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Welcome.
If you’re new to Evolving Enneagram — or curious about our contemplative approach to the Enneagram — this page will help you orient and take your next step.
What is the Enneagram?
The Enneagram is often introduced as a personality typing system. It describes nine fundamentally distinct patterns through which we perceive and engage the world. Yet it is far more than a personality framework. The Enneagram offers a precise and dynamic map for conscious awakening.
It reveals the habits of attention and the locus of identity that shape our relationships — to ourselves, to others, and to the God of our understanding. Rather than inviting us to label ourselves or others, the Enneagram serves as a companion on the wisdom path. It helps us gently and honestly recognize the patterns that both protect and limit us — so that we may transcend and include them.
In this way, the Enneagram can either reinforce our identification with personality — or become a path toward the liberation of the soul.
What is Contemplation?
In our work, contemplation is a way of being — of belonging to ourselves and inhabiting the world with grounded presence, open‑heartedness, and clarity of mind.
It is not about striving, self‑improvement, or spiritual performance. Rather, it is cultivated through slowing down, releasing preconceptions, and opening to what is most real. By bringing gentle, spacious awareness to body, heart, and mind, what once operated unconsciously begins to come into compassionate view.
Contemplation creates the inner space where the truth of our radiant being unfolds naturally.
What is the Contemplative Enneagram?
Evolving Enneagram’s unique approach is where contemplation and the Enneagram meet — where the wisdom of the Enneagram and the spaciousness of contemplation are held together within a field of intentionality and compassionate relationship.
The contemplative path — while not limited to these — emphasizes postures of silence, solitude, and stillness. Through these practices, we gradually loosen our attachment to self‑protective agendas and rigid identities — without making any part of ourselves “bad” or wrong.
Drawing from contemplative wisdom traditions around the world, we begin to see our habitual ways of thinking, feeling, and behaving not as failures, but as limited strategies that once helped us survive. What we once clung to for safety can now be held with compassion.
Without contemplation, the Enneagram is merely a map.
Without the Enneagram, contemplation can become a way of spiritually bypassing our human experience.
With contemplation, the Enneagram becomes embodied — guiding us to live truthfully in the territory of our everyday lives.
The Enneagram helps us see the patterns we have lived inside for years. Contemplation gives us the steady presence to meet those patterns with compassion — in a way that transforms them. As we are transformed from the inside out, our lives begin to change. And as our lives change, so too does the world around us.
This work is not about fixing, correcting, or improving ourselves. It is about releasing what obscures the goodness that is already here. It is about becoming more honest, more awake, and more free. What once felt rigid begins to soften. What once felt shameful can be held in love. What once felt separate begins to belong.
This is a path of remembering.
A path of integration.
A path of coming home.
We are all just walking each other home.
— Ram Dass
Where Should I Begin?
Each path is sacred and uniquely your own. Wherever you find yourself — seeking personal, private guidance or longing for shared journey — we trust you will find the support you need to take the next right step in this season of your life.
Personal or Professional Guidance
You may begin by working with one of our Contemplative Enneagram Guides in a private 1:1 session or a relational session for romantic or professional partners. These spaces offer individualized contemplative accompaniment, thoughtfully attuned to your lived experience.
Whether you are navigating transition, relationship challenges, vocational discernment, or deeper questions of identity and faith, these sessions create space for honest reflection, compassionate insight, and meaningful integration.
Shared Journey and Community
You may choose to begin in community through a Book Journey, a Contemplative Practices & the Enneagram (CPE) group, a retreat experience, or other Upcoming Offering.
Contemplative work deepens in shared space. Practicing alongside others invites courage and clarity as we walk the path together.
Deeper Formation and Training
If you feel called to sustained formation, explore the Contemplative Enneagram Practitioner (CEP) yearlong certification program or the half-day (self-paced) Enneagram of the Soul facilitator training & certification.
These pathways are designed for those who desire ongoing transformation — and for those who feel drawn to embody and share contemplative Enneagram wisdom in the world.
Vision, Website & Digital Presence
We believe in using technology to give voice to the sacred. If you seek an online presence that reflects the depth, integrity, and truth of your authentic calling, we help you create a grounded and beautiful digital home that honors your voice, your values, and your vision.
Propose a Customized Journey
Our work is co‑creative. It has been shaped and enriched by those who have journeyed with us over the years — whether for a brief but meaningful season or across the nine‑plus years of our core community’s life together.
Is there something you are longing to participate in that does not yet exist, yet feels aligned with our purpose? A gathering, a cohort, a retreat, a book study, or a particular focus of study or practice?
We welcome your vision. If you feel called to help bring something new into being, we would love to hear from you. Share your proposal. Together, we will prayerfully discern whether it aligns with our team’s call in this season.