The Shift Network Blog

Seeing Shadows

Seeing Shadows
Susan L Olesek
By Susan L Olesek

It was dark out as I approached my parked car one night last month, but I saw the light was on inside the vehicle. Seeing a shadow inside, I felt an eerie, gut-sinking-knowing that someone was in the front passenger’s seat. In a bizarre instant, I realized that I was being robbed. I felt at once terrified and equally incensed at the injustice, but kept walking towards my vehicle despite my mounting panic. What do I do? I asked myself, turning and looking frantically around.

The irony of the timing of this happening immediately struck me, since I was returning home from a three-hour volunteer training at San Quentin State prison. I work there with lifers teaching the Enneagram, a psychological system which elucidates why we do the things we do. Feeling primed by the Correctional Officer, who punctuated the training with shocking stories of the horrible acts people are capable of committing, I grabbed my wits and searched for help. I didn’t want to be the mom of three boys, shot dead in a Trader Joe’s parking lot, any more than I wanted to be a fool who stood idly by while being violated.

I pleaded with a passing man to help me, who pulled the passenger door open and startled the trespasser. A young, scruffy looking 20-something-year-old man spilled out of my car. The contents of my glove compartment were recognizable in his half-opened back pack. Never before have I experienced my Inner Witness more perceptibly than in the surreal five minutes that followed; never have I felt more outside of myself while observing my own thoughts.

I felt my body begin to shake as I screamed at this total stranger in an uncomfortably intimate face-to-face and demanded: “What are you DOING?! EMPTY YOUR BACKPACK, PUT EVERYTHING ON THE GROUND!” I felt like a cop. Oh my God, who are YOU?! I questioned myself, shocked at my own behavior…

[Aside: Since learning the Enneagram, I have identified with a Type One, a dutiful, rule-abiding, “perfectionist,” an “anger type” with a serious record of swallowing rage “for the good of” all kinds of things, but at a severe cost to myself.  Allowing anger to move through me freely is like the wild frontier for my Type.]

Who WAS this person shouting, and from where did she come? I felt my fury at what was unfolding in front of me fuel me into outraged action, and yet, I also felt both my feet on the ground. This was uncharted territory for me, for sure, and I watched with a rubber-necked fascination at this unfolding of a new part of me – quite beside myself.

Amazingly, the man did as he was told. Crouching down, he furtively began dropping items on the pavement between us – a pair of tennis shoes, an eyeglass case, someone else’s wallet - I collected my things, clutched them to my chest, and senselessly began to eat one of the carrots out of the half opened bag I just bought minutes before. What’re you DOING?! I chided myself, incredulously, watching my own incoherent behavior with one eye, and that of the man in front of me with another.

I started to gather that he was actually not violent. In an odd way, I already felt sorry for this kind of harmless thief and his sorry lack of savvy.  Nevertheless, I heard myself continuing to scream at him. He seemed queerly detached – like maybe he’d been yelled at in his lifetime, I considered. I only half wanted to detain him until the police arrived. The small, indignant part of me felt this was the “right(eous) thing” to do. A slightly wiser part of me knew their arrival would solve nothing.

I’ve been working with people convicted of everything from bank robbery, to murder, to rape in prisons and jails for the last six years. One thing I know, for sure, is that by the time people are acting out in the ways in which this man was behaving, they’ve long since justified their own dysfunction with a litany of wrongs that have been “done to them.”  All human behavior is an attempt to get a need met. I teach this. Somehow, in that tense moment I recalled it, and knew this to be also true for him. Though I could judge him in a heartbeat - and, in fact, was - his behavior was just part of his desire to survive and this, apparently, was his strategy.

Remarkably, in a twisted sort of demonstration of his moral cognizance he tried to right the wrong-doing in which he was enmeshed. “Here!” he said, pulling a plastic bag of pot out of the backpack and shoving it towards me. I could recognize his barter – my receipt of this valuable contraband for his hopeful pardon – but I couldn’t quicken my self-observations to keep pace with the spin of my own ego which was still bent on adjudicating his “misconduct.”

“I DON’T WANT YOUR DRUGS!” I barked back, shunning this ill-begotten bribe and reached my hand into his bag to see what else of mine he had. Offended now, his willing window of appease slammed shut and he snatched his bag from me, showing anger for the first time: “Now you’re stealing MY stuff!” He accused me and stood up.  I shook my head at his reasoning and felt his last statement shift our exchange so far beyond surreal that I was jolted back to reality. I stepped back and looked at this human being. I considered his wildly rationalized indignation with just a little more presence. His willingness to cooperate exhausted now, we assessed each other face to face once again, for a few more fleeting seconds.  

I come by compassion for others readily. Too readily, I’ve been told. I’m quick to recognize the traps we lay for ourselves; the repetitive habits of thinking, feeling and behaving we call personality and how we get in trouble with it, again and again. I regularly sit inside the bars – real or metaphoric - offering this “key to freedom” called the Enneagram to people. On this peculiar night, however, I felt the key turn in the lock of my own cell.

Until I went to prison (to teach the Enneagram), my own ego kept me shackled to the narrative I began to tell myself after my mother’s suicide at age five: “You’re not good enough.” I’ve served a self-imposed life-sentence while trying to square my mother’s inability to find her own worth with my own struggle to do the same. This is my personal prison. I catch my inner critic in the act regularly; it’s uncompromising rage at the unfairness in the world seems always just below the surface. The scariest place, for me, is to recognize – in real time – that I’m angry. Being willing to follow my fury to it’s source is akin to looking under the bed when I was eight - terrified of what I might find. But I take heart in what David Whyte says:

“Anger is the deepest form of compassion for another, for the world, for the self, for a life, for the body, for a family and for all our ideals, all vulnerable and all possibly about to be hurt. Stripped of physical imprisonment and violent reaction, anger is the purest form of care, the internal living flame of anger always illuminates what we belong to, what we wish to protect and what we are willing to hazard ourselves for.”

I was angry at the distress this man’s actions triggered in me that night – absolutely. But, as it turns out I had a litany of wrong-doing I was tapped into myself. I was irate at the Correctional Officer who scared me enough to question the viability of my work earlier that evening. I was infuriated by the mass incarceration in the state of California, enraged by this man’s lack of care for his own soul and at my own lack of faith in the justice system. I was exasperated at the lack of opportunity our system provides incarcerated people to actually heal.

Honestly, though, much deeper than any of these ideological distractions, I was mostly angry at how many years it took for me to find self-worth enough to put a convincing voice to it. For years and years I have awakened in a panic from dreams in which, though someone was harming me, I did not speak up.  In this man’s desperate self-sabotage that evening I dimly recognized my own terrified reflection and this is what I was shouting at until my voice went hoarse.

My own wrath nearly spent, the intruder must have realized that I wasn’t going to physically apprehend him. Without struggle, he side-stepped the way I had been boxing him, corralling the scene, and then suddenly, with little ado, disappeared quickly into the night.  As I stood there silently watching him go, my heart still pounded so fast it actually hurt, but I knew that the baffling turn of events that I had just witnessed contained the paradox with which I wrestle most.

My Type defaults to right and wrong, good people and bad people, should and should-not’s. I suddenly saw things with better measure. Good/bad is a construct of my ego; an axle of seeming truth around which I have wrapped my personality. There are human beings to whom things have happened, out of which we each try to survive. Life is not black and white, it’s actually totally murky.

This experience begged the question I have often used in my own marketing slogans: “Who are you, really?” I am about forgiveness, but I often come by compassion far more easily for people whom society labels “offender” than I can hold for myself. I think, in fact, that by immersing myself in my work with the incarcerated, I can distract myself from this unwillingness to work on this part of myself. That night I got schooled in how to come into balance; how not to leave myself out of the equation. Compassion is an exchange of energy that needs to be directed inward as much as to another, not more, not less.

With the hindsight of that moment, I’ve begun including myself in the justice I purport to seek. As I reflect on the ways in which I can leave my history of self-abandonment in the rear view mirror, I know better how to model this for others trying to do the same. The lesson: “teach what you need to learn” comes in unsuspecting classrooms. This homeless man – whom the police knew by name when they arrived belatedly– was every bit my teacher. I can be furious at his behavior and care about him, see him and see myself, hold him – best I can – whilst holding onto myself.


After working with hundreds of inmates and the Enneagram, Susan witnessed the powerful influence ego has on the choices people make and realized that, “We are all in a prison of our own making in the way we suffer our personalities.” Seeing firsthand how this “road-map” to personality systematically explains not just what we do, but incisively unearths the reasons why, Susan began to appreciate the Enneagram as the “missing piece” to criminal reform and founded The Enneagram Prison Project (EPP) in 2012. With unwavering compassion for the human condition, Susan Olesek brings her profound appreciation for the Enneagram System to those living behind bars – both literally and metaphorically. Certified in two schools of Enneagram Studies (Palmer-Daniels and Riso-Hudson), Susan also holds a Bachelor’s degree in Sociology from Occidental College. She teaches across the US, in corporations, in her private practice in the San Francisco Bay Area, and to her favorite audience – inmates. Susan’s driven by a wholehearted conviction that anyone brave enough to take an honest look at themselves is deserving of the personal liberation possible as a result.