As an EnneaType 8, often called the “Challenger,” “Leader,” or “Boss,” my life has been marked by a complex relationship with power, control, and vulnerability. The journey from my deeply ingrained patterns of domination and self-reliance to a more open, compassionate way of being has been as challenging as it has been rewarding. In this personal reflection, I’ll share my inner landscape’s evolution, highlighting the strengths and struggles inherent in being an Enneagram Type 8.
Audio Insights from Armor to Heart
Armor All: Strength, Independence, and Control
For most of my life, this need for control felt natural. It wasn’t just about physical dominance or assertiveness but extended into all areas of my life—work, relationships, and even spirituality. Independence was the driving force behind my personality, shaping how I approached life. My deep-seated anger stemmed more from a rebellion against authority than anything else. The idea of someone else imposing their will on me was intolerable, so I became determined to assert control. The Enneagram became a powerful mirror, showing me the cracks in this seemingly invincible armor. It revealed how my fixation on control was a defense mechanism—one that not only kept me safe but also kept me isolated from my true self and others. It was a tool that helped me see the prison I had built for myself, a prison made of the very qualities I believed were my strengths.
Mastering others is strength; mastering yourself is true power.
Lao Tzu
Mysticism Before Psychology
My path into the Diamond Approach® and the Enneagram came not from psychological or therapeutic work but from mystical experiences. I had inherited my father’s belief that psychology was a bunch of crap and that feelings were best left to women and wimps. So, I avoided delving into “my feelings,” those pesky irritants that complicated much of my life.
I had already been on a spiritual path for 13 years, emphasizing out-of-body experiences as a way to explore reality. This fits perfectly with my connection to point Five. I didn’t have to suffer through the needy mess of emotions and relationships; I could escape into the cosmos and have mind-blowing spiritual experiences. But as exhilarating as that was, it didn’t change that my life was still a mess. I was still a jerk despite all the “spiritual experiences” I was having. None of it was changing me; I was hiding from the vulnerable parts of myself. So, I left that path, looking for a way to become a real human being. I stumbled upon Diamond Heart Book One: Elements of the Real in Man through a weird but regular series of events. That book didn’t just change the direction of my life—it changed my life and the person living it.
The ego is a protective shell, but it is also the very thing that keeps us from experiencing the fullness of our true nature.
A.H. Almaas, The Point of Existence
Discovering My Type
Friends of mine in the Diamond Approach introduced me to the Enneagram. I first read Helen Palmer’s book, followed by Claudio Naranjo’s. After a few months of familiarizing myself with the Enneagram, I flew to Boston to participate in Helen Palmer’s and David Daniel’s Enneagram training. Many of the friends I made there have since passed on, but many, like me, are still around—though maybe not all of us are still “kicking!”
The Enneagram is not just about types, but about the dynamic movements within us, especially under stress.
Helen Palmer
During these trips and connections in Boston, I came into contact with Jack Labanauska and Andrea Issacs, founders of the Enneagram Monthly. Initially, I wasn’t immediately sure of my type.
Like many, I started by exploring the character traits of different types, but this left me circling multiple possibilities—was I a Three? A Seven? Perhaps a Five? It wasn’t until I stopped focusing on the surface traits and began paying attention to each type’s dynamic movements under stress that I realized my type. What ultimately made it clear was the recognition of how I moved from eight to five during periods of emotional stress.
This movement from Enneqagram Type Eight to Type Five was an intellectual retreat and an emotional detachment. I would go a million miles away from my feelings, pulling back so far that it felt like I had left them behind. It was as if I needed to figure everything out in a cold, detached space before I could return. And when I did return, I did so with a vengeance. Eighty percent of my life had been lived in this pattern. Whenever things became overwhelming or I felt emotionally vulnerable, my instinct was to withdraw, creating a protective distance from my emotions, not in a healthy, reflective way, but instead in this defensive, emotional, and intellectualized withdrawal.
Discovering Fear
Eights deny fear. Under stress, Enneagram Type Eight moves to the withdrawn, detached qualities of Type 5. I had repeatedly lived out this pattern of retreat throughout my life, though I didn’t fully recognize it until I dove deeper into the Enneagram. Whenever I felt emotionally overwhelmed or vulnerable, my instinct was to withdraw—not just intellectually, but emotionally. It was more of an emotional detachment, pulling away from the rawness of my feelings. I would create a cold, distant space where I didn’t have to face the messy vulnerability I feared. In that space, I believed I could regain control. But what I was doing was distancing myself from the very emotions that needed to be faced—fear, vulnerability, and the feeling of being attacked.
The cave you fear to enter holds the treasure you seek.
Joseph Campbell
This withdrawal didn’t just involve introspection; it was a defensive, intellectualized withdrawal. I believed I could reengage with the world more potent than before once I had sorted everything out mentally. Yet, this cycle only reinforced my avoidance of emotions and deepened my reliance on control. Rather than resolving anything, it created a cycle of withdrawal and re-engagement, fueled by the fear I was running from. One of the most profound revelations the Enneagram gave me was recognizing how often I used spirituality to escape this pattern. For years, I immersed myself in spiritual practices, seeking transcendence and profound insights, but none of these experiences changed how I related to my emotions or the world. I was locked in the same pattern of emotional and intellectual detachment, avoiding the vulnerable, raw emotions that lay just beneath the surface.
It Wasn’t All Peaches and Cream
When I finally reconnected with my feelings, I went on a roller-coaster ride of emotional highs and lows that I was honestly surprised to survive. People plumped up! I lived in a world filled with two-dimensional cardboard cutouts, and dealing with the flood and overwhelm of emotions was challenging. The Diamond Approach’s work on essential compassion opened me to inner resources. These resources supported my movement toward becoming a more authentic human being.
The Road to Compassion and Vulnerability
The most transformative aspect of my journey has been learning to move from the fierce independence of Type 8 to the compassionate, connected qualities of Type 2. This shift, which I call “the redemption of point eight,” is one of the most difficult for Eights because it requires us to face the emotions we’ve spent a lifetime avoiding—neediness, vulnerability, and dependence. At first, this transition felt like a betrayal of everything I had built my identity on. How could I, someone who prided themselves on strength and self-sufficiency, admit to needing others? How could I let down my guard and allow myself to be vulnerable?
Vulnerability is not winning or losing; it’s having the courage to show up and be seen when we have no control over the outcome.
Brené Brown
But as I began to allow these feelings to surface, I discovered that true strength comes not from avoiding vulnerability but from embracing it. Compassion, particularly self-compassion, became a crucial part of this process. The Diamond Approach helped me see how I had armored myself against the world, believing that compassion was a weakness, something to be avoided. But as I allowed myself to feel my pain and the pain of others, I realized that compassion is one of our most blessed resources. It will enable us to hold our pain without needing to fix or control it, creating space for natural healing and growth.
The Hurt Beneath the Anger
Another profound revelation came from the Diamond Approach when I learned that anger was a secondary emotion; beneath the anger is always hurt. Since anger was my primary emotion and “go-to” reaction in life, I spent a lot of time asking myself, “Where’s the hurt?” The Diamond Approach’s teachings on essential strength and its connection to anger were life-changing, much like my experience with essential compassion. But this shift impacted a whole different sector of my personality. These two forces, essential compassion, and essential strength, began to have their way with me, and I reluctantly but willingly went along—except for the times when I had to be dragged!
True strength is not in resisting vulnerability but in fully allowing it. In that openness lies the depth of our being.
A.H. Almaas, The Unfolding Now
The Power of Open-Ended Inquiry
Open-ended inquiry, as taught by the Diamond Approach, became both a microscope and a laser for me, peeling back the layers of armor and revealing what lies beneath the hood of this Model 8. Through this process, I’ve gradually lost my obsession with seeking something in the future. What once seemed so important now pales in comparison to my interest in the question, “What’s happening right now?”
The Wonderful Dream and the Illusion of Fulfillment
Like many Eights, I fell prey to what A.H. Almaas calls “the wonderful dream”—the belief that fulfillment, wholeness, and happiness are just around the corner if only I can achieve, control, or experience enough. For years, I lived in the illusion that spiritual enlightenment or material success would finally bring me the satisfaction I craved. The dream of fulfillment became the driving force behind my spiritual pursuits, masking my need to face my vulnerability. This “wonderful dream” is seductive for Eights, who often believe that strength and control will solve all their problems. But the truth I eventually confronted was that the dream was a lie. The more I tried to control my external world, the more disconnected I became from my inner life. No matter how intense my spiritual experiences or how successful I became, a part of me consistently recognized, “This isn’t it.” The fulfillment I sought wasn’t going to come from mastering my outer world—it could only come from facing and integrating my inner one.
The wonderful dream is the ego’s illusion of fulfillment. True fulfillment comes not from control or achievement, but from being present with reality as it is.
A.H. Almaas, The Inner Journey Home
I’ve come to appreciate what A.H. Almaas calls “the fruit of the work”
—the simple enjoyment and depth of being present.
Thank you, John! I very much appreciated your presentation of the enneagram in a personal way. Makes the teaching very alive and present.