How is the Enneagram a Transformational Path?

03 Dec

In some ways, The Enneagram is a sneaky backdoor to transformation. Upon first glance, the objective data profiled around this unusual, nine-pointed star seems like an amazing, insightful short-cut to understanding the seemingly crazy behaviors we’ve reverted to our whole lives. While the Enneagram definitely cuts to the chase, anyone who persists in overriding the ego-ridden habits of heart and mind will eventually see that stepping around the predictable suffering of personality can lead us to a profoundly spiritual path. The fact that the spiritual dimension of the Enneagram is not always immediately apparent to us can be a saving grace, however, a gift. For, if we knew the amount of discomfort that can arise in the revealing work of self-exploration, many of us might not dare to look in the first place.

It’s quite possible to think dualistically about who we are for some time. We may see ourselves alternately as spiritual beings who happen to have a personality, or just as people primarily driven by psychological structuring without much awareness that anything deeper is going on. We can even work on these two processes simultaneously, but without “integration.” Because personality forms due to the loss of connection with our essential nature, an understanding of where this disconnection first occurred (and continually recurs) can open us to the mutual terrain of spiritual and psychological life. While their integration is necessary to the path to personal liberation, it is still a choice.

That choice can be a murky one. To get to the point where we are willing to look inside ourselves for the more mystical answers to why life is so hard is a slippery slope because, quite frankly, the more wounded we are the better defended and so the harder it is to look. Our attention is habitually drawn to something external to us, someone else’s bothersome behavior, for example. It’s not just the Sixes who are adept at projection. We all love to hate the parts of ourselves that we can’t accept about ourselves by locating these parts in other people. We distract ourselves with something, anything besides ourselves. There is inevitably this disconnection from spirit, essence, Source, God – call it what you like — and it happens for all of us. For most of us, however, this concept is elusive for us to grasp not to mention flat out terrifying to admit.

I recall going in to a therapist’s office during the height of a depression who said: “This must be quite scary for you.” I instantly deflected her comment, “Hey, I’m paying you! I thought to myself with great annoyance. “I called you. I’m not scared.” And then the way that that one comment bumped around in my head all week as I grappled with how right she was, Type 1 Anger my ever-reliable tell.

If you’re looking for a less confrontational start, an equally revealing but seemingly safer place to gain personal awareness can be in relationship, especially in the company of people who share our own type. A Type 7, the style which can have tendencies towards narcissism if left unchecked, recently returned from an Enneagram training and reported how “excruciating” the other Sevens were for him to work with. When he consciously decided not to speak in the Seven circle, “No one even noticed because they each had so much to say!” So it is with self-awareness, the more we look external to ourselves, the more avenues we notice are actually leading back to some truth inside of us. Nothing bothers us unless we have something to defend.

I am fortunate to have found the company of a few Social Type 1s with Type 2 wings whom I shall call “my perfect mirrors.” Occasionally, I recognize behavior in these folks which makes me cringe because I see the judging, angry, critical side of me. What is equally revealing, though, and honestly just as hard to sit with, is observing their characteristics which are the positive shadow in myself, like how a Type 1 moves into action for their high ideals and gets so much done. How do they do that? I ask myself with admiration as I belatedly recall that whole anger thing – the mobilizing passion of Tyoe 1. So, we can teeter in the humanness of self-discovery between text-book, fascinating psychological patterns we see in ourselves (and repeat relentlessly) and the more esoteric realm of from which this behavior is actually keeping us.

Once we make this connection, we can more readily and rapidly unravel why this loss of connection occurred in the first place. Investigating our childhood patterns, the earliest building blocks of personality, is a good place to start. Our inner “realities” are our own private story lines which play out the archetypal themes of our unconscious childhood messages. I like Riso-Hudson’s succinct summary of these voices we all carry around, how Type 6 learned that “It’s not okay to trust yourself.” As a Type 1 I can tell you all kinds of corroborating evidence I’ve gathered to prove why “It’s not okay to make mistakes.” The 2 adamantly defends how “It’s not okay to have your own needs.” The Superego can have quite a hold on us. Deconstructing this mess is a massive effort if we take the task to heart.

We come into the world so magnificently embodying the essential qualities – we are full of faith, totally innocent, we are love and are utterly perfect. I think, in fact, the reason holding babies is so mesmerizing is because they remind us of these qualities in ourselves. Perhaps even in utero, but certainly long before most of us can remember, we start to experience that the world is dangerous — it requires some defending — and then, voilà, we have personality.

Incidentally, early on in my parenting and understanding of the Enneagram I had a protective urge to keep my children from this suffering. I wanted to keep my children from experiencing the world as dangerous. Knowing how fiercely defended I’d become, I didn’t want my boys to have to launch their own defenses. I actually felt (with such chagrin now I tell you) that if I could be a “good enough” mother, they wouldn’t have to grow up in the painful world I’d experienced. So I went over-the-top to shelter them. In my futile effort to control so many aspects of their world — from media images to swearing relatives – I believed that I was “protecting them” from experiencing what the Universe was so lovingly and reliably attempting to teach them. As I took my ideological resistance of reality to its logical conclusion, however, I eventually saw that keeping children from developing a personality is not only impossible, it’s not even “good” mothering at all. Far from it! There is a reason why we don’t introduce the Enneagram to young children. They need to form a personality before they can deconstruct one. Personality is very useful, albeit limited.

So, we grow into our personalities, and as we do we find ourselves alternately digging into our psychological structures to loosen their hold, or bolstering them up to keep ourselves out of the pain from which they seem to protect us. We do this until we cannot bear to continue playing out these habits. My favorite quote by Henry Cloud is that: “We change our behavior when the pain of staying the same becomes greater than the pain of changing. Consequences give us the pain that motivates us to change.” Thank goodness the consequences are taken care of for us. It’s not up to us to arrange the circumstances necessary to bring transformation about. All we need to do is tolerate our own presence; the rest is, shall we say, handled.

There is something to the timing of leaning into the spiritual realm of self-discovery, however. What is it with us and our forties? I could barely make it to this tell-tale life marker before I fell apart. Of course, plenty of people do serious self-work before forty, but it’s as though we need a good many years in our life to allow our ego to be something, before we can withstand the experience of becoming nothing. Once we have grown into our personality type enough, gotten sick enough of our own patterns to investigate the defensive structures we’ve embedded in our styles, we can, if we so choose, slowly but surely (or sometimes with excruciating swift totality) blow our own cover.

As the personality armoring falls away it becomes unbearably obvious that it is necessary to ground ourselves in something greater than ourselves. Eventually our survival strategies, with their limited mechanisms, no longer work like they used to. It is with great relief that we realize, they need not. It is at this point when many people find that indeed there is an undeniable link between psychological and spiritual work as we begin to grasp at something outside of ourselves in order to ground ourselves again.

The superego is always seeking to set-up camp somewhere, and it doesn’t like it when we begin to act outside of the familiarity of our egoic stance. For this reason, it will continually reassert itself. It is useful to know, then, that any move toward our essential nature is an unequivocally good thing. It is not to be considered an escape, or a turning away from ourselves, but a liberation from those aspects of ourselves which have made us suffer in the past. Whenever we are recognizing and acknowledging our identifications, fears, resistances, etc. and bringing our attention to the present moment we are able to become more aware of and open to essential qualities which exist perfectly within ourselves. The healthier we become in our type structure, the more access we have to all of the Essential qualities.

“The unfolding of Essence becomes the process of living. Life is no longer a string of disconnected experiences of pleasures and pain but a flow, a stream of aliveness.” — A.H. Almaas

I don’t mean to imply that allowing our higher qualities to arise necessarily feels comfortable. I have had many folks I teach in prison tell me that: who they were when they committed their crime is not the all of whom they really are. Of course not! When we’re acting out of profound fixation none of us are our True Selves. Interestingly, I have witnessed some of these same people as they begin to experience their True Nature as separate from their personalities for the first time, who are just as uncomfortable, humiliated and humbled by this glimpse of their own gentle, loving nature.

As a Facilitator and lover of this system, I embrace the spiritual dimension of the Enneagram in equal ardor to its psychological aspects. It is my hope and enduring practice to continue integrating both facets within myself to make manifest the transformation I alternatively grasp and resist in my own humanness.

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What is EPP?

Published on November 30 by webmaster for susan olesek Category: what-is-epp Tags: , , ,

EPP stands for Enneagram Prison Project, a nonprofit organization built on a conviction. It is dedicated to making a much needed difference. EPP is a tiny group of committed people who set out to impact a system that really, really needed a new possibility.

EPP is each of us doing our own work and each of you doing yours — the best we can. But, as George Ivanovich Gurdjieff himself said,  “It’s not just difficult to do this work alone, it’s impossible.”

Forming an organization on this single, profound thought, and around a tool as profoundly self-revealing as the Enneagram means that we do the work together. EPP takes Enneagram teachers, who’ve embodied a deep understanding of the human psyche and spirit, inside of prisons and jails. Our clients value the process of self-understanding enough to offer it to the people in their custody.

At EPP, we think the incarcerated are most deserving of this razor-sharp self-assessment tool that helps them to see why they do what they do. Historically, the Enneagram has found itself primarily taught in privileged, educated, white, esoteric circles, but truly, its wisdom has always been intended for anyone and everyone with a genuine desire to know who they really are.

EPP has made it its mission to bring this invaluable tool to the people who need it the most.

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How EPP Came to Exist

Published on November 28 by webmaster for susan olesek Category: how-epp-started Tags: , , ,

Going to prison brought Susan face to face with her ego. When she was given the chance to sit with people behind bars, she began to understand what it really means to come up against the self.

Susan says, “I finally got how fiercely (and unconsciously) we defend, deceive, and depend upon psychological mechanisms and constructs to keep others from knowing us and ultimately from knowing ourselves.”

Witnessing all that transformation was like going to church, without the guilt. Susan kept going back to learn more, to see herself more clearly, to experience more of “that kind” of raw change that going to prison and working with inmates provided.

Eventually, Susan says she started to feel like she was getting away with something profound. She was witnessing transformation, change, and the human potential coming online as no one had ever told her would be possible.  As a result, Enneagram Prison Project (EPP) was born. Susan become convicted that self-awareness, self-regulation training, via the Enneagram system of self-assessment and self-knowing, had to be brought to those in need of understanding themselves.  EPP is about bringing invaluable insights to those who deserve the best possible chance, at a second chance.

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The EPP Ambassadors

Published on November 25 by webmaster for susan olesek Category: epp-ambassadors Tags: , , ,

Society calls them “career criminals,” but many have come to know them as “EPP Ambassadors.” Soon enough, when they hear about 5% recidivism rates, our government may just be calling them “the proof.”  Anyone paying attention can see the profound evidence that change is not just possible, it is happening real-time; gradually and sometimes in startling strides. The most radical demonstration of all, however, is when determined “former felons” return to prisons not as recidivism stats, but as the next generation of EPP teachers and inspirations.

That’s right, what we know as “the work” of self-realization starts from the “inside out,” and therefore so does the EPP Ambassador recruitment process. I have often joked, in mock self-deprecation, that I am just “some white lady with a poster,” until a program participant really does “the work.” Because you know, the Enneagram is flat out an amazing system, however, unless and until it is practically applied to a real life, a genuine human dilemma, it’s merely theory, just another tool in the box.

But, it takes more than a minute to do this work…

Currently incarcerated inmates “doing time” spend hours and weeks on end unpacking defense mechanisms, avoidance patterns and idealizations, a process many of them have affectionately coined “doing me.” While we “do time” together, EPP students (and I, too) vacillate between admitting to our own antics and aggressively defending them. Fairly predictably, though, people who may start out with a big egoic defense: “Well, that’s just me!” follow up with a more somber: “Oh, $#*!, that’s also me!” and so goes the process of waking up.

By the way, this is not unlike the awakening that happens inside of corporations, or the monthly workshops in my own little sheeshy town in California. Because the human condition is just that, human. Somehow, though, when we get wind of how this magnitude of change happens in prisons and jails we all sit up in our chairs just a little more. We all try hard not to ask ourselves a really difficult question, and I’ll just be blunt: “If they can do it, what’s my problem?” I can venture this guess about you because I’ve asked it about myself.

Ambassadors who are willing to continue their self-study upon their release have already turned some necks in the Enneagram trainings they’ve attended at retreat venues around the country. People frankly just don’t see these guys coming. Time and time again, EPP Ambassadors end up surprising the pants off of everyone – themselves, corporate CEOs, and quite honestly myself included.  For the most part Enneagram rookies report, in hindsight, that they didn’t anticipate the kind of revelations they’d have from this kind of self-study. How could we? It is a journey, and who would have thought that a trip around a funky little diagram could pack such a punch?

The people poised to carry the work of human transformation furthest forward are those who have traveled the furthest depths of themselves.  We have an eye for this potential inside of EPP. When we see someone who gets the Enneagram all the way under their skin, we are so inspired that we can barely contain how much we care to see them succeed.

Men and women who have survived serious abuse, familial dysfunction, and then our criminal justice system and who have managed to keep their hearts open earn a different kind of badge. Holding out for oneself long enough to try to change “one more time” after that kind of trip is as humbling as it is heroic. Frankly, these are the folks who get me out of bed in the morning. These guys fuel my willingness to tolerate the tantrums of incredibly powerful people, running massive organizations as they frantically do exactly what folks behind actual bars have done – hide from themselves.

Anything EPP might hope to say about “the theory” behind bringing the Enneagram to criminal reform pales in comparison to hearing what someone who has done hard time and who has applied the Enneagram could offer. I know a little bit about this population EPP hopes to serve, but truly, these women and men are the experts and have much to teach those of us who want to help.

Before I went to prison, I imagined myself to be much more open-minded about the people I’d find there than I actually was. I told my colleagues how surprised, how blown away I was, actually, by the humanity I found within prison walls. Witnessing the projections and assumptions I made (and continue to find myself sometimes making) and that others so innocently make about inmates remains humbling and eye-opening.

Those incarcerated men and women who have taken the Enneagram teaching to heart are the future for all of us “doing our work” and are the future of the Enneagram Prison Project. They have demonstrated the tenacity for self-inquiry, they “did their time” and figured out what got them in so much trouble with their personality in the first place. If this only lowered the recidivism rate, their efforts would be absolutely worthwhile, but these guys bring a level of credibility to EPP and to the Enneagram itself, that is indescribable.

These willing men and women have come to mean the world to me.


“”As an inmate, I found myself lost and struggling to find out what had gone so wrong in my life that I no longer deserved freedom. As a student in one of Susan Olesek’s first prison classes, however, I learned that I not only deserve freedom but that I also hold the key to my own personal freedom by simply taking an honest look at myself, my choices, and my behavior. I directly credit Susan for being part of the most positive change my life has ever experienced.”

— Clay Tumey | Former Inmate and Current EPP Ambassador | Cleveland Correctional Facility | Austin, TX

“The work that my teacher and mentor does is like no other I have ever been involved in or introduced to. Susan Olesek has such passion for what she does and for the people that she teaches. It’s great, and to tell you the truth, it’s because of the way that she teaches that I stayed with the program and her class. It works and it was working for me and still is. The compassion and genuineness that she displays and gives is unheard of compared to other teachings and programs that I have taken. I have had the pleasure of co-teaching a class with her not too long ago and I will tell you this, it was a little intimidating, because she is that good at what she does, and I as the student just don’t want to mess up! But it turned out to go very well; I want nothing more than to make her proud, and I think I have. Working with Susan has really changed my life to a life I really never thought was possible, but learning from her was the tool that was missing. She gave me the answers and guided me to the right path in life. The person who is writing this letter is a real person today. Someone who takes care of himself, because, he knows he matters today! My needs are important and these are some of the things that I did not know only three years ago. It’s crazy how a teacher can come in and make you feel like a real person and see you for who you really are, and that’s what Susan does! She has a gift, and everyone should get to be part of it.”

— Victor Soto | Former Inmate and Current EPP Ambassador | Elmwood Correctional Facility | Milpitas, CA

“From sitting in a prison cell, considering myself to be apt enough to anticipate any and every move and playing mental chess as my way to survive, I took pride in knowing what’s going to happen three moves ahead of time. I have to admit now, while I am sitting here in this moment writing this, I never saw “her” coming.  That “her” is Susan Olesek. And thank the Universe that I didn’t, because this woman has taught me so much, mentored me when no one else would, and saw something in me that I couldnt see. Susan Olesek helped me to become a better man and become the father I so desperately wanted to be.  For that, I am eternally grateful. But that’s not what gets me.   Susan impacts everyone’s life in such a beautiful way, in a way that makes them feel like I do.  Susan Coleman Olesek, I am so honored to have had you come in to my life and allow me to be a part of this big beautiful EPP family of ours!”

— Elam Chance | Former Inmate and Current EPP Ambassador | Cleveland Correctional Facility | Austin, TX


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Make a Donation to EPP

Published on November 9 by olesek Category: donate Tags:

A contribution can start as small as $25.00, or it can be airline miles, or it can be a stock donaton too. A contribution of $500 or more puts one incarcerated man or woman through the Introductory 8-week EPP Enneagram program and gifts you your very own “Key to Freedom.” On behalf of all of EPP and its supportive colleagues, associates, we THANK YOU for your support!

Your contribution allows us to further the goals and activities of the Enneagram Prison Project (EPP). EPP is a nonprofit 501(c)(3) and relies on its colleagues and friends as well as government institutions to carry out its mission of transforming the possibilities of those incarcerated through self-awareness training and practices made possible via the Enneagram. Contributions directly support EPP’s ability to build its infrastructure, create curriculum, market itself to the many prisons (and the incarcerated), reach more people,  train Enneagram specialists, and stay in contact with its network of supporters, participants, teachers, and facilities.

Contributions to EPP are tax deductible.

Make A Contribution Today

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“The White Lady with the Poster”

Published on September 6 by olesek Category: what-is-epp Tags:

I went to prison on a leap of faith and an idealistic prayer, fully intent on teaching something that I had — ironically — yet to fully learn myself: that we are all in a prison of our own making in how we suffer our personalities. Almost immediately, I realized that an application of the Enneagram within this demographic was perhaps the most moving thing I had ever witnessed, but it took me more than a minute to overcome my own projections. “You’re too inexperienced, too white, too female, too sheltered…” — too many things — my ego told me, to be as effective as I felt those guys deserved a teacher to be. A nagging truth relayed to me by a mentor kept arising during this time:”You can’t take anyone where you haven’t been yourself.” Boy, did she have that right.

Working with myself on the inside, as I persisted in working alongside others “on the inside,” was simply the only way I could sense how to break out of my own personal prison. By unpacking defense mechanisms, avoidance patterns, and personal idealizations with hundreds of incarcerated participants, I slowly turned the key in the most confounding, locked up parts of myself. By alternately admitting to our own antics and seeing how aggressively we could go about defending them, I can say that I have learned a thing or two over the time I’ve done in prison. For one, I can now recognize an inner critic when I see one. What is more, I’ve replaced that inner-criticality with a far kinder, more developed inner guide. It is with my own self-knowing that I have been able to go where imprisoned men and women, literally and metaphorically, need to go in order to know themselves. We venture “there” together.

I don’t purport to know anyone else’s pain, nor expect you to know mine. We really must walk in our own shoes. But I daresay, I can pull up a chair. I’ve now sat with hundreds of men and women peering through the bars of their personal prisons together and know, that I know, that I know…that this “Enneagram thing” works when — and only when — we start from the inside out. Come and see for yourselves.




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A Team, A Vision, An Organization

Published on May 11 by olesek Category: what-is-epp Tags:

One opportune trip to prison and the whole trajectory of my life — professionally and personally — was absolutely inspired. Seeing how one hundred incarcerated men took learning about themselves so much to heart compelled me to follow this exhilarating example of realizing the human potential with everything I had. Three years later in April of 2012, flanked by two dedicated founding board members: my partner, Rick Olesek and my colleague, Suzanne Dion, Enneagram Prison Project (EPP) was born.

Standing at the helm of a fledgling non-profit as an executive director with more vision than I had experience, I was delighted to encounter a newfound passion for social entrepreneurship. With my wits in one hand and my poster in the other, I talked my way into a local jail and before anyone could finish shouting, “You cannot possibly teach the Enneagram to prisoners!” EPP was on the map with a 5% recidivism rate. Boom.

We set out with this vision, based solely on what I had witnessed firsthand:  To free the incarcerated from the prisons of their own making in every prison and jail in the United States and around the world. To that end, in the few short years since its inception, EPP has contracted with two government agencies in two different Californian counties, and offers a year-long program to lifers in San Quentin State prison. There are waitlists. We are developing an International Affiliate Program with pilots starting in Copenhagen and Helsinki. In short, this Enneagram thing works for “those folks” just like it does for my corporate clients, just like it did for the three of us. What do you know, we’re all human. We are ecstatic to grow this paradigm-shifting idea as we each grow along with it.

In fact, equal to our joy in seeing something so personal to me flourish, is the satisfying opportunity that running an organization offers me and our team to “walk our talk.” Whether it is writing company policies, defining our company culture, forging strategic partnerships, or resolving conflict, one core value we share at Enneagram Prison Project is that “We do the work together,” and, work there is to do!

I’ve got my Type 1 sleeves rolled up and am hanging on to my bursting heart as we keep pace with some incredible momentum. We are never short on material to work with, including, “The prisons of our own making” and how to move beyond them inter-personally, professionally and now organizationally.

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