The day I went to prison was one of the most transformative days of my life.

That might sound crazy but it’s true. Last week, I traveled to California to meet some of my colleagues at Defy Ventures to participate in a graduation event at the Medium Security California City Correctional Facility or “Cal City” as it’s referred to. Defy is a national nonprofit that provides entrepreneurship and personal and professional development training for currently and formerly incarcerated individuals. This event was the culmination of nearly 9 months of programming inside this facility, essentially helping these men prepare to make the most of their second chance.

Defy’s mission is to shift mindsets so that people with criminal histories have their best shot at this kind of second chance. And while I’ve been a first-hand witness to our work shifting people’s mindsets (including my own) on the reentry side, my two and a half years at Defy had gone by with barely seeing the inside of a prison. The pandemic halted all of our in-prison programming, so this would be my first experience truly going inside.

The anxiousness and excitement built inside me as the days neared. Then, a winter weather advisory loomed over the Tri-State area the night before my plane was due to take off. I held serious doubts that my trip might be canceled. I thought to myself, “Has anyone ever wanted to go to prison this badly?” But the morning came and went with nothing but flurries and some wind, and soon I was in Los Angeles boarding the bus to Cal City.

The bus ride to prison was oddly scenic, supposedly a rarity due to the rainy weather the landscape had recently seen. As we got deeper into the 90 minute drive, several wide lanes soon became a narrow two and the noisy LA traffic became a distant memory. And as we pulled into the facility’s parking lot, I realized just how isolated things felt. That effect hit before even stepping into the prison. I looked around, being encircled by the vast Mojave Desert, expecting to see a tumbleweed go by. I was a long way from Manhattan. But the stillness wouldn’t last long.

After clearing the gate check and being processed by security, the door to the event room opened up and music began blasting. A group of EITs (short for Entrepreneurs in Training - which is what we call our participants) cheered us on, high-fived us, and put leis around our necks as we came in. Many were smiling with ear-to-ear grins. It was like coming out of the tunnel at an NFL game. The EITs were just as excited as I was. And after playing a networking game and sitting for the event introduction, I—along with Defy’s volunteer business coaches— danced down the aisle as if we were at Jim and Pam’s wedding in The Office.

 

That day, I was no longer Kyle O’Connor. I was officially “Kind Kyle,” my Defy moniker since Defy uses fun, alliterative first-names as a positive label. I like to think that Kind Kyle brought out the best dance moves in me, but I can’t be so sure. 

This was all a stark contrast to the menacing appearance that a prison has from the outside, the dehumanizing element that the American prison system is infamous for. It was also a stark contrast to who we’ve been programmed to think currently incarcerated individuals should be. Mass media makes us picture hulking tough guys with no emotion, and uses labels that Defy rejects, like inmates/prisoners/convicts. That’s not what I saw at all. I saw just the opposite.

And the joys of the day were just getting started. Much of the afternoon was spent listening to the EITs pitching their business ideas in small coaching groups. These are ventures that many of them have hopes to launch at some point after returning home, something that Defy will also help them with, as a productive outlet and means of economic empowerment. They thanked us incessantly for our feedback through words of affirmation and appreciation cards. 

After the initial coaching rounds, we participated in Defy’s signature “Step to the Line” activity. “Step to the Line” is an empathy building exercise where EITs and volunteers stand facing each other a few feet apart across two lines on the floor. The moderator reads out statements based on things in our pasts and belief systems and, if each of us as an individual finds it true, you step to the line. A few examples of prompts are:

• “I have earned a four year college degree.”
• “I have done criminal things for which I could have been arrested but did not get arrested.”
• “Violence took place in my home growing up.”
• “Not forgiving others is hurting me.”
• “When I was 18, I didn’t think I’d make it to 21.”

 

The room remains silent except for the moderator. All you see is people stepping to the line or staying back. It’s hard to tell how much time goes by because it’s so moving. You can imagine how deep this gets…crying is not uncommon…I was on the verge of tears myself.

It’s the ultimate activity that not only highlights our similarities and differences as humans, but it’s also the best visual representation of the effects of systemic racism I have ever seen. For context, based on my personal observations and assumptions, the majority of Defy’s volunteers would identify as White whereas the majority of the EITs would likely identify as African American or Latin American. 

Towards the end of the event and after the pitch competition, where five EIT finalists won IOUs ranging from $100-500 upon their release, there was the graduation ceremony. This was the portion where EITs wore caps and gowns and came up to the front of the room to accept their Certificate of Entrepreneurship from the Drucker School of Management at Claremont Graduate University. One EIT even sang a song he wrote called “Defy the Odds” while playing a guitar. EITs’ parents could be in attendance and many came up to hug their sons.

 

In the final hour of my first full day in prison, as the event winded down, I got into a conversation with the mother of one of the graduating EITs, “Amazing Adrian.” She pointed to him and said, “I have three sons. He’s my oldest, but he’s still my baby.” She agreed with my acknowledgement of how proud she should be. He was now not only the CEO of his new life, but a man who is well on his way of his own journey of personal transformation. We spoke briefly about the importance of programs like Defy for the lost men in our society today and how Defy, in particular, was a stellar program.

It made me think about my own graduation and how happy my parents were that day. I remember my family glowing. Their every expectation was that I’d graduate college, but they still showed up on that day as proud as if I had won a Nobel Peace Prize. 

In no conceivable way was prison ever a destination where I thought I’d end up. My sheltered upper-middle class childhood in Bergen County, NJ, was the furthest thing from that environment. But life takes us on many twists and turns, some that take us through the Mojave desert. And it’s beautiful moments like this that remove us from our bubbles and force us to start seeing things from another perspective. 

After leaving the prison gates behind for good and shuffling my way to our bus back to Sherman Oaks, I double checked my pockets to make sure I had collected my ID back from security. Thankfully, I had. But there was another piece of paper rustling around in there as well. As the bus pulled away from Cal City, I looked at the paper in my pocket…

 

 

Thanks for that, Amazing Adrian. Kind Kyle hopes to talk with you again soon.