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Why My Mom and I Opened Up About My Incarceration

My name is Roy Waterman and for 12+ years, I was incarcerated. I’ve faced many challenges in my life and overcome many obstacles, but none more devastating or impactful for my family and myself than the time I spent in prison; yet none of those experiences have been discussed or shared between me and my family — until now.

As part of a video series that explores the ways formerly incarcerated individuals are #StillNotFree, my mother and I finally sat down for one of the most difficult — and powerful — conversation we’ve ever had.

It took a lot of convincing to get my mother Donna comfortable with going through with this experience. It came to a point where I thought she wouldn’t agree to be on camera discussing the most troubling memories from our past; and I didn’t blame her.

While the conversation was long overdue, it was very difficult and took a toll on our emotional and mental health. I knew that recording this raw conversation would reopen many old wounds, and it did.

I also knew that it was extremely important for us to publicly share this conversation, and that doing so would help people who have not been personally impacted by incarceration understand our experience.

Since my release from prison, becoming a chef, and starting my own catering business Caribbean Soul Caterers, I learned very quickly that formerly incarcerated people are not getting enough opportunities to show what they can bring to the table. And I think a big part of that is the stigma associated with being labeled as an “ex-offender” or a “felon.”

Starting out, I did everything I could to make sure that my business and its marketing didn’t have any associations with my criminal history. I would never have called myself a “second chance” employer or been open about the fact that I was formerly incarcerated — because I was afraid of that stigma and the negative impact it could have on me and my business.

But I quickly realized that I was doing a tremendous disservice to the millions of people like myself who are impacted by incarceration in America. That’s when the light bulb went off in my head; I decided to fully engage in the process of criminal justice reform — making it a part of all that I do, including my business.

So I started hiring formerly incarcerated people to work as prep cooks, servers, and greeters for my catering business. Now, I am proud to call myself a Fair Chance employer.

Fair Chance employees at work for Caribbean Soul Caterers

But even still — as a business owner in a position to provide opportunities for others directly impacted by mass incarceration — the stigma associated with having gone to prison still follows. After recording this conversation with my mother, I remain fearful that some people may disregard our experiences and view me as an outsider because of my past.

I hope that everyone who watches this moment between my mother and I understand that I am human.

I hope this conversation provides non-impacted populations with a window into what incarceration does to families.

I hope that it leaves those who have never met an incarcerated or formerly incarcerated person with a sense of empathy for our experiences.

I lacked many things prior to my incarceration which ended up serving as contributing factors to the crime I committed, among them positive role models to provide me with a sense of community, belonging, and hope.

As a grown man, I now understand the power of strangers to influence children, and recognize mentorship as one of the most valuable things we can offer youth in our communities — especially those at risk of becoming system involved.

If I could go back in time and gift a six year old version of myself anything, it would be hope. But unfortunately, six year old me lacked adult mentorship when I needed it most and as a result, I grew into a young man who took away from my community instead of investing in it.

The pain that I consequently caused my family, friends, and neighbors is unacceptable by my standards today.

But I’m not a young man anymore. I’m a Fair Chance Employer, a dedicated son, and a criminal justice advocate.

Now I’m in a position to give to at-risk youth what nobody gave to me when I was young: hope.

I thank you for watching this conversation with my mother and meditating on not only how difficult my personal circumstances might have been, but also the experiences of the millions of others impacted by a criminal justice system that is in urgent need of reform. And lastly, I hope you’ll join me in taking action to fix it.

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