My Time in Prison

I’m a privileged white girl who went to prison last week.

I was brought up in affluence, with a great family who told me they loved me every day and a promise — more like a mandate — of a 4 year college degree. As I moved to Los Angeles and met people from all walks of life, I legitimately used to be embarrassed at my family’s wealth and my privileged experience. I participated in every volunteer activity I could think of, from building houses in Uruguay to spending my Sundays with kids below the poverty line, to wash away this shame that I was given life on a silver platter and yet some of my college roommates were working two jobs just to stay in school.

I’ve always been philanthropic of mind and known that I need to use my privilege for good, but before I moved to LA I had never been truly aware how much of my success, and that I was the volunteer rather than the one being helped, were due to the situation I was born into. I’ve learned something recently though, that you don’t have to feel shame for the way you were brought up, whether that be in poverty or in a mansion in Calabasas. That while guilt, pain, sadness, anger, confusion are all normal emotions, shame is not something to carry around. I learned this in prison.

At enso, we spend everyday working on projects with the mission to create impact at scale, but we often spend a lot of time theorizing, strategizing and creating in front of a computer. A few times a year we take the time to get outside our office and volunteer as a team and this time, we took the hour drive from LA to CDCR (California State Prison, Los Angeles County) with Defy Ventures. Defy Ventures is an entrepreneurship, employment, and character development training program for currently and formerly incarcerated men, women, and youth (source: Defy website). Since I do a lot of career development training in my personal time, I thought this would just be a fun day of giving back and practicing my skills. What I didn’t realize was that I would not only learn a lot about myself in prison, but learn even more about my unconscious biases about the incarcerated and how truly lucky I am that I was born in my situation.

The best thing we did during the day was an exercise called “walk to the line.” There was a line drawn down the middle of the gymnasium, with EITs (inmates who are “entrepreneurs in training”) on one side, and the volunteers on the other. The exercise is meant to show what we on both sides of the line have in common with one another, and what we experienced differently. One thing was immediately apparent before we even started the exercise — 90% of us on the volunteer side were white, and 90% of the EITs were black.

Catherine, the leader at Defy Ventures, would call out a phrase ranging from deep thought provoking to light and funny, and you were to step to the line if that phrase rang true for you. Right off the bat she asked “who feels uncomfortable in their own body.” I’ve always struggled with body image as a ballerina so I timidly stepped forward, and was greeted at the line with confirming hugs from volunteers and respectful handshakes from EITs who look 100% different than me but struggled with the same issues.

Then the questions got even deeper, and to be honest they were questions I didn’t even realize needed to be asked:

“Did you have a person who told you they loved you every day as a kid?”

Horrifying enough, I think only a handful of EITs out of the 90 participating in the program stepped forward. Almost all the volunteers did. I literally (yes, literally) cannot even imagine what this must have felt like for those EITs — not just growing up, but witnessing that in the room. Think about what a difference that makes to a person’s self esteem and future prospects to never be told they’re worth something and that someone loves them.

“Had one or both of your parents ever been incarcerated?”

Almost all EITs stepped forward, and only a handful of volunteers. How are children supposed to thrive when all they know is life with family in prison? When I spoke with several of the EITs about this over lunch break, they explained that when your mom is a drug addict and your dad is already in prison, the only way you know how to feed your family is to sell drugs. Or join a gang. My biggest downfall in life was being kicked off dance team for being “too fat.”

“Has someone been killed in front of you?”

Not only did almost all the EITs step forward during this section, but they stayed at the line when the question expanded to “was that person your friend?” “Was that person in your immediate family?” When violence is all you know — and not just from playing Call of Duty on your brand new Xbox One — how are you supposed to learn that violence is not the answer? Especially when one or both of your parents has already committed a crime of that level?

During this exercise, I noticed that my shame was the same shame that the EITs wore, but for vastly different things. They were ashamed that they grew up in poverty and were forced into gangs. They were ashamed that 100% of them stepped to the line during the question “have you dropped out of high school” and that 100% of the volunteers stepped forward during “do you have a 4 year college degree.” And I felt ashamed that I couldn’t have given these 90 men who are clearly trying to turn their lives around a better chance at a successful, happy and free life. And that I didn’t have to struggle to be successful — sure I work as hard as I can, but a lot of where I am today is based on my privilege.

Catherine reminded us several times throughout the day that the family you were born into is nothing to be ashamed of. Feeling empathy and sympathy for those with less than you, or striving to attain the wealth, security and education of those with more than you, are healthy and fantastic emotions. But focusing on something you can’t control — like the class you were born into — is nothing to be ashamed of.

I never thought I would have the same emotions as convicted murderers, or ever understand that there was a distinct systemic reason that they ended up there and not me, but this is what happened over and over during the event. These men weren’t inherently bad, or even inherently that different from me, they were just born into different circumstances. They weren’t less intelligent or less driven, they didn’t love their family any less, and they didn’t feel more confident in themselves than me.

My biggest takeaway is that something needs to change systematically in our country. We need to find a way to give these men a chance when they’re children. We need to find a way to stop viewing someone who’s committed a crime as a lost cause or a horrible person. We need to stop being ashamed of where we came from, but rather learn from it and rise above. We need to stop making snap judgements about people and strive to learn more about them, using that as a learning experience to help shape our future generations.

I want to live in a world where a kid born in Compton has the same chance to be a CEO as a Jewish white princess born in the suburbs of Chicago.

To get involved with Defy Ventures, please visit their website at

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