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Susan Olesek, Enneagram Prison Project

Published on 01/18/2018

What is your life’s purpose?
Freeing myself and others from the prisons of our own making.

How are you living your purpose?
I am working to solve the problem of mass incarceration from the inside out.

Historically in the U.S. our approach to correcting bad behavior has not worked. We know this because there has been a nearly 700% increase in incarceration over thirty years. Our criminal justice system is badly broken and the epidemic of incarceration is hurting many more people than just those behind bars. African Americans are incarcerated at nearly six times the rate of whites, and the poor are disproportionately represented behind bars. We need change.

This is not a criminal’s problem, this is everyone’s problem. As Bryan Stevenson said: “All of our survival is tied to the survival of everyone.” We must recognize the collateral damage of systematically imprisoning those already marginalized economically, socially, and psychologically. Locking people up without offering them the resources or psychological and emotional safety to really change is not right.

In 2012, I founded Enneagram Prison Project (EPP), a nonprofit which supports men and women in prison who are desperate to change, but have no idea how to do so. Our curriculum is designed to support participants in taking 100% percent responsibility for their thoughts and emotional reactivity, and ultimately, their outward behavior. We accomplish this by teaching an incisive psychological system called the Enneagram that identifies the repeating patterns of thoughts, feelings, and behaviors people are in the habit of expressing to cope with themselves and others, meet their needs, and pursue their lives.

The Enneagram provides a “map” to recognizing the strategies that have unconsciously been used to survive and the ways these predictable habits can get acted out in healthy and unhealthy ways. When an individual is unconscious of underlying hurt and pain, they are frequently unaware of how they may be acting out, discharging their own negative beliefs and needs on themselves, others, and society as a whole.

In the past eight years, I have worked closely with some of society’s toughest “career criminals,” those whom society has all but discarded. I found two things to be true:
1. Hurting people hurt people and
2. The incarcerated are some of the most willing agents of change.

In the most practical sense, “their” healing is for the protection of “our” society as a whole. Impacting a problem of this epic proportion requires a radical, massive shift in consciousness, a shift in caring.

One of the most meaningful aspects of my work with EPP is when those who have fallen in love with themselves and “the work” with the Enneagram, are released. Many of these returning citizens have come to join us as EPP Ambassadors. Together with our partnering Enneagram schools, we scholarship these students to go on to deepen their Enneagram studies and become spokespeople for this project. These courageous women and men have presented at universities, high schools, and Fortune 500 companies about the transformational power of self-knowing. Some of these students are now certifying to become Enneagram teachers in their own right and will one day soon return “on the inside” as EPP Guides. Ambassadors are the proof that change is possible and they remain my biggest inspiration.

How did you find your purpose?
When I was five years old, my three siblings and I left our dinner on the table and followed the sound of my father’s scream downstairs. We stopped short at the scene of my mother’s suicide. The night she hung herself, my mom must have decided that her life had no worth, and I decided, as a child does, that my mother’s decision was because of me. I would spend the next three decades of my life telling myself versions of, “If I was good enough, horrible things wouldn’t happen.” Living under the habitual obligation to improve myself, and the world around me, ran me like a junkie. This became my own personal prison.

In my 20s, I married, had my first son (and then a second and a third), and promptly put myself into a parenting class that introduced me to something called the Enneagram. An incisive, psychological tool, the Enneagram showed me that people’s neurological organization is so patterned that we are actually predictable. Like a “map” of ego-structures, this curious, nine-pointed diagram pointed out the cognitive, emotional and behavioral strategies all of us use to survive our childhoods.

Reluctantly, I recognized myself as a Type 1, a Perfectionist/Reformer, whose pattern it is to suppress anger, and to reframe it into something more appropriate. Utopian at heart, Type 1s forget that our “goodness” is inherent, not earned, so we set standards for ourselves (and others!) that leave us eternally idealistic, but chronically frustrated—a nicer word for angry. For the first time, I understood. The contempt that I held for myself was directly connected to my fury at the world for abandoning me when my mother disappeared from my life. I saw how I could temporarily suppress my outrage by staying above and beyond my own reproach until my ego caught up to me with its self-critical judgment and seething resentments.

There was nothing “wrong” with me, it turns out, just an intelligent response to a massive hurt and my fierce compulsion to avoid it.

Slowly I began to realize that in nine different ways we all come to suffer that we are “not enough.” This is the human condition. I wish I could say that’s when I became enlightened, but I would not find any lasting reprieve from my inner critic until 10 years later when I found myself in a little Texas prison, as a newly certified Enneagram teacher, face-to-face with over 100 men who were in for everything from drug dealing to murder. I was hired to teach something that I believed, but had yet to really learn, “that we are all in a prison of our own making in the ways that we suffer our personalities.”

Sitting with people at the unhealthy, rock bottom of themselves as we found our breath and located an inner witness to ourselves—in a place like prison—was a miracle, because their practices of self-sabotage, self-abandonment, and self-hatred, I sheepishly realized, were also mine. Years of therapists and healers, workshops and self-help books could not rival the extraordinary journey inward I received from teaching in that prison, with those men, over the next four years.

Feeling like I was getting away with something inside those walls, I wanted to share with others what was happening and I somehow got permission to bring a filmmaker inside the prison with me. As I sat interviewing several men about their personal transformations using the Enneagram, I was blown away by their vulnerability. Then, my client at the prison asked each of the men “What was it like to work with Susan?” and I watched as each one of them started to cry. I suddenly saw that my story of being “not good enough” was a tired one, and what a fraud I would be if I refused to take my own teaching, the teachings of the Enneagram, to heart. Right in front of me, I watched as those hurting men began to wake up to themselves and as they did, they literally held space for me to do the same.

I knew then what “the work” really meant and that I was not only doing it, but that my purpose was to facilitate how others could also learn to love themselves as I was learning to do.

What advice do you have for purpose seekers?
Know yourself. “The work” of self-understanding is not like anything else and there is no substitute. Knowing what motivates us, what drives us, what we avoid and precisely how we do this deep inside of ourselves is profound and empowering. The Enneagram is a map of ego-structures that provides so many inroads to who we truly are that it will continue to unfold and guide us as we open to our truest selves.

What resources do you recommend?
Enneagram resources:
The Wisdom of the Enneagram: The Complete Guide to Psychological and Spiritual Growth for the Nine Personality Types by Don Richard Riso and Russ Hudson
Essential Enneagram: The Definitive Personality Test and Self-Discovery Guide — Revised & Updated by David Daniels and Virginia Price
Enneagram Institute
Enneagram in the Narrative Tradition

Resources on the history of incarceration:
The New Jim Crow: Mass Incarceration in the Age of Colorblindness by Michelle Alexander
Just Mercy: A Story of Justice and Redemption by Bryan Stevenson
Between the World and Me by Ta-Nehisi Coates

Other resources:
There Is Nothing Wrong with You: Going Beyond Self-Hate by Cheri Huber and June Shiver
Daring Greatly: How the Courage to Be Vulnerable Transforms the Way We Live, Love, Parent, and Lead by Brené Brown


Connect with Susan Olesek, Consultant and Human Potentialist
Email:  Susan@SusanOlesek.com
Tedx Talk
EEP Ambassador video

An unapologetic idealist, Susan Olesek is a consultant and Human Potentialist in passionate pursuit of what is possible for people. In 2012 she founded the Enneagram Prison Project (EPP), now a burgeoning California Bay Area nonprofit offering self-awareness education and self-regulation training to the incarcerated in Santa Clara and San Mateo County jails and San Quentin State prison with an international affiliations in Helsinki, Finland and soon to be Belgium and Australia. Using the Enneagram, her favorite foundational tool for human transformation, Susan delights in the facilitation of individuals, groups, and society reaching for the highest parts of our collective selves. She is a sought after international speaker and teacher of the Enneagram residing in Los Gatos with her three boys and her husband, Rick, her “steady Seven” and EPP’s Executive Director.

HeleneTStelian Musing
I’m Hélène Stelian, the Midlife Mentor with a passion for facilitating personal development in women 40+. Through my THRIVE Courses, I help introspective, curious, action-oriented women 40+ deepen their journeys of self-discovery and growth—and create their next chapter with courage and intention.



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  1. Rena

    Fascinating. I had never heard of this before, but I love what you’re doing! Such important work.

    • Susan Olesek

      Thank you so much for seeing this work. For me, I feel incredibly lucky to be allowed to go in and out to work “on the inside” with people who are just so determined to change their lives and empowered with such a powerful tool to do it.


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