The Enneagram: The Missing Piece in Criminal Reform

By: Susan Olesek

I had to obtain extra security clearance to first bring them in, but now regularly, on week five of the eight-week program we teach in jail, we purposely drop two, 100-piece puzzles, a pair of kittens made “for under five years old,” onto the floor and direct 45 supposed “hardened criminals” to divide into two groups to assemble. Personality comes online like giving a ball to boys at recess.

I am now part of a growing team of people who teach self-awareness to the incarcerated, using primarily “the Enneagram,” a human consciousness map of sorts. This incisive tool points to the cognitive, emotional, and behavioral patterns we unconsciously and conditionally developed to deal with our heartbreak — our panic, our terror, and our rage — when we came to believe that who we really are was not okay. We call these patterns “personality.” This habitual, human response to protect ourselves is intelligent. It is necessary. And, though it helps us to survive the brutal unconsciousness of those around us, over time, it is a deeply painful experience and one that leads to a lot of loss of our emotional self. The incarcerated know this better than most.

On puzzle day, Type 3s, “The Performers,” immediately create a competition. Type 5s, the “Observers” withdraw from the crowd. At least one Type 6, the “Loyal-Skeptic” almost always suspects we’ve withheld a piece. The “Helpers” Type 2s, are likely to finish their own puzzle and move over to support the other group. I’ve seen a Type 8, the “Boss,” begin egging on the other group, and once, magnanimously demand that everyone work together. The way we do anything is the way we do everything, as Father Richard Rohr is apt to say.

It’s downright predictable how people will demonstrate their type structure on the Enneagram system, but what happens beyond this interesting display is something I didn’t anticipate: They banter, they play, they support each other, they laugh out loud... They’ve often told me: “Doing this puzzle made me forget I was in prison. I haven’t done a puzzle since I was a kid and it just felt like I was one again.” They thank us, sometimes profusely, and across cultures, gender, race and age, inevitably, five weeks into their self-study, they then make a notable turn inward.

As we explore how the basic conditioning of personality comes from childhood, incarcerated students share things that happened to them, which sicken me. One man shared how his mother prostituted herself and did drugs in front of him, that when child protective services came for him, his mother could only say: “Just take him!” And then he was beaten in foster care. His tragic story is, sadly, not unusual. In an infinitely intelligent move towards their own survival, the people who share these stories that I cannot even make up, realize how they have silently locked away parts of themselves, piece by piece and sometimes in one fell swoop, just to survive.

It has never been so obvious to me, so logical, why humans are self-forgetting. We come by our tactics so innocently as children, and by the time we are adults, we are using them quite unconsciously, and almost totally habitually. I will tell you, though, what is even more astounding than the horrors that people endure, is the way in which they emerge from the unthinkable, having somehow managed to hold onto their hearts. At Enneagram Prison Project (EPP), we use the Enneagram to understand how to contact those denied parts of self, which are often the most precious pieces. The process is every bit like a puzzle, one student stated EPP’s approach precisely:

“I’ve been from program to program, but never in my whole life have I found anything like the Enneagram. I’ve been in recovery a lot of years, in and out of prison, in and out of jail. I have so much potential. It’s a puzzle, you know a puzzle? You put it together piece by piece, but there was one piece missing. There was one piece that was missing and I came and I found it here [in Jail]. I don’t regret being here anymore, but I betcha I won’t come back. “ — Elizabeth, Type 2

This week, I started a program with a new group and was approached by a student hastily before the class started. He literally said to me: “Ma’am, I’m 19 and I have never been to jail before, I just got here. I was wondering if this class could help me remember who I am? I feel like I used to know, but I thinkI forgot. His words were so profound and I told him so.

There is no knowing more important than self-knowing and the Enneagram system is the most human potentiating tool I have ever come across for self-recovery. This tool is for the recovery of the authentic, disenfranchised self. The incarcerated have suffered greatly and this is something we all need to deeply examine as it affects all of us, just as the healing, and awakening of each person profoundly impacts us all.

BIO | Susan Olesek is a “Human Potentialist,” a consultant in pursuit of what’s possible for people. Born outside of Boston and schooled in Hong Kong, Tokyo, and England, she obtained a sociology degree from Occidental College and is certified by two Enneagram schools:Palmer-Daniels andRiso-Hudson. Susan runs Enneagram workshops across the United States and in her local practice in Northern California, and is the Founder of theEnneagram Prison Project (EPP). Today, EPP is a burgeoning, paradigm-shifting model of self-awareness education for the incarcerated and is spreading rapidly across the globe. Susan lives in the Santa Cruz mountains with her three children, dog, three cats and dozens of chickens, along with her husband, Rick, who is the Executive Director for EPP.

You can learn more about Enneagram Prison Project, or contribute to this work, at:

You can read previous articles by Susan Olesek featured on Enneagram Prison Project for The Catalyst here:

2015: See Shadows - click here

2014: My Own Personal Prison - click here


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This article appears in: 2016 Catalyst, Issue 9: Yoga Day and Enneagram