Maurice Nicoll, a psychiatrist and one of G's students, wrote a small book titled "A New Man" where he talks about the Gospels, their language and meaning as understood from The Work point of view (more or less). He devoted a whole chapter to the parable of wise virgins. Basically, most of his points have been already mentioned and discussed in this thread, so for what it's worth, with a few things possibly added or put differently. (Apologies for any repetitions, he does it ad nauseam and I did try to leave out as much as possible. Emphases and notes in color - mine)
From introductory chapter: The Language of Parables
Chapter: The Idea of Wisdom in the Gospels
[wise]
There is a connection between the words phrónimos, diaphragm and shrewd (perspicacious) that I think is quite interesting:
http://biblesuite.com/greek/5429.htm
Back to Nicoll and the parable of the ten virgins "five of whom were wise, phrónimos, and five foolish or silly":
From introductory chapter: The Language of Parables
ALL sacred writings contain an outer and an inner meaning. Behind the literal words lies another range of meaning, another form of knowledge. According to an old−age tradition, Man once was in touch with this inner knowledge and inner meaning. ...
The idea behind all sacred writing is to convey a higher meaning than the literal words contain, the truth of which must be seen by Man internally. This higher, concealed, inner, or esoteric, meaning, cast in the words and sense−images of ordinary usage, can only be grasped by the understanding, ... A person's literal level of understanding is not necessarily equal to grasping psychological meaning. To understand literally is one thing: to understand psychologically is another. ...
The Gospels are from beginning to end all about this possible self−evolution. They are psychological documents. They are about the psychology of this possible inner development—that is, about what a man must think, feel, and do in order to reach a new level of understanding.
...Everyone has an outer side that has been developed by his contact with life and an inner side which remains vague, uncertain, undeveloped. Teaching about re−birth and inner evolution must not fall only on the outer side of a man—the life−developed side. Some people reach a stage where they realize that life does not satisfy them, where they genuinely begin to look in other directions and seek different aims, before they can hear any teaching of an order similar to that of the Gospels. The outer side of a man is organized by life and its demands ...
A parable is cast in the form of ancient meaning. A parable in the Gospels is cast in the form of an ancient language now forgotten. There was a time when the language of parables could be understood. This language—the language of the parable, allegory and miracle—is lost to the humanity of to−day. But sources still remain which enable us to understand something of this ancient meaning. Since the object of the parable is to connect higher and lower meanings, it can be thought of as a bridge between two levels, a liaison between literal and psychological understanding.
Chapter: The Idea of Wisdom in the Gospels
[wise]
IN many of the parables and sayings of Christ a word is used which is translated as wise. For example, Christ said to his disciples on one occasion: "Be ye wise as serpents and innocent as doves. " "Innocent" means "harmless", "not doing any harm", and has not the moral sentimental Western meaning of not knowing anything: it would indeed be impossible to be "wise" and at the same time not know anything. But the word translated as "wise" does not exactly mean "wise" so much as "clever" or practically intelligent. The Greek word is φρόνιμος [phrónimos] which meant in its earliest use being in one's right senses and so having presence of mind or having one's wits about one. ... To know how to do and actually to do the right thing at the right time is to be φρόνιμος. You will remember that the "Steward of Unrighteousness" (wrongly translated as the Unjust Steward) was called "wise"—that is, φρόνιμος—being commended by his lord because he saw what to do in a very difficult situation and acted with great presence of mind.
This word, φρόνιμος, has therefore a strong, bracing, practical meaning. It is used in the Gospels to define the right action of an intelligent man seeking a higher level of himself through inner evolution. Christ talks of those who are useless in this respect. He compares them with salt that has lost its savour and is not even fit for the dunghill: "If the salt have lost its savour, wherewith shall it be seasoned? It is fit neither for the land nor for the dunghill: men cast it out. " (Luke xiv, 34, 35. ) And here the word translated as "have lost its savour" means literally "has been made foolish". The dunghill is life. ...
There is a connection between the words phrónimos, diaphragm and shrewd (perspicacious) that I think is quite interesting:
http://biblesuite.com/greek/5429.htm
phrónimos (an adjective, derived from 5424 /phrḗn, "personal perspective regulating outward behavior," and the root of the English term "diaphragm" which controls key body functions from the inside out) – properly, "how we size things up," reflecting our personal ("visceral") opinions, i.e. what we consider "savvy" (smart). This always roots to our personal perspective ("inner outlook") which regulates our definition of being "shrewd," i.e. reflects personal mind-set (insight).
5426 phronéō (from 5424 /phrḗn, "the midriff or diaphragm; the parts around the heart," J. Thayer) – properly, regulate (moderate) from within, as inner-perspective (insight) shows itself in corresponding, outward behavior. 5426 (phronéō) essentially equates to personal opinion fleshing itself out in action (see J. Thayer). This idea is difficult to translate into English because it combines the visceral and cognitive aspects of thinking.
Back to Nicoll and the parable of the ten virgins "five of whom were wise, phrónimos, and five foolish or silly":
... This is a parable about reaching a higher level by inner evolution, here called directly the Kingdom of Heaven.
The wise virgins are distinguished from the foolish virgins by possessing oil in their lamps. Notice that they refuse to give their oil to the others, but tell them to go and buy it in life. All of them had lamps but only half had oil in them and these are called "clever" or "not silly". ...
What does it mean that they had oil? They are those who ... have understood something that the others have not understood and this is represented by their having oil in their lamps.
[A lamp - the first stage of inner evolution]
... A lamp is to give light. But, psychologically, it means here something that can give light, not in a physical sense, but in the sense of light as used in the Gospels—the light that shines in the darkness of the mind... and [can] illuminate the understanding.
When a man lives only from his senses and takes the spectacle of outer life, lit up by the sun, as his sole end, he is in darkness. John says the darkness does not comprehend the light; the lower does not understand the higher level. When a man becomes aware that he is internally incomplete and lost, and that the full meaning of his existence is to undergo a change, an inner evolution, and receives a new understanding about himself and what he has to do, he already begins to see this light, this real meaning of his creation.
... Because the Kingdom of Heaven is within a man, he can only get contact with it internally. The way is in himself, not outside. He can experience flashes of another consciousness, moments of entirely new meaning, which show that a higher level exists in him. They are moments of this light. But to reach this level permanently a man must be taught the Word and taught it first of all externally, via the senses. He must hear it: but this does not mean merely to hear it literally, but to begin to understand it, to hear it with his mind, to ponder it, to think of its meaning, to take it into his inner consciousness and to see himself in the terms of what it teaches. For his mind must slowly be prepared in order to change because this higher level is different from a lower level and so the thoughts belonging to a lower level are not of the same order as those of a higher level.
Something new must be formed in his mind to receive "light"—so he must gradually come to "think in a new way" (or "repent" as it is so wrongly translated). This gradual change in thinking forms the lamp in him. ... But the lamp is not enough by itself. It cannot give light alone—but it is necessary, as the first stage of inner evolution.
[Oil - the second stage]
The second stage, in this parable, is the stage of having oil in the lamp. This means that what he knows and sees as new Truth must be applied.
Christ said: "Everyone that heareth these words of mine and doeth them, shall be likened unto a wise man... and everyone that heareth these words of mine and doeth them not, shall be likened unto a foolish man." Here the two words wise and foolish appear in the same sense as in the parable of the wise and foolish virgins. To act inwardly from the teaching of Christ, to begin to do it, to begin to work from the understanding of its meaning, to begin to use it and apply it to oneself practically—this is to be wise. This is to use the Word intelligently. This is to be practically clever. And this gives oil in the lamp, individually.
[on sitting on the fence]
But people can accept Truth of this higher order and yet continue to act only from the level of life. They do not internally obey the new Truth, the new knowledge they have learned, which comes from a higher level, but they continue to obey life and its good when it comes to the point. They have lamps but no oil. These are called the foolish, who must go and buy oil from those who sell it. This means that they must continue to get the kind of oil gained from meritorious actions in life which is the only kind of Good they value. "Those who sell it" are those who tell you what is meritorious, what will pay best.
To act from merit and reward makes one sort of oil. To act from the teaching of the Word and its internally understood meaning is to act from a level higher than life, and nothing in outer life will reward you for such actions.
[The foolish]
The foolish virgins with lamps and no oil are those who are on one level of Truth and knowledge intellectually—a higher level—but live and do according to another level. They know one thing, and live and do another.
These in the very nature of things shut themselves out from the Kingdom of Heaven—that is, from the attainment of this higher level possible to Man which is his real meaning. It is not that the door is shut on them. The door is not shut; they shut the door on themselves.
The kind of oil they get from "buying and selling", the oil of merit, is not that required for entry into another level of humanity. So they are said to be "not clever". They are not clever because they do not see that it is to themselves and the kind of people they are that the teaching of Christ applies. They must not merely think in a new way, through the ideas of the Word, but must themselves become different kinds of people.
They may know and even believe the Truth on a higher level, and at the same time live on another level, not applying the Truth to themselves. This is their problem: their actual lives are not governed by their knowledge. They know one thing and will another thing.
The foolish, ... knowing the teaching, continue to seek their Good from life, from rewards, from reputation, from being first, getting to higher and higher positions, having better morals than others, being thought well of, from outwardly conforming to laws and social standards, when internally they are quite different and are only restrained by fear. This is the only Good they know and so they must follow it.
And since the whole question lies in what a man deems is Good, and because a man acts solely from what he deems is Good, they are told to go to what they deem Good and get at least that kind of oil, for this is all they can do. They are told to go to those who buy and sell this Good. ... They have no idea of acting from a form of Good beyond life, beyond reward in life, for the sake of what they see is Good in the light of a higher teaching of what is Truth and Good. So they shut themselves out because they mix up two different levels of knowledge as two different levels of Good.
If you look narrowly at what is meant by "Good" in the Gospels you will see what is meant.
[Knowledge and Being - a lamp and oil]
To bring down the teaching about higher Man to the level of Man as he is, to follow the idea of what is Good from the basis of life and its rewards, its merits, its values, its insistence on reputation, outer appearances, and so on, is to shut oneself out from the Kingdom of Heaven, because a man beginning to reach the level of the Kingdom of Heaven does Good for no reward in life but from what he sees internally as Good in the light of the Truth of the Word taught him. And it is of no use for any of us to pretend that we already know this kind of Good and act from it. We act from life and its Good, however much we know.
To be a Christian a man must will what Christ taught and do it. If he cannot see the Good of what he is taught, he will not act from it. No matter how much knowledge is given and how true it is, he will not act from it unless he sees by his own inner understanding that it is desirable and good and begins to will its existence. A man is not merely his understanding but what he wills from it, and this is what he does, and this is the whole man. The Word—that is, the psychological teaching in the Gospels—is to make a man different, first in thought, and then in being, so that he becomes a New Man. Merely to know about the Word and to make one's oil—one's Good—from the advantages, intrigues and merits of life is not to have the oil that belongs to the lamp of Christ. To act from the Word, to act from this teaching about inner evolution, this higher state of Man, to begin to do a very few things in the light of Christ's words through seeing what they mean and liking the ideas and so being able to will them, without any sense of reward, is another matter. One single act done from willing some truth belonging to that order of teaching called the Word will lift a man for a moment far beyond his usual level. In such an act there is no question of bargaining, no question of "how much?", no question of "where do I come in?" and no boasting about it afterwards. One such thing done in the purest part of your understanding because you see the necessity and reality and so the Good of it, one such thing done from the inner will, can begin to set in motion something that has hitherto remained silent and motionless. The seed starts to life. The man, as a seed on which the Word can fall, begins to awaken. Light enters into his inner darkness. Truth is one thing, the spirit another—and a man must be re−born, from water and spirit, before he can become a New Man. Water is the Truth, the knowledge and teaching about a higher level; and spirit is a man's will passing into this knowledge and uniting it with him, through his seeing its Good, its value. No amount of external teaching will bring about this result. A person may have a lamp—but only through his own most intimate will, only through his deepest consent, only through obeying in secret the knowledge that has formed the lamp in him, will he make oil for it. It is just here that everyone is free. It is just here that everyone, through an inner action, can evolve or not evolve.
