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.