Day 5

Russ Hudson

Discriminating the Higher Qualities of the Enneagram

What you will learn in this session:

*Learn to recognize the essential gifts, virtues, and holy ideas unique to each Enneagram type that often get overshadowed by personality patterns.

*Understand how true healing requires addressing both psychological wounds and spiritual growth, avoiding both spiritual bypassing and endless self-analysis.

*Gain tools to help clients reconnect with their inner light, creating a safe, attuned environment where lasting change and deeper self-recognition can emerge

Russ Hudson is a renowned Enneagram teacher, scholar, and co-author of several bestselling books with Don Riso, including The Wisdom of the Enneagram.

He is a co-founder of The Enneagram Institute, the founding Director of the International Enneagram Association, and the co-developer of the scientific Riso-Hudson Enneagram Type Indicator (RHETI) personality test.

Gift: Russ Hudson & 2025 Enneagram for the Helping Profession Handout and Other Resources


Joseph Howell

These Are the Times That Try People’s Souls

What you will learn in this session:

*How to move beyond quick judgments and skillfully explore clients’ true Enneagram core types, respecting their deeper selves beyond surface behaviors.

*The concept of the Soul Child—the pure, authentic self beneath the ego—and how reconnecting with it can transform healing and growth.

*Practical ways to integrate Enneagram wisdom into helping others navigate grief, suffering, and conflict with compassion and presence.

Dr. Joseph Howell, Ph.D., is a clinical psychologist, author, and founder of the Institute of Conscious Being. As a young man, he was privileged to be mentored by the one and only Henry Nowen.

With degrees from Yale Divinity School and the University of Virginia, Howell integrates psychology with spirituality, focusing on the Enneagram’s power to transform consciousness. His book, Becoming Conscious: The Enneagram's Forgotten Passageway, explores how individuals can uncover their true essence by moving beyond ego-driven patterns.

A sought-after speaker, Howell, alongside his wife Lark, leads retreats and seminars across the U.S., helping people cultivate spiritual growth and inner-healing.

Gift: A Soul Child Reunion: A correlation of the soul child and the ego types


Kristen Oberly

The Enneagram and Dreamwork

What you will learn in this session:

*How dreams reveal unconscious motivations and help us see beyond our fixed Enneagram personality patterns.

*How working with dreams intentionally can expand our awareness and bring more flexibility to our type.

*Tracking dream themes, especially around instincts, offers personalized insight into how our type and life history influence us.

Kristen is an artist/illustrator who has been exploring the landscape of dreams and the Enneagram.

She has worked one-on-one with clients interested in their internal world, and offers classes on TheEnneagramSchool.com. Kristen also hosts the podcast 'Sinsomnia', where the topic of the unconscious, dreams, and personality are discussed in depth.


You can find Kristen on www.inkstoryrebel.com. She's a host on the podcast 'Sinsomnia', and a recurring host on the YouTube channel and podcast 'House of Enneagram'


Andrea Isaacs

The Enneagram and Shadow Work: How We Can Help Clients Embody Unshakable Confidence and Live with Meaning and Joy

What you will learn in this session:

* Exploring how the entire Enneagram system uniquely expresses itself in each client’s personality and life patterns, allowing for tailored insight and support.

* Understanding the critical value of identifying the “First Domino” — that initial key factor or belief that, when addressed, triggers meaningful and cascading change.

* Learning how to effectively apply embodiment practices to speed up the process of transformation by engaging the mind-body connection for deeper, more lasting results.

Andrea Isaacs is founder of The Isaacs Method for Emotional and Life Mastery. For over 30 years, she has empowered holistic coaches and entrepreneurs to master the inner game of business so they can have clarity about their dreams, unlock their potential and experience more vitality, visibility, and velocity in business and life.

She was a trailblazer in the Enneagram field pioneering new approaches in 1994 with the creation of EnneaMotion, a groundbreaking system integrating the wisdom of the Enneagram with embodiment practices and neuroscience, and her EQ Quiz based on the Enneagram.

For 25 years, she was a founding faculty member for the Enneagram Institute Professional Training Program shaping the next generation of Enneagram teachers and practitioners.

Her unique coaching method empowers her clients to step across the edge of their comfort zones into bigger versions of themselves with unshakeable confidence, achieve extraordinary results and create lives of purpose, impact, and joy.

Gift: The Emotional Mastery Toolkit


Susan Olesek and Troy Williams

Enneagram Prison Project and The Human Potentialists

What you will learn in this session:

* What does it really mean to “do the work” with the Enneagram—and why is it so crucial? Find out here.

* Practical ways to stay committed to your Enneagram type growth and avoid falling back into old patterns.

* Troy’s inspiring journey with the Enneagram, and how he is now a beacon of light for others

Susan Olesek is an unapologetic idealist, a Human Potentialist in passionate pursuit of what is possible for people. Born outside Boston, raised in Hong Kong and Japan, and educated in England and California, she earned her BA in Sociology from Occidental College in 1993. Throughout her life, she has developed a compassionate interest in human behavior.

Susan brings her conviction that there is something inherently “good” in people to anyone in her presence. During her 15 years of developing self-awareness training for Fortune 500 executives, corporate teams, schools, and those experiencing incarceration, she became known for her compassionate approach to the Enneagram. In 2012, she founded Enneagram Prison Project (EPP), a 501(c)(3) non-profit dedicated to the self-awareness education of those imprisoned, now scaling around the globe.

While working with wildly diverse groups of people using the same insightful tool, Susan became convinced that the Enneagram has always been meant for everyone. In 2021, she founded The Human Potentialists (THP), a Benefit Corporation with a vision to democratize the Enneagram. THP's mission is to guide people to their highest potential while connecting them to the core of our shared humanity. THP is dedicated to doing business for good.

Susan is writing her first book, a memoir, which she plans to publish later this year. She is married to Rick, EPP’s Executive Director, with whom she raised three young men. They live in the Santa Cruz mountains with 12 chickens and three cats.

Troy Phillips is an EPP Ambassador and consultant for The Human Potentialists. He was introduced to the Enneagram through his work with the Enneagram Prison Project, while serving a three-strikes to life sentence at San Quentin. Troy says, "Mentally, I was…locked in a box, living in a cage in my mind. I didn’t even know… I needed to unlock that door."

Troy embraced The Work of self-understanding, where his Enneagram Type Six gifts for tenacity and truth-telling shine through. He’s learned that while he will always seek safety and security, he can address any issue or circumstance by paying attention to his thoughts and feelings and expressing them safely. In his own words, Troy says, “I’ve learned to respond and not react when triggered.”

Today, he is a co-pilot of EPP’s compassionate curriculum in custody, virtually, and the “free” world. He regularly returns to prison as a co-facilitator, bringing hope and healing to those incarcerated. He is the proof that doing The Work works. In 2023, he co-presented EPP’s curriculum to the California Board of Parole Hearings.

Troy knows that “I don’t have to live in a cage anymore. I choose to reach out, and EPP has helped me with that." He is a father and a grandfather, living in Bakersfield, California, positively impacting his family, his EPP family, and the world.


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