Enneagram Heart Work Cohort
An 8-Week journey for heart healing, connection, and Enneagram learning in community
Beginning April 2025
You know the Enneagram has the power to transform relationships — now it’s time to do the work.
You’ve studied the Enneagram, resonated with its insights, and seen glimpses of its transformative power. But knowing isn’t the same as embodying.
Welcome to the Enneagram Heart Work Cohort — a space for those ready to move beyond theory into the experience of healing.
Here, you’ll deepen your understanding of the Enneagram, explore each type’s journey, and engage in your own inner work within a supportive community.
The Heart Center of the Enneagram isn’t just about feelings. It’s the part of each of us — not just heart types — that seeks attunement, connection, identity, and belonging. It shapes how we want to be seen, how we suppress our needs and desires, and how we react when they go unmet.
The work we do with our Heart Center determines whether and how much we can truly receive in our relationships. And it’s some of the hardest work we’ll ever do.
In Enneagram circles, turning toward our tender hearts — toward pain rather than away from it — is called the unpopular proposition. It goes against our protective impulses. And, it’s the path to deep healing.
It’s time to do the Heart Work — to open, to receive, and to let in what you’ve been longing for. And we can’t do it alone.
In a world that feels more disconnected than ever, we need spaces that bring us back to ourselves and each other — to understand why connection is so difficult, how it shapes our relationships, and what it takes to soften, open, and truly belong.
This isn’t something our Enneagram type can solve on its own.
We need skillful means—ways to draw upon our Essential nature to heal the wounds we’ve been carrying.
This isn’t just about learning. It’s about feeling, integrating, and transforming — together.
Through shared stories, compassionate witnessing, and embodied practices, we’ll explore how each type navigates these themes and relates to the wisdom of the Heart.
Learn the Art of Compassionate Heart Work
This is for you if:
💔 You find yourself deeply attuned to others’ emotions — picking up on their pain, joy, and unspoken feelings — yet struggle to stay present with your own grief, needs, and boundaries.
💔 Grief and heartbreak have shaped your journey, whether through the loss of a relationship, a major life transition, or a deep longing that’s gone unfulfilled, and you’re seeking a space where your experience is truly seen and honored.
💔 You crave deep, authentic connection but hesitate to fully open your heart — perhaps due to past wounds, fear of being too much (or not enough), or difficulty trusting others — but you’re ready now and want support in navigating that vulnerability.
💔 You’re drawn to healing work — personal, relational, and/or collective — but often feel unsure how to hold space for both yourself and others in a way that is sustainable and nourishing.
💔 You want to understand the Enneagram beyond written descriptions and surface-level stereotypes — witnessing how each type’s emotional world unfolds through real people, real stories, and the raw, transformative process of heart work.
"My sincerest gratitude for your ability to hold a container. You’ve really made this space nonjudgmental. You have a way of helping me go to places I avoid, or because I’m scared I don’t want to go there alone. It’s meant a lot to have such a steady guide. The gentleness with which you approach this has been incredibly appreciated, and it’s very much a gift."
— Chelsea, Type 7
What
A cohort experience to explore each Enneagram type’s journey of grief, gratitude, and beyond.
We’ll meet 8 times, focusing on 1-2 Enneagram types each session. I’ll share brief teachings and guide experiential practices that get to the heart (😉) of each type’s patterns of reactivity. We’ll learn to work with this somatically (using Somatic Enneagram™ Facilitation techniques), while compassionately including all 3 centers (head, heart, and gut).
Each participant will have the opportunity to engage in inner work through a panel, with the group offering compassionate witness to the process.
Panels are my favorite way to deepen our understanding of Enneagram type structure & really see where the rubber meets the road when it comes to inner work!
Who
Seekers who want to deepen their self-awareness, build emotional resilience, and foster authentic heart-to-heart connections in a supportive, healing environment—through the lens of the Enneagram.
You know your dominant Enneagram type (or have a solid guess). Beginners and advanced students are both welcome. Either way, this group learning experience will bring new insights, a deeper connection to your heart, and a supportive community of real people living and working with their ego patterns.
Where
We’ll meet on Zoom for live sessions.
You’ll also have access to a private homepage (not on social media) to view recordings and share reflections, and a group chat will be available for ongoing connection between sessions.
Live attendance and participation are strongly encouraged, especially during the week of your type!
(See the live session breakdown here.)
When
Meeting times will be finalized soon - please weigh in here!
We’ll meet for two hours each week, starting in April 2025.
What’s Included?
📚 Foundations of Somatic Enneagram Work Mini Course — Learn the guiding principles of Somatic Awareness Practice and how it supports Enneagram work.
🧠 16 hours of live instruction — Teaching, practice, and panel-style learning.
🌐 Homepage — Access session recordings and additional resources (available for a limited time).
🤝 30-minute 1:1 integration session — Connect with Caryn to go deeper with any content and work through your own process. Plus, you’ll have the option to add more 1:1 sessions at a discounted rate.
💬 Group chat — Ongoing connection, conversation, witnessing, and support throughout the cohort (participation optional).
How Much?
Early bird price is $475. After that, the group will be offered on a sliding scale of $500 - $700.
Payment plans are available.
Head to the FAQ section for more details!
"Throughout the group, Caryn's openness was obvious - never judgmental - and she is very good at accepting people for where they are at. Caryn's willingness to be open about her own practice is very inspiring and her leadership inspired the group to be vulnerable and feel comfortable enough to do so. Her focus on learning how to listen to our bodies is a new level of support that I have never experienced before. I jokingly tell people that Caryn is a magician — what I mean by that is she is able to get so much out of a person just by encouraging them to consider themselves in a way they may not have before."
— Colleen, Type 9
You’ll Leave This Program With:
💗 A Deeper Understanding of the Heart Center – Insight into each Enneagram type’s emotional landscape, their experiences of grief, heartbreak, and healing, helping you navigate emotional dynamics with greater awareness and offer meaningful support to others.
💗 Greater Capacity for Compassion – Practical tools for practicing compassionate heart work with yourself and others, allowing you to mitigate conflict, strengthen relationships, and contribute to the collective healing that’s so needed right now.
💗 Embodied Emotional Awareness – Somatic practices to help you stay present with your own heart and the emotions of those around you, deepening your ability to respond with resilience, prevent burnout, and foster authentic connection.
💗 Powerful Storytelling & Witnessing – A firsthand experience of how shared stories create space for transformation and collective healing, equipping you to hold space for others, facilitate deeper conversations, and nurture environments of trust and vulnerability.
💗 Authentic Connection & Community – A sense of belonging with others who value deep, heart-centered relationships, ensuring you have a supportive network that fosters mutual growth and understanding.
💗 A Felt Sense of Co-Regulation – The experience of being held in a community that nurtures healing through presence and shared understanding, enabling you to cultivate emotional safety, bring ease to group dynamics, and create spaces where people feel truly supported.
"Caryn is very compassionate, highly skilled and effective in her work. She has a way to guide us through our experiences and find hidden beliefs or pain. She helps us deconstruct those beliefs in an open and gentle way, enabling us to see more clearly. Her method is the magic, because the process allows us to deeply understand our patterns and how the drive or influence us, our beliefs and their impact to our created realities and our pain. She guides us there, never dictating, though I suspect she often knows where we are headed. After that I can see the areas we have focused on so clearly and it brings immense relief. The power to release the pressure and the pains is there, within us, waiting for us. She guides us to it."
— Riann, Type 1
Frequently Asked Questions
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I highly recommend this style of learning to folks at any level of awareness! In our time together, we’ll be focusing on a small portion of Enneagram teachings, related to attention, fixation, & core beliefs. It is not a comprehensive overview, but rather a chance to experience the type in action and to learn together in community. That said, this group is best for those who have done some self-observation and who have sense of their dominant type.
If you’re called to join but not fully certain of your type, there are a few options:
a) Reach out for recommendations on who to work with to get clearer on your dominant type! (I don’t currently offer typing interviews but I have some wonderful colleagues who do!)
b) Sit on the panel of a type you are exploring to see how the material shows up for you
c) Join the cohort and work with the material without sitting on a panel
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Practicing and learning in community brings a richness to the inner work. Every time a group gathers, a unique field is created and highlights pieces that are ready to be witnessed and worked with in real time.
When we earnestly observe what is alive in the present moment, there is always an opportunity for new insights to emerge. Additionally, I will be teaching and facilitating from the perspective of identifying the somatic roots of our patterns and working with a somatic approach that is different from many approaches to the Enneagram.
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Live attendance is encouraged, especially during your type’s week so you can have the experience of sitting on a panel. (See the live session breakdown section for dates.)
Recordings of the teachings and practices made available to group participants. Panels will be also be recorded* for members who are unable to attend. Recordings will be viewable for one month following the final session.
*Panelists will have the option to request that their portion of the recording not be shared.
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Payment is nonrefundable*. Please consider if this cohort is right for you, and reach out if you have any questions.
*In the case of extraordinary circumstances, payment may be applied toward 1:1 coaching.
"Caryn has an incredible ability for making space for different responses without losing the heart of the group experience that participants came for."
~ Jen, Type 9
Live Session Breakdown
Community is at the heart of transformative inner work. In this group, we’ll create a space where we can truly see and be seen — a place to connect, practice, and grow together. Through shared experiences and intentional practices, we’ll learn to shift our attention with purpose, cultivating the ability to view ourselves, each other, and the world from new perspectives.
Each week will include insightful teachings and practices designed to tap into the essence of the type(s) we’re focusing on. You’ll also have the opportunity to engage in a panel experience, where each participant will be invited to step into the spotlight during their type's week, with compassionate guidance and witnessing from the group.
Session 1: Introductions + Enneagram Heart Work Overview
Session 2: Intro to the Frustration / Flow Triad + Type 4 Panel
Session 3: Type 7 Panel + Type 1 Panel
Session 4: Intro to the Rejection / Power Triad + Type 2 Panel
Session 5: Type 8 Panel + Type 5 Panel
Session 6: Intro to the Attachment / Blend Triad + Type 3 Panel
Session 7: Type 9 Panel + Type 6 Panel
Session 8: Reflections, Questions, and Closing Circle
"I appreciate the accessibility from approaching the Enneagram through a non-religious lens and the intentionality around non-judgmental and empowering language. Caryn’s vulnerability to share about her past and present experiences model approaching life through an Enneagram lens in a very human way. I felt that I was able to show up exactly as I was in any given moment and be seen and valued for however that was."
— Anonymous Group Participant
What is Enneagram Heart Work?
There’s a reason the heart is one of the most physically protected organs in the human body — second only to the brain and spinal cord.
But it’s not just our physical heart that needs guarding. The Heart Center, as taught through Enneagram wisdom, is intimately connected to our sense of identity, value, and our attunement to our needs.
The Heart Center, as taught by Enneagram wisdom teachings, is responsible for attunement to needs and sense of identity and value.
When we experience misattunement from caregivers early in life, it can leave lasting emotional scars. These wounds ripple throughout our relationships, often affecting us for a lifetime. A loss of identity and questioning our worth can stir deep feelings of shame and grief, making it incredibly difficult to access the love, connection, and depth we deeply crave.
No wonder our egos set up defenses to avoid facing the pain we fear could break us.
But this avoidance often leaves us feeling disconnected, empty, or fundamentally flawed.
This journey isn’t just about understanding the Enneagram on a cognitive level — it’s about connecting with each other as humans, beyond our type structures.
Throughout the 8 weeks, I’ll guide you through teachings and experiential practices to help you recognize and shift your patterns. We’ll also engage in panel demonstrations for each Enneagram type, where every participant will have the opportunity to do inner work on a panel, with the group holding compassionate witness and offering support.
Together, we’ll explore:
➡️ Why grief is a necessary part of spiritual development.
➡️ How reactivity in the Heart Center shows up in each Enneagram type.
➡️ Skillful tools to heal heart wounds and cultivate compassion for our own tender hearts.
This shared experience will help build compassion, understanding, and a deeper connection to the unique healing work we each need to do in this lifetime.
Panels are one of my favorite ways to bring inner work to life. They give us the opportunity to witness our patterns in real time, showing us where the rubber truly meets the road. This is where real transformation happens! Being part of a panel — or witnessing others on theirs — is a rare and profound experience that can create deep shifts and lasting healing.
Are you ready to dig into the heart of the inner work?
Take this first step toward healing, understanding, and a deeper connection to your Heart Center in community!
Space is limited!
Meet Your Guide
My name is Caryn (she/her)
I am a
Conduit of Compassion;
Transmitter of Truth;
I Hold Hope,
Inspire Insight,
& Wield Wisdom
in service of your Inner Knowing
Trained as a social worker, I now play the roles of Enneagram Teacher, Somatic Practitioner, and Transformationalist. Through deep relationship, compassionate curiosity, and the framework of the Enneagram, I guide others to become responsive stewards of the ever-emerging present.
Some of my credentials include:
Bachelor of Arts, Psychology - Cornell University
Master of Social Work - Portland State University
Master Awaken Your Life Coach - Awaken Your Life Training [Accredited through the Association for Coaching]
Certified Narrative Enneagram Teacher - The Narrative Enneagram
Certification in Enneagram-Informed Conscious Living, Year-Long Program - Russ Hudson, Jessica Dibb, & The Shift Network
Certified Professional Enneagram Teacher - Russ Hudson, Jessica Dibb, Gayle Scott, & The Shift Network
The Somatic Enneagram™ Facilitator and Faculty - The Somatic Enneagram™, Marion Gilbert
My favorite credentials come from my lived experience and 3-centered practice.
Through direct experiences of presence, I have learned…
It’s not enough to understand ourselves conceptually - we have the potential to sense into embodied belonging in our whole beings.
It’s not enough to know our value - we have the potential to receive unfathomable compassion and love from the world around us, from others, and from ourselves.
It’s not enough to free ourselves - we have the potential to create conditions that foster liberation for all.
Though the work is never done, you are always enough. Wherever you are on your path - here and now - you are worthy.
