Undefining Moments on the Journey

with John Harper

This session explores the difference between the moments that define us and the moments that quietly undo our identification with personality. While defining moments often help us recognize our Enneagram type and organize our sense of self, transformation tends to arise through undefining moments—experiences that challenge the belief that we are our thoughts, emotions, or strategies.

Drawing on lived experience, this talk examines pivotal realizations about the mind, presence, anger, agency, and the superego, revealing how personality functions without actually being who we are. The objective is not to move beyond the Enneagram, but to deepen its purpose: shifting from self-definition to self-recognition.

For Enneagram students and practitioners, this perspective is essential because it reorients the work from managing personality to loosening identification, allowing greater freedom, humility, and genuine presence to emerge.

In this session, you’ll:

• Distinguish between defining moments that shape personality and undefining moments that loosen identification

• Explore how Enneagram patterns organize identity — and how transformation begins beyond them

• Reflect on what it means to shift from self-definition to deeper self-recognition

• Consider how loosening identification allows greater freedom, humility, and presence

When the world feels divided, practitioners are called to hold a wider lens.

with panelists: Russ Hudson, Mario Sikora,  Michael Naylor, Clare Loughrige

The world feels increasingly divided. Conflict, uncertainty, and fear are shaping the emotional landscape many people are living in. In moments like these, conversations can quickly collapse into sides and tribal thinking.

Practitioners are called to hold a wider lens.

Rather than reinforcing division, our work invites people to move beyond rigid either-or thinking toward a more unified way of seeing. Peace begins within each of us, and the way we hold space for others matters now more than ever.

In this session, you’ll experience:

• Short reflections from leading Enneagram voices as Russ Hudson, Mario Sikora, Michael Naylor, and Clare Loughrige share perspectives on the role of practitioners in times of division and uncertainty.

• A deeper exploration of how practitioners can hold space differently—moving beyond either–or thinking toward a more integrated and compassionate lens.

• Experiential breakout conversations where participants can reflect with peers on how these themes show up in their own work with clients, communities, and organizations.

• An opportunity to connect insight with practice, considering how the inner work of practitioners influences the way we guide others through conflict, fear, and change.

• A shared moment of reflection with a global community of practitioners who are committed to supporting human development with wisdom, humility, and presence.