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?

Jeff sits down with therapist Lindsay Taylor of Hope Springs Counseling in Alabama for a wide-ranging, honest conversation about the inner world of Enneagram Ones—especially what it takes to stay grounded when everything feels like it’s on fire. Together, they explore the One’s visceral experience of brokenness, the exhausting question of “what is mine to do,” and why the Serenity Prayer keeps showing up as a lifeline.

Along the way they unpack autonomy, boundaries, grief disguised as anger, the temptation to escape into “future-fixing”, and why past-work can feel both threatening and essential—less about reliving pain and more about gaining compassion, clarity, and a fuller relationship to time (past, present, and future).

You can connect with Lindsay at : www.HopeSpringsCounseling.net

Y’all, this one is REALLY GOOD. In the first half we talk typical 6 stuff: counter phobic vs phobic, reading other people’s emotions, etc. But in the second half, we get into some new stuff and it’s one of my favorite episodes to date.

There are a few seconds of audio issues around the 47 minute mark (we had some technical problems during recording), but hopefully you all can still understand!

Find Hunter Mobley’s book here

In this exchange, Kristin and Joey explore how differently the types move through the world—especially around communication, authority, affirmation, and intensity. They also examine crisis strengths, autonomy, vulnerability, and the common mistyping of bold people.

The discussion broadens into themes of parenting, growth, and self-awareness. Joey reflects on raising children with an understanding of stance and wiring, while Kristin speaks candidly about discovering her own fear and authority patterns later in life. Together, they emphasize that the Enneagram doesn’t change hardwiring—but it can transform how we relate, how we repair, and how we take responsibility for the impact we have on others.

Links

Inside Story episode (Apple): HERE

Kristin Messegee's Coaching: HERE

All Joey Schewee's work at WE Solutions: HERE

Joey's Upcoming book: "When Working Together Doesn't Work" : HERE

Jeff sits down with grief expert and Enneagram guide Mandy Capehart to unpack what national grief really feels like — not just personal sorrow, but the deep cultural distress many Americans carry today.

Together they explore the emotional impact of polarized culture, lost shared reality, and fear-driven responses in our relationships and communities. Mandy offers insight into how regulation, one-on-one connection, and lived values can help us navigate overwhelm and reclaim humanity in a fractured world.

If you’ve felt disillusioned, scared, or unsure how to engage with big problems without burning out, this episode invites you into deeper awareness, compassionate action, and hope rooted in connection — not just outrage.

About Mandy & Where to Listen:

This episode features Restorative Grief with Mandy Capehart – Podcast Page, a show that explores grief in all its forms — from loss of loved ones to life transitions, identity shifts, and the heartbreak of unsolved cultural pain.

👉 Listen to Restorative Grief on Apple Podcasts, Spotify, or your favorite player for compassionate stories and practical tools for navigating grief and growth.

Connect with Mandy:

1. Website: mandycapehart.com
2. Instagram: @mandycapehart

In this episode, Katie talks with a local friend about all things 6. We discuss why some 6s might mistype as 4s or 8s, what rebellion looks like and why 6s do it, procrastination, and much more!

Find Ava's interior design account here: https://www.instagram.com/rose_junction_/