Contemplative Enneagram
Guidance & Support
The need for inner awakening is universal, yet the path of awakening is deeply individual — unique to each of us.
Our contemplative Enneagram guides offer personalized spaces for reflection, integration, and relational insight. Whether you are navigating transition, exploring questions of identity or faith, strengthening a partnership, or seeking deeper embodiment of Enneagram wisdom, this work is rooted in attentive presence and compassionate inquiry.
These sessions are open to individuals and partners — romantic, professional, or both — who desire thoughtful, grounded accompaniment in this season of their lives.
What to Expect
Each session unfolds at a contemplative pace — attentive, spacious, and grounded in presence. Drawing from the wisdom of the Enneagram and contemplative practice, our guides are steeped in compassionate, soulful listening. They are trained to listen deeply and reflect thoughtfully, helping you notice patterns of attention, identity, and relational dynamics as they arise in real time.
You may explore:
- Recurring patterns in thought, emotion, and behavior
- Questions of vocation, identity, and faith
- Relational dynamics in partnership or leadership
- Practices that support embodied awareness and integration
This work is not about fixing or improving yourself. It is about cultivating honest awareness, compassionate self-understanding, and the freedom to respond rather than react.
How Sessions Work
Evolving Enneagram believes that trained professionals thrive when given creative space to lovingly and wisely discern how to structure their relationships with private clients. Below, you can learn more about each guide’s philosophy and training, and you can reach out to them directly about their format and pricing.
Private sessions are offered virtually, except when scheduled in tandem with an in‑person retreat or special event.
Individual sessions are typically 60 or 90 minutes. Relational sessions for romantic or professional partners are generally 90 minutes to two hours, allowing for spacious conversation and shared reflection.
Some guides offer stand‑alone sessions. Others work in packages that support mutual commitment to the journey over time. We recognize that some individuals come for a focused season of discernment, while others engage in longer‑term contemplative accompaniment as an ongoing way of life.
To begin, meet the guides below and reach out to any who resonate with you.
We are also happy to help you discern the next right step. For general questions, contact us at info@evolvingenneagram.com.
Meet Our Contemplative Enneagram Guides
Each guide brings unique training, lived experience, and calling to this work. We encourage you to explore and reach out to the guide whose presence and approach resonate most with you.
Aliyah brings a compassionate, embodied, and gently courageous presence to contemplative Enneagram work. As a spiritual director, musician, and healer, she creates spaces where vulnerability is honored and healing can unfold at a steady, attentive pace. Those navigating grief, chronic illness, faith shifts, or the longing to integrate mind, heart, and body often find resonance in her soulful and depthful approach.
Additional Background: Certified Spiritual Director; Spiritual Life Facilitator and Worship Leader; CPE Facilitator Team Member; Musician and educator
Angela brings a wise, expansive, and quietly powerful presence to contemplative Enneagram work. She is especially attuned to those navigating spiritual evolution, faith shifts, or the desire to move beyond inherited limitations into a more spacious and embodied way of being. Individuals drawn to courageous inquiry, cultural awareness, and transformative depth often resonate with her grounded yet visionary approach.
Additional Background: Adjunct Faculty, Evolving Enneagram; Certified Book Journey Facilitator for The Enneagram of the Soul; Contemplative Practices & the Enneagram (CPE) Team Facilitator; Facilitator of transformational book studies and retreats; formation in contemplative spirituality
Kristina brings a steady, nurturing, and quietly spacious presence to contemplative Enneagram work. Rooted in years of contemplative practice and spiritual formation, she deeply trusts the inner wisdom of each person and gently supports clients in listening to their own unfolding. Those drawn to reflective depth, contemplative prayer, and a grounded, compassionate guide often find resonance in her approach.
Additional Background: Certified Spiritual Director; Learning Lab Facilitator (Conscious Living); Commissioned Presenter of Centering Prayer (Contemplative Outreach), Adjunct Faculty, Evolving Enneagram; Certified Book Journey Facilitator for The Enneagram of the Soul; Contemplative Practices & the Enneagram (CPE) Team Facilitator
Jill brings a steady, theologically grounded, and deeply compassionate presence to contemplative Enneagram work. With doctoral training in Christian spirituality and decades of pastoral experience, she is especially attuned to those navigating faith transitions, spiritual reconstruction, or the longing to reconnect with their truest self. Individuals seeking thoughtful theological depth, gentle honesty, and grounded spiritual companionship often resonate with her wise and courageous approach.
Additional Background: Doctor of Ministry (Christian Spirituality); Master of Divinity; Integrative Enneagram (iEQ9) Accredited Practitioner; Enneagram Certification in Conscious Living (Russ Hudson & Jessica Dibb); Adjunct Faculty, Evolving Enneagram; Certified Book Journey Facilitator for The Enneagram of the Soul; Contemplative Practices & the Enneagram (CPE) Team Facilitator
Macha brings a seasoned, compassionate, and deeply steady presence to contemplative Enneagram work. With over four decades of experience supporting individuals and small groups, she meets people exactly where they are — honoring both the complexity of their stories and the wholeness that remains intact beneath them. Those navigating long‑held patterns, addiction recovery, trauma healing, or questions of identity and belonging often resonate with her grounded and gently transformative approach.
Additional Background: MSW; degrees in adult mental health, psychology, and women’s studies; Adjunct Faculty, Evolving Enneagram; Certified Book Journey Facilitator for The Enneagram of the Soul; Contemplative Practices & the Enneagram (CPE) Team Facilitator
Nhien brings a profound capacity for listening for what is real and emergent beneath the chatter of our minds and the tempest of our reactivity. Steeped in contemplative presence and shaped by more than two decades of inner and outer work with the Enneagram, she accompanies individuals, couples, and small groups in discerning vocation, deepening spiritual connection, and living more fully into their authentic calling.
Those drawn to spiritual maturation, vocational clarity, faith evolution, or the integration of inner awakening with outward life often resonate with her clarity, depth, and steady invitation into wholeness.
Additional Background: Founder, Evolving Enneagram; JD, Stanford Law School; professional mediator; Master of Divinity, Unity Institute & Seminary; Ordained Unity Minister; Certified Somatic Enneagram™ Facilitator; Awareness-to-Action Certified Enneagram Professional; IEA Accredited Professional with Distinction; Author of The Enneagram of the Soul.
