My Day in Prison: The Day I Became a CEO Mentor with Defy Ventures
Last week, before the sun was even up, I got in my car and began the long drive to Logan Correctional Facility in Lincoln, Illinois. I knew I was headed into a prison. What I didn’t know was that I was about to walk into one of the most meaningful, perspective-shifting experiences of my life.
I volunteered with Defy Ventures, a nonprofit that works with currently and formerly incarcerated men and women – people they call Entrepreneurs in Training (EITs). Their program, CEO of Your New Life (CEO YNL), uses entrepreneurship, personal development, and career readiness training as a path to transformation. It’s part business school, part character course, part healing space. And volunteers like me play a key role in bringing it to life.
I thought I was going there to help. I didn’t expect my life to be changed forever.
Walking In
After the security checks, a series of reinforced doors, and a walk through the prison yard to another multipurpose building, I finally stepped into the room where the day’s work would happen. More than 40 people – EITs, volunteers, and alumni – were gathered. The energy was almost electric: part nervousness, part anticipation, part something like hope.
What struck me immediately was the warmth. Women in state-issued uniforms clapped for us as we walked in, smiled, and welcomed every volunteer like we were long-lost coworkers returning to the office. Not out of obligation, but out of gratitude – genuine gratitude for time, for presence, for being seen.
We were told we weren’t allowed to touch one another – no hugs whatsoever. We were allowed to shake hands, high-five, or fist bump – nothing more.
But this wasn’t the prison atmosphere we see on TV. This was a community. A classroom. A room full of human beings doing the hard work of becoming someone different than the person who first entered those gates.
The Humanity We Forget Exists
One of the first exercises we participated in was called “Human Bingo,” an icebreaker of sorts. We were given a bingo card with things like “Likes to run,” “Has more than two siblings,” “Has a child,” and other shared traits. It was our job to introduce ourselves, mingle, and start conversations about who we were.
In this moment, I was able to meet the EITs for the first time and learn a little bit about them. They ranged in age from very young to probably their late 50s. Some had been in prison for a short time; others had been in for nearly 30 years. As we chatted, I learned small but meaningful things about them: Jerni, who was a vegetarian and struggling with what to eat in prison; Brittany, a veteran with a passion for teaching people how to garden and eat healthy foods; McCarah, who loves spicy food with a passion; and Jackie, a young mother who gave birth to her daughter while incarcerated.
The game moved fast, but it made us comfortable with one another before the business pitches and the competition to see who would “win” began.
After the icebreaker, volunteers stood up one by one and introduced themselves at the front of the room. We were only allowed to use our first name and an adjective that described us (I was Tenacious Trish), what industry we were in and our job title, and a “win” to share with the EITs.
When I introduced myself, I decided to share something I’ve shared with very few people.
“My name is Tenacious Trish. I am the CEO of a marketing and PR firm, as well as a film production company. My win is that I started my company 19 years ago as a way to escape domestic violence in my marriage and provide for my son. Since then, I’ve worked to empower women and give back to others who have walked in my shoes.”
Entrepreneurship as Redemption
For most of the day, I had the chance to sit with EITs as they worked through business plans they had been developing for months, then stood up and gave Shark Tank–like pitches to groups of volunteer mentors. The level of effort, creativity, and grit in those plans would rival many pitch decks I’ve seen in the corporate world – especially considering everything was done without internet access, using only the prison library and resources from Defy.
An adult preparatory program for skilled laborers.
A clothing line.
A traveling workout program for veterans.
A mobile tattoo shop.
An eco-friendly cleaning supply company.
Every idea had purpose. Every pitch had heart. Every presenter had a story.
Some EITs had never given a presentation in their life. Some were so nervous they shook. But they stood up anyway and delivered visions of what they hope to build when they are released – legitimate businesses, meaningful careers, better futures.
That’s the magic of Defy Ventures: it gives people something bigger than their sentence. It gives them a plan. It gives them belief. It gives them the tools to disrupt a cycle that too often feels predetermined.
And volunteers like me – business leaders, CEOs, marketers, managers, entrepreneurs – get the chance to help shape those futures in real time.
We had several rounds of pitches that led to the semi-finals and finals. At the end, judges’ scorecards were added up and the winner was crowned: Briana, whose “Prepping for Success” company helps tutor skilled laborers like electricians when they need to take certification exams.
There were prizes for first through fifth place – small cash awards to be given upon release.
These pitches also marked the end of their program; once they presented, each EIT officially graduated – quite the feat after this nine-month-long journey. In addition, each EIT is awarded a Chromebook upon release to help them reenter society and their new life.
The Exercise I’ll Never Forget: Step to the Line
One of the most powerful moments of the entire day was the “Step to the Line” exercise. Volunteers and EITs stood facing each other on two parallel lines. A facilitator read a series of statements – some light, some deeply personal – and if a statement applied to you, you stepped forward. Then you stepped back. Forward. Back. Over and over. What started as a simple physical movement quickly became one of the most vulnerable, humanizing experiences I’ve ever witnessed.
As the prompts grew heavier – “Step to the line if you’ve ever felt abandoned.” “Step to the line if you’ve ever struggled with self-worth.” “Step to the line if you’ve ever made a decision you deeply regret.” “Step to the line if you’re a veteran.” “Step to the line if you’ve been arrested.” “Step to the line if you didn’t have enough to eat as a child.” – something remarkable happened. The line between “us” and “them” disappeared. We stepped forward together. We stepped back together. We shared pain, fear, shame, joy, resilience, and humanity.
The young woman I stood across from, Keisha, and I locked eyes. Each time we stepped forward, we would fist bump – an acknowledgement of our similarities. As the questions got heavier, our eyes stayed locked in the most emotional way – tears glistening as we tried to hold it together. I saw her pain. I felt her emotion. I saw into her soul. It was intensely profound and powerful.
In those moments, you could feel the room shift. The uniforms stopped mattering. Our résumés stopped mattering. What was left were humans with overlapping experiences, mirrored emotions, and stories that looked far more alike than different. It was raw. It was uncomfortable. And it was deeply, profoundly connecting.
It also showed us how any of us volunteers could be standing in their shoes. One wrong move, one bad decision, one unfortunate circumstance could land any one of us right there.
It took my breath away.
It made me love each of these women and feel such gratitude for their vulnerability.
The Story That Shook Me to My Core
I heard many stories that day that impacted me forever – from Fefe and Desiree, who spoke openly about faith and God, to Dawn, who told me about growing up with no money for food or clothing and how hard her life had been. But the person who made the biggest impact on me was Jacki – a young Latina woman who was as stunningly pretty as she was sweet.
She came up to me later in the afternoon and said something that shook my soul:
“Hi Trish. I wanted to come over and say how sorry I am that you experienced domestic abuse. I have too. Thank you for sharing that with us.”
What?
This young woman standing in prison was saying she felt sorry for me?
It blew my mind to see her standing in front of me, tears in her eyes, filled with compassion.
I looked into her almond-colored eyes with tears in my own. Earlier, I had noticed a gorgeous little girl in the crowd of loved ones who looked identical to her. I knew it had to be her daughter.
“Is that beautiful little girl your daughter?” I asked.
“Yes,” she said.
Then she told me her story.
While pregnant with her daughter, her child’s father was physically abusive. One winter night he came home and threw her dog, her beloved companion, outside into the cold. She was terrified of him, so she grabbed a small knife from her bedside to check on the dog and bring him inside. As she stepped outside, he hit her hard in the face with a boot. In raising her hand in self-defense, she stabbed him, and he subsequently died.
“I didn’t mean for that to happen. I didn’t mean to kill him,” she said.
I looked at her with compassion.
“I know you didn’t,” I said. “I was in that very same situation. What happened to you could’ve been me. I understand, and I hope you’ve forgiven yourself.”
She went on to tell me she had her daughter, who had just turned five, while incarcerated. Her daughter is now getting old enough to ask why Mommy doesn’t come home – and where her Daddy is.
“Someday I will tell her the truth,” Jacki said. “But for now, I’ve told her I’m in school and will be home soon – and that her Daddy is in heaven.”
Jacki was given 15 years for her crime, but with good behavior she may be released in two years, when her daughter is seven.
I have thought about Jacki and her story every day since I left Logan, waking at times in the middle of the night in tears. How could the system be so broken? Why is this the story of so many women?
And I think about how it could’ve been me.
Graduation: The Moment That Hit Me Hardest
At the end of the day, there was a graduation ceremony for EITs completing their CEO of Your New Life program. Caps. Gowns. Certificates. Applause that shook the room. Some of them had never graduated from anything in their lives – not even high school. This was a defining moment.
Some graduates had family there – parents hugging their children, partners crying, toddlers clapping without fully understanding why. For others, Defy staff and volunteers were the family in the room.
Each graduate was called up to the stage to accept their certificate. Photos were taken. Then they had the opportunity to bring family members up and introduce them to the entire group. Many used the moment to thank their loved ones for support; many parents spoke about how proud they were and how much they loved their child.
There wasn’t a dry eye in the house.
I cried like a baby.
“This segment is sponsored by Kleenex”, a volunteer next to me whispered.
We cried some more.
One graduate, FeFe, said something to me I’ll never forget:
“In here, you keep your head down. You can’t trust anyone. Defy was the first time I was able to be vulnerable and make true friendships. It was the first time since I’ve been in prison that I didn’t feel like I have to walk on eggshells. It gave me hope.”
That sentence alone made every mile of the drive worth it.
What I Learned
I went to Logan Correctional Facility thinking I would teach something. Instead, I learned more about humanity, humility, and hope in one day than I have in most business conferences combined.
Here’s what I took away:
1. People are more than their worst decision.
Behind every crime is a story. Behind every sentence is a person who could be doing something incredible with the right support.
2. Redemption is real—but it requires opportunity.
Transformation isn’t magic. It’s mentorship, education, community, belief.
3. The world changes when we show up.
Volunteering doesn’t just impact the EITs. It changes you – your assumptions, your biases, your understanding of justice and mercy.
4. Programs like Defy work.
Graduates find jobs faster, stay employed longer, and have dramatically lower recidivism rates than national averages. When people are given a real pathway out, they take it.
My Call to You
If you’ve ever wondered how to make a meaningful impact – not just a donation, but a human-to-human impact – Defy Ventures gives you the chance.
You don’t need to be a CEO. You just need to be someone who believes in second chances.
One day inside that facility reminded me how much potential sits behind bars in this country. How many brilliant, talented, passionate people are waiting for someone to say, “I see you. And I believe you can do this.”
It showed me that we shouldn’t be defined by our worst mistake.
It taught me that people can reform and change.
It showed me that good people can make bad decisions.
I walked out of Logan with a heavier heart – but also a brighter sense of what is possible.
And I can say this with absolute certainty:
It won’t be my last day volunteering with Defy.