Self-Knowledge · Contemplative Practice
The Wisdom Enneagram
Not a personality quiz. Not a type label. A precise instrument for seeing the unconscious patterns that shape your life — and for beginning to step outside them.
Enroll Now — $199 Learn More
What This Is
A map of your conditioning.
The Enneagram is one of the most penetrating systems of human psychology ever developed. It does not categorize you into a type and leave you there. It shows you the pattern of your fixation — the unconscious structure that shapes how you see, feel, and respond to life — and then points beyond it.
Most Enneagram work teaches you to identify your number and understand its characteristics. The Wisdom Enneagram goes further. It asks: what does it mean to actually see your fixation in real time? And what becomes possible when you do?
The goal is not to understand your type. The goal is to see through it — and discover the freedom that lies on the other side of that seeing.
I have facilitated groups in this work for close to two decades. My husband Matthew and I developed this course together: he maps the system with precision and philosophical depth; I bring it into embodied, contemplative, and practical life.
The Difference
Not a type label. A lived practice.
Ways to Engage
Choose your entry point.
Self-Study Course
The Wisdom Enneagram
33 video lessons with Matthew and Holly. Begin the moment you enroll. Return as often as you need — the material reveals new layers each time you encounter it.
$199 · One time · Lifetime access
- 22 lessons: origins, fixation, 9 types, 3 centers, movements & drives
- 11 lessons with Holly: from understanding to lived practice
- Guided meditations and self-observation practices
- Practitioner's Circle members: 10% off at checkout
Live Facilitation
Bring Holly to Your Community
Nearly two decades of facilitation. This work is designed to be experienced in community — where participants can witness their fixations reflected in one another.
Retreats · Workshops · Ongoing Groups
- Half-day and full-day introductory workshops
- Multi-session group series for deeper exploration
- Retreat integration alongside somatic and equine work
- Organizations, faith communities, wellness spaces welcome
Your Guide
Nearly two decades in this work.
I came to the Enneagram through the contemplative tradition — through Father Richard Rohr's work, through recovery, through years of sitting with the question of what it actually means to see yourself clearly.
What drew me, and kept me, was this: the Enneagram does not ask you to fix yourself. It asks you to see yourself. That distinction is everything.
I am an internationally certified yoga therapist, a contemplative teacher, and the founder of Circle Yoga Shala. I bring this work into retreats, workshops, and ongoing groups — and into this course alongside my husband Matthew, who has studied the system's philosophical and historical roots for thirty years.
Live Facilitation
Bring the wisdom of the Enneagram to your community.
Whether you are organizing a retreat, leading a faith community, or hosting a wellness event, this work creates profound shifts when experienced together. I would love to explore what is possible for your group.
Contact Holly →