Like the Enneagram, our Generation--its technologies and events--shape how we see the world.

In this conversation with Katie Whitlock, we will be exploring the values and cultural markers of Gen X, Millennials, and Gen Z, weaving together films, music, shared culture, and the defining experiences that mark each era.

Connect with us at www.aroundthecircle.org

Get connect to all our work at www.aroundthecircle.org

In this episode, Jeff sits down with counselor Ben from Los Angeles for a live Enneagram mistyping session—could he be a principled One, a justice-driven Eight, or an analytical Five?

From his early years in LA to a career in corrections and counseling, Ben shares stories of resilience, accountability, and the ongoing work of channeling anger into growth.

Along the way, we highlight how Ones and Eights approach clarity, control, and problem-solving differently, giving listeners a front-row seat to the art of discerning type through real conversation.

Like the Enneagram, our Generation--its technologies and events--shape how we see the world.

In this conversation with Katie Whitlock, we will be exploring the values and cultural markers of Gen X, Millennials, and Gen Z, weaving together films, music, shared culture, and the defining experiences that mark each era.

Connect with us at www.aroundthecircle.org

See all of our best material at: aroundthecircle.org !

In this Mistyping session, Sandy from Chicago—a leadership and development coach—traces how infertility,and a bruising conservatory experience pushed her from “just tell me what to do” health coaching into deeper inner work. We talk holding space for grief without “positivity bullying,” growing up Midwestern “everything’s fine,” motorcycles as moving meditation, the love–hate of French horn performance, and learning to listen to her body. Then we press into typing: the pull between Five and Nine (with Four in the wings), what it means to prefer clarity over calm, intrusion over conflict, conserving energy, and hearing the heart-message that “your needs aren’t a problem.” Along the way: birding, butterflies, boundaries, and finding a voice that can move to Eight when needed. Connect with Sandy: swansoncoaching.com.

Like the Enneagram, our Generation--its technologies and events--shape how we see the world.

In this conversation with Katie Whitlock, we will be exploring the values and cultural markers of Gen X, Millennials, and Gen Z, weaving together films, music, shared culture, and the defining experiences that mark each era.

In this episode we tackle Gen X: from latchkey kids and divorce to the rise of the internet and shifting individualism, we ask what makes each generation unique, how those shifts impact personality and relationships, and why the Enneagram found fertile ground in Gen X’s world.

Connect with us at www.aroundthecircle.org

Jeff sits down with Elliot, a Kiwi in London. They trace Elliot’s deconstruction and church life, his work building inclusive spaces, and how the Enneagram has helped him sort clarity from certainty.

Sexuality isn’t just behavior—it’s an internal experience. We sit down with researcher-coach Dr. Sam Greenberg to map how Enneagram type and instincts shape desire, cues, assertiveness, and intimacy. Sam outlines the gifts and challenges of each instinct, why instincts often predict sexual patterns more than type, how repressed instincts show up in the bedroom, and what happens in common pairings (like self-pres x sexual). We also hit evolutionary frames, honeymoon-phase myths, “service sex,” stress/context loads, and practical ways couples can reduce friction and increase connection—without shame.

• A working definition of sexual desire vs. sexual behavior
• Why instincts set the framework and type adds nuance
• Gifts/challenges of self-pres, social, and sexual dominance
• How repressed instincts derail empathy, safety, or passion
• Common pairing dynamics (self-pres × sexual, etc.) and best practices
• Why stress, sleep, money, and context change desire—and what to do about it

• IG: @enneagasm (Sexy First Fridays with therapist Lindsay Frazier)
• Web: EnneagramSexpert.com

AS always : all our best material is at : www.aroundthecircle.org

Tammy joins Jeff for a live mistyping session that moves from opera halls to IT dashboards—and into the deep stuff beneath type. A lifelong Michigander with three degrees, a choir section-leader, and a self-described “walking contradiction,” Tammy is blunt and kind, fiercely independent, and devoted to care (for people…and five cats). Together we explore comparison, authenticity, and the tension between being known and staying buttoned-up. 

Jeff had a stellar conversation with Enneagram Coach, Spiritual Director and Founder @reflecttheoriginal , Sarina Sherring.

You can connect to her work here: www.reflecttheoriginal.au

For the full interview go to: aroundthecircle.org

This week we are joined by Amanda from Michigan. This was an excellent conversation!

If you are interested in our mistyping guide : GO HERE

The guide is only in the print version.