Understanding Yourself: The Enneagram Meets Stoicism

I was in my early twenties and living in a monastery when I first encountered the Enneagram. It answered a couple of questions for me: Why do we keep doing what does not serve us? Why do we suffer in familiar, almost rehearsed ways?

The Enneagram did not offer simple answers. In fact, it was very challenging. It showed me how I had learned to cope with the world. I began to notice what I paid attention to. I discovered what I avoided. I realised how I tried to earn love, safety and meaning. It did not ask me to change. It asked me to notice.

That was over thirty years ago. Since then, I have returned to it again and again. I have used it with students, staff and colleagues. At one point, I brought it to the department I led in a British higher education institute. What happened there was not a performance improvement plan. It was something subtler and far more transformative. People began to understand themselves and each other. Real understanding. The kind that softens edges and opens doors.

And still, for all its depth, the Enneagram was not enough on its own for me. It showed the patterns, but not always the path. This is where Stoicism entered my life. It offered a practice to move beyond some of the habits I noticed in myself.

The Stoics were not interested in personality. They were interested in freedom. They asked, again and again, what is within our control? And how do we live in alignment with that?

Over time, I began to see how the Enneagram and Stoicism speak to one another. One reveals the trap. The other offers the key.

I have known people who live as reformers, their lives shaped by a relentless inner critic. On the Enneagram they are known as Ones. They cannot rest until things are right, morally, structurally, even grammatically. There is something noble in their vigilance, and something exhausting. For them, Stoicism offers gentleness. Marcus Aurelius reminds us that we can correct without condemning. That virtue is not perfection, but integrity.

I have seen those who live to serve, who give with open hands and tired hearts. These Enneagram Type Twos anticipate the needs of others with grace, but sometimes forget their own. They want to be loved, but often settle for being needed. Stoicism, in its stillness, teaches them that love is not earned through sacrifice. Seneca wrote that the wise are content with themselves. It is a difficult teaching, and a liberating one.

The Threes are those who chase success, who shape-shift to match what the world applauds. They move quickly, always onto the next goal, the next version of themselves. They are admired, and often deeply alone. For them, Stoicism is a call inward. “Do not try to seem,” said Epictetus, “but to be.” To act not for applause, but from purpose.

Fours are driven by feeling. They experience a kind of archetypal ache. It is a longing to be seen. They wish to be understood in all their depth. They are sensitive to beauty, and to pain. For them, Stoicism is not about suppression, but orientation. It teaches them to feel without being swept away. To anchor in what is true, not just what is intense.

Type Fives tend to retreat. They observe, analyse, withhold. They do not want to need, or be needed. Knowledge becomes a kind of shield. The Stoic invitation here is into the world. Courage, said Cleanthes, is not found in knowing everything, but in facing what must be faced. For the intellectual withdrawer, action becomes the medicine.

Then there are the doubters. The Sixes. The loyal sceptics. Always scanning for threat, preparing for the worst. They are often the most courageous people I know, though they do not see it. Stoicism meets them with steadiness. It says: trust what you know. Take the next step. “You have power over your mind,” said Marcus Aurelius. “Not outside events.” Anxiety fades in the presence of clarity.

I have watched the optimistic Sevens, too. They are the ones who fill silence with stories and sadness with distraction. They move fast, not because they are frivolous, but because they are afraid to stop. For them, Stoicism is a homecoming. A reminder that joy is not out there, but already here. The pleasure of presence. The sweetness of enough.

I have seen power, raw and unsentimental, in the Eights. The kind that seeks control, not to dominate but to survive. People who lead, often instinctively, and resist vulnerability with all their strength. Stoicism refines their fire. It speaks of self-mastery. Of restraint. The best revenge, wrote Marcus, is not to become like your enemy.

And I know the peacemakers, the Nines. The ones who merge, defer, soothe. They keep things calm, but sometimes disappear in the process. For them, Stoicism is a call to wake. To speak. “First say to yourself what you would be,” said Epictetus, “and then do what you have to do.” In that moment, the Nine begins to rise. Not as a reaction, but as a presence.

We are not our types. We are not our patterns. But we are responsible for them.

The Enneagram helps us see. Stoicism helps us choose. Together, they offer something rare in a noisy world: the freedom to know ourselves without flinching. And to act, not from habit, but from wisdom.

I think sometimes of a staff meeting from years ago. It was late autumn, the kind of grey afternoon where the windows dim early and everyone stays a little quiet. We had been working with the Enneagram for a few months. People knew their types by then, though we rarely named them aloud. What changed, slowly and without fanfare, was how we spoke to one another.

That day, someone disagreed with a decision I had made. There was a pause. A few years earlier, it might have been awkward. Someone might have softened it too much, or pushed back too hard. But this time, someone else, someone who was usually reserved, nodded and added a thoughtful question. Another colleague, someone who once carried every meeting with effortful cheer, stayed silent, but present. No performance. Just listening. And eventually, we found our way to a better decision.

It was not dramatic. It was not the kind of moment you write up in a report. But it was the kind of moment that stays with you, because something subtle had shifted. People were speaking from their centre, not their strategy.

It was just a meeting. But it was also something quieter and rarer: the sound of self-knowledge in conversation with wisdom.

One response

  1. shinystranger7db6299b71 avatar
    shinystranger7db6299b71

    A skillful interweaving of two different perspectives of the human condition, introducing both principles of Stoicism and the Enneagram to an openhearted reader. It’s an invitation to explore each and/or both in greater depth … and to plummet the essential question in the process. Beautifully written.

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