Journeying With the Enneagram is a 5-month experiential Enneagram course, for your personal transformation, supported by intentional community.
Next Cohort Starts September 14, 2026
In this course, you will apply the wisdom of the Enneagram to your everyday life, learning to get in touch with your True Self. You don’t need to cut yourself off from the world and join a monastery to gain deeper peace and freedom. With the proper guidance and community support, you can become a more whole and happy human being right in the midst of your messy life.
The result of doing this work together is deeper understanding and compassion for self and others, and an improved relationship with yourself, others and your spiritual life. By committing to show up with willingness and honesty each week, you will shed habitual patterns of suffering through the cultivation of contact with supportive and loving mindfulness, aka “Presence.”
Apply now by completing the “Readiness Assessment Survey.”
Here’s why I LOVE teaching this course, and why you will love it too.
Join the Journey on Sept 14th.
What’s Included
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We will meet as a group weekly on Monday evenings, from 6:30-8:00pm CST, beginning Sept 14th, 2026 and ending on Feb 15, 2027. All calls will be recorded and shared with the group, so you can watch the call on weeks you need to miss. These calls will be a time to do Presence Practice together, share check-ins, insights, successes, struggles, questions, and discuss the chosen topic of the week.
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This book by master teachers Don Riso and Russ Hudson is the foundational text and guiding curriculum for this course. The path they have laid out is, I believe, divinely inspired wisdom that takes the reader’s mind, heart, and body through immense transformation. Each week we will read one chapter of the book and then come together in a group call to discuss our questions, reflections, insights, and breakthroughs.
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You will be encouraged to do the weekly homework reflection together with a classmate. Like many things in life, the more you put into this course and into these relationships, the more you will receive in return. There is something healing about having another human witness your process. Not only does it add a layer of accountability, but the insights that arise solidify much more quickly than could ever happen if you decide to only do the exercises alone in your journal. With a compassionate witness to observe your personality patterns with all its quirks and shadows, you will begin to internalize compassion for yourself in a much deeper way.
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The course includes 5 confidential coaching sessions with Chelsea on Zoom. This is a time for you to explore what is coming up for you personally in response to the course material, readings, and insights or struggles that arise. You will have the freedom to share things you may not be comfortable sharing in the large group, and to get more direct support on specific issues in your life. (Chelsea is a certified Spiritual Director, and trained in Enneagram Coaching and teaching from master teachers Anne Mureé, Russ Hudson, and Marion Gilbert). You will receive one session per month while attending JWE (5 sessions total).
Schedule
We meet every Monday night on Zoom from 6:30-8:00pm (Central Time Zone)
Next cohort starts September 14, 2026, and runs through Feb 8, 2027.
Investment:
Sliding scale of $250 - $325 per month
There is a small amount of scholarship money available for young people, people in marginalized groups, or those going through a difficult financial season. Please reach out to Chelsea here if you are in need of financial support.
Those seeking to become Accredited Professionals through the International Enneagram Association can credit the hours in my JWE course toward their certification.
Kind words from past students
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I am so grateful to and for Chelsea and the Journeying with the Enneagram program. I came in with content knowledge of the Enneagram, but here, I began the real work: Personal Transformation. Weekly readings, partner homework, and class time, coupled with monthly 1:1 sessions with Chelsea opened my eyes to my auto-pilot behaviors, thoughts, and feelings. Seeing it means I can begin to have a choice moving forward. Thank you, Chelsea and JWE!
– Lisen Roberts, Ph.D., university professor
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Aaahhh!!!!! Chelsea is such a knowledgeable and energetic teacher and guide. Far from dry academics, Chelsea’s JWE class unites deep wisdom with our own daily experiences, inspiring very real personal and spiritual growth. This course has enriched my own understanding of those I try to serve and love in my ministries, and, I believe, has made me a more empathetic husband and father.
– Christopher Wojcik, Priest of the Orthodox Church; Husband, Dad, and Grandpa
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Chelsea facilitates and energizes Journeying with the Enneagram with insight, wisdom and commitment. She creates bubbles of space that make us feel like we belong. She continually creatively engages and challenges me with my own inner work and provides opportunity after opportunity to grow and work alongside others on the same quest. JWE is worth all the time and energy put into it. After I finished the 10 months, I signed up for another semester!
– Barb L., retired educator
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My experience with the JWE course has been powerful. Class time with Chelsea & monthly connection sessions with her have helped me explore & discover so much more about the mysterious & enchanting world of the Enneagram. Chelsea has challenged & encouraged with her insightful questions & knowledge. Sharing her own stories along with my open-hearted classmates has motivated me to continue to discover more about myself and to always approach this gradual knowing with curiosity, compassion and love.
– Cindy Craig, Retired nurse, mother, reiki healer
How to Apply
The first step is to fill out this Readiness Assessment Survey to determine if this course is a good fit for you at this time.
If you are still feeling called to this course at the end of the Assessment, you will be directed to schedule a Zoom call with me to discuss your responses, any concerns or questions you have, pricing and payments. Please plan for 30-45 minutes for this call.
Take time after our call to discern if this is a good fit for you at this time. If we both determine you are a good fit for this course, you will be invited to join!