A deep exploration of personality, conditioning, and the path toward conscious living — with Matthew Krepps and Holly Krepps.
The Enneagram is one of the most precise and penetrating systems of human psychology ever developed. It does not categorize you into a personality 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 courses teach you to identify your number and understand its characteristics. This course goes further. It asks: what does it mean to actually see your fixation in real time? And what becomes possible when you do?
This is the Enneagram as a contemplative tool — not a personality quiz, not a social media type description, but a serious instrument for self-knowledge and conscious living.
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.
Matt maps the system with precision and depth. Holly brings it into embodied, contemplative, practical life. Together they cover the full arc — from understanding fixation to actually working with it.
Matthew brings his background in philosophy, religious studies, and thirty years of contemplative practice to a precise, rigorous, and deeply accessible mapping of the Enneagram system. His 22 lessons cover the full architecture — from the origins of the system to the movements of each fixation and the instinctual variants that shape how each type navigates the world.
The Enneagram is not a personality label. It is a precise instrument for seeing the structure of your own suffering — and for finding the door that leads beyond it.
Holly's 11-lesson section — "So What's Next?" — is where the Enneagram becomes a lived practice rather than an intellectual framework. Drawing on her decades in the recovery tradition, her study with Father Richard Rohr, and her own fearless self-observation, Holly guides you from understanding your fixation to actually working with it — through meditation, contemplation, and the honest discipline of self-remembering.
Knowing your type is the beginning. Learning to see it in the moment — without judgment, without escape — that is where the real work begins.
The Enneagram has become widely popular — and widely misunderstood. Most people encounter it as a typing system: find your number, read the description, share it online.
This course treats it as something far more serious and far more useful: a contemplative instrument for seeing the automatic patterns that run your life — and for beginning to step outside them.
The difference between those two approaches is not subtle. It is the difference between reading a map and actually making the journey.
The Wisdom Enneagram is a self-study course — available to begin immediately and return to as often as you need. There is no expiration. No subscription. No rush.
This is the kind of material that reveals new layers each time you encounter it. Students regularly report watching the same lessons multiple times across years — finding something different each time.
Practitioner's Circle members: use your 10% discount at checkout.
No. The course begins from the very beginning — including the origins of the system and the concept of fixation itself. Many students discover or confirm their type during the course rather than before it.
Most Enneagram courses focus on typing and description. This course treats the Enneagram as a contemplative instrument — the goal is not to understand your type but to see your fixation in real time and begin to work with it. Holly's "So What's Next?" section is particularly rare — practical, meditative, and grounded in decades of lived experience.
Yes. This is a self-study course — all 33 lessons are available immediately upon enrollment. You can move through them as quickly or as slowly as serves you. Many students find it valuable to sit with individual lessons for days or weeks before moving on.
Not currently. The course is self-study with lifetime access. Live cohort options may be offered in the future — join the Practitioner's Circle to be notified first.
Yes — active Practitioner's Circle members receive 10% off all Study courses, including the Wisdom Enneagram. Apply your discount at checkout.
101 students have already begun this journey. The course is open now and available to start immediately.