Coaching for Enneagram Sixes with Kristin : HERE

Pick up Joey Schewee's new book : HERE

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On this episode of Inside Story, host Kristin Messegee sits down with Enneagram teacher and workplace consultant Joey Schewee for a candid, surprisingly personal conversation about what it’s actually like to live inside Type Eight.

Joey opens with her upcoming book, When Working Together Doesn’t Work—a guide born from 17 years of consulting and leading teams—and then Kristen pivots into the heart of the episode: Eight confidence, intensity, and the misunderstood inner world beneath the “big presence.” Joey challenges common stereotypes (and mistypes), reframes Eight “reactivity” as fast-moving anger that clears quickly, and names the real fuel behind Eight conflict: injustice, low effort, and compromised integrity.

Together they explore the push-pull between autonomy and connection, why Eights often feel uncomfortable when attention turns toward them, and how “wanting” energy from others can feel intrusive—especially when it isn’t grounded in authenticity. Joey also shares what changed after facing something she couldn’t control, how anger can cover tenderness, and why gut types may be the most intuitive in the system.

Again, Joey’s book When Working Together Doesn’t Work is available for pre-order now on Amazon and releases in March, and you can get it : HERE .

In this conversation, Jeff Cook sits down with Milton Stewart—an Enneagram Seven, business leader, and President of the International Enneagram Association (IEA)—for a wide-ranging look at where the Enneagram stands right now and where it’s headed next. Milton shares what the IEA exists to protect: integrity, ethics, and responsible teaching, along with a growing commitment to global community and cross-cultural nuance. They talk about the rise (and fading) of Enneagram “buzz” on social media, the expanding push for scientific credibility, and the difference between trendy typing and real transformation.

Milton also tells his personal Enneagram origin story (including his early “mistype everybody I know” phase), how the tool shaped his work in under-resourced education settings, and what it’s like to learn from teachers whose presenceteaches as much as their content. The conversation lands on a core theme: the work—and Milton names two practices that keep it real no matter how much you’ve learned: humility and presence. If you’ve ever wanted a bigger-picture view of the Enneagram world—especially beyond American culture—this one will widen your lens and deepen your hope.

1. Milton’s website: https://kaizencareers.com
2. Milton’s podcast: Do It For The Gram: Enneagram Podcast
3. International Enneagram Association (IEA): https://internationalenneagram.org
4. IEA Events (“Nine Points”): https://internationalenneagram.org → Nine Points (events posted by accredited professionals)

In this Early Access episode, Katie Whitlock welcomes Imogen, a 24-year-old from Shanghai, China.

Imogen shares how she found the Enneagram through a friend, why she identifies as a Five without tests, and how “avarice” shows up as a fierce protection of time, energy, space, and purpose.

Together they explore the Five’s impulse to offer information as a form of connection, the tension between deep internal emotion and discomfort with outward emotional exchange, and the relief that comes when the Enneagram gives a framework for accepting difference.