We both stepped to the line. Here he was, a 45-year-old man incarcerated for 25-to-life, and here I was 25 years old, staring at each other eye-to-eye, tears dripping off the side of our faces. Though we stood on opposite sides of the line, we couldn’t have been more alike. Realizing how human we both were, both feeling judged for our past, there was a sense of freedom behind these prison bars.


I found many excuses the morning of. My husband had been serving in this program called Defy Ventures — an organization empowering recently released inmates to become entrepreneurs by way of coaching from professional business men and women. The program added another opportunity to serve, this time behind bars. He had gone to the prison in October while I was on travels, and said I couldn’t miss the next opportunity in December. As the night came before the day to go, my list of reasons to skip out were endless.

I couldn’t get my earrings off.
My only suitable pants had a hole.
I had a flight to catch the next day.
My throat was sore.
I was tired.
I was nervous.
I was lazy.

And when I got to the bottom of it, I didn’t feel like keeping my commitment I had made weeks prior.

The 5 a.m, brutally-early alarm set off, and I still was trying to decide whether or not to go. My type-A personality decided, irregardless of the excuses I could think of, to honor the commitment I had made weeks prior. Thus the hour and half journey to Solano County Prison began with the sun.

It was nerve wrecking to consider I would be spending a whole day with fifty inmates, of which had been incarcerated for acts of murder, rape, armed burglary, and more. My mind raced as we made the trip. What would I say? What do you ask them? How do you relate? Can you relate?

As we entered Solano Prison, my heart was pounding. I hadn’t sweat like that in ages, and the extra shot of espresso wasn’t adding confidence to my ability to sit face-to-face. Over 50 entrepreneurs and business men and women like myself entered the prison yard. We were greeted by over 80 inmates or EIT’s (Entrepreneurs in Training as Defy fondly calls them) with the friendliest, most welcoming love. Many shared they had been looking forward to this day for months, preparing their business plans and speeches.

I was shocked. My perceptions and expectations immediately turned upside down.

Back to the 45-year-old man. To break the ice, Defy’s founder, Catherine Hoke, has an activity called “step to the line.” The EIT’S and the business leaders stand on opposites sides of a long line — statements are said, and if it resonates with you or it is true, you step to the line. The only rule, you must keep eye contact with those on the other side the entire time, not looking down or away — truly embracing everything you and they are and feel.

Easy statements came in the beginning, causing an uproar of laughter throughout the room.

“I like hip hop music.”
“I like country music.”
“I like sports.”

Then it began. The honesty of what it meant to feel hurt as a human being.

“I grew up in a household where there was abuse.”
“I felt like I wouldn’t amount to anything.”
“I grew up with only one parent.”
“I grew up in a neighborhood where we heard gunshots.”
“At 18, I could only rely on myself.”
“In my past, I had to keep my feelings to myself to stay alive.”

“Do you feel like you can’t forgive your past?”

This one sunk home. I avoided stepping to the line at first.

As I kept eye contact with this 45-year-old man, his eyes were watering, mine had been too for a while, I saw him make his step to the line — it gave me courage. I stepped forward too. We kept eye contact the whole time, looking at each other, embracing this moment of similarity, of hurt, of shame, and of courage.

It was freeing to be honest with myself, and with others.

Though we were on different sides of the line, we had all had pasts marked by shame, by hurt, and by disappointment — something that surprised both sides. Even greater though, it was clear how different the cards were that we had been dealt in life.

The birthing lottery was in plain sight.

So often questions around our childhood only brought the EIT’s to the line. I can’t relate to growing up in neighborhood where gunshots were heard, or in a household of abuse, or a single parent home, or having to rely on myself at 18. This broke my heart, to see these men who had endured suffering I would never be able to understand. Stepping to the line was emotional, it tore down walls, it changed each and every one of us, no matter which side of the line we stood on.

The day continued. Each mentor gets paired with one to two EIT’s to help advise and give instruction for how to better share their personal statement and pitch their business idea. The afternoon was marked by encouragement and honest critique to these men inside prison. Getting an opportunity to coach these remarkable individuals was incredible. The day capped off with a business pitch competition, and the support of fellow EIT’s and mentors rang through the room.

What Defy Ventures is doing for both men and women on either sides of the line is something so contagiously amazing. Giving these incarcerated men and women an opportunity to be potential business owners and value-creating employees under the coaching of professionals is truly a second chance at life. Giving these mentors like myself, an opportunity to serve and coach is an opportunity to break down walls and to be changed from the inside out.

As we drove back to San Francisco, feeling exhausted and emotionally spent, my eyes filled again. Breaking down, I couldn’t stop replaying the face of the one man who could of been my dad’s age. I was filled with a swirling of sadness and hope. Sadness for the lives damaged and years lost, and a hope that myself and others can make an impact and that these men might finally realize the redemption and reinvention they so desperately crave.

I am so grateful that I made the journey to spend the day in Solano Prison.

I can’t wait to go back to see my friends again.

+ To learn more about how you can participate with Defy Ventures or donate to funding needs, see here.

*All images via Defy Ventures.

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