I spent an entire day in a maximum security prison and it was one of the most profound experiences of my life. Myself and 50 other entrepreneurs from the Mastermind Talks community participated in a program called Hustle 2.0 led by an incredible human named Catherine Hoke.

Our day at Kern Valley prison started with these words “we do not fire warning shots… if you hear gunshots, get against a wall immediately”. Shit got real, real quick.

I’m fortunate to say that I’ve never spent a day or night in jail and that’s part of the reason why I was so inspired to be a part of this very unique experience. I will openly admit that there are things I’ve done in the past that had I been caught I very well may have spent more than a few nights behind bars myself. I’m sure some of you reading this might also share this possibility.
Growing up in Scarborough I could count on two hands friends who had killed or been killed before the age of 20. Needless to say, my life could have gone in a very different direction had I drifted to the other side of the tracks. What made this opportunity so interesting for me is, I wanted to meet these men and learn about their personal journeys and hear their perspectives on life after decades of reflection. The men we met with are called “Maverick’s” in the program. Many are serving life sentences, some are eligible for parole and many will never experience freedom ever again.

I spoke with several of them one to one. Hearing them share the circumstances of their childhood, the challenges and unfair odds while growing up and ultimately the criminal act that resulted in them being incarcerated, was a very eye opening experience. Despite the harsh reality of the crimes that these men committed, sitting across from them you would never imagine that the soft spoken, polite, vulnerable human in front of you is the same person that was sentenced years or decades ago.

We also spoke about what life will be like if and when they are released. They shared their business ideas with us and we engaged in mock job interviews, giving them coaching and constructive feedback. I truly felt connected to each one of the Maverick’s that I spoke with and can honestly say that a few of them could even be one of my homies had we met under different circumstances.
The highlight of the day for me was Step to the Line. This is an exercise that involves all the guests and Mavericks lining up face to face, standing a few feet apart with only rows of tape separating us. The way it worked was we each stand on the first row of tape in front of us and we answer a series of intimate questions by stepping forward to the second row if our answer to the question is yes. The questions got deep and some got pretty dark. A few examples are:

“Have you lost a parent to gun violence?”
“How old were you when you first got arrested? 18, 16, 14, 12, 10, 8, 6…?”
“Have you lost a child?”
“Have you ever thought of killing yourself?”

The intention of these penetrating questions was to not only give some context to the reality of the Maverick’s lives before their incarceration, but to also show that there are serious issues that the men on each side of the line shared when they both stepped forward standing inches apart. By the end of the exercise, each and every one of us had a much deeper sense of compassion and empathy for the Mavericks and for one another.
Seeing who stepped to the line reinforced my belief that regardless how rich, successful and famous someone is, they may be suffering in ways that you can’t even imagine. It’s often those who’ve “made it” and reached the pinnacle of their success, that are the ones who are closest to losing it. They’re at the top of their mountain feeling that they have no one to talk to about what’s really going on so they numb their pain with whatever way they know how, which can often be self-destructive. Thankfully experiences like this provide the opportunity for those who need to open up the chance to share and receive the support they need. 

After we completed Step to the Line, it was time to battle the Maverick’s in a lip-sync dance off (which we sadly lost). The Maverick’s got some moves and showed us how to put it on. It was a true Cat Hoke dance party.

As our day was coming to the end, Cat requested that we take the time to fill out our “sweet sheets” and write down some positive, encouraging words for the Maverick’s we spoke with. She reminded us that in 15 minutes we will be on our bus traveling back to LA and the Maverick’s will be back in their cells and may not have another visitor for years. These sheets will hang on their cell walls and provide them with a bit of positivity and optimism. They also gave us our own sweet sheets and shared kind words of appreciation for our time together.
At dinner that night I felt an overwhelming sense of gratitude for my freedom and the great guidance I’ve had that has kept me on a positive path in life. I am so grateful to my parents for teaching my brother and I positive moral values at a young age. I couldn’t help but think how my life would be so different if I had made just one or two wrong choices during my teen years. I may have ended up on the other side of the tape.

My big take aways from this experience are to seek to understand others before passing judgement on them. Yes, some of these men committed crimes that are very wrong, however when you learn what led them to that moment you can understand how and why it happened. By no means does that justify the crime, but it does give us some insight on how these harmful actions can be intervened. My other take away is to keep believing that people can change with the right support and guidance and that everyone deserves a second chance. I will not forget these men and their stories. The lessons I left prison with will help me enjoy every moment of freedom I have.

If you’d like to learn more about Cat Hoke and Hustle 2.0 click here

I was given the privilege to bring my camera in to Kern Valley prison. These are a few of the photos that I captured. If you would like to see more you can see them here.