A Prison of Our Own Making

And What’s Actually Right About You

By Susan Olesek

I cut my teeth learning how to teach the Enneagram in prison. I first went “inside” as a 36-year-old, at-home-mom of three young boys, armed with a BA in sociology and an idealism that often landed me in risky pursuits, but never behind bars. Among my first incarcerated students were a man on the FBI’s “most dangerous” list who spent 26 years in the correctional system; a serial bank robber; a former PhD student with a 16-year crystal meth addiction; a gang leader of the Nortenos; and a 65-year-old grandma in for embezzlement. 

By the time I met my students in the jails and prisons that housed them, they were serving sentences ranging from a few years to life-without-the-possibility-of-parole. They “did the crime and were doing their time,” as people like to say. According to the correctional system, justice was served. But, as I listened more closely to the people actually living behind the walls, I began to hear something deeply important in the stories they told me. Their narratives revealed our sameness, the distinct, yet patterned ways people get into trouble with their personalities - those traps of shame, grief, rage, and fear which are so predictable they can be plotted on a diagram. The Enneagram system does not discriminate, or care, which sides of the walls we are on; it reflects everybody back to themselves with absolute fairness. 

“What is different about teaching self-awareness to those in prison?”, people always ask. The difference lies in the injustices that incarcerated people suffered long before they got locked up. Those incarcerated don’t come into the world as murderers, rapists, embezzlers, robbers, or drug dealers. These roles are fostered inside families and social systems like secret, dark recipes, silently passed down, with no one ever naming the toxic set of ingredients that created the conditions and environment out of which they grew. 

Countless people have told me that they were guilty of their crimes, but that the person who committed them was not who they really are. People commit horrible acts, yes. But, it’s hurting people who hurt people. We tend to dismiss what came before. As a society, we have not dared ask what oppression and violations happened to these people when they were too young to do anything about it. And yet we absolutely must. We need to grasp the crucial context of childhood trauma. When we refuse to understand that this is the crux of what is driving adults to discharge their pain onto others, we remain complicit in the perpetuation of its consequences. 

Twelve years ago as an inexperienced, newly certified Enneagram teacher, some might say - some did say - that I had no business helping “career criminals” learn such an incisive, psychological tool inside of one of America’s oldest and, arguably, most dysfunctional institutions. I was told that this was dangerous, that I could “set them off.” But on my first visit behind prison walls I immediately understood that I had one undeniable thing in common with my incarcerated students; something no degree or certification could have better equipped me with, and something much more valuable. Like my students, I knew what it was like to be in pain. 

Short of doing actual prison time, I quickly realized the many years I’d spent trapped inside of myself gave me a kind of “cred” and, for a time, allowed me to get away with trying to teach something that I was still desperately trying to understand. Being in the company of people who were as determined to defend what was wrong with them, as I was to see what was right in them - and vice versa - brilliantly revealed how strenuously we avoid the truth of who we really are. My incarcerated students have been my greatest guides while I worked the edge of a classic adage that has become my mantra: “Teach what you need to learn.” 

I was cautioned that the folks in prison would manipulate me if I taught the Enneagram to “them.” But, that is not what happened. With this insightful psychological tool and loving support, those who had been practically thrown away did what almost no one expected them to do; they began to heal. I have thousands of examples of this, but here will share just one. 

A man with whom I’d worked for many months once waited patiently after a class and asked to speak with me. This was a student who rarely talked without being invited into a conversation, but that afternoon I could sense he was holding something with great weight. I learned that after serving nearly a lifetime in prison he had “gotten a date” with the parole board where he would have his first face-to-face opportunity to be accountable to his victim’s loved ones. Enneagram Prison Project’s curriculum is designed to help our students take responsibility not just for what they have done, but also to be able to articulate the reasons why. This tender student wanted my support in learning how to talk about his past directly with people who were impacted by his actions, something he had never done before. 

This man identified with Type Nine, “the Peacemaker.” Nines come to teach the rest of us about belonging. An awake Type Nine can sense the importance of every being in the room. One of our EPP Guides says that, when you sit next to a Nine, you get the feeling that everything is okay and that they need nothing from you. That is exactly how I felt in this man’s presence. His energy was so mild it was almost possible for him to disappear in class, he seemed to ask so little from the rest of us. The young Type Nine comes to believe that if they make a big deal about themselves they will be left behind, or even annihilated. Personality is a cover, a survival strategy. Type Nine’s dissociate from their anger and learn to tolerate it by checking out. The bigger the ego – in this Type Nine’s case, the more invisible he made himself– the bigger the pain. What happened to you? I immediately began to wonder and marveled at the courage it took for him to show up for himself like this. 

This man’s whole chest and legs were shaking. I offered him a chair and he sat, gratefully. He faced me with his back to the door, a vulnerable move men rarely make in prison, and one which, he later told me, was an effort to eliminate his chance to escape our conversation. With great measure, he dared to tell me that he had assaulted and raped a woman over three decades ago. His admission came swiftly, but the words following it were thick with shame and stuck in his throat. His eyes filled with tears. It was as if this horrible incident had just happened yesterday. He raised his eyes to meet mine for the first time since we sat down and I could see how clearly he was grappling with his remorse. I nodded my encouragement to him. 

The stakes are so high for incarcerated students. Often those inside are literally fighting for their freedom and need to be able to figure out what’s been driving them in order to put a stop to the very long sentences that come with their crimes. That he took the “right action” to put himself in the chair across from me showed me his determination to move the mountain of shame off of his chest. “Tell me about your childhood,” I said. 

He then told me about the many physical and emotional assaults he endured as a little guy; about how he was beaten by his own mother when he was very small and later watched her be physically assaulted and raped. He told me that, for the last 30 years, he had never felt worthy or safe enough to tell anyone what he had done, never mind share what had happened to him. Small wonder, I thought. 

English Psychologist D.W. Winnicott once said, “There are things that happen in childhood that should never happen. And, there are things that should have happened, that never did." How would it have changed the trajectory of this man’s life if just one person had reassured him that the beatings and violations he endured should not have happened — to him or to his mom? No child should ever witness his own mother get raped. But the little boy who did see such things desperately deserved someone to gather him up in their arms and tell him that this horror was not okay--and not his fault. In the absence of such holding, a child’s psychological last resort is to surrender his own fragile connection to himself. In doing that, this man lost his deep sense of belonging and right action with which he, as a Type Nine, had come into the world; acting out the hurt for which he had been given no words at all. 

There was no justification, and no judgment between us, just pure understanding of how the unmetabolized traumas of childhood played out in this man’s devastating actions. There was an intelligence to his rage which underlied the acts for which he was serving a life sentence. Yes, he was one hundred percent responsible for what he had done. He was the first to admit his guilt. But, where were the adults and systems that could have helped him to hold the pain he had suffered when he was arrested – quite literally – in childhood? By not sharing in the culpability for his predicament and that of so many incarcerated others like him, there is a clear omission of justice going on in our “correctional” system. 

My own son is a Type Nine. Knowing the personality structure of the “Peacemaker” personality as I do, an understanding of the logic that fueled this man’s fury opened up inside of me. I offered him empathy for the disregard of his personal boundaries that came before he disregarded his victim’s. I saw the little boy who wanted someone to help him make sense of himself. I reminded him of what we teach in our early Enneagram classes, of the intelligence driving aversive emotions. This man’s greatest resource was his own instincts, information that comes without thinking or feeling. Anger tells us when our boundaries are crossed, when we don’t have any agency, or when something is not okay. The little boy who could not heed his body’s own wisdom survived by dissociating from it. He checked out while his outrage lodged in his soma. 

With just a little validation, I could see a flash of his anger, and gradually also the enormity of his hurt as he allowed himself to realize that he, too, was violated. A layer or two of the deep grief and remorse that he carried with him for years was peeled away that afternoon. We talked about having compassion for the little boy who really had nowhere safe to just be, who could only belong to a raging family by dissociating from the gentle soul that he truly was, and still is today. 

As we spoke, he stopped shaking and became calmer. It is remarkable what happens when someone is simply seen. When we are witnessed for who we are in the present – not judged for what we have done in the past - our self-judgment can be suspended and our humanity resurfaces without effort. 

In the weeks following our talk, I noticed this man’s countenance change. He raised the bar for sharing in our classroom and contributed more than ever. He began to meet other people’s eyes more readily, and when he came into the classroom he brought a magnificent new presence with him. Several weeks after his confessional, we walked through the yard one afternoon and he told me that he had been sharing with other men what had happened to him as a child, and how he connected it to his criminal past. The outward change in him was evident, but what was most inspiring is that he had apparently changed his mind about his own importance, dropping the façade of not mattering and disappearing before our eyes. For the first time, it seemed, this man mattered to himself. He was on his way to healing and forgiving himself for his past, a crucial step to seeking forgiveness from his victim’s family and society when he heads to his parole board hearing. 

The Enneagram has always been meant for everyone. The early pioneers of what would become Enneagram Prison Project (EPP) were incarcerated people who made this obvious. I am astounded by the appetite for self-understanding I have found among those in prison. Those in prison are bewildered that such a tool as the Enneagram even exists. For nearly a decade EPP has been on a mission to help people to understand why we do what we do, using the Enneagram to inspire transformation on both sides of the bars. 

While founding EPP, I simultaneously adapted my approach to facilitating self-awareness programs for people running Fortune 500 corporations, teens, parents, and spiritual circles, but my heart has inexplicably been drawn to those in jails and prison. Over time I have seen the same caliber of inner work happening in increasingly diverse populations, while using the exact same curriculum. It’s become crystal clear to me that across age, race, gender, and socio-economics, whether behind bars or in the upper echelon of Silicon Valley’s most renowned and powerful corporations, we are all in a prison of our own making in the ways we suffer our personalities. 

If the “justice” system has taught me anything, it is that real and lasting change only comes when we come clean to ourselves. We need to hold people compassionately culpable for what has gone wildly wrong — on both sides of the bars: for those locked up in our correctional system, and for those running it. But, we cannot change what we cannot see. We have to be willing to take a look at what is actually, really going on, “on the inside;” on the inside of government, of corporations, of our jails and prisons, on the inside of our family systems, and inside of ourselves.

This article is an excerpt from Susan's forthcoming book, 
A Prison of Our Own Making: And What is Actually Right About You.

Susan Olesek is an unapologetic idealist, a Human Potentialist in passionate pursuit of what is possible for people. Born outside of Boston, raised in Hong Kong and Japan, and educated in England and California, she earned a BA in Sociology from Occidental College and has cultivated a compassionate interest in human behavior during her lifetime. In 2012 she founded Enneagram Prison Project (EPP): a 501(c)(3) nonprofit dedicated to the self-awareness education of those imprisoned, now scaling around the globe. She has the vision to democratize the Enneagram and is on a mission to guide people to their highest potential while connecting them to the core of our shared humanity. 

For the first time, Enneagram Prison Project is offering our compassionate approach to the Enneagram to the public. Previously taught only to those in prisons and jails, 9PrisonsONEKey is a foundational 8-week, online course taught by certified EPP Guides and now available to everyone.

Catalyst is produced by The Shift Network to feature inspiring stories and provide information to help shift consciousness and take practical action. To receive Catalyst twice a month, sign up here.

This article appears in: 2020 Catalyst, Issue 25: Enneagram Global Summit