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Susan Olesek – Enneagram Types: The Key For Humanity?

By Gwen Dawkins

Susan Olesek, 49, willingly goes behind bars to compassionately connect with those incarcerated by teaching them the Enneagram. Referring to herself as a human potentialist, she wants them (and you) to know that their true essence is something amazing. Her Enneagram Prison Project (EPP) utilizes this universal psychological tool to cross all cultures, borders and boundaries to get down to what makes us human.

What is the Enneagram Prison Project?

We help people on both sides of the bars understand why we do what we do through a psychological system called the Enneagram (pronounced “ANY-a-gram”). The Enneagram is a self-awareness tool that “maps” the strategies we unconsciously used to survive our childhoods. These can potentially be healthy, unhealthy, and even self-sabotaging –– and they’re all predictable based on nine personality structures. This can be especially enlightening for incarcerated people to understand their underlying pain, why and how they have repeatedly discharged that pain in unhealthy patterns, and how to better self regulate. Pre-Covid, we taught 15 Enneagram programs in jails and prisons in California, in addition to programs in Minnesota, Belgium, and France. We also have affiliates now forming in the UK and Australia. Since Covid, we’re now offering our “in-custody” curriculum in classes virtually for the first time to the general public.

How did the Enneagram Prison Project come to be? 

A spiritual leader, who knew I was recently Enneagram certified, invited me to teach 100 incarcerated students at a small Texas prison. It made so much sense, and I loved the idea, but I was worried that the students would be too tough or angry to want to learn about it. Despite my insecurities, I decided to go. As it turned out, the students were so grateful that someone cared, and they were hungry to learn about themselves. It was beautiful. I commuted from California to Texas to teach the program for three years. But I was also a mom to three young children aged one, five and nine, and I wanted to do this work closer to home. So I contacted jails and prisons in the Bay Area. Elmwood Correctional Facility offered me a classroom for 12 weeks. Fifteen men self-selected to join the class, and it turned into an unbelievably inspirational time for all of us. In fact, from that first class came two of our nine “Ambassadors,” who learned the Enneagram while incarcerated and now teach and speak for Enneagram Prison Project. From there, we received a grant which enabled us to teach in additional facilities in Santa Clara and later contracted with Maple Street Correctional Facility in San Mateo. I was invited to speak at San Quentin State Prison; then got invited back again. The men were really curious, and we began teaching there as well.

Are you ever in fear while working with incarcerated men and women? 

I have never been afraid for my safety. But in the beginning, I was terrified that I wouldn’t do a good job or that no one would come. They came. I’m no magician. The only way the Enneagram works is if people want to be there to learn.

What do you hope the EPP to accomplish? 

My goal is to help people fall in love with themselves and all of the types. There’s something incredible about each one of us as we are.

What types of changes/revelations have you seen with EPP participants?

One thing we see is that people relax and become more connected to themselves. There are nine different ways people defend. Humans often operate with some idea that we have a deficit. All, but especially those incarcerated,  focus on the bad things they’ve done –– we help them understand that’s not the crux of who they are. We teach about self-forgiveness. Transformation happens gradually, and it can only be achieved when people open their hearts. Since Covid, many incarcerated folks have been released. Our EPP Ambassadors help our students and their families make the fragile transition back into our community. 

For the first time, your courses are available to the general public.

Yes! That’s always been our long-term goal, but we’ve been focused on bringing our program to additional correctional facilities. However, once Covid hit, we were suddenly forced to pause all prison programming. The silver lining is that it created the opportunity to pivot and start offering our courses online publicly. “9 Prisons, ONE Key™” is a foundational course designed to illuminate how we are all in a prison of our own making in the ways that we suffer our personality and makes clear that we all hold the key to our freedom. Our “Path to Freedom” training program moves deeper into the Enneagram for those interested in growing their self-understanding or potentially becoming “guides” in our prison and jail programs taught worldwide.

Can you talk a little about your own path to the Enneagram? 

I’ve always been a seeker. I love people and want to understand why I’m on the planet. Tragically, my mother committed suicide when I was five-years-old, and somehow I believed it was because of me. For the next three decades, I told myself versions of a story that, “If I was good enough, horrible things wouldn’t happen.” My obsession with constant self-improvement became my own personal prison. After marrying and becoming a mom, I took parenting classes –– always trying to meet the ideal. I took an Enneagram class with other moms who were trying to figure out our kids. But I learned “the work” was really about us. It woke me up, and I wanted to learn more and get certified to teach the Enneagram and know more about myself and others.

Your approach seems especially focused on the positives of the 9 Types. Is that a result of working in prisons? 

The Enneagram points us to our profoundly unconscious behavior; it’s not all rosy. Many Enneagram practitioners start with the dysfunction of the types. But I realized it didn’t feel good to focus on the distortion. I am interested in what’s good and right about all of us. For example, I personally identify as a Type 1, which many call the “Perfectionist.” But being perfect is not attainable, and I always cringed when I heard that word. The way we at EPP see it, Type 1s teach us the sensibility of wanting to do the right thing. We call Type 1s “Idealist/Reformers” because they want to line up with their true north, with integrity, what’s fair, and doing meaningful work in the world. Anger is the instinct that points us to what is fair and right, but Type 1s often avoid displaying anger, thinking that’s not a “good” emotion. But instinctually, anger actually lets us know that we really care when things aren’t going the way we think they should. Type 1s become perfectionistic when trying too hard to be good; it comes from an innocent place. We are all filled with paradoxes, and the ego is simply a mimic of who we essentially are. When it comes to those incarcerated, many people don’t take the time to see the person’s essence. All of us at EPP are open and focus on every person’s positives because we know we become who we think we are –– where our attention goes, our energy follows. 

What’s your major source of funding for EPP? Can others help? 

We receive grants from various entities as well as philanthropic contributions from foundations and individuals. And our online courses are donation-based.

How can others get involved in EPP? 

Start at the EPP website for more information about our projects, courses, and donation opportunities. We’re running the “9 Prisons, ONE Key™” and “Path To Freedom” as live virtual courses, offering multiple cohorts over Zoom to accommodate many schedules across many time zones. These courses are wonderfully enlightening and create healing opportunities. There is no fee to participate in these courses, and EPP uses a donation-based model, which is voluntary and paid at the end of the course.

Enneagram Prison Project is a 501(c)(3) non-profit dedicated to serving those incarcerated and their potential future.

Check back with Zest & Aplomb for additional blog posts about The Enneagram and understanding your type.

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2 Comments

  • Reply Christina Morgan March 2, 2021 at 12:48 pm

    I discovered the Enneagram on PBS in 2000 and became a forever fan. I often thought of how wonderful it would be to spread this knowledge to those that wanted to learn. The path that Susan has taken to share this tool to help individuals be the best version of their type is truly inspirational.

    • Reply gwendy79 March 4, 2021 at 2:20 pm

      I agree Christina! I ran out of room in the article, but Susan has also piloted an Enneagram program for high school students — the idea being that the sooner we can begin to understand ourselves, all the better! Thanks for reading and commenting! 😁

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