Why The Odyssey Still Speaks to Us: The Enneagram and the Human Journey Home
Beatrice Chestnut | July 30, 2026
With all the recent excitement surrounding the new film adaptation of The Odyssey, I've been thinking about a connection I explored in my first book, The Complete Enneagram: 27 Paths to Greater Self-Knowledge. Long before Hollywood’s most recent return to Homer, I was fascinated by the way Odysseus's journey mirrors the Enneagram, a powerful map of human development with roots in ancient wisdom teachings.
At first glance, these two traditions seem to have little in common. One is an ancient Greek epic about a king struggling to find his way home after war. The other is a diagram that re-emerged in the 1960s that maps universal patterns of human personality and transformation. But early in my Enneagram studies, I learned that The Odyssey isn't simply an adventure story—it’s an archetypal story of “homecoming”—of coming home to our “true self”—it is an account of the inner journey that every one of us must make on the way to becoming our truest self.
And, the journey home that Odysseus takes leads him through nine “lands” where he meets mythic characters that create challenges that he must overcome on his way home. And these nine lands with their nine sets of challenges parallel the Enneagram types. And, they are arrayed in the same order we find in the contemporary Enneagram typology!
One of the ideas that has guided much of my work is that the Enneagram is not merely a framework for understanding personality. I believe it reflects universal archetypal patterns that have surfaced throughout humanity's great wisdom traditions for centuries. We find echoes of these same patterns in sources as diverse as the Kabbalah, Dante's Divine Comedy, and Homer's The Odyssey.
Interestingly, Odysseus encounters each of the psychological challenges in the very same sequence as the nine points of the Enneagram. Each island presents not merely an external obstacle, but an inner challenge—one that must be understood and transcended if he is to continue his archetypal journey home.
What fascinated me most was not only that the encounters in The Odyssey echo the nine Enneagram archetypes, but that the character’s primary defining trait is usually what leads to their undoing. This is exactly what the Enneagram teaches us: that to come home to ourselves we need to challenge the very aspects of our personality that we most identify with.
And perhaps that is why The Odyssey continues to resonate nearly three thousand years after it was written. Home is not just a place. It is a metaphor for returning to our essential nature. Odysseus's voyage is ultimately the journey each of us undertakes: the long, difficult process of waking up, confronting the patterns that keep us asleep, and finding our way back to who we really are.
Many parallels between Odysseus’ journey and the Enneagram as a map of the archetypal hero’s journey. Both draw on the symbolic meaning of the numbers 3, 7, and 9. Both describe what we need to develop—and watch out for—given our human condition, if we can succeed going from a lower level of awareness to a higher level of consciousness. Through the action of the Odyssey, we learn that to arrive “home,” we need to be humble, clever but not arrogant, and we need to work with universal forces and strive to do what’s right and what has integrity.
To demonstrate just a bit of the way the Odyssey aligns with the Enneagram map, I will outline the parallels between the nine lands Odysseus visits and the Enneagram types—the nine lands depicted in the second of three sections in the book, known as “The Great Wanderings.”
The Nine Stops on the Journey Home
After fighting for ten years in the Trojan War, Odysseus longs to return to his home on the island of Ithaca to reunite with his wife, Penelope, and his son, Telemachus. But what should have been a relatively straightforward voyage becomes a ten-year odyssey filled with storms, monsters, temptations, and seemingly endless trials.
Type Nine: The Lotus-Eaters
Odysseus's first stop after leaving Troy is the Land of the Lotus Eaters. There, the challenge is not violence or danger; it is forgetting. The Lotus-Eaters are a friendly group who have a habit of eating a plant called lotus, which makes them go to sleep to themselves. They symbolize the temptation to fall asleep to our deeper purpose, settling for comfort instead of rising to the challenge of remembering who we are and where we are meant to go. Like the Nine personality, the journey begins by awakening to the desire to come home to ourselves and not just stay addicted to things that cause us to forget ourselves and our higher purpose.
Type Eight: The Cyclops
In the second land that Odysseys and his men visit on their way home, they encounter Cyclops, “lawless brutes” who don’t fear gods or humans (Homer/Fagles, 1996). The Cyclops embodies raw power, self-reliance, and the belief that strength alone is enough. But the portrayal of the Cylops shows us that myopic, unchecked power becomes blindness. The Cyclops Polyphemus, in particular, gives us a close look at the Type Eight archetype. He takes what he wants when he wants it, eating Odysseus’s men without care. After he fails in his effort to trap Odysseus’ men in his cave, Polyphemus ends up hurling boulders at the sea in a (literally) blind rage after Odysseus’s men spear his eye after intoxicating him with potent wine. This encounter reminds us that appetite, anger, and a narrow focus on our own viewpoint, when unrestrained, can lead our downfall.
Type Seven: Aeolus and the Island of the Winds
Odysseus and his men next arrive at Aeolia, the floating island, which is a Type Seven’s dream: life is easy there—it’s comfortable, happy, and filled with feasting and celebration. To help the men get home, Aeolus, the island’s ruler and controller of the winds, captures all the troublesome winds in a bag, leaving only the favorable West Wind to carry the ships safely toward Ithaca.
After sailing successfully for ten days, Odysseus falls asleep just as Ithaca comes into view. But his men are tempted by the bag of winds, which they think is filled with treasure, and they open it. The winds are unleashed, creating a violent storm that blows them all the way back to Aeolia. The Seven challenge reminds us that pleasure, distraction, and the desire for "something more" can cause us to lose sight of what matters most. Real freedom isn't found in chasing endless possibilities—it comes from staying committed to the journey home, even when that requires focus and self-discipline.
Type Six: The Laestrygonians
After visiting Aeolia, Odysseus and his men land in the territory of the Laestrygonians, a race of enormous, powerful giants. What first appears to be a peaceful harbor quickly becomes a nightmare as the giants attack without warning, destroying nearly every ship in Odysseus's fleet. Only his own vessel escapes.
The Laestrygonians represent the Type Six archetype taken to its extreme. They assume anyone approaching them must be an enemy and react immediately with overwhelming force. Demonstrating the fear that drives Type Six, they illustrate how vigilance can become paranoia and fear can become aggression. When fear completely takes hold, we lose the ability to distinguish real threats from imagined ones—and we react in ways that can be destructive.
Type Five: Hermes and Circe
The next stop’s main characters embody the Type Five archetype. After escaping the Laestrygonians, Odysseus and his remaining crew arrive at the hidden woodland home of the sorceress Circe. She welcomes his men inside, but soon transforms them into pigs with a magic potion, symbolizing how easily human beings can become consumed by greed, appetite, and the fear of not having enough. Before Odysseus confronts Circe himself, the messenger god Hermes appears and gives him a protective herb that allows him to resist her spell.
Both Hermes and Circe are keepers of secret knowledge, but they use that knowledge differently. Hermes represents discernment, healthy boundaries, and the wisdom to reveal hidden truths when the time is right. Circe tests whether Odysseus can use that wisdom without falling prey to fear, greed, or self-protection. Because he resists her magic, Odysseus frees his men, earns Circe's respect, and receives the guidance he needs to continue his journey into the underworld. Like the Type Five personality, this episode reminds us that true wisdom isn't simply accumulating knowledge; it's knowing how to use it skillfully in service of the journey ahead.
The Underworld: After visiting Circe’s land, Odysseus makes a visit to the underworld, as many other heroes of epic poems from ancient times do. This visit is exactly halfway through the poem, and this is reflected by the gap between Types 4 and 5 on the Enneagram diagram—which symbolizes a descent into a positive “darkness” or “Shadow” territory—or Dark Night of the Soul—that humans must traverse to complete the journey of homecoming.
Type Four: Hades and the Sirens
Circe directs Odysseus to descend into Hades to receive more guidance, and there, he encounters the spirits of the dead. He speaks to many, but they are consistent: they consistently describe their regrets and envy the living. Soon afterward, he must sail past the Sirens, whose songs offer the chance to truly know human longing and depth of emotion. But they are temptresses, who–if listened to–bring travelers to their deaths.
Together, Hades and the Sirens reflect the emotional landscape of Type Four. Hades represents the grief, longing, and unfulfilled desires that every human being must eventually face. The Sirens symbolize the temptation to become lost in those emotions, believing fulfillment lies in endlessly exploring our pain. Odysseus prepares carefully for this encounter, tying himself to the mast while preventing himself from acting on the Sirens' call. In doing so, he demonstrates that emotional depth can become wisdom—but only when it is experienced consciously rather than allowed to consume us.
Type Three: Skylla, Charybdis, and the Island of Thrinakia
After passing the Sirens, Odysseus faces one of the greatest leadership challenges of his journey. He must navigate between Skylla, a six-headed monster, and Charybdis, a deadly whirlpool capable of swallowing an entire ship. Knowing he cannot avoid both dangers, he chooses the course that will save as many of his men as possible, even though, as Circe explained, it will require him to sacrifice six men. Here we see themes connected to Type Three—to succeed in making it through this difficult passage, Odysseus must have a clear goal and do what’s necessary to effectively reach his goal.
Later, on the island of Thrinakia, Odysseus warns his exhausted crew not to slaughter the sacred cattle of Helios. While he sleeps, they ignore his instructions, believing they know better, and their decision ultimately leads to their destruction. These episodes capture both sides of the Type Three archetype: authentic leadership that remains focused on the larger mission, and the dangers that arise when ambition, entitlement, or the desire for immediate reward eclipse wisdom and restraint.
Type Two: Calypso
By the time Odysseus reaches Calypso's island, he has already survived years of hardship and has nearly completed his journey home. Calypso is a beautiful goddess who welcomes him into an idyllic paradise. She gives him everything he could want: the best food, comfort, safety, and even the promise of immortality if he will stay with her forever. But there is one thing she cannot give him—his home. While Calypso wants Odysseus to remain with her as her husband, Odysseus longs to return to Ithaca, to Penelope, and to the life that is truly his.
Calypso represents both the gifts and the shadow of the Type Two archetype. She genuinely nurtures and provides for Odysseus, but beneath her generosity lies a desire to keep him with her for herself. Under the guise of helping, she tries to control the outcome of the relationship so that her own needs are met. Only after Zeus commands her to let Odysseus go does she embody the higher qualities of Type Two. Knowing he will never return her love, she still helps him prepare for his voyage home. By finally releasing him with no strings attached, she demonstrates what authentic love without reciprocation can look like.
Type One: The Phaeacians
The last people Odysseus encounters before finally reaching Ithaca are the Phaeacians of Scheria. They are disciplined, orderly, courteous, and deeply committed to doing what is right—much like Type Ones. Their kingdom is beautiful and well-governed, their ships are expertly navigated, and they ultimately feel morally obligated to help the weary traveler complete the final leg of his journey home.
The Phaeacians embody many of the admirable qualities of the Type One archetype: integrity, responsibility, conscientiousness, and a commitment to virtue. But Homer also reminds us that even our greatest strengths have their limitations. The Phaeacians' perfection and moral certainty can become rigid and self-righteous. And despite all of their discipline and virtue, they are not spared from fate. After they help Odysseus, Poseidon turns their returning ship to stone and threatens their harbor, reminding us that striving for perfection and righteousness cannot protect us from life's uncertainties.
Why These Stories Endure
One reason great works like The Odyssey continue to resonate is that they are about far more than the adventures of a legendary hero. They speak to recurring patterns of human experience that transcend culture and time. Whether we encounter them in Homer, Dante, the Kabbalah, or the Enneagram, they remind us that the journey toward greater consciousness has always followed familiar terrain.
That is one of the ideas at the heart of The Complete Enneagram. While the Enneagram offers a powerful framework for understanding personality, it is ultimately much more than that. It is a map of the universal human journey—a journey from unconscious habit toward greater presence, freedom, and wholeness.
On the occasion of the release the new 2026 edition of The Complete Enneagram this August, I'm delighted that so many people are rediscovering The Odyssey. I hope this ancient story encourages you to look beyond the monsters and adventures in your own life, see them as learning opportunities that can further your growth, and recognize your own journey home.