revealing our own vulnerabilities and the shared humanity that connects us all.

When I signed up for a prison simulation exercise through my Women’s Connection group, I had no idea how deeply it would affect me.

The organization behind it, Why Not Prosper, was founded by Rev. Dr. Michelle Simmons. Inspired by her own experience of incarceration, she decided to support others like her. This grassroots approach immediately spoke to the power of personal wisdom in driving change.

As part of the exercise, we were all given a name and post-release scenario. I was “Harriet,” newly released after five years in prison. The seemingly insurmountable obstacles to reintegration overwhelmed me. Each station in the room represented a unique challenge: getting identification, finding transportation, securing employment, and locating housing. In the seven minutes allowed per station, I never seemed to have the correct document for the next stop on the way to living “on the outside”. The experience was a jolt to the senses about how much we take for granted in our cushy lives.

My journey didn’t end with the simulation. A subsequent opportunity to assemble “Love Bags” for women in a Philadelphia correctional facility brought me face-to-face with the real impact of incarceration. As part of the experience, we also agreed to serve a Thanksgiving meal the next day. Along the way, I met Faith, a 60-year-old operations manager for Why Not Prosper.

Faith’s story is a testament to resilience. Growing up with an alcoholic mother, she shouldered adult responsibilities from a young age.

As the oldest, it was up to her to get her brother and sister off to school, then feed them dinner. Mom’s drunken rages and beatings prevented her from a basic education. A six-year stint in the army followed, but after that, a life of dependency and prison.

As we served Thanksgiving dinner in the prison gym, the atmosphere was a mix of hope and stark reality. White tablecloths and flowers adorned the tables. Watching the women arrive in groups of thirty-five, the diversity of their stories and the common thread of humanity that bound us all, struck me.

… genuine kindness often requires stepping out of our comfort zones and confronting tough realities

This experience taught me that genuine kindness often requires stepping out of our comfort zones and confronting tough realities. It showed me that vulnerability — both in those we serve and in ourselves as we open our hearts to their struggles — is not a weakness, but a powerful catalyst for connection and change.

I learned, most importantly, that we all have the ability to help others. It’s a power we all possess, regardless of our past or present circumstances. Faith’s transformation from a life of addiction to one of service is a convincing reminder that everyone has the capacity to make a difference, no matter how dire their situation may seem.

Painting at the Formerly Incarceration Renaissance Museum (F.I.R.M.)

I asked Faith, what was the turning point for her to leave drugs and become Reverend Michelle’s right hand?

“Reverend got the best out of me when I could not see it in myself. The Lord keeps me strong.”

Faith’s journey from thirty-years of addiction to a college degree, then becoming a pillar of support for other women, was inspiring. Her words, “I gave myself forgiveness. I don’t want to live that life,” resonated deeply, highlighting the power of self-compassion in the face of past mistakes.

As I looked around at the women sharing a meal, each with their own complex journey, I was humbled by the realization that change often starts with one person extending a hand of kindness. In that moment, the line between volunteer and beneficiary blurred, and I understood that in helping others, we often find healing for ourselves.

Anna Maria DiDio is an author whose memoir and adoption-themed children’s books and more can be found on her website: amdidio.com . Her latest book, Grace’s Write Time, is a middle grade chapter book about friendship and belonging.

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In Prison For a Day was originally published in New Writers Welcome on Medium, where people are continuing the conversation by highlighting and responding to this story.

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Published on February 15, 2025 16:05
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