On Penances and their Use
Dr. Lewis Patsavos
Professor Emeritus of Canon Law at Holy Cross Greek Orthodox School of Theology
[T]he pastoral nature evident in the canons of the Fathers is... easily discernible in the canons of the synods. It is because of this characteristic that the canons have been referred to as “fruits of the Spirit,” whose purpose is to assist mankind in its quest for salvation. Certainly such a lofty purpose can only be appreciated when the canons are understood as pastoral guidelines and not as legislative texts. Viewed simply as legislative texts, the canons differ little from laws to be upheld rigidly and absolutely. Recognized, however, as the pastoral guidelines which in fact they are, the canons serve the purpose for which they were intended with compassion and flexibility. It is this latter understanding of the canons which makes comprehensible the exercise of “economy” as practiced in the Orthodox Church today.
Penances have a therapeutic, not a legalistic, character and are imposed in accordance with certain principles which stem from the holy canons.
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Elder Paisios the Athonite
—Geronda, does the precise observance of the commandments help us feel God near us?
—Which commandments? Those of the Mosaic Law?
—No, those of the Gospel.
—The observance of the commandments does help, but it must be a correct and proper observance, for it is actually possible to observe the commandments wrongly. Spiritual life requires divine righteousness, not a dry observance of the law. We see the discernment with which the Holy Fathers guided people even in the application of the Sacred Canons! Saint Basil the Great, the strictest Father of the Church who has written the most demanding canons, refers to a canon that applies to a particular sin, but then he himself adds, Do not examine the time but the manner of repentance. 
In other words, if two people commit the same sin, the Spiritual Father may impose on one man the penance not to receive Holy Communion for two years, while on the other he may impose only two months. There can be that much of a difference!
—Does penance help one to cast out a passion?
—One must understand that penance is meant to help someone. Otherwise, what can one say? If you attempt to correct someone by physical punishment, you will accomplish nothing. If you try to correct someone by force, Christ will turn to you on Judgment Day and say, “Were you a Diocletian?” To the punished one He will say, “What you achieved, you did so because you were forced to.” We don’t strangle someone in order to ensure Paradise for him; we try to help him seek some fruitful ascetic discipline for himself. He must come to the point of being joyful because he is living, and joyful because he is dying.
Penances are left up to the discernment of the Spiritual Father. The Spiritual Father must be uncompromisingly strict with him who sins callously. The one who is overcome by sin but who repents, becomes humble, and modestly asks for forgiveness, will be helped with discernment by his Spiritual Father to approach God again. This is what many of the Saints did. Saint Arsenios the Cappadocian as a Spiritual Father did not usually give the people penances. He tried to bring them to an awareness so that they themselves, out of philotimo, would choose to do some ascetic discipline or act of charity or other goodness. Whenever he observed a little child who was possessed or paralyzed and understood that the parents were the cause for the child’s suffering, he would first heal the child and then impose a discipline on the parents to make them careful in the future.
Some people say, “Oh, this particular Spiritual Father is very patristic. He is very strict! He is smart, has a good memory, and knows the Pedalion  by heart.” A Spiritual Father who applies precisely the rules contained in the Pedalion, however, may harm the Church. Does it do any good when the Spiritual Father takes the Pedalion and begins: “What sin have you committed? This one. What is written here about it? This many years abstention from Holy Communion for you! And what have you done? This. What is written here? This rule applies here!”
—So, Geronda, one must take into account dozens of things.
—Yes, especially in today’s society, one cannot just go and apply the entire canonical tradition of the Church with blind, indiscreet austerity; he should cultivate a sense of philotimo in people. In order to be able to help other souls, the Spiritual Father must first do considerable work on himself; otherwise, he will go around breaking heads.
The Pedalion is called the Rudder because it guides man toward salvation, sometimes in one way and other times in another way, as the captain of the ship turns the rudder to the left or to the right in order to bring the ship to shore. If he were to navigate the ship in a straight line without turning when needed, he would bring it upon the rocks, sink it and everyone on board would drown. If the Spiritual Father uses the Canons of the Church as if they were... loose military cannons—and not with discernment, in accordance with each person’s needs and the repentance demonstrated—then instead of healing souls, he’ll be committing a crime.
2. See Saint Basil the Great, Letter 217, par. 84, PG 32, 808B: “For we do not always judge such things by means of time, but observe rather the manner of the repentance.” (By “time” Saint Basil means the imposed duration of penance.)
3. A collection of the Canons of the Orthodox Church, containing the Sacred Canons of the Oecumenical Councils, the Apostolic Canons, as well as the Canons of the Holy Fathers of the Church, with a brief interpretation. It was compiled in 1793 by Agapios the Priestmonk and Saint Nicodemos of the Holy Mountain.
From Spiritual Struggle, by Elder Paisios of Mount Athos (Souroti, Thessaloniki, Greece: Holy Monastery of St. John the Theologian, 2010), pp. 307-309.
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Elder Porphyrios of Athens
To begin with, when I first started to hear confessions, I used to really “scald” those who came to make confession. I used to have at my side Saint Nikodemos’s Confessor’s Guide (Exomologitarion) when someone would come for confession. If he confessed a serious sin then I would look up the book and would see that it wrote: “Not to receive Holy Communion for eighteen years.” I didn’t know; I was inexperienced. And so I imposed the corresponding penance. Whatever the book said was law. But then the people would come back the following year—they would come from various places, from various villages, from far and near—and when I asked them, “How long is it since you made confession?’ they would answer, “I confessed to you this time last year.” Then I would ask, “And what did I tell you?” They would reply, “You told me to do a hundred prostrations every night.”
“And did you do them?”
“Well, you told me that I couldn’t receive Communion for eighteen years so I thought to myself, Since I’m damned anyway, I might as well forget about the whole thing.”
You understand? Then another person would come and say the same thing. So I thought, “What do I do now?” It was then I began to become a little wiser. The confessor has the power to bind and to loose. I remembered one of Saint Basil’s Rules, and I took that as my basic guideline and changed my tactics in confession. The Rule says: “He who receives the power to bind and to loose, when he sees the great remorse of one of the sinners, let him reduce the time of the penance. Don’t let him judge the penances in terms of time, but in terms of disposition.”
And so I started to encourage the people to read the poetic canons written in honor of the saints, to read short prayers, to make prostrations and to read Holy Scripture. And in that way they began to pay attention to the things of our religion. Their hearts were softened and without any external prompting they desired to observe the fasts, to enter the spiritual arena and to come to know Christ. And one thing I have understood is that when someone comes to know Christ and love Him and is loved by Christ, everything thereafter proceeds well in holiness and joy and everything is easy.
From Wounded by Love: The Life and the Wisdom of Elder Porphyrios, pp. 43-44. Edited from an archive of notes and recordings by the Sisters of the Holy Convent of Chrysopigi. Translated by John Raffan (2005, Denise Harvey (publisher), Limni, Evia, Greece).