In this Early Access conversation, Katie Whitlock sits down with Delian, a creative Enneagram Four from upstate New York’s Finger Lakes (which she calls “the speakeasy of New York”)—and the two of them immediately turn a “re-record” into a surprisingly rich deep dive. Delian shares her four-ish world: running a classic car shop with her husband and mother-in-law, pursuing acting, and writing new Enneagram-inspired poetry that blends fantasy, core wounds, and even Greek mythology retellings.

From there, the conversation moves into the messy, honest terrain of typing: why Delian first tested as a Two, flirted with being an Eight (because wouldn’t it be nice to be action-forward?), and only felt fully “seen on the page” when she discovered the self-pres Four subtype. Together they unpack the difference between stress and excess, the role of time orientation, and why gender expectations can shape how “thinking” shows up in Fours and Fives.

The heart of the episode lands on shame, significance, and the Four’s tension between longing for authenticity and using “brokenness” as an excuse to delay real life. It’s warm, funny, personal—and quietly brave.

Kristin Messegee flips the script on Inside Story and lets herself be the Six, handing the interviewer role to Jeff Cook. They dig into how Sixes read strength, why reliability feels magnetic, and what “pushing against” someone really means when you need the ground to hold.

We talk about triggers, control, and the specific places anxiety shows up—her husband’s health, her kids, her work, and a divided world that fuels her distrust of groupthink and institutions. They talk about unproductive thinking, why encouragement often doesn’t land, and what actually helps: interrupting the spiral through the body, regulating the system, and building an internal voice that stays kind and steady.

Along the way: independence as freedom (hello, car rides), “escape” as an eject button, and a funny, skeptical detour into AI and certainty.

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Jeff Cook sits down with coach, author, and deconstruction theologian Stacey Wynn to clear up common misconceptions about Enneagram Eights—and name what often gets missed about their inner life.

Stacey talks about being labeled “intimidating,” why many Eights aren’t loud bullies, and how they often “fill the vacuum” when leadership lacks integrity. They explore the Eight’s small circle of trust, how Eights can care deeply (and sometimes “care aggressively”), and how anger functions less as outbursts and more as a steady internal signal—especially around dismissal, betrayal, and justice. The conversation also touches fear, control, and “decisioning,” plus the Eight-Five dynamic in relationships. They close with a brief turn toward theology and deconstruction, focusing on power, hierarchy, and healthier communities, and Stacey shares where listeners can find her work.