One of the problems with vainglory, according to St. Isaac the Syrian, is that “it hands that person over to” either fornication or pride.  But before we can talk about how vainglory hands one over to either fornication or pride, we need to understand what vainglory is.  Nowadays the word vain means to have a high opinion of oneself, but that is not what it originally meant, nor what it means in the Bible or in the hymnology of the Church.  This is why many English-speaking Orthodox Christians have no idea what vainglory means. 

The word vain used to mean (and still sometimes does mean) empty, powerless, or useless.  This is what vain means in the Bible when, for example, it speaks of vain idols.  The idols are empty, powerless and useless.  When the Orthodox prayers speak of vain thoughts, they are referring to thoughts that are empty, powerless or useless.  This is why Orthodox prayers often pair vain thoughts with evil imagination.  They are not the same thing.  Vain thoughts are not necessarily evil, they are just empty, valueless thoughts.  But such vain thoughts often lead to evil imagination, as St. Isaac and other Church Fathers have pointed out.  

The second part of vainglory is glory.  Glory, at it’s core, and especially in Hebrew, is a word that means weight, value or substance—not substance in the abstract theological sense, but substance in the overwhelmingly powerful sense of a semi tractor trailer, fully loaded, moving at 80 miles per hour.  Glory is the weight that overpowers you so that you cannot stand in the presence of an angel, for example.  Glory is the worth, the worthiness of God that so overpowers the angels closest to God that the seraphim must cover their faces to be in God’s presence.  

Vainglory, then, is to overvalue, to praise, or to give too much importance (weight or substance or worth) to something that is unimportant or not very important.  So, for example, it is vainglorious of me to give too much attention to my clothes.  It’s not that what I wear is absolutely unimportant. One should dress as appropriately as one can for the weather or the situation.  But clothes are much less important than kindness, or mercy or faithfulness or generosity.  It is much more important that I be kind and generous to others, even if it means I am not quite appropriately dressed—as we see in the example of St. Martin of Tours who cut his military cloak in half to cover a cold beggar. 

But one can be vainglorious about many things.  In the Headings on Spiritual Knowledge (2.25), St. Isaac divides vainglory into two levels.  There is the level of the body and the level of the soul.  When our mind thinks that things of the body are more important or valuable than they really are, vainglory tends to hand us over to fornication, says St. Isaac.  Things of the body include attention given to appearance, health, feeling happy, clothes, possessions, status, rank, reputation.  While some of these are almost completely unimportant, others have some importance.  So, for example, it is relatively important for me to be healthy enough so that I am not a burden to others.  But attention to my health becomes vainglorious when it takes my attention from love of God and love of neighbour.  A good reputation is desirable, but it has no value at all compared to actually being good.  

The second level of vainglory according to St. Isaac is of the soul.  Vainglory of the soul hands one over to pride.  St. Isaac specifically mentions two areas where vainglory is particularly manifest in the soul.  These are excellence of conduct or of knowledge.  When I praise myself or enjoy it when others mention my excellent conduct, my piety, the right way I do things, then I have fallen into vainglory.  This is true of knowledge also, even correct knowledge (maybe especially correct knowledge).  When I know the right answer, the right teaching, the right practice then I must be very careful.  Especially when I know I am right, I am on the precipice of failing into vainglory, which, according to St. Isaac, “increases in us the ulcer of pride.”

Again, it is not that right conduct and correct knowledge are unimportant.  It is rather that right conduct and correct knowledge are seldom the most important matters.  The most important matters have to do with our relationships: relationship with God and relationship with one another.  The most important matters are the virtues, the fruit of the Spirit, love of God and neighbor.  When being right—even if (or especially if) I know I am right—is more import to me, is weightier to me, has more value to me than loving and caring for my brother for whom Christ died, then perhaps I have moved into vainglory.  And if I am vainglorious in these matters of my soul, then perhaps I am already suffering from what St. Isaac calls “the ulcer of pride.”

As with so many areas of the spiritual life, vainglory is not simply a matter of black and white.  Like almost all spiritual things, discernment is necessary.  I am not loving my brother if I don’t bathe, but if cleanliness is more important to me than kindness, I may be suffering from vainglory.  Correct, Orthodox faith and practice are very important, but if I judge others based on what I know to be correct, then even very good and true Orthodox piety itself can become a cause of vainglory.  I must never forget that the Pharisee whose prayer was rejected fasted and prayed and even tithed.  The Pharisee did everything right, as for as he could tell, and he was not justified.  The publican who did very little right begged for mercy and was justified by God.