Looking into the eyes of an inmate: a powerful exercise in empathy

We’re all ex-somethings. I wish we’d ask ourselves, ‘What would it be like if I was only known for the worst thing I’ve done?’ Moved by empathy, we’d recognize people for who they are today and not for the mistakes they made yesterday. Millions with criminal histories would unlock their potential.
- Catherine Hoke, Founder and CEO of Defy Ventures

A bit of background

On December 7th, 50+ Atlassians logged 15+ hours of Foundation leave (out of the 40 hours we are given each year to volunteer) by journeying to volunteer at Valley State Prison: an all-male, medium security facility in a very small town called Chowchilla, CA. The volunteer opportunity was hosted with Defy Ventures: an entrepreneurship, employment, and character development training program for currently and formerly incarcerated men, women, and youth. We arrived on the day of their business pitch competition and graduation ceremony from a program called CEO of Your New Life that nearly 70 currently incarcerated Entrepreneurs in Training (EITs) had been taking part in over the past 6 months. This was a huge accomplishment for the EITs, and for many, the first time they would walk in a cap and gown. They had completed hundreds of hours of training and coaching aimed at turning their street hustle into legal startups, and had been working hard on Shark Tank-style pitches that we would soon judge to get them ready to pitch to VCs upon release from prison.

We had insight into some general logistics of what to expect that day (i.e. I knew I had to go shopping for an outfit that fit their very strict volunteer dress code), and we had been told that it would be a jam-packed and inspiring day. But as we walked off our bus and into the metal gates, it was clear none of us really knew what the next 8 hours had in store.

I am still processing my full experience that day, and nursing a pretty massive emotional hangover. An experience so transformative is proving pretty hard to put into meaningful words, but I gained some breathtaking perspective that I want to try and hold onto by documenting my thoughts. I hope that my reflections may also compel you to get involved through a similar volunteer trip or donation to Defy.

The facts, figures, and media representations

I knew going in that the United States has a huge mass incarceration problem; that our criminal justice system disproportionally targets people of color and low socioeconomic status (African-Americans are nearly six times more likely to be incarcerated than whites and Latinos are nearly twice as likely to be incarcerated than whites); that though we are one of the largest and richest countries, we are also the nation with the highest incarceration rate in the world; and that the U.S. represents about 4.4% of the world’s population, yet houses 22% of the world’s prisoners.

I’ve also read a decent number of articles and books, listened to podcasts, and watched documentaries and television shows that represent different versions of how American prisons operate, who the criminals in our country are, and what life in prison is really like. Some of these do an incredible job of illustrating the realities of mass incarceration in America (Just Mercy, The New Jim Crow, 13th), while some, especially TV shows, are sensationalized and can tend to fall back on stereotypes (looking at you, Orange is the New Black). But no number of facts or figures, nor pre-established perceptions of prisons and prisoners from the media, could have prepared me for the real men I met and the firsthand stories I heard.

A powerful exercise in empathy

I don’t know what type of people I was expecting to find in prison, but it certainly wasn’t the deeply empathetic, articulate, and motivated men I encountered throughout the day. In fact, the first EIT that approached me during an icebreaker game shook my hand, looked me straight in the eyes, told me I was in a safe environment and had nothing to worry about, profusely thanked me for caring about him and his “brothers” enough to visit, and told me what he knew about Atlassian and our products more eloquently than most. By the end of the day, some men had even told me that we were the closest thing they had to family. They felt a genuine sense of love and admiration for volunteers choosing to spend a day with them when we could have made a number of excuses to be anywhere else.

The experience I’ll reminisce about most often is a game we played called “Step to the Line.” The activity could definitely be called “Step towards the deepest feelings of empathy you have ever experienced,” which is not as catchy, but it’s what I felt throughout the activity, and what I will continue to feel every time I look back on the day. Defy actually produced a film called Step to the Line using Oculus VR if you want to learn more.

Two parallel duct tape lines ran down the center of the gym floor we were in. All the volunteers were behind one line and EITs were behind the other. Each volunteer and EIT stood face-to-face while remaining behind our lines, and we were encouraged to look into each others’ eyes, no matter how uncomfortable it got. Cat (the founder of Defy) read aloud a series of statements, and we were told to step up to our line if the statement felt true to us. Statements quickly escalated from “I graduated from a 4-year university,” to “I was the victim of violence in my home growing up,” to “I have seriously contemplated suicide.” The honesty and vulnerability both sides showed was staggering, humbling, and often, really damn heartbreaking. There were some notable similarities and some very stark, telling differences where our lives diverged that gave us connection and compassion like nothing else could.

“Step to the Line” exercise. Images from 2017 Fast Company article.

Looking into the eyes of an EIT

Looking into the eyes of an EIT I was reminded that deep down, we are both the same. We both have fears, anxieties, scars, and regrets. We both have hopes, dreams, and deep loves in our lives. We were both born into a world that judged us for our socio-economic standing, skin color, culture, gender, hair, voice, body, opinions, and beliefs — but some of us had identities that gave us more privilege than others. We have both been hurt and have hurt others, though in different ways and to different magnitudes. And we have both regretted the hurt we have caused. We have all — legitimately every single volunteer and EIT — attested to doing something stupid or illegal (or both). But the EITs were disproportionately caught in the act and received the harsher consequence. And nearly all of us volunteers graduated college, while only one EIT was able to step to the line with that statement. Most volunteers grew up with support systems and healthy ways to cope with pain and anger in our lives, while most EITs did not have that same help. And pain on both sides of the line often originated from the same source — a parent’s divorce, the death of a loved one, and/or deep feelings of shame.

Looking into the eyes of an EIT (and looking down the line of volunteers) I was reminded that everyone has a backstory and everyone is fighting battles you can’t always see. Everyone deserves to forgive themselves, to forgive others, and to be forgiven with a second chance. No one should be forever be defined by the worst thing they have ever done. And no child should be born with the odds stacked against them from the start (70% of children with an incarcerated parent will follow in their parents’ footsteps). We were not able to hug the EITs, but we were able to reach across the line and give them a handshake as a physical representation of the empathy we were feeling. There was a flurry of hand squeezing and many same-side-of-the-line hugs (those were allowed!) throughout the exercise.

Looking into the eyes of an EIT I felt such a deep sense of sadness for the mass amounts of potential that was never able to be realized. And looking around I imagined many others felt the same, as there was not a dry eye in that gym. Even the seemingly hardest of men had completely let down their guard. I could feel the love the two men immediately across from me emitted as they saw my tears and felt my pain. One told me it was the first time in his adult life he could remember being brought to tears.

For those few brief moments we shared a visceral feeling of respect and compassion that I don’t think I could replicate if I tried. This was perhaps the most humbling and human moment of all. We were one collective unit, bound by memories, injustices, prejudices, pain, and a desire to forgive and be forgiven. By the end, it really didn’t matter which side we were on.

Far from monsters

Prior to visiting prison and hearing personal stories from EITs, I could have easily labeled these men as “monsters”. But as they recounted stories of joining gangs for protection and belonging, trafficking drugs to put food on the table, and stupidly getting behind the wheel while intoxicated and killing a 16-year old girl — a moment they replay in their mind most seconds of most days and would do anything to take back — they were humanized.

These are no doubt terrible things, many of which unfortunately resulted in horrible tragedies. But the scarlet letters they now wear screaming “murderer” or “drug trafficker” last an eternity, even after they serve their time. It’s no wonder it’s so hard to get a job or reintegrate into society when a resume still screams “monster” years after the offense. It’s no wonder recidivism rates are so high and intergenerational cycles of incarceration are so common. Even murder becomes forgivable (at least in my eyes) when you hear a backstory that he killed the man that was repeatedly raping and beating his young daughter. How would you feel in that situation? What would you choose to do? We all hope we would not commit a violent crime, but I don’t think you ever really know until you are in the unthinkable situation.

Future CEOs

I mentioned earlier that the program these men went through is called CEO of Your New Life. They are taking control of their lives so they can go on to become self-sufficient members of society. I have no doubt that some of them will go on to become actual CEOs. The business pitches we watched were brilliant, convincing, and very well thought out despite the lack of market research they are able to conduct from prison. The winning pitch was for a product an EIT had already made a prototype of in the prison textile factory: an eco-friendly, bamboo fabric shoe bag that keeps your favorite shoes from breaking down and falling apart. Other notable pitches I heard included a DIY patio kit, a service that enables electronic money transfers into LA jails called convictcash.com (it is actually already live and was launched entirely from prison), and a marriage proposal planning service for men that feel they lack time or creativity.

Lessons learned

It’s cliché, but I went in expecting to help the EITs, and came out realizing they had overwhelmingly helped me.

The day gave me a huge dose of perspective. It’s hard to feel upset or annoyed by disappointments, inconveniences, or annoyances in life when you see these men — many who have been without their families and their freedom for 20+ years — smiling, laughing, and working their asses off for a second chance.

I’ve learned to channel the guilt of my privilege into meaningful actions through programs like Defy. The EITs couldn’t stop thanking us for showing up and helping them, and never showed any sign of resentment towards the fortunate lives we live on the outside.

I learned about forgiveness and the necessity to forgive ourselves before we are able to forgive anyone else. Listening to two teenage girls (who have lived their lives with a father behind bars) tell their their dad, “We forgive you” is unreal powerful (and instantly created a room of ugly criers).

I realized that being free is so much more than being free from the walls of a prison. Defy recognizes that true freedom requires mental, emotional, and spiritual wellness, but sadly most prisoners in this country never get that kind of support or therapy, setting them up for failure on the outside.

I saw that hope is stronger than fear and gives even the man who at one time had a 399 year life sentence the drive and motivation to keep working towards a second chance.

And I witnessed the power of a parent’s love. Unfortunately not every EIT had family members attend their graduation ceremony, but those that did were pretty exceptional examples of unconditional love. One mom that sat in on her son’s business pitch told our judging panel, “I know I might be biased, but I have always known this was the capable and successful man my son was meant to be”. And the most common phrase that parents told their EIT during a “love bomb” ceremony where EITs and families could exchange heartfelt words on stage, was how happy they were that the world could now see their little boy live out the potential they always saw inside.

The experience of a lifetime

I am not against prisons in and of themselves, but I do believe in a more rehabilitative, rather than punitive, system than we currently have in this country. I know that criminal justice reform is an extremely complicated issue and I am not pretending to have the answer. What I do know is that way more prisoners than not that deserve a second chance (or as one EIT put it, a legitimate shot at a first chance), and there’s way more that we can do to help than we think. I had, and continue to have, a lot of what Oprah would call “aha! moments” of deep understanding of people and circumstances far outside my every day reality, that I could have never realized without the connection I got to experience with these men.

I am 100% guilty of hyperbole in my life: This is the best thing I have eaten in my entire life; This is the most fun I have ever had; I have never been colder than I am right now; I’ve never been sleepier…you get the idea. I feel the need to call this out before I confidently say, with zero hyperbole, that volunteering with Defy was hands-down the best volunteer experience I have had, the most humbled I have ever felt, and the most motivated I have been to take real action on an issue.

Help me Defy the odds

My birthday is next week, so in another attempt to use my privilege for good, I set up a campaign to receive Defy donations in place of gifts — all of which will be doubled through Atlassian’s matching program. I have a goal of $250, which, with a match, will equal the $500 it costs to enroll one incarcerated EIT in the CEO of Your New Life program. I can 100% guarantee that any investment in these EITs will make a more lasting and visible impact than you can imagine. Giving someone a second chance to transform the hustle and defy the odds > any birthday gift I could dream up.