Our monthly Second Saturday gathering continues as we explore the high side of the Enneagram through conversation, reflection, and lived experience. This is our recording from last month.

Do join us March 14th. Become a member of aroundthecircle.org and go HERE to sign up.

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In this session, we focused on Twos and Threes—looking closely at the fears, patterns, and excesses that can pull these heart types off center, and the deeper messages that begin to move them toward freedom. Together, we explored how Twos relate to need, care, pride, and control, and how Threes wrestle with validation, achievement, image, and the longing to know their worth apart from performance.

What made this conversation especially rich was the honesty in the room. Participants shared stories about relational risk, self-love, grief, retirement, emotional presence, and the challenge of letting go of the need to manage how others feel or how they see us. We also reflected on the heart’s message, the holy ideas, and the virtues that begin to emerge when these types loosen their grip on old survival strategies.

This gathering is part teaching, part discussion, and part crowdsourcing—an opportunity to listen deeply to one another and to consider what real movement toward wholeness looks like from the inside out.

In this conversation:

1. the “45-pound weight” each type carries through fear and fixation
2. why Twos struggle to name and honor their own needs
3. how pride, control, and the longing for reciprocation show up in Twos
4. why Threes often tether worth to achievement and validation
5. how grief, stopping, and emotional honesty become part of healing for Threes
6. the role of the heart’s message, holy ideas, and virtues in moving toward the high side of type

We’ll gather again on March 14 as we continue the conversation with Fours and Fives.

If you want, I can also make this a little shorter, a little warmer, or more promotional.

Katie sits down with Emma, a 35-year-old Enneagram Six, for a thoughtful and personal conversation about fear, preparedness, relationships, and the long road toward self-trust.

Emma shares how she first found the Enneagram through podcasts, what it was like to recognize herself as a Six, and how that discovery helped make sense of patterns she had carried for years. Together, Katie and Emma explore the inner world of Sixes: the search for safety, the struggle to trust themselves, the experience of rumination, and the deep need to find what feels “just right.”

They also talk about Emma’s relationship with her boyfriend, an Enneagram Three, the differences between Six and Three achievement, and how the Enneagram helps illuminate the push and pull of connection. Along the way, Emma reflects on growing up between cultures, including her childhood in Saudi Arabia, and shares how an early medical emergency became one of the defining moments in her relationship to preparedness and control.

So … what does it mean to be happy anyway?!

In this episode of The Morning Show, Jeff is joined by Enneagram teachers Jackie Contessa and Kristin Messegee to explore the relationship between the Enneagram and happiness.

Together they consider whether happiness is something we pursue, something we cultivate, or something that emerges when we begin to see through the patterns of personality.

Along the way we explore ideas like enjoyment, satisfaction, meaning, purpose, and the sense of a life well lived.

The conversation also explores:

• how different Enneagram types might approach happiness differently

• the role of struggle, maturity, and personal development

• whether happiness can coexist with grief or hardship

• how relationships shape our experience of happiness

• why growth may require surrendering older versions of ourselves

If the Enneagram is a map, this episode asks a deeper question: where is that map actually trying to lead us?