Reflections Parallel: Love & The Enneagram


Exploring the Stages of Growth in Love using the Wisdom of the Enneagram

What’s Included
Ten 75-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 Love & The Enneagram”

About this Reflections Parallel Series

Join Robert Holden, with special guest Caroline Myss, for a 10-part journey on how to use the Enneagram to navigate the stages of growth in love and to expand your capacity to love and be loved.

The Enneagram is a powerful self-awareness tool that dates back 2,500 years. Its origins are the wisdom schools of ancient Egypt and Greece. It’s based on Plato’s and Aristotle’s sacred mathematics, spiritual philosophy, and natural laws. It offers timeless wisdom to help you deepen your understanding of love and spiritual practices to widen your circle of love.

Enneagram is a Greek compound word for “nine” (ennea) and “written” or “drawn” (gramma). It is a model of nine personality types that helps you to cultivate a more conscious and enlightened relationship to love. It’s also a mandala of nine meditation points with spiritual practices for finding your wholeness, loving the “true Self”, blessing your relationships, fuelling your activism, living your purpose, and being a truly loving presence in the world.

In Love and Enneagram, Robert explores the nine Ennea-types and their relationship to love. For each Ennea-Type, he shares a creative mix of readings from spiritual literature, much loved poetry, inspiration from the wisdom traditions, musical references, meditations, and prayers. Caroline Myss will respond to Robert’s offering with spiritual direction for the stages of growth in love for each type.

Over the ten webinars, Robert and Caroline will cover,

9 Types in Love – learn how each Ennea-Type relates to love, and likes to express love in their relationships, work, and life.

Blocks to Love – identify the inner blocks to love that each Ennea-Type must work with to experience ever-expanding love.

Stages of Growth – use the Enneagram to assist you on an ever-evolving journey into greater love.

Power of Love – live a love-centered life to access higher inspiration and creativity and fulfill your sacred contract on Earth.

9 Soul Meditations – work with a spiritual practice at each Ennea-Point, led by Caroline Myss, to help you participate in the great love story of Creation.

“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:

The Enneagram of Love

What is the Enneagram, and how can I work with it on my spiritual path? In our first class, Robert sets the scene with a story from the Desert Fathers and Desert Mothers of the 3rd century AD, a community that included Evagrius Ponticus, the grandfather of the Enneagram.  Robert introduces you to the nine Enneagram Types – including the Helper, the Investigator, the Perfectionist, and the Peacemaker.  Caroline offers guidance and inspiration for our journey ahead.


  • Great Commandment – how the enneagram can help you to love yourself, to love your neighbours, and to love God.
  • The Enneagram Types – an introduction to the nine personality types – the Ennea-Types – and how they like to love and be loved.
  • 3 Centers of Love – tuning in to love as a universal energy, as an infinite intelligence, and as the substance of your true self.
  • 9 Facets of Love – exploring the nine meditation seats – Ennea Points – of the Enneagram and the qualities of love they represent.
  •  A Love-Centered Life – working with love as a spiritual path and as our most necessary spiritual practice.

   * Caroline Myss’s reflections on the stages of growth in love.

Lesson 2:

Type One: A Perfect Love

Plato described love as the “desire and pursuit of the whole.”  He wrote, “Love is born into every human being; it calls back the halves of our original nature together; it tries to make one out of two and heal the wound of human nature.”  Learning to love and be loved is our best chance for experiencing Plato’s Law of One – that restores us to the original Oneness of Creation, wholeness of the Universe, and Goodness of God.  In this class, we explore the basic anatomy of Ennea-Type One, the Reformer or Perfectionist, and meditate on a love that is perfect and whole.


  • A Higher Love – aligning with a perfect love that appears in sacred geometry and in the natural laws of the universe.
  • Love and ethics – recognizing that love is always ethical, the conscience of humanity, and source of our original goodness.
  • Beyond Self-Improvement – the crucial difference between the paths of self-improvement and self-acceptance.
  • Love’s Prayer – laying down the ego-fixation of judging to experience true vision, serenity, and holy perfection.

   * Caroline Myss’s Spiritual Practice on perfect love.

Lessons 3:

Type Two: An Unconditional Love

The Sufi poet, Hafiz said, “And still, after all this time, The sun never says to the earth, ‘You owe Me.’ Look what happens with A love like that, It lights the Whole Sky.”  In this class, we focus on Erich Fromm’s work on The Art of Loving, and how love is the deepest need of humanity and “the only sane and satisfactory answer to the problem of human existence.”  We look at the basic anatomy of Ennea-Type Two, The Helper, and meditate on an unconditional love that wants us to give and receive love freely and in equal measure.


  • The I AM of Love – love is not a coin to bargain with or a thing to give and receive. Love is who you are.
  • Secret to Self-Love – understanding why the ego is unable to love itself, and why self-love is a spiritual practice.
  • Giving up your Role – how relationship roles – like helper, giver, carer, rescuer – can block the flow of giving and receiving love
  • Loving Each Other – exploring the difference between helping someone and loving them.

  * Caroline Myss’s Spiritual Practice on unconditional love.

Lesson 4:

Type Three: Love in Action

“Work is love made visible,” wrote Kahlil Gibran.  Here, at Enneagram Point Three, we look at love as the great work of your life.  Learning to love and be loved is how you participate consciously in the greater story of creation.  We explore Robert’s work with Success Intelligence Ltd (S.I.)  One of Robert’s S.I. mantras is, “If your definition of success has little or no mention of love, get another definition!” In this class, we examine the basic anatomy of Ennea-Type Three, The Achiever, and explore the relationship between love and work, love and success, and love and purpose.


  • Instrument for Love – your sacred contract is to make yourself an instrument for love.
  • Loveability – your ability to love and be loved is the inner work that helps you to accomplish our life purpose.
  • Death of a Salesman – giving up your self image – your attractive package or commercial personality – so as to reveal your authentic self.
  • Sacred Activism – bringing love to your activism. Activism is love in action. A true activist performs acts of love.

   *  Caroline Myss’s Spiritual Practice on love in action.

Lesson 5:

Type Four: Secret Beaut

“Love is our true destiny. We do not find the meaning of life by ourselves alone – we find it with another,” wrote Thomas Merton.  Robert begins this class with a mystical vision that Thomas Merton shared in his classic work Conjectures of a Guilty Bystander. Merton is standing on the corner of 4th and Walnut, in Louisville, when suddenly the secret beauty of every passer-by is revealed to him. In this class, we examine the basic anatomy of Ennea-Type Four, The Individualist, and explore the relationship between love and beauty, and love and our original face i.e., the essence of who we are.


  • Plato’s Ladder of Love – taking the journey from eros (romantic love) to Agape (spiritual love).
  • Love and Healing – exploring the difference between healing yourself and loving yourself.
  • The Artist’s Muse – expressing yourself creatively in your life, your art, your work, your relationships with love’s help.
  • The Beautiful Prayer – “O God, show me the truth about myself no matter how beautiful it is.” Macrina Wiederkehr

    *   Caroline Myss’s Spiritual Practice on secret Beauty.

Lesson 6:

Type Five: Omniscient Love

Love is intelligent. Love knows how to love. You can ask love to show you how to love and be loved.   At Enneagram Point 5, we explore omniscient love and the relationship between love and wisdom.  “Love expands intelligence – and intelligent living is extended when we live in the emotion of love,” wrote biologist Humberto Maturana. We also explore love and mysticism, and our capacity to appoint love as the teacher for our life. In this class, we look at the basic anatomy of Ennea-Type Five, The Investigator, and we meditate on love as the access point to universal wisdom.


  • Beyond Theology – Love is not a theory; it is an experience of reality. “Love is the abridgement of all theology,” wrote St. Francis de Sales.
  • Love’s Philosophy – getting inside the mind of love with Percy Bysshe Shelley
  • Love is Medicine – “We must begin to love in order not to fall ill.” wrote Sigmund Freud.
  • Loving Kindness Meditation – contacting your heart and the whole world through loving kindness.

  *   Caroline Myss’s Spiritual Practice on omniscient love.

Lesson 7:

Type Six: Life Loves You

Do we live in a friendly universe?  Is life for us or against us?  In this class, Robert focuses on themes from the book Life Loves You, which he co-wrote with Louise Hay.  Life Loves You is a treatise on basic trust i.e., knowing that there is love and support to guide you at every turn on your spiritual journey – and especially when you feel lost, undecided, and at a crossroads.  In this class, we look at the basic anatomy of Ennea-Type Six, The Loyalist, and we meditate on listening to the Inner Voice of love that is always here to guide us.


  • The Ground of Love – developing a basic trust in the field of love that holds you when you are flying and falling.
  • Love and Fear – learning to meet every fear with love and making sure your psychology is guided by love.
  • Love is your Guide – allowing the loving hand of the universe to guide you and bless you.
  • I am Sustained by Love – a meditation from A Course in Miracles on love and spiritual resilience.

   *  Caroline Myss on love and spiritual guidance.

Lesson 8:

Type Seven: Omnipresent Love

“What you are looking for is what is looking,” said St. Francis of Assisi.  There is no worse feeling than looking for love.  Everyone knows this!  Love is not a search; it isn’t a “thing” to find.  Looking for love is a spiritual blindness. You do not find love by looking for it.  Love is everywhere you are, but you must be present to experience it. In this class, we look at the basic anatomy of Ennea-Type Seven, The Enthusiast, and we meditate on being the love we are looking for.


  • Finding Love Everywhere – the nature of love is both infinite and eternal. There is nowhere where love is not.
  • Let Love Find You – stop running from love, come out of hiding, and let love find you.
  • Be Love NOW – working with Ram Dass’s loving awareness meditation to help you find love everywhere.
  • I am what I seek – allow yourself to be a beloved child of the universe both on earth and in heaven.

    *   Caroline Myss’s Spiritual Practice on omnipresent love.

Lesson 9:

Type Eight: Omnipotent Love

Martin Luther King Jr said, “Love is the greatest force in the universe. It is the heartbeat of the moral cosmos. He who loves is a participant in the being of God.”   At Enneagram Point Eight we will focus on some key teachings from Martin Luther King Jr’s classic work Strength to Love. In this class, we look at the basic anatomy of Ennea-Type Eight, The Challenger, and we will meditate on the relationship between love and power.


  • A Higher Power – love is your higher power and you can access it only by surrendering to it
  • Undefended love – what is the ego defence you must let go of to increase your capacity to love and be loved?
  • Dysfunctional independence – are you too independent for love?
  • A Cosmic-Sized Love – you cannot play big and be powerful if you will not surrender to a love that is bigger than you.

    *   Caroline Myss’s Spiritual Practice on omnipotent love.

Lesson 10:

Type Nine: Holy Love

Maya Angelou said, “Love keeps the stars in the firmament and imposes rhythm on the ocean tides. Each of us is created of it and I suspect each of us was created for it.”  At Enneagram Point 9, Robert will share some stories from the three occasions he interviewed poet and activist, Maya Angelou. In this class, we look at the basic anatomy of Ennea-Type Nine, The Peacemaker, and we meditate on what it takes to come out of our cage, to sing our song, and to be a truly loving presence in the world.

  • Bhakti Yoga – love as a spiritual path that helps us to remember who we are and to experience union with God.
  • Calling all Angels – why your presence matters, and how you can participate in Love’s Plan for Creation.
  • Practising Presence – “To love is to be present,” said Thich Nhat Hahn. Ask yourself, who needs my presence today?
  • Love’s Special Agent – you did not fall, you gave your consent, it was love that sent you to earth.

*  Caroline Myss’s Spiritual Practice on holy love.

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.