Reflections Parallel: Spiritual Growth & The Enneagram


Learn about the Wisdom of the Enneagram, and Experience 9 Deep Soul Meditations for Personal Growth and Global Transformation.

What’s Included
Ten 60-minute webinars - lifetime access to streaming video & downloadable audio recordings.

Headphones On the go? All Sessions are available as downloadable MP3 files.


Terms: Due to the nature of this offering, there are no refunds for this purchase.

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Learn more about Spiritual Growth & The Enneagram”

About this Reflections Parallel Series

Join Robert Holden, with special guest Caroline Myss, for a 10-part deep dive on how to use the Enneagram to support you in your spiritual growth in these uncertain and vital times.

The Enneagram is one of the oldest self-awareness models on our planet, dating back 2,500 years. Its origins are the esoteric schools in ancient Egypt and Greece. It blends sacred mathematics from Plato and Aristotle. It was developed further by the Desert Fathers and Mothers in the 3rd century AD. And it was brought to the West in the early 20th century by G.I. Gurdjieff.

Enneagram is a Greek compound word for “nine” (ennea) and “written” or “drawn” (gramma). It offers a model of nine personality types – Ennea Types – which are similar in some ways to the archetypes that Carl Jung excavated from our collective unconscious. The Ennea Types include the helper, achiever, perfectionist, peacemaker, etc.

The Enneagram is a sacred journey. It takes you on a spiritual path and offers you a rich mix of practices, inquiries and meditations for inner work. As we journey around the circle of the Enneagram we stop at each point – the Ennea Points – and we enjoy nine soulful meditations that dive deep into big inquires like spiritual growth, loving relationships, sacred contracts, living your purpose, mysticism and divine consciousness.

In each class, Robert will introduce you to one Ennea-Type at a time, and Caroline Myss will lead us on a spiritual practice (a deep soul meditation) for the corresponding Ennea-Point.

Over the ten weeks you will learn about

Purpose of the Enneagram – how to use the Enneagram to add more body, heart and soul to your life.

Know your Type – look into the basic anatomy of the nine personality types.

Your Journey of Growth – how to use the Enneagram to be more soul-centered and inspired in your life.

Heal the Inner Blocks – identify and work with the basic fear, the fixation and the passion of each type.

Recognize your Soul Gifts – appreciate the signature strengths and soul gifts of each type.

Nine Soul Meditations – work with a spiritual practice at each Ennea-Point, led by Caroline Myss.

“I’m so grateful I know about the Enneagram. It has helped me in every area of my life – my spiritual practice, my writing, my work, my relationships, being a parent, everything!”

Robert Holden

Lesson 1:

Working with the Enneagram

What is the Enneagram, and how can you work with it?  The Russian philosopher, Peter D. Ouspensky, met G.I Gurdjieff in 1915.  Gurdjieff introduced the Enneagram to Ouspensky.  In Ouspensky’s classic work In Search of the Miraculous, Gurdjieff says, “A man may be quite alone in the desert and he can trace the enneagram in the sand and in it read the eternal laws of the universe. And every time he can learn something new, something he did not know before.”


  • The Enneagram Symbol – drawing the Enneagram symbol and getting to know some of its key teachings.
  • The Enneagram Types – an introduction to the nine personality types of the Enneagram.
  • The Enneagram Points – an overview of the nine meditation seats – Ennea Points – of the Enneagram.
  • Spiritual Growth Inquiry – some basic ways to work with the Enneagram for your spiritual growth.

Lesson 2:

Type One: The Way of Perfection

Teresa of Avila wrote, “Each of us has a soul, but we forget to value it. We don’t remember that we are creatures made in the image of God. We don’t understand the great secrets hidden inside of us.”  In this class, we explore the basic anatomy of Ennea-Type One, the Reformer or Perfectionist, and learn about the teachings available to everyone here at this first point on the Enneagram.


  • Original Blessing – experiencing your basic goodness and how perfectly made your soul is.
  • Fall from Grace – how we fall from grace and how to open up to grace again.
  • The Good Deed – contemplating the work we are here to do for the greater good and the whole of Creation.
  • Rumi’s Field – using the Virtue of Point One, which is Serenity, to move beyond right and wrong to a consciousness of unconditional love.

Lessons 3:

Type Two: The Road of Salvation

In the Gospel of Thomas, Jesus tells his disciples, “If you bring forth what is within you, what you bring forth will save you. If you do not bring forth what is within you, what you do not bring forth will destroy you.”  What does this mean for you?  What are you being called to bring forth?  In this class, we look at the basic anatomy of Ennea-Type Two, The Helper, and learn about the gifts available to us all at this point on the Enneagram.


  • Anam Cara – being a true soul friend to yourself and to the world.
  • Radical Discontinuity – repairing the sense of separation and disconnection with each other, with Gaia, and with God.
  • The Good Samaritan – sharing your talents and being of service to the world.
  • Divine Assistance – using the Virtue of Point Two, which is Humility, to call upon greater divine assistance for your life.

Lesson 4:

Type Three: A Path with a Heart

“Look at every path closely and deliberately, then ask ourselves this crucial question: Does this path have a heart? If it does, then the path is good. If it doesn’t then it is of no use to us,” taught Carlos Castaneda.  What is your path with a heart?  In this class, we look at the basic anatomy of Ennea-Type Three, The Achiever, and we work with the invitation that awaits all of us here at this point on the Enneagram.


  • Clouds of Glory – we come trailing clouds of glory, and we are here for a great work.
  • My Father’s Business – what is a successful life and how do we live it.
  • From the Unreal lead me to the Real – learning not to betray yourself and to be more authentic.
  • Your Heart’s Prayer – using the Virtue of Point Three, which is Truthfulness, to journey on a Path with Heart.

*  Caroline Myss’s Spiritual Practice on the path with heart.

Lesson 5:

Type Four: No Direction Home

“I was born very far from where I’m supposed to be, and so I’m on my way home.” said Bob Dylan, in the movie No Direction Home.   Do you ever feel like a spiritual misfit?   Where is your place of origin?  Where do you feel most at home?  In this class, we look at the basic anatomy of Ennea-Type Four, The Individualist, and we dive deep into the holy waters at this point on the Enneagram.


  • Original Face – “I’m looking for the face I had / Before the world was made.” W B Yeats
  • Holy Longing – what is it that I truly long for, and where do I hope to find it?
  • The Black Madonna – meeting yourself where you are on your path.
  • Palace of Nowhere – using the Virtue of Point Four, which is Equanimity, to come home to yourself.

*   Caroline Myss’s Spiritual Practice for coming home to yourself.

Lesson 6:

Type Five: The Path of Illumination

“The eye through which I see God is the same eye through which God sees me; my eye and God’s eye are one eye, one seeing, one knowing, one love,” said Meister Eckhart.  Who taught you how to see?  What is your vision for your life? How do you see the future for humanity? In this class, we look at the basic anatomy of Ennea-Type Five, The Investigator, and we look deep into the wisdom available to us here at this point in the Enneagram.


  • The Nous – opening the doors of perception and learning to see with the eye of the heart.
  • Bad Scholarship – undoing the spiritual blindness – “the bad scholarship” (William Butler Yeats) – of the world.
  • Direct Knowing – you don’t have to search Google to listen to the inner voice for truth.
  • Ordinary Mysticism – using the Virtue of Point Five, which is Transparency, to see everyday life in a new way.

Caroline Myss’s Spiritual Practice for an intimate conversation with the divine.

Lesson 7:

Type Six: The Path Less Travelled

“In the middle of the journey of our life I came to myself within a dark wood where the straight way was lost. Ah, how hard a thing it is to tell what a wild, and rough, and stubborn wood this was, which in my thought renews the fear!”  These are the opening lines to Dante’s Divine Comedy.  When have you felt lost in your life?  How do you experience spiritual guidance? In this class, we look at the basic anatomy of Ennea-Type Six, The Loyalist, and we will pay attention to the spiritual guidance that is available to us now.


  • An Infinite Intelligence – how do you experience the infinite intelligence of creation?
  • Love and Fear – when you come to a fork in the road how do you choose which way to go?
  • The Farewell Discourse – connecting with the holy spirit of universal inspiration that is available to everyone.
  • The Road Less Travelled – using the Virtue of Point Six, which is Courage, to travel on the path you are destined for.

*   Caroline Myss’s Spiritual Practice for spiritual guidance.

Lesson 8:

Type Seven: Life as Pilgrimage

“It is good to have an end to journey toward, but it is the journey that matters in the end,” wrote Ursula K. Le Guin, author of the Earthsea series.  Everyone is on a voyage.  What is your journey?  Where are you coming from and where are you going to?  In this class, we look at the basic anatomy of Ennea-Type Seven, The Enthusiast, and we examine what is the next step we are being asked to take in our life now.


  • The Inner Pilgrimage – where are you on your pilgrimage?  Who is your guide? What is your destination?
  • The Holy Grail – what is your holy grail?  Have you found it?
  • Chalice Well Prayer – where do you stop to source inspiration, to quench your thirst, and to nourish yourself. Are you looking for it in the right place?
  • Avalon Sunset – using the Virtue of Point Seven, which is Sobriety, to experience happiness now.

*   Caroline Myss’s Spiritual Practice for your inner pilgrimage.

Lesson 8:

Type Eight: The Path of Surrender

Martin Luther King Jr said, “Power without love is reckless and abusive, and love without power is sentimental and anaemic. Power at its best is love implementing the demands of justice, and justice at its best is power correcting everything that stands against love.”    In this class, we look at the basic anatomy of Ennea-Type Eight, The Challenger, and we will explore how we can show up more powerfully in our life at this time.


  • Small Beginnings – working with the fear of being too small and not big enough for your life.
  • Playing Big – how big are you playing in your life?  Where are you playing small?  How would you like to Grow?
  • The Bigger Picture – how to decrease the “False Self” and increase the “True Self”
  • Higher Power – using the Virtue of Point Eight, which is Innocence, to connect with a higher power..

*   Caroline Myss’s Spiritual Practice for the path of surrender.

Lesson 10:

Type Nine: The Hero Journey

“The big question is whether you are going to be able to say a hearty YES to your adventure,” said Joseph Campbell, author of Hero With A Thousand Faces.  How do you relate to the hero archetype?  What sort of a hero are you?  In this class, we look at the basic anatomy of Ennea-Type Nine, The Peacemaker, and we explore the inspiration available to us all at this Enneagram point.


  • Sleepers Awake! – it’s time to stop dreaming, and wake up to our true self and the path before us.
  • Cloud Nine – identifying the ways we withdraw from life and how this causes conflict and disturbance.
  • Practising Presence – showing up fully for your life and the part you have agreed to play.
  • Follow Your Bliss – using the Virtue of Point Nine, which is Engagement, to honour your sacred contract.

*   Caroline Myss’s Spiritual Practice for the hero archetype.

Caroline Myss

About Caroline Myss

Caroline Myss is a five-time New York Times bestselling author and internationally renowned speaker in the fields of human consciousness, spirituality and mysticism, health, energy medicine, and the science of medical intuition. Caroline established her own educational institute in 2003, CMED (Caroline Myss Education), which offers a diverse array of programs devoted to personal development and draws students from all over the world. In addition to her written work, Caroline maintains a rigorous international workshop and lecture schedule and has produced more than eighty audio/visual products on subjects that include healing, spirituality, personal development, and the study of archetypes.

About Robert Holden

Robert Holden’s work on psychology and spirituality has been featured on Oprah, Good Morning America, a PBS special Shift Happens! and in two major BBC-TV documentaries. He runs a public program of Enneagram workshops each year and also Leadership & Enneagram programs with clients Dove & the Real Beautiful Campaign, Unilever, Hay House and Google.

Robert is this year’s keynote speaker for the International Enneagram Association annual conference. He has taught Enneagram retreats on Spiritual Growth in Jerusalem, Assisi, Findhorn, Greece and Montserrat (home of the Black Madonna).

He is a New York Times best-selling author of 10 books including: Happiness NOW!, Shift Happens!, Authentic Success, Be Happy, Loveability and Life Loves You (co-written with Louise Hay). Robert’s new book Higher Purpose: How to Find More Inspiration, Meaning and Purpose is out now.