Once, when we were on the way to Orthodoxy, the leaders of our community were taking a retreat at a Benedictine monastery. One of the monks casually asked me what I was looking for: what did I (a Protestant) hope to find at a Roman Catholic Benedictine monastery. At the time I had read the Rule of St. Benedict several times and one word particularly bothered me. It was a word for which I could find no definition. I said to the monk, "I want to know what humility is. I have no idea what that word means."
The monk did not respond and did not ask me any more questions. Over the years since then, I still ask myself that question: What is humility? What does it mean to be humble? In the Rule of St. Benedict, humility is very important. Humility is the ladder by which one climbs to the knowledge of God. According to St. Dorotheos of Gaza, "In as much as [a believer] is always making progress in virtue, he is always growing in humility. The more humble he is, the more help he gets [from God], and so he advances through this virtue of humility." So we see here too, that humility is a kind of foundation, it is the virtue through which all other virtues are attained.
[By the way, "virtue" is just the traditional Christian word used to refer to Christ-like qualities. So to grow in virtue is to become more like Christ in specific ways: gentleness, peace, self-control, etc.]
Harry Boosalis in his book, The Orthodox Spiritual Life according to Saint Silouan the Athonite, offers this definition of humility based on his understanding of the teachings of the Orthodox Church Fathers: "Humility could be defined as an honest and contrite recognition of one's own shortcomings and weaknesses together with a focus on the mercy of God." I find two aspects of this definition quite helpful.
First, is the word contrite. Contrition is a difficult feeling to find and nurture in a world in which anything goes and the strong finish first. A humble person does not merely acknowledge her weaknesses (any moderately successful person does that). A humble person is heartsick over them. So long as we nurture in ourselves the thought that we could change if we really wanted to, we could have done differently if we had really tried, and our mistakes are our mistakes (the mistakes we chose) and we could have done differently if we had wanted to and had tried harder--so long as this is our thought, we may feel guilt, we may feel remorse, but we will not yet feel or be contrite.
A contrite heart, I think, comes from a knowledge of brokenness. Yes I am sad. Yes I am also guilty. But what breaks my heart is that even when I try really hard, I still fail miserably. This brings contrition, and it is dangerous. The experience of such contrition can be hellish, or even the beginning of hell because it brings one to the door of despair. But there is also another door here: the door of humility.
And now the second particularly helpful aspect of Professor Boosalis' definition: "with a focus on the mercy of God."
Contrition leads to despair when one forgets the mercy of God. Humility continually looks for the mercy of God. The humble person continually calls out to God for mercy because she is contrite, she knows her many weaknesses and she knows that only God can help her.
And here, with despair never far behind her (yet nonetheless behind her) and the mercy of God ever before her, the child of God experiences mercy, an feeling that many have called a "bright sadness." Joy and brokenness; hope and an honest recognition of weaknesses, all weaknesses, mine, yours, the world's. God's greatness and love and mercy incarnate in our messy, brutal reality. Jesus crucified, and we crucified with him. Jesus resurrected, and we resurrected with him. At the same time. All at once.
This my friends, is normal Christian life, at least as far as I can tell. This is the process of transformation from glory to glory.