Access to all past Rewired Episodes at : www.aroundthecircle.org

In this crossover episode of Rewired x Early Access, Jeff sits down with Katie Whitlock to reflect on what has emerged after months of interviewing Enneagram voices under 35. What begins as a behind-the-scenes conversation quickly becomes a deeper examination of how listening—real listening—reshapes both teaching and understanding.

Katie shares what surprised her most as an interviewer: that one-on-one conversations were easier than expected, that people speak about their inner worlds with remarkable clarity when given space, and that the Enneagram begins to change once you stop talking long enough to hear how others describe themselves. Along the way, she reflects on how this process forced her to confront her own habits as a Type Three, learning to step back, listen more carefully, and teach from lived patterns rather than rehearsed explanations.

Together, Jeff and Katie explore how stereotypes begin to break down when you attend not just to behavior or stated motivation, but to patterns—how people speak, where their attention goes, and the inconsistencies between how they describe themselves and how they move through the world. They discuss why newer students often over-type too quickly, why mature learning leads to a season of “I don’t know,” and why that valley is not failure but growth.