Sail the Wine Dark Sea: Enneagram series with Kathryn Grant

Ten sessions: January 21, February 11, March 4, April 8, May 13, June 10, September 16, October 14, November 11, December 9.

8:30-10:30am Pacific Time

Cost: $35 each, or $300 for all ten sessions* ($50 discount).

*If you take advantage of this discount, you will have access to all 10 sessions. We will email links to watch all of the previous videos in the series and send you links to join the future sessions live on Zoom.

Set sail on the wine dark sea with Odysseus as he travels from Troy to Home in Ithaca. A distance of 565 nautical miles, a two-week sea cruise. It takes ten years! Sail the sea, meet the monsters, applaud the help-mates. Partake of bread, cheese and wine – even if metaphorically. On our way home we will travel the Enneagram in counter-clockwise order. Every encounter along the way has lessons, questions, warnings and encouragement for us. Odysseus arrives home – not to spoil the ending – a changed man. A different sort of hero. We will arrive home changed as well. His journey is ours.

Using Michael Goldberg’s brilliant book, Travels with Odysseus, we will leave Troy, victorious in that infamous war. Spoils of war filling 12 ships to sail home to Ithaca. The journey mirrors our necessary travels to home, loosening our egos and discovering our gentle strengths, our values, our virtuous selves. 

January 21  Troy has been destroyed, Odysseus and crew load their bounty – silver, gold, swords, armor – the spoils of war into ships and sail off. They don’t get far before being tempted to land and continue their conquests. Pillaging, looting and ravaging. Second stop -The Lotus Eaters. Almost stalls the entire trip to home. What do we need to learn about resignation, narcotization and nines?

February 11  An encounter with the Cyclops. Who is the bigger bully? Brute strength versus clever manipulation. For some a tragic stop – for all, it sets the tone for the rest of the journey. Poseidon enters the story with lasting consequences. Focused on our own strength, might we be blind-sided by cleverness? What do we need to learn about denial, excess, lust and the eights?

March 4. An island that floats – no fixed location. The inhabitants and the island itself do not want to be tied down, limited. A grand on-going party. The King’s refusal to help a second time. Sounds rather like those folks who do not want to acknowledge or encounter pain, and become fixated on “the good stuff.” What do we need to learn from the overtly “happy” sevens?

April 8  The opposite of being the big one is the fear that you are the small one. The Laestrygonians are physically huge, but lean into fear, pre-judging and pre-emptive actions. Fear can motivate but it can also cripple or exaggerate. The action here results in a huge loss for Odysseus and is a turning point in the story. Perhaps a lesson for us in this as well.   What can we learn about being right-sized from the fearful, watchful sixes?  

May 13. After the horror and loss of the encounter with the Laestrygonians a much needed rest, replenishing supplies and the beautiful goddess, Circe to give directions and encouragement. But first to the pig sty. Hermes the god of change, intersection, turning points, enters the story, introduces us to Moly – a very handy drug if you intend to deal with witchy-goddesses like Circe. Has Odysseus become humble, as well as flexible to take directions, and connect the dots, understand the intricacies – and steady enough to follow those directions -his life and the life of his crew depend on this.  What do we need to learn from perceptive, reclusive, steady fives?    

June 10.  To Hades and back. Letting go of our regrets in order to return to our lives. We must make peace with the shades of Hades, as Odysseus did. Given directions by Tiresias he sails past the Sirens who sing his song, who understand his longings and he is not be pulled off course. Do we, like fours yearn to be understood? The Sirens offer a test and a resolution. What can we learn from the strength of the creative, sensitive, emotional fours?

September 16. We pick up our journey with the challenge to sail through the straight and narrow to avoid Scylla and Charybdis.  Take necessary losses – a three quality. See the goal, set the course and go. Stranded on the island of the sun God, Helios, hungry, thirsty, far from home – can we hold ourselves to the truth, be persistent and follow strict instructions (again from Tiresias of how to survive) – or do we make our own rules – as threes have been known to do. What can we learn about arrogance and swagger from the threes

October 14. His crew and ships destroyed, Odysseus floats – alone, battered, naked. What sort of hero now? How is he to survive? What does he need? He needs to be rescued, cared for, nursed back to life. To be reanimated.  Learning to give and receive nurture and help is a “two-way” street. Calypso, the quintessential two, saves Odysseus and then captures him. What can we learn from the twos about helping, over-doing and interdependence – and freedom?  

November 11. Poseidon shows up again and Odysseus with help from Zeus escapes with his life – barely. Once again floating in the salty sea – rescued by the high-minded Phaecians who personify honesty and integrity. No shortcuts here. Practice our best selves, our virtues – that is what ones have been telling us all along. This is the last stop of rejuvenation and story-telling before Odysseus returns to Ithaca – to encounter great trouble

December 9. Nine stops. Nine lessons. On to the “third half of life.” Can we enter the symbolic/spiritual life, bringing the earth, ourselves and heaven together – as they must be? Odysseus is given a specific task to entertain symbolism, to embrace the spiritual life. We need to determine for ourselves how and if we will enter the symbolic life, embrace our sense of spirituality. What is my legacy? What task? What is mine to do? The purpose of the quest.

Register Now!!!

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Register for one or more Individual Sessions – Held on Saturdays, 8:30-10:30 a.m. Pacific Time
OR… Register for the Entire Series (We will email you links to all of the recorded sessions that you have missed and you will be enrolled in all future live sessions.)
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Jan 21 2023


8:30 am - 10:30 pm






Journey Center Online


  • Joanna Quintrell
    Joanna Quintrell
    Spiritual Director, Journey Center Online Executive Director

    Joanna Quintrell serves as the Executive Director of the Journey Center Association. It was in the year 2000 that she found herself in a spiritual crisis and first learned about spiritual direction, a gift that was life-changing and heart-transforming for her… no one had ever taught her how to nurture her own inner life with God. Joanna began her training as a spiritual director in 2003 (trained at the Mercy Center, Burlingame and the Center for Spiritual Direction in Chicago). She served as the founding director of Journey Center Santa Rosa in California through 2016 and then established the Journey Center Association in 2017. She has been the co-director of the Association’s 2-year Spiritual Director Formation Program since 2009. In addition to the joy of holding sacred space for others, Joanna loves organic gardening, hiking, traveling and grand-parenting. She and her husband live in Santa Rosa, California.

  • Kathryn Grant
    Kathryn Grant
    Certified Enneagram Instructor, Spiritual Director

    Kathryn Grant is a spiritual director and Certified Enneagram Instructor. She completed her spiritual direction training through Stillpoint/Centerpoint in Santa Barbara, CA. Her Enneagram training and certification was with Jerome Wagner, PhD. (EnneagramSpectrum Master Trainer- working with Jerry to train Enneagram instructors). She, Jerry and a colleague, Mysti Rainwater are developing an online Enneagram training course specifically for Therapists. Kathryn is an International Enneagram Association Accredited Professional. She holds degrees from the University of Illinois, Urbana, IL and Roosevelt University, Chicago, IL. She is also a Life Coach, trained with Clegg Coaching and Training and Mario Sikora’s Enneagram International Certification. She is honored to have co-taught Travels with Odysseus with Michael Goldberg and is an authorized workshop presenter. A confirmed storyteller, Kathryn loves the richness of good stories to enhance our learning experience!
    Visit my website:, 805-479-4117

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