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Sail the Wine Dark Sea!
Sail the Wine Dark Sea!

Sat, Mar 04


Online Workshop

Sail the Wine Dark Sea!

Using Michael Goldberg’s book, Travels with Odysseus, we will leave Troy, victorious in that infamous war. Spoils 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.

Time & Location

Mar 04, 2023, 8:30 AM – 10:30 AM PST

Online Workshop

About the event

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. 

Our hero, Odysseus meets help-mates and monsters. The helpful characters give him strength, courage, instructions for the journey – and also importantly, cheese, bread and wine. The vengeful monsters, shipwreck and sabotage him, killing his crew, sinking his ships and wreaking havoc on supplies and lives. He makes it home, alone: no spoils of war. Tired and sea water soaked – to great troubles at home - 

And then – a surprise! 

Set sail on the Aegean Sea – and never leave dry land. No need to re-read the Odyssey – (or for the first time.) The story will be told. No sunscreen required. No Dramamine. A gripping adventure and brilliant Enneagram wisdom awaits. Book your cruise now. A hat might be a good idea.

We will meet once a month – usually the second Saturday morning. January, 2023 through June and September through December.

Cost: $35 each session.

This workshop is presented in partnership with the Journey Center. Register here on the Journey Center website:

Voyage Itinerary:  

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.

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