In our earliest days of teaching the Enneagram, Don Riso and I were became aware of something that we had not anticipated: that the work we were doing was reaching prison populations and having a positive effect. We received letters from incarcerated people sharing their realizations with us, and we were always deeply moved by these testimonies. We felt renewed in our conviction that with the right information and the right holding environment, that people with very difficult histories could turn their lives around. We met with a number of individual counselors who were training with us over the years and who were using the Enneagram effectively with people in prison and were always inspired by their stories. We felt that a concerted effort from individuals in the Enneagram community could perhaps make a big difference in the lives of the incarcerated, but we were not the ones to start such a major initiative.
Enter Susan Olesek and Suzanne Dion, who contacted us with just such a proposal. We were deeply impressed with their sincerity, their sense of mission, and their humility in wanting to really learn the Enneagram material from the deepest place—a process that is of course much more than merely learning the information. In short, we saw that Susan and Suzanne, as good Enneagram Ones, were devoted to walking their talk, and in a relatively short time, they were gathering talented Enneagram students from both our Enneagram Institute as well as the Narrative Tradition, and a number of other schools—all drawn together by the vision of using this amazing tool to make a difference in the world. Don and I enthusiastically backed this project and made any teaching resources we had available for the good work that the nascent Enneagram Prison Project needed to accomplish their mission.
Our next great delight was meeting a number of the first “ambassadors”— formerly incarcerated men and woman who had learned the Enneagram through EPP and were motivated to share their experiences both inside and outside the prison systems. I was deeply moved by their stories, their realness, and their genuine turn toward what in my view is what the Enneagram is really about: not simply typing people, but using this profound system for the genuine transformation of the human psyche. And hearing the stories, the transformation was real, obvious, and affecting. I now count a number of the EPP ambassadors as close personal friends, and feel this work is perhaps one of the greatest gifts that has come out of this system of self-understanding.
As you may know, Don Riso passed away in 2012 after a long and brave battle with cancer, but he left the world knowing some of the good that we had done, and encouraged me to continue to work with EPP in any way possible. I wholeheartedly agreed, and was honored to become an official advisor to the Project along with my dear friend and colleague David Daniels, who had already done some work with the team in a prison. Still, I wanted to taste firsthand the work EPP was doing, and was determined to find a way to contribute more directly. I had several conversations with Susan about coming to one of the prisons with her, but given my very heavy teaching and travel schedule, the opportunity did not arise until this March, 2016.
In short, I was scheduled to come to the San Francisco Bay Area for a retreat, but came a few days early to be able to join Susan and Suzanne on teaching trips to two prisons: Elmwood Correctional Facility in Milpitas, and San Quentin Maximum Security Prison in Marin County. After a couple days rest in San Francisco, I was brought at dawn to Elmwood to have my first session.
Many years of meditation practice and inner work come in handy when you enter an environment as intense as a prison. Yet, I noticed in Susan and Suzanne a lightness that was supportive, and actually found myself feeling much more at ease than I would have imagined. We passed through security into this inner world, and after some brief organizing ourselves and our materials went with Susan to my first class, which was about the third session in a series for a group of men who for various reasons were being isolated from the rest of the prison population.
What struck me immediately is that the faces I saw there were much like any class I have ever taught. I saw quite a range of expressions; everything from eagerness to wariness, from soft relaxation to tense defensiveness—in other words, like just about every other Enneagram class. What was different was that I could feel the enormous hunger for something real—these men did not want to be “cheered up.” They wanted truth, something that they could live with.
Susan masterfully got things started and asked the men to check in about where they were at, and to say something that they had come to appreciate about themselves. A lot of my work with people ends up being about helping them to have some kindness toward themselves, and to better manage their potentially brutal super egos—or inner critics. I saw instantly that Susan had grasped the importance of this crucial holding, and was skillfully and sensitively getting the men to look at themselves from a bigger perspective than they were used to. After everyone weighed in, at Susan’s suggestion, I took a little time to go around the Enneagram and talk about what was true, real, and beautiful about each of the nine points. I could feel a softening in the room as these men took in that whatever their misdeeds, there was a logic to what had happened, and there was still something awake and good in them. I could feel even the more tentative and suspicious members of the group were opening up, having some laughs, and feeling okay to join in with what was happening.
At the end of the session, the guys were downright effusive in their enthusiasm, and their gratitude. There were many hugs and actually a feeling of affection quickly formed. It is like that when people are present with each other. I have noticed over the years that people in Enneagram trainings often form bonds of friendship with each other that can be among the strongest and most important in their lives, even though they were only together for a week or so. When people are present with each other, they actually meet each other. What was touching and amazing was that it was just as powerful with these incarcerated men, and in fact, happened even quicker. I felt perhaps these guys had not much to gain in any pretense, and recognized correctly that for them to change their lives, some more radical form of showing up would be required. I can still feel the connection in that room as I sit writing this now.
I did not really want to leave, feeling we had just got something good going, when it was time for me to go to join Suzanne who was in the midst of an ongoing class for some of the women in the prison. These women were lively! I felt instantly a very different atmosphere than with the men. We sat in a circle, and as with the previous group, the women took turns sharing what was up for them. Instead of teaching anything formal, I participated in a conversation, listening as much as sharing. These ladies had many questions which I did my best to answer, and they seemed particularly interested in what it was like for me to be a writer—how I had fallen into such an unlikely profession as writer and teacher of the Enneagram! We talked also about relationships, and the challenges of being vulnerable to another human being. Needless to say, this was a big topic, and the conversation was free of religious or New Age clichés of any kind: just straight talk from one human being to another, based in experience and presence. Again and again, the theme of openness vs self-protection came up in these prison sessions, but it became for me a big theme of the days starting with these women. I talked with them about how all of the personality types were based in some kind of split in us, and the terrible point at which we human beings feel we have to leave parts of ourselves behind. I explained that the whole point of the inner work with the Enneagram was to find those splits, and to let presence, really a form of healing “grace” help us experience what we are in more wholeness, beyond any such splits. I could tell how well Suzanne had been teaching this group, because they followed what I was saying with relative ease, asking powerful questions along the way.
After the women’s group, we had a quick lunch, and I did a video interview for EPP which was rich for me, having just taught my first two classes in a prison environment. I also noted that in the room where we did the interview, there was an art project made by the prisoners, a set of tiles painted to create the image of “The Sleeping Gypsy” by Rousseau. It is a beautiful painting—the original hangs in the Museum of Modern Art in New York. But it was striking to see it there because it was Don Riso’s all-time favorite painting. I took it symbolically as a “wink from the beyond” about what we were doing.
After lunch, we had our third and final session of the day which was with a large group of men who had been doing the Enneagram work with EPP for a longer stretch. There were a few in the class who were taking it as a repeat course having gained so much benefit from previous classes. What was evident was the greater level of listening, presence, and maturity in these men. I could feel “The Work” in them, and they were ready and able to participate in a deeper level. They all checked in, and I felt moved to share with them more of my own personal journey, including some of the difficulties I had traversed in my younger years.
Again, the comments, and the sharing would have been extraordinary in any setting. I heard and felt real self-knowledge and real humility. I felt that a lot of these men, if they stayed the course, might do some wonderfully positive things both in the system, and “on the outside” when that day came. Having met my friends who were now Ambassadors, who had been through these courses and come out the other side, it was moving for me to see these men in the midst of this alchemical process, on their way to be truly amazing human beings.
A highlight for me of this section was near the end of our time, when Susan and Suzanne had us break into groups to discuss what each of us had been realizing about ourselves through the work. I was given the privilege of working with the guys who had taken the course several times and who had some profound things to share and to ask. It was amazing to me how quickly I bonded with these guys, and felt so much hope for them.
Many of them had histories of drug abuse and criminal records which stemmed from their use, but also from activities that grew out of their addiction. We talked about learning to stay present with kindness, even to our difficulties, and that we could see the real transformation in each other. One of them shared that this seemed almost like some kind of magic, but that he could not deny the effect it was having on him and on his friends in the group. There were laughs and tears, and intimate human moments. I can still see their faces vividly in my mind’s eye. I wish so much for these guys.
The following day was yet another completely different journey. I was picked up by Susan and Suzanne in San Francisco, and we traveled over the Golden Gate Bridge to Marin County to enter San Quentin Prison. I have to say this place had resonance for me from my childhood. One of my cousins fought in Vietnam and lost his eyesight there. When he returned to the USA, after his hospitalization, he came to live with my family in Colorado. He and I were both big music lovers and he had the then new album of Johnny Cash in San Quentin. I remember thinking it remarkable that Johnny Cash was allowed to go in and entertain the inmates at this famous maximum security prison, and what it must have been like. Now, nearly a half a century later, I was going to be working with inmates at the same place.
I was struck immediately by the much greater security measures. Yet we entered the prison with relative ease—Susan told me this was quite unusual. I was going to be working with a group of “lifers,” men with life sentences, who had been meeting together for some time, and who had created a place for themselves in the tough prison environment in which they could let down their guard a bit, and share more of what was inside their souls. Susan and Suzanne had been working with this group for several weeks, and they knew the basics of the Enneagram and many seemed to know their types. Shortly after we arrived, I was introduced to the man who had created this group, and he seemed incredibly centered and open. As it turned out, earlier in the morning, this man who had served some 33 – 34 years in prison, had been granted parole. He shared with us how he managed to hold himself together during his interview/hearing. But after stepping outside of the room in which the interview had occurred, he fell to his knees weeping with gratitude. No wonder there was so much softness in him. He greeted me warmly and seemed delighted to see Susan and Suzanne.
After this short but powerful exchange in the courtyard, we went directly to a smallish room with a group of chairs arranged in a circle, and one by one, the men from this group entered and took a seat. I could feel them regarding me with great curiosity, and some of them started chatting with me before the rest of the group arrived. They shared over and over how amazing it was to be seen, to be treated as a human being. They offered that this was one of the main things they loved about working with Susan and Suzanne, and how healing it was for them. One of them offered that if we could see him with such kindness and realness, knowing that he had committed very serious crimes, it enabled him to do so too. It was very apparent that Susan and Suzanne had done tremendous work to build trust with these guys, and their affection and appreciation they held for these two women was palpable. It made it easy to enter a more intimate conversation and to use our time together most powerfully. And the session was very intimate indeed.
I would emphasize that all of these men were well aware that they had done some terrible things, and they were not “easy on themselves” at all about this—quite the contrary. Most of them had been in prison for 30 years or more. One “youngster” was there only 27 years! They had few illusions about themselves, but they were, against all odds, willing to see that there was something more to who they are, and to feel all that would arise in the process of seeing that. I could see too that these men were in different stages of this journey. Some were still very hesitant to trust. Others were just beginning to open up, and still others were beginning to face the legacy of childhood trauma and deprivation that had led them to such extreme actions. Some made breakthroughs during the meeting. One man sitting near me was initially quite resistant, but upon hearing the conversations and feeling that we really were there to see him, began to tear up silently. When we had a closing meditation, he held my hand tightly and kept saying “thank you.”
As with the last group at Elmwood, this meeting was more of a conversation than a class. And again, these men wanted to know about me, where I came from, and how I got into the work I was doing. They told me that they could tell I “understood the streets.” When I shared with them that I was from New York City and that I had lived in the East Village “back in the day” there were laughs of recognition. One of them shared he had been worried that I would be some kind of “Ivy League professorial a**h***” but was much relieved that I was a “real guy.” The theme of realness was there throughout all of the classes, but most clearly here in San Quentin. There was really no room for spiritual posturing, or patronizing language of any kind. And I loved it! I had a great time with these men, talking about “real stuff.”
In Elmwood, and in San Quentin, I noticed the copies of the book I had written with Don Riso, The Wisdom of the Enneagram, and it was really moving for me to see how carefully the people in these programs had been reading the book. Writing a book is so different from the performing arts. In the latter, you get instant feedback about how the audience is responding to your work. But in writing, you send your message out to the world and hope for the best. So over the years I have been privileged to sign many heavily annotated copies of our books, but it was especially poignant for me seeing these people using the book as a kind of life line—as a way to remember a bigger picture of themselves which is exactly what we wrote the book to do.
The only teaching I did grew out of our conversations. I talked a lot about mercy as something distinct from self-pity and that mercy was a sign of real strength. I talked about how mercy could only grow from a genuine empowerment that came from self knowledge and self mastery—from being powerfully present in ourselves. I talked about how the ego substitute for empowerment is control, and the more disempowered and scared we feel, the more we need to control everything around us and inside us. The men got very excited about this concept.
I was aware that they lived in a world were vulnerability was seen as weakness and to be avoided at all costs. But I shared with them that real strength had sensitivity in it: like a great martial arts master. And who was going to be better able to take care of himself? The tough guy or the sensitive martial arts master? In other words, we were exploring the split between self protection and openness. I wanted these men to have a taste that from presence, grounded in themselves, they could be both, and in fact, they were already both.
After our meeting, a man who was in charge of the special programs at San Quentin checked in to see how we were doing, and then invited us outside to get some group photos. We were all in a great space and I really look forward to seeing those photos. As in Elmwood, I was reluctant to leave the group, but gave and received some big hugs, and let them know I would love to come back. We left the prison feeling great about the meeting and celebrating our friend who was finally being released. The sun was shining gloriously and it was one of those moments were it is obvious that our lives actually do have a purpose.
I do hope to work with EPP again, and will continue to devote my resources and those of the Enneagram Institute, to supporting this very necessary work. For those of you already involved, thank you! And for those of you thinking about it, I am sure there is a place for you in the greater work of transformation that the Enneagram is part of, and to which those of us in EPP are dedicated. And I especially give thanks for Susan, Suzanne, Rick, and Mark, and all of the core team for carrying this work forward, and I give thanks for meeting these men and women who like me, are on a new path to a true and real humanity.
Author and Enneagram Master Teacher
President of the Enneagram Institute