Finding the True Self, Part 9: Navigating Past Pride

Odysseus and the Enneagram
TIMEJuly 19, 2019

We left Odysseus at type Three on the Enneagram almost totally destroyed. His ship and crew were completely so, and he himself is hanging on by a thread to life on some makeshift raft from his boat’s wreckage, drifting away from the whirlpool, Charybdis, and lost on the high seas. He has deceived himself about his own capabilities, and along the way deceived his men, and this is the result of such self-deception.

Now, Odysseus drifts for nine days until he is washed up on the island of Ogygia.

So far, the perils have meant encountering seven deadly sins of the soul: sloth (at type Nine), lust (type Eight), gluttony (type Seven), fear (type Six), avarice (type Five), envy (type Four), and deceit (type Three).

We come, then, to the last two personality types, and in the “Odyssey” we learn from Book 1 that Odysseus has been stranded on Calypso’s island of Ogygia for seven years’ duration! In short, of all the dangers, this is most serious delay to his journey to Ithaca, suggesting that the Calypso episode represents the deadliest sin of all, but how so?

The Deadliest Sin of All

To remind ourselves, the type Twos’ self-image is “I help,” and their basic desire is to feel love and to be a loving person; but their deadly sin, again often hidden even from themselves, is pride.

This coupling of love with pride is surprising, but it arises because, in their desire to help others, Twos often develop a sense of superiority over those they help: But-for-my-help, what a mess you would be in.

Furthermore, while wishing to help others, they can deny that they need help themselves. This denial can perversely, then, create exactly the opposite effect of the love that type Twos intend.

But to return to the question, “But how so?”—How is pride the deadliest sin?—we need to consider a number of factors. First, that pride, perhaps the equivalent of hubris for the Greeks, has always been viewed as the worst of all the sins. Lucifer fell from heaven because of pride.

Second, this idea is reinforced by considering the etymologies of Ogygia and Calypso. “Ogygia” means something like “primeval” or “primal” or “at earliest dawn.” Odysseus, therefore, is landing, as it were, on the root and most primitive sin that humans practice (a lot!).

No wonder, then, that it takes him some seven years to escape from this peril. And note the magic number of seven, the number of perfection, of completion—God rested on the seventh day and hallowed its rest—so only in the seventh year can Odysseus rest from the effects of this deadly sin.

Third, the word “Calypso” or “Kalypto,” means, according to Michael J. Goldberg, to hide. And “apo-calypse” means a revelation. So, it means something like to hide some revelation. Another translation has it as “she that conceals.” We talked in earlier articles about some types that are driven by body or mind issues; clearly, hiding or concealing is in the heart. The type Twos (as are the type Threes and Fours) are Enneagram heart types, and one consequence of this is a preoccupation with image, and so with concealing (in the heart) what is really going on.

However, saying all this still leads to a big problem to understand: namely, how being loved by Calypso is such a bad thing? Isn’t love good? What has happened?

Calypso and Her Offer of Love

With Odysseus arriving on Ogygia, Calypso, “the dangerous nymph with glossy braids,” an immortal goddess, falls in love and wishes to marry him. As Odysseus says, “she loved me.” She loves him so much that if Odysseus accepts her offer of marriage, she will make him an immortal too.

“Calypso, the Blonde-Haired Goddess,” by Jan Styka. (Public Domain)

Furthermore, even without the marriage, she caters to Odysseus’s every need, including sleeping with him, as lovers. Odysseus even admits to her that his own wife, Penelope, “falls far short of you. Your beauty, stature.”

But the reality is: “He had no choice.” He was an unwilling lover, and she was “all too willing.” And the result of this over seven years is that Odysseus spends his days sitting on “rocks and beaches, wrenching his heart with sobs and groans and anguish, gazing out over the barren sea through blinding tears.”

He cannot leave her; she will not let him. And he no longer has any resources of his own—no crew, no ship, no way to return to Ithaca—so he is stuck.

Odysseus pining for home
“Ulysses (Odysseus) on Calypso’s Island,” 1830, by Ditlev Blunck. (Public Domain)

To our Western minds and culture, this sounds almost too good to be true: a gorgeous, immortal goddess wants to look after you, and love you forever! How can an action man like Odysseus really want to leave? But just as this—to the West—seems such a good deal, the reason it is not touches on one of the most serious addictions that beset our culture: namely, dependency.

As James Hollis expresses it: “Children are supposed to leave; if they didn’t, it would mean you had failed to empower them, ask enough of them to develop the wherewithal to conduct their lives without you. We may miss them, but if we cling to them, we are not loving them; we are revealing our own dependencies.”

This is the trap of the type Two: “I help” and “I am a loving person” comes to mean, “You need me and cannot do without me; I have become indispensable to your life.” And the pride creeps in because in such a position, there is always the sense that because you need me, then “I” am superior to you.

Hermes orders Calypso
“Hermes Orders Calypso to Release Odysseus,”1810, by John Flaxman. (Public Domain)

Help From Other Gods

As Hollis also observes: “The gods want us to grow up, to step up to that high calling that each soul carries as its destiny.” This is what it means to actually live, as opposed to being in some immortal play zone where actions seem inconsequential. Thus, at the council of the gods, Zeus hearkens to the voice of his daughter, Athena, goddess of wisdom and protector of Odysseus, and sends Hermes to instruct Calypso to release Odysseus.

It is no accident that it is the god Hermes who is the one sent to release Odysseus from the grip of Calypso. We met him before on the island of Circe (where Odysseus was detained for a year by another goddess) and where his expertise saved Odysseus from Circe’s wiles; now he is the one to unlock Odysseus’s destiny.

For let us remember that Hermes is the discoverer of secrets. He is the one from whose name we understand that things might be “hermetically sealed,” or that “hermeneutics” means precisely the art of interpreting what is subtle, obscure, arcane and difficult. So what is hidden—concealed—in the heart of Calypso must be revealed now.

Of course, Calypso is not very happy about it. Her plans for Odysseus are about to be quashed, and all the real desires of her heart revealed—namely, that all her love for Odysseus is really more about love for herself, keeping Odysseus for herself, and quite pointedly, as the text reveals, wanting to be superior to Penelope, Odysseus’s own soul. In this way, what she is attempting to do potentially thwarts the will of the gods themselves.

At first, she is very angry. She blames the gods, calls them “cruel, jealous” and points out their deep hypocrisy, for it was Zeus himself who shattered Odysseus’s ship, destroyed his crew, and set him loose, abandoned on the seas.

Calypso was most likely a Two, the Lover. “Calypso Calling Heaven and Earth to Witness Her Sincere Affection to Ulysses,” 18th century, by Angelica Kauffmann. (Public Domain)

And she is right; this is what the type Two is very good at discerning: the intentions of the hearts of others and also their internal contradictions. She, as she reminds Hermes, “welcomed him warmly, cherished him” and vowed to give him immortality.

At this moment, though, she realizes that she has said as much as it is wise to say, for “there is no way for another god to thwart the will of storming Zeus.” So she agrees to let Odysseus go and, in the Walter Shewring translation, remarks that she will help him “without concealment.” No more play-acting. Her intentions will be true and without masks, as she will now really help Odysseus.

Indeed, this is highly necessary as Odysseus is rightly suspicious of her motives when she informs him that she will help him leave. He has had seven years of her seductive “forever trying / to spellbind his heart with suave, seductive words / and wipe all thought of Ithaca from his mind.” These are the worst aspects of the Two: flattery and manipulation.

But now she says candidly, “All I have in mind and devise for you / are the very plans I’d fashion for myself / if I were in your straits … I am all compassion.” This is the Two type at its very best. Now she really does help Odysseus: not building the ship for him, thus promoting the dependency on her that he has experienced these long seven years, but enabling him to build it for himself.

Interestingly, one of her gifts at this point is a double-edged (Two edges!) ax: It seems to me to symbolize the effect of Twos in anyone’s life. They can cut both ways: for the good, “I am all compassion,” and for the ill, the co-dependency and enervation that results.

Calypso can heal but she can also entrap. Thus, when you are dealing with a Two, you have to clarify what is really essential in your life, what is your real mission; you have to keep a clear head—the wisdom of Athena always in mind, and you must not be distracted no matter how targeted and customized the offering is for your personal needs. In this way, you can sail away and reach the high destiny of your hero or heroine’s calling—to find Ithaca and your own soul.

And for a Two—Calypso herself—she is saved from her own pride and hubris when she hearkens to the messenger god who helps her re-interpret what is really going on (in terms of the order of the cosmos, which is the will of Zeus) so that she can back off, be straight, and contribute without manipulation. In this way, she herself prevents the retribution from Zeus that Hermes says will “make your life a hell.” This acceptance of the word of Hermes is a form of humility and an antidote to the pride of the Two.

In this multipart series, “Finding the True Self,” we will discuss nine types of personalities, their flaws, and show how Odysseus, through his adventures, overcame them to find his way back home.

James Sale is an English businessman whose company, Motivational Maps Ltd., operates in 14 countries. He is the author of over 40 books on management and education from major international publishers including Macmillan, Pearson, and Routledge. As a poet, he won First Prize in The Society of Classical Poets’ 2017 competition, recently appearing at New York’s Princeton Club.

James Sale
James Sale has had over 50 books published, most recently, “Mapping Motivation for Top Performing Teams” (Routledge, 2021). He has been nominated for the 2022 poetry Pushcart Prize, won first prize in The Society of Classical Poets 2017 annual competition, performing in New York in 2019. His most recent poetry collection is “HellWard.” For more information about the author, and about his Dante project, visit