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.

Jeff sits down with Drea from Alabama for a fresh round of Mistyping—and what starts as casual catch-up (football fandom, life with a five-year-old, and the chaos of caregiving) turns into a layered conversation about responsibility, control, justice, and self-criticism.

Drea shares her story: born and raised in Alabama, married nearly five years, mom to Porter, and currently balancing work as an air compliance specialist with caregiving for her mom, who’s living with early-onset Alzheimer’s with dementia.

Along the way, she opens up about finishing her master’s in environmental management, her growing awareness of environmental justice, and what it means to “take up space”—especially after postpartum struggles and a desire to create supportive community for other women.