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.

This is our Second Saturday Workshop from January!

Members can sign up for all of our coming workshops : HERE

In this conversation, we return to motive—this time on the high side: what it looks like to be your type when you’re grounded, centered, and flourishing (not in stress, not in security). We lay out a simple map for transformation—from our Shadow → through the Holy Idea → awakening our Virtue—and invite real-time reflection from our community on what changes when we begin to trust a bigger reality than our fear.

We tackled the body triad—891s—in January.

Eights wrestle with Holy Truth and the possibility of innocence without naivety. Nines explore Holy Love, self-worth, and what it means to take up space without losing peace. Ones confront Holy Order, naming resentment, control, and the long journey into serenity, flexibility, and joy.

We end by celebrating the gifts that show up on the high side: the Eight’s empowering strength and demand for what’s real, the Nine’s steady presence and non-dualistic wisdom, and the One’s persistent care for justice—turning chaos into order with a deeply rooted heart.

Members can sign up for all of our workshops : HERE

On February 14th, we will talk through 234s—so bring your heart-triad people and come ready to talk about what “going high” can look like in real life.

Continuing the 4 journey, Katie talks to Lucas, a 28-year old musician. They talk acceptance, growing up, and what it feels like to be a male who lives so much of life deep in the feeling center.

Find Lucas on Instagram at ofthoughtandfeeling

Find Lucas' music on Spotify

Kristin Messegee sits down with Lindsey Davis for a Type Seven installment of Inside Story—and what starts as a “get to know you” quickly becomes a rich, surprisingly tender exploration of how Sevens actually experience their inner world.

Lindsey shares the personal upheaval of 2025 (divorce, re-finding herself, and realizing she’d been mistyped as a Two for nearly a decade), and the two of them unpack what changes when you’re finally looking through the right lens: why boundaries can feel hard for different reasons, how reframing works as both a gift and a defense, and what it’s like to feel “a good day” while quietly bracing for it to disappear.

Along the way they talk somatic awareness, the body as truth-teller, the “good girl vs good woman” shift, anger as a boundary signal, and even why some Sevens show up publicly for hard topics (like politics) while avoiding the friction one-on-one. It’s funny, honest, and deeply practical—an episode for anyone trying to build self-trust, tell more of the story, and stay present when life gets complicated.

In this Early Access conversation, Katie sits down with Jeremy (“Remy”), an Enneagram Four from Texas whose life has moved through music, church work, divorce, and the long aftershocks of abandonment.

Together they get underneath the classic Four questions—wanting to be “not misunderstood,” protecting a kind of mystery, and carrying a quiet fear that people will leave once they’ve seen too much. Jeremy tells the story of watching his father hand his mother divorce papers in kindergarten, then later losing his job, his mother, and his marriage—experiences that shaped both his intensity and his caution.

From there, the episode pivots into healing: what it means for Fours to realize they’re already “glorious,” to stop chasing constant extraordinariness, and to learn how the ordinary can still hold real beauty. The conversation also gets timely, exploring how social media and algorithm-driven platforms raise the threshold for what feels meaningful—flattening art, attention, and even identity into “what will perform.” Jeremy offers a grounded, artist’s critique of the attention economy, and Jeff closes by teeing up a part two—because they only scratched the surface of Jeremy’s story.

Spoiler! This episode has a surprise ending!

Jeff welcomes longtime friend Collin Cannon for a Mistyping conversation that moves easily from friendship into depth.

Jeff and Collin explore the tension between Ones, Twos, and Sevens—digging into optimism, duty, anxiety, relationships, and what happens when things break. What emerges is a thoughtful, honest exchange about motive, freedom, and care, leaving listeners with a clearer picture of Colin and a felt sense of how real Enneagram work unfolds in conversation.