What Visiting a Maximum Security Prison Taught Me About Entrepreneurship and Life
I recently spent a day coaching and mentoring inmates at a maximum security prison in California.
This experience was organized by Hustle 2.0, a dynamic nonprofit organization founded by Catherine Hoke, author of A Second Chance: For You, For Me and For the Rest of Us, which was published by Seth Godin, and with the forward written by Sheryl Sandberg. Hoke is on a mission through her programs for employment, entrepreneurship and personal development to help inmates reenter society as successful entrepreneurs and employees.
I jumped at the chance to go but I didn't expect to come away with such powerful insights and lessons. Those 12 hours changed my life permanently.
“If you hear a gunshot, lie flat against the wall.”
Kern Valley State Prison is a two-and-a-half-hour bus trip from Los Angeles. It was 5:30 a.m. when I joined a group of other entrepreneurs to get to the prison on time. We were all pretty nervous and on edge. I’d never been in a room with a convicted killer before. Despite all the protection we had, there was still danger. Kern Valley is a level 4 maximum security prison with a reputation for violence.
So when we were told to lie flat against the wall if we heard gunshots, I knew they were serious. After passing through an endless stream of locked gates, I felt confused and knocked off center.
I don’t know what I expected, but it wasn’t a DJ pumping out loud rap music! The inmates weren’t sitting quietly around a table. Instead, they’d formed an archway with their hands and were throwing out high fives with an explosion of excitement. This felt more like a party than a level 4 security prison. This was a celebration of life, not a time for punishment.
“Tell me your life story in one minute.”
We broke the ice with speed dating.
I sat across from a guy in his early 40s. He’d killed at 19, been incarcerated for 22 years -- four of those in solitary confinement -- and still has nine years to serve. He told during his time of forced isolation is when he’d had his pivotal moment.
I was curious to know more…
He said that during his time in isolation, he had nothing to do but ask himself why. Why had he killed? What led to that life-changing (and life-defining) choice? He told me that during this time of intense reflection and introspection, he’d learned to love, accept and forgive the person he’d been.
He had made peace with his choices to the point where the man he was back then no longer exists. This blew me away. I realized I’d come in with a “judgy” attitude. I hadn’t expected to meet someone so self-aware in prison. This conversation taught me that your past doesn’t need to define your future.
You may not be able to erase past events, but you can reach a point where they no longer have to define who you are. How often do you get stopped because an old identity is dictating how you act in the present?
If an inmate can let go of who he was and love his way to an entirely new identity, then so can you.
“Who here has considered committing suicide?”
Next up, we formed two lines facing each other. Inmates on one side; entrepreneurs on the other.
Our instructions… if your answer to the question is yes, then move back five spaces. If not, stay where you are. These questions got deep. Did you lose a parent before you were 18? Have you ever considered suicide? Have you ever driven a car while under the influence? Have you ever thought about killing someone?
For every single question, at least one person moved from both sides of the line -- without exception.
Inmate or entrepreneur, we were all connected by shared experiences. Some of us had been caught, some of us hadn’t. Some of us were just one degree of separation from those inmates serving time. Some of us had done stuff (such as driving under the influence) that, if we’d gotten caught, would have landed us in jail.
This was such a powerful moment for me.
We all make mistakes -- some more life-changing than others -- but most of us get a second chance to make a different choice every single day. The real question is, are we making the most of that freedom?
If you’re reading this, you are privileged.
If you’re reading this, there’s a good chance you won the birth lottery! You were born into a country and a community full of opportunity. You have family, friends and access to resources, information and tools.
You have your liberty, and you’re free to live your life however you want. The only thing limiting you is you.
We closed out the day with a lip sync battle. I was exhausted. Emotionally drained and suffering from a huge vulnerability hangover. I’m known for throwing good moves on the dance floor, but even I wasn’t playing all out when it was our turn to battle. The inmates beat us hands down. They weren’t tired or drained. Instead, they were exploding with life, giving it everything they’ve got. I couldn’t understand their surge in energy.
Until it hit me…
When I leave this room, I go back to my beautiful Austin apartment and my “privileged” life. They go back to their cells. For me, this was just another day where I hold the reins. For them, this was an isolated moment of experiencing something that resembles “normal.”
This brings me to my biggest takeaway.
If you have your physical liberty, you can live an unrestricted, extraordinary life. There’s literally nothing stopping you but you. No incarceration. No systemic oppression. Just your thoughts, beliefs, choices and perceived limits.
As Andre Norman, a former convict turned international speaker, said, “I know people in the world today who aren’t free. They’re slaves to work, they’re slaves to stereotypes and slaves to cultures and customs they don’t even believe in. Not being in jail does not mean you are free.”
If you have the privilege of free choice, perhaps you also have a responsibility to use it. Go after the scariest of goals. Set your sights higher. Take risks. Dream bigger and bigger. Ask for more and more. Grab life as hard as you can and create a life that’s worth living -- instead of allowing glass walls to keep you locked away.
That’s what the inmates I met taught me. They reminded me I have so much. They reminded me just how limitless I really am. I walked away from that maximum security prison with an insane zest for life. A deeper appreciation for all the beauty and opportunities that surround me every single day.
I feel inspired to step up and take action -- to leverage the incredible privilege I have.
And I hope by sharing my experiences with you, you’ll feel the same way.