There is something very misleading about "reading about humility" as if one could learn about true humility from a book. In fact, St. John says this precisely: "Do you imagine that talk of such matters will mean anything to someone who has never experienced them? If you think so, then you will be like a man who with words and examples tries to convey the sweetness of honey to people who have never tasted it. He talks uselessly. Indeed I would say he is simply prattling. Our theme sets before us as a touchstone a treasure stored safely in earthen vessels, that is, in our bodies. This treasure is of such quality that it eludes adequate description. It carries an inscription of heavenly origin which is therefore incomprehensible so that anyone seeking for words for it is faced with a great and endless task. The inscription reads as follows: Holy Humility."
Therefore, St. John approaches this step with some concern. His hesitancy to write about humility stems from at least two sources. First, as he insists, humility is a virtue won through struggle. There is a very real sense in which humility can only be learned existentially - through the experience of the struggle for God. In the context of this struggle, we are taught by God Himself what it means for us to be humble. It is one thing to write about it and to give mental assent to it. But how many of us really know that this is true, how many of us feel that it is true, how many of us experience the torturous presence of pride moment to moment? There is only one way to learn: life-long struggle with oneself.
Second, it is difficult to write about it because humility expresses itself in different ways in different people. Since humility is a grace of God in the soul, learned existentially in the context of my own individual struggle to find God, it is inescapably personal. What it means for me to be humble is tied to who I am, where I have come from, where I am going and how I am supposed to get there. The uniqueness of my own road to God means that humility is going to be different for me than for anyone else. Furthermore, as I grow older and my life changes, humility will take on new meaning and new expression.
However, as beginners we are in need of some direction. St. John gives us general guidelines to follow in the specifics of our own struggle. First, he reminds us that the struggle for humility is the most important struggle of our spiritual lives. Humility is victory over every passion, a love of prayer, and the guardian of all other virtues.
Second, he teaches us how to recognize the presence of humility in our hearts. (Remember: his purpose in giving us these "signs of humility" is not to make us proud because they are there, but to make us humble because they are not!) Sign number one of humility is "the delighted readiness of the soul to accept indignity, to receive it with open arms, to welcome it as something that relieves and cauterizes diseases of the soul and grievous sins." Sign number two is "the wiping out of anger - - and modesty over the fact that it has subsided." Sign number three is "the honest distrust of one's own virtues, together with an unending desire to learn more."
Third, he teaches us how to cultivate the presence of humility in our hearts. Here St. John reminds us that there is not one way to humility. The heights of humility may be scaled from various vantage points: 1) We can develop humility by reminding ourselves often of our sins. Nothing keeps us from thinking that we are "holy" like the remembrance of what we have done and are doing wrong, 2) We can develop humility by reminding ourselves of how much grace we have received. If we cannot "handle" the constant remembrance of our sins or if this grace has not been given to us, then perhaps we can humble ourselves by the constant remembrance of God's mercy and grace. True gratitude leads to humility, 3) We can develop humility by reminding ourselves of how weak and vulnerable to sin we are. If we cannot continuously remind ourselves of our sin, and if we cannot remain continuously thankful, at least we should be able to remember at all times how easy it is for us to fall. We are not strong in and of ourselves; we are vulnerable, we cannot defend ourselves spiritually or physically. Let us be humbled. This is why the holy fathers say that physical labor, vigils, fasting, etc. are important aids to humility. They reveal the weakness of our flesh, so that we might put no trust in it. Recognition of our own mortality and frailty leads to humility.