Link to the upcoming EnneaSummit : HERE

Link to all of our other work : HERE

Jeff sits down with Tyler Zach to preview his upcoming Midlife Summit (Oct 21–24). They dig into why “midlife has a branding problem,” the U-curve of happiness, and how the second half can move us from productivity to fruitfulness. Tyler shares tear-worthy moments from the panels (don’t miss the Sevens), why 60 is still “midlife,” and what happens when elders step into being elders—sages who lend hard-won wisdom across generations.

In this episode:

• Midlife ≠ crisis: redefining the forties, fifties, and sixties as seasons of ascent
• “Rehiring,” not retiring: purpose, reinvention, and new risks later in life
• From skills to wisdom: becoming an elder instead of just getting older
• Integrating the three centers with age—and why that brings real joy
• Generational cycles (spring/summer/fall/winter) and what Gen Z can build next
• Stories of resilience through illness, loss, and the long cocoon

About the Summit:

The Midlife Summit runs Oct 21–24 and streams free for four days (with optional lifetime access at an early-bird price). Panels feature respected voices from the Narrative tradition, the Enneagram Institute, Personality Hacker, and more. Grab the link in the show notes to register and see the full lineup.

Early Access on iTunes: HERE

Early Access on Spotify: HERE

Our inaugural Episode! In this discussion on Early Access, host Katie Whitlock sits down with her close friend Michael —an Ironman-in-training, soon-to-be husband, and a reluctant but curious student of the Enneagram.

Enneagram Two gets a fresh look. Jeff sits down with coach and creator Jackie Contessa to unpack why “the Helper” label misses the mark and how that shortcut fuels mistyping. They trace the real motives at play—pride, flattery, intrusion, hidden grief, and the drive to “etch a role” in others’ lives—and name how gendered expectations distort typing (why many women lean Two and many men avoid it). Jeff and Jackie contrast Twos with Ones: duty and betterment vs. relational payoff, resentment from suppressed anger vs. resentment from unmet exchanges. They also hit possessiveness, boundaries as relationship-keepers, external energy vs. inner world, and the Two-to-Eight stress move. If you’ve ever wondered, “Am I a Two—or just helpful?” this one gives you a sharper lens.

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