Natasha Ortega Shepperson is a master’s student in the School Leadership Program at the Harvard Graduate School of Education.  Before coming to Harvard, she taught for five years as a first and second grade teacher in Chicago.  Through the Petey Greene Program’s partnership with the Boston University Prison Education Program, Natasha volunteered as a TA for a college course on the Supreme Court that was taught at MCI Framingham during the spring of 2015. Next year, she will be working in a principal residency program at a school in Chicago.




What made you decide to volunteer with the Petey Greene Program?

I had never had any experience working in or being in a prison. Period. My intersection with it was through this educational lens.  I had never thought about education in prison at all and I was just thinking that there could be some skill set that I have worked on in the past in terms of leading students and leading adults that could be transferable to a prison education program.

Also, for me, it really came from a place of curiosity.  I felt very ignorant having worked in education for my whole professional career and a) never had a conversation about prison education and b) never been pushed to think about it, so I never did. I’ve had a lot of experience in education and this is a conversation that I’ve never had with any of my peers in the last six years.  It felt important and I wanted to learn more.


What were your perceptions of the criminal justice system before this experience?

I did have a family member who had gone to prison and is now done serving his sentence. I think that when I heard about the program, it made me think about that person and how he had continued to struggle on the outside. I wonder whether, if there had been stronger supports and opportunities for him, if he would have had a more successful transition into mainstream society. 

I also had a lot of assumptions that were very influenced by media and the dominant narrative that we should be fearful of people who are incarcerated. I saw Petey Greene as one opportunity to create a restorative approach in a place that might not always encourage that.  It really wasn’t until this school year that I even learned about the school-to-prison pipeline, that’s how sheltered my conversations about education had been.  I was struck by the similarities between our schools and prisons and the statistics that back up where our Black and Latino students end up going.  Hearing about the Petey Greene Program gave me an opportunity to proactively try to work against that.


What was your role in the classroom?

The professor teaching the course very much took me under his wing in terms of navigating the system and having conversations about: “what do we believe about education in general? What do we want this class to be? What do we want the women to get out of it?”

I was coming more from the pedagogical angle with my experience and background and he was coming more from the experiential lens of ‘these are some of the challenges of working with women in prisons that I’ve seen before’ and, so we were thinking about how to blend those two to create the optimal learning environment. We incorporated more collaborative learning and group work into the class and for their final project, the students did a class presentation on their beliefs about the Supreme Court being an agent of social change in our society.  Many of these students had been too petrified at the beginning of the year to even talk when they were asked a question.  But by the end of the semester, they were giving a 20-minute presentation with four of their peers around them.  So, that was part of my role: social and emotional support for the women, so they could get to that point.


What has surprised you the most about working in a prison?

I’ve been surprised by their willingness to welcome me into their community as a complete outsider.  I have just been met with so much grace from them and so much kindness and hospitality. It has astounded me and it’s made me truly believe that the desire to connect with other people is part of our humanity and a human condition that we all desperately need.  I really don’t think it was anything that I deserved or earned from these women.  They really allowed me to be part of their community and shared parts of their life with me, knowing that at the end of the three-hour class.  I would walk out of that facility and that was not an option for them. And they never held that against me.  It’s been very humbling and it was probably the most unexpected part of this experience for me.


What sort of conversations have you been having with non-volunteers about your work as a TA?

Sometimes, when people hear about what I’m doing, they’ll say, “that’s so good and noble of you.” That’s a hard conversation to have because I would like to be having the conversation more around “how could I be a part of that” instead of “that’s someone else’s work,” because it is a reflection of all of us.  And so that’s where I try to take the conversation to: “How is this situation indicative of where we are as a country and what is our collective role in that?” I think that’s hard because I spent the semester trying to figure out what that is myself, and I’m not sure if I’m there yet.  I do think we all have a role in it though and so that becomes the conversation: what role are you going to choose to have? 


Have you had any realizations through this work that have been hard to explain to people who don’t have a similar context?

One of the things I noticed within the women’s prison during the first few weeks was how unaccustomed I was to doors closing on me all the time.  I would go to open a door and it would be locked.  I just did this out of second nature – I don’t live in a world in which doors are locked on me. I can open any door that I want whenever I want to.  Something so small as that is just a constant reminder of the environment that these women are living in. And I wonder, what would that do to you? Day after day, year after year of not being able to open a door? Every door is locked. Every door, unless someone is letting you walk through it. I feel it’s very symbolic of how my life is vastly different from the students lived reality.


What were some of the moments when you felt like you were having a positive impact through your role as a TA?

One moment was the first time that the women disagreed with each other. We had noticed that a lot of the women were constantly looking for the right answer and it was the first time in which there were two different answers. We had talked a lot about how there’s not necessarily a right answer. There’s evidence to support your ideas. This was the first time that two women took that evidence, took a stance of their own and actually disagreed with each other.  It was really empowering for them and for all of us.

One woman, initially, never raised her hand in class. We always had to call on her and the first words out of her mouth were always either ‘I can’t remember’ or ‘I don’t know.’  By the end of the semester she got up with her peers and was a part of that presentation group and was able to get through her sentences without stuttering, without saying I don’t know and really feeling confident about what she was saying in a way that we hadn’t seen before. 

There was also another moment. The whole semester I had been constantly saying to the women, ‘speak up, speak up, speak up,’ because we couldn’t hear their voices because they were talking so low or mumbling their words when answering.  There was one moment when one student couldn’t hear what another one said and she said ‘I need you to speak up.’  And then, it wasn’t us doing it anymore; they’re taking ownership of this and they are feeling empowered to advocate for their own learning and model for each other what they want to see and hear.  All of it has been tremendously exciting, the different ways in which the women have been finding their voices.  


What was the last day of class like?

The women were leaving and I shared my final reflections about what I’d seen them learn.  I talked about voice and agency and building a community together and my hope that they continue to do that. And I thanked them for letting me be a part of the experience. 

I was having a hard time saying goodbye, feeling that I didn’t know what was next for them. None of the perfunctory end of the year conversations seemed appropriate. It wasn’t like I could say “have a good summer,” or “what are you doing next?” It was different. 

Then one of the women came up to me, and hugged me and held me there for a few moments. I felt like she was saying ‘you can go, you can go, and we’ll be okay.” I think it was powerful because that’s what I needed. It was a moment of closure that felt powerful and I cried for hours after I left because she knew what I needed even when I didn’t know what I needed. How did she know? 

I feel like these are some of the smartest women that I’ve ever met and they are so much more aware of things that I am.  And that was a moment she just knew exactly what I needed. I needed a hug and then she just held me with her glance to say you can go, it’s okay. So I could end by feeling things will be okay - or really, I’ll be okay. 


What are you taking away from this experience?  What do you want to do with what you’ve learned?

From a big picture lens, I’m taking away a deep commitment to education for all, including those who are literally out of sight all the time.  That’s something I had never previously considered. For my particular next steps as a principal, I’m taking away a few smaller technical pieces, in terms of how I can set up systems and structures at my school to support our families that have a parent or family member who is incarcerated. Even something like sending report cards to incarcerated parents could be a really powerful and exciting opportunity for them to share in their children’s lives, to be part of a conversation even when they are not present. That’s something that I am committed to doing.  If a family shares that they have a parent who is incarcerated, then I’ll inquire if I can send a report card to them, see if it’s possible to set up a conversation with them, and even if they could be on speakerphone for our parent-teacher conferences. I’d also like to create support groups for those who have a parent who is “away,” whether “away” means military deployment, incarceration, a death in the family, etc.

I’m also thinking that we just need more people working in prisons.  I’m very personally motivated to find a way to be a part of an Inside-Out program or summer tutoring options in Chicago.  A resounding theme that I heard from people at the prison was that outsiders’ presence means so much to them and if that’s all I can do right now, I’m more than willing to do that.  I’m committed to being present for them and that means finding a way inside prisons. 


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