Rethinking Repentance

It’s been a long hiatus, about four months, and in that time my daughter Caitlin married a wonderful young man, John, whom we love very much, and I have recovered from all the wedding stress and holiday busyness.

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And here we are, past mid-January. This is the traditional time for people to give up on their new year’s resolutions, in a sort of collective domino effect, where the act of surrender cascades through early February. At that point, resolutions are not so much broken as completely forgotten.

I raise my coffee mug to those of you who, like me, try to avoid new year’s resolutions for precisely this reason. And if your resolution was to cut back on caffeine, I apologize.

Resolution is the noun form of “to resolve,” which basically means to decide on a course of action. At this time of year especially, a resolution is more than a decision to do something, as in, “We determined to resolve this dispute.” Instead, a new year’s resolution is an expression of an intention to make a change in our lives, because we understand that change is needed. Whether we are able to sustain that change is a different question.

My hubby Rob pointed out to me that this annual urge for change and improvement is really a secular form of repentance. “Repent” is not a word that is used in polite conversation anymore, because it contains a lot of religious baggage. If you have any doubts about that, next time someone is complaining about an aggressive coworker, try saying, “Well, he just needs to repent,” and see what happens. It’s a real conversation stopper.

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But why does repentance have such negative connotations? A large part of the answer, of course, relates to said religious baggage. Many of us carry what is often described as “religious trauma” from legalistic, judgmental church backgrounds and perhaps from hypocritical and even abusive leadership. I’ve also noticed over the years how frequently I encounter ex-Catholics who talk about all the guilt they grew up with.

Yet when the holy Fathers of the Orthodox Church talk about repentance, it’s in such a positive, life-giving way. Even when they talk about tears of repentance, the deep sorrow over one’s sinfulness is experienced in the context of the tender mercy of God.

I am grateful that I didn’t grow up in a church context where God was viewed as a harsh judge ready to yell “Gotcha!” every time I failed. Throughout my heterodox Christian past I knew repentance was an important part of spiritual life that removed the blockages between God and us, which means it’s a good thing. But I wasn’t exactly excited about it. I would characterize my understanding of repentance as an “eat-your-spinach” view. It was good for me, but not the part of the banquet of Christian life that I really looked forward to.

So when I was learning about Orthodox Christianity, I was a bit taken aback when an acquaintance, a recent convert, told me, “I love confession.” I thought, “Whaaaaaat?” He went on to describe how freeing it was, and how close to God he felt afterward. At the time I was still struggling with the theological concept of confessing to a priest, and his sister, a good friend of mine, affirmed what he said. She said something like, “I want to shout to my Protestant friends, ‘You don’t know what you’re missing!’” Both converts spoke of repentance and confession in terms of freedom and healing and restoration of relationship with God, not as a grit-your-teeth necessity.

Right now we’re not going to explore the Sacrament of Confession. For a deeper dive into that topic, you can read the Walking an Ancient Path posts “Cautious about Confession” and “What a Priest Really Thinks about His People during Confession.” Instead, right now we’ll look at the larger topic of repentance itself. Of course, Orthodox Christians can’t really separate the two—true repentance also involves partaking regularly in the Sacrament of Confession with a priest for forgiveness and renewal. But we need to acknowledge our need for repentance before we schedule that appointment with the priest.

What do the Fathers have to say about repentance, and why do we sometimes—or often—try to avoid the topic?

Before we delve into these questions, it’s important to define our terms. What is repentance?

What Is Repentance?

[Photo from the Greek Orthodox Archdiocese website,]

In the New Testament, the word translated “repentance” is the Greek word μετάνοια (metanoia)—pronounced “meh-TAHN-yuh”—and it means a change of mind accompanied by regret and changed behavior. So, repentance is a change of mind and heart, a turning away from sin and back toward God. Of course the best illustration—and the greatest icon—of repentance is Jesus’ Parable of the Prodigal Son, where the son literally turns away from his old way of life and goes back to his father’s house.

One of my favorite modern elders, Elder Thaddeus of Vitovnica, Serbia, who died in 2003, writes, 

What is repentance? Repentance is a change of one’s way of life; it is discarding the old man and all of his evil habits and turning toward God, toward the Truth. Repentance means becoming quiet, peaceful, humble, and meek. (Our Thoughts Determine Our Lives: The Life and Teachings of Elder Thaddeus of Vitovnica, p.166)

I highly recommend this book. In fact, I need to re-read it soon.

On the surface, repentance sounds simple, doesn’t it? We admit our failings, turn to God, and allow Him to transform us. And when we’re serious about repentance and spiritual growth, we schedule confessions with our spiritual father regularly.

But, it’s not always that simple, psychologically and emotionally. We want to grow and experience theosis, to be united to God. And our negative thoughts get in the way.

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What images come to your mind when you hear the word “repentance”? I’ll tell you mine: A report card in school. Going to the principal’s office. Meeting with the fifth-grade teacher because she intercepted a really nasty note that you passed to a friend. (Not that this ever happened to me.)

What comes to my mind are tools of measurement: A ruler. A scale. A balance. A frowning judge peering down at me with a scowl on his face and a gavel in his hand. With each measurement, I come up short. And punishment awaits.

Sheesh. No wonder many of us like to talk about repentance in an intellectual, theological way: It’s very distancing and thus safe. We keep repentance at arm’s length and don’t run towards it.

But are these negative images valid?

For those of us living in the West, even if we’re cradle Orthodox, we are surrounded by a very juridical view of God. The message in the various forms of Christianity all around us is that we have done wrong, we have offended God’s honor, and we need to confess this to the heavenly Judge so that we can be restored to His good graces. In Roman Catholic circles, this includes penance as part of that restoration, which is viewed as punishment for our sins.

But this is not the way of Eastern Christianity. The saints and elders throughout the centuries understood that repentance is medicine for healing. It’s a radically different paradigm from the negative images that linger in my mind.

But don’t take my word for it. Instead, read the words of a dearly loved fourth-century bishop and author of our most-used Divine Liturgy, St. John Chrysostom. He wrote, “Sin is a wound… Repentance is a medicine.” And medicine is all about healing, not punishment.

Even if we understand this, or think we do, we also tend to think, Repentance is depressing. I already feel bad about myself, and I’ll just feel worse if I catalog all my sins.

Man, do we have baggage. All of us. Including me. So let’s look at some of the reasons for our negativity. What follows is not a comprehensive list, but I think it covers most of our struggles. I will be including a lot of the saints’ words about repentance because I have no authority. I’m just a gal in the pews. But these saints have authority in the Church because of their grace-filled lives in Christ, and they offer life-giving words for us while we’re walking this ancient path together. 

As we consider what they have to say, notice the spiritual unity across the ages. From the second century through the twenty-first, these holy saints and elders proclaim the same unchanging Faith, the same unchanging truths about God. No other Christian tradition compares.

Reasons behind Our Negative Attitudes toward Repentance

1. Discouragement over recurring sin

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I do the same things over and over. I’m embarrassed in confession that I sound like a broken record. (Side note: For our younger readers, a record is a disk made of vinyl with lots of grooves in it. A record player drags a needle along these grooves, and music comes out. On a record player we can play the same sad tune over and over, just like our lives when we fall into the same sins, over and over.)

So, if I repent of something I’ve already repented of, and this happens again and again, is my repentance even real? 

In the early 19th century St. Herman of Alaska offered these words of assurance for sinners like me:

A true Christian is made by faith and love toward Christ. Our sins do not in the least hinder our Christianity, according to the word of the Savior Himself. He deigned to say: not the righteous have I come to call, but sinners to salvation; there is more joy in heaven over one who repents than over ninety righteous ones.

Saint Paisios of Mt. Athos, who died in 1994, agreed:

The person that is struggling to the best of his abilities, who has no desire to live a disorderly life, but who—in the course of the struggle for faith and life—falls and rises again and again, God will never abandon. And if he has the slightest will not to grieve God, he will go to Paradise with his shoes on. The Benevolent God will, surprisingly, push him into Paradise. God will ensure that he takes him at his best, in repentance. He may have to struggle all his life, but God will not abandon him; He will take him at the best possible time.

I find it difficult to understand this unconditional love of God, and I need these reminders.

Also, if we’re honest with ourselves, often there is a specific reason underneath our discouragement and embarrassment: pride. In his wonderful little book Way of the Ascetics, author Tito Colliander notes, “If you are remorseful because later on you fell anyway, and if you are full of self-reproach and resolutions ‘never to do so again,’ it is a sure sign that you are on the wrong road: it is your self-reliance that has been wounded” (p. 53). 

Ouch. So. Let’s talk about . . .

2. Pride

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The societal pressure to appear that we have everything together in our lives is strong. And certain religious backgrounds can discourage taking a good, hard look at ourselves.

During the years when I floated through the charismatic movement—this would have been the early 2000s (or maybe, the “aughts”?)—I attended a few prayer conferences featuring nationally known speakers. They were men and women of deep faith in Christ, and the thing I loved most about these conferences was the racial diversity and harmony. I remember looking around during the worship time and seeing fellow believers who were African American, Latino, Asian, and White, and I thought, “This is what heaven looks like.”

But the worship music made me uncomfortable. Not because of the pop radio style—I was used to that. Or because of a crowd of people singing in tongues, with ad hoc harmonizing, although that felt really awkward.

What bothered me most about the music was its triumphalistic and spiritually militant lyrics, focused on spiritual battle, claiming the victory that Christ had won, and banishing Satan. The lyrics contained kernels of truth, but quiet reverence was missing. Searching our hearts for sin was missing. Repentance was missing. And any connection to historic Christianity was long gone.

If I’m constantly singing about victory in Jesus, how can I admit that my life is a mess, that my family is falling apart, and that I’m struggling with an addiction? Those who grew up Orthodox have been mercifully spared this type of emotional excess and unmoored theology, but some parishes are all about tradition and routine, and there is strong pressure, once again, to have your bleep together. How can we admit our needs in these environments?

Even when covered with spiritual jargon, this refusal to deal with our sins and failings is a type of pride. 

Archbishop Averky, the abbot of Holy Trinity Monastery in Jordanville, New York, who died in 1976, advised:

“Repent”—that is, lay aside your pride, acknowledge yourself as a sinner, and hasten to God not with a feeling of self-satisfied superiority, but with the feeling of your spiritual poverty, your nothingness, your indecency, and pray to God for the forgiveness of your sins and for mercy. (From The Struggle for Virtue: Asceticism in a Modern Secular Society, p.5)

Sometimes we’re just too proud to admit our spiritual poverty. Other times, we’re too ashamed to admit our sins to anyone. Which leads to the next problem:

3. Believing that God is a harsh judge.

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Occasionally I see an important reminder on a bumper sticker or a sweatshirt: “Be kind, for everyone you meet is fighting a hard battle.” Some of the battles we fight are secret, and they are sources of great shame. We feel so defeated that it’s hard to admit these sins to ourselves, much less bring them to God. 

Often we keep these things to ourselves because we believe, deep down, that God cannot or will not forgive us. We see Him as the Judge, not the Great Physician. Evidently St. John Chrysostom saw this struggle in the flock he shepherded so many centuries ago. He advised them, “Did you commit sin? Enter the Church, repent for your sin, for here is the physician, not the judge. Here one is not investigated; one receives remission of sins.”

We forget that the mighty King David, the author of so many psalms, was an adulterer and a murderer. We forget that Moses murdered an Egyptian, and St. Paul presided over the stonings of early Christians. Saint Mary of Egypt was a prostitute. Yet all of them repented, turning away from their sins and turning to God, and the Church recognizes them as saints.

Abbot Nikon Vorobiev, who reposed in 1963, wrote,

Many desperate robbers and murderers not only received forgiveness following their sincere repentance and change for the better, they even achieved sanctity: Moses the Black, Barbarus the former robber (May 6), Daniel and others. The Lord gives us these examples in order that we not fall into despair like Judas, but repent and thereby receive salvation. (Abbot Nikon: Letters to Spiritual Children, p.108)

Elder Ephraim of Arizona, who reposed a few years ago, reminds us of some good news:

How easily God forgives! The only thing that must occur is to open the door of your souls to Him. God does not wait for any reward for that which He gives to men. And even if your sins are millions or billions, for God this is counted as nothing. What is the worth of a small amount of sand to the ocean? All the sins of the world are like a virus to the ocean. There is no sin which conquers the mercy of God. Thus, the sins of man are zero. When the child returns to the bosom of the Lord, all things cease before His mercy.

The type of shame and guilt that keeps us from turning to God is different than sorrow over our sins that drives us to Him. It is a demonic burden that weighs us down rather motivating us to imitate the prodigal son and turn around and make our way back to God. If this is your struggle, I encourage you to talk to your priest about it. You will need his prayers and counsel.

But the great spiritual tragedy of our age is, I think, the opposite of the struggle with guilt and with the wrong belief that God will not receive us when we turn to Him. It is far more common for people to think that we’re all okay, and God’s forgiveness is to be expected.

4. Believing our sins really aren’t that bad.

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This is the Cosmic Santa Claus view of God, and this Santa would never put coal in anybody’s stocking. Well, maybe Hitler’s, but not mine.

This minimizing of sin is common in Western societies. If we use the word “sin” at all, it is a label for really bad deeds, like murder—unless the murderer had an abusive childhood. Speaking for Americans, as a society we really don’t think in terms of sin anymore. We think in terms of psychology, and, like Adam in the Garden, we do a lot of blame-shifting. Sure, I’m angry, but it’s my parents’ fault. I lie because people back me into a corner. I cheat on my taxes because the government is corrupt. And if we’re theists of some sort, we believe that God is loving, which is true, and that he is merciful, which is also true. But the seriousness of sin is not acknowledged.

This attitude is a pendulum swing to the opposite side of God as a harsh Judge. It’s a modern view, but it is not new. Read what St. John of Kronstadt had to say about 19th-century attitudes:

Let us fear hardened insensibility to our sins; let us fear the pride of our hearts, which says: ‘I do not need any forgiveness of sins; I am not guilty, I am not sinful’; or else: ‘My sins are trifling, they are only human ones’—as though it were necessary that they should be diabolical; or: ‘I do not feel amiss living in my sins.’ This is the pride of Satan, and it is Satan himself speaking these words in our hearts.” (My Life in Christ, p.352)

I don’t feel a need to belabor this point. If you’re reading this blog, you’re probably living as a Christian in the world, not in a monastery. You are well aware that the world values self-actualization and self-expression as ideals, whatever that means to the individual. “You do you.” Sin is not acknowledged around the water cooler, and in many cases, it is celebrated. We are surrounded by indifference to sin, by the pursuit of pleasure, acquisitiveness, and careerism.

The ancient Church, in contrast, does not encourage us either to minimize sin or to beat ourselves up. Her teachings are marked by a steadfast consistency and balance. 

The Balance of the Church

Is sin serious, or is God merciful?  The Orthodox Church responds, “Yes.” Sin is serious, with eternal consequences, and God will judge us. And our God is full of compassion and mercy for sinners who return to Him. 

Both/and. Not either/or.

Saint Silouan the Athonite, who lived in the 19th and 20th centuries, expressed this balance well: “We should think this way: I am a great sinner, but the Lord is merciful. He loves people very much, and He will forgive my sins.” 

We proclaim this truth during every Divine Liturgy when we pray the pre-communion prayers. Translations vary, but the message remains the same. We recite together, 

How shall I, who am unworthy, enter into the splendor of Your saints? If I should dare to enter into the bridal chamber, my vesture will condemn me, since it is not a wedding garment; and being bound up, I shall be cast out by the angels. Cleanse, O Lord, the filth of my soul, and save me, as You are the one who loves mankind. In Your love, Lord, cleanse my soul, and save me.

“In Your love.” “You are the One who loves mankind.” In one breath we admit “the filth of my soul” and the need for cleansing—no sugarcoating reality here—and also recognize God’s steadfast love for us. This too is reality.

[Photo by Jack Sharp on Unsplash]

Elder Thaddeus of Vitovnica expands on this idea:

The Lord hears our prayers when we pray from the heart, even though we are great sinners. The Lord is always looking into our hearts, and if we turn to Him from the heart, He will be there. He will hear our prayers even though we are very sinful, but He also expects us to repent while there is still time. (From Our Thoughts Determine Our Lives, p.161)

These words are a tonic for those of us who grew up with lots of guilt, and a corrective for those of us who grew up in an churches that stressed positivity and emotional experience and didn’t really talk about sin very much. With either extreme, repentance becomes a duty rather than an opportunity for spiritual growth and maturity.

Repentance in the Context of Hope

Saint Nektarios of Aegina, who lived in the 19th and 20th centuries, gave this advice:

Do not despair if you keep falling into your old sins. Many of them are strong because they have received the force of habit. Only with the passage of time and with fervor will they be conquered. Do not let anything deprive you of hope.

The saints with one voice talk about repentance—even tears of repentance—as an opportunity for growth, healing, and drawing close to God. Saint Isaac the Syrian defined repentance as “the gateway to mercy which is open for all who seek it,” a way of entry “into the divine mercy.” An unnamed Desert Father, probably in the third or fourth century, said, “To repent is to look not downward at my own shortcomings, but upward at God’s love; not backward with self-reproach but forward with truthfulness. It is to see not what I have failed to be, but what by the grace of God I can become.”

[Photo by Faris Mohammed on Unsplash]

This is such a positive view, bathed in hope. There’s a different quality to this attitude than the one I grew up with. Of course, I didn’t have the Sacrament of Confession; I was encouraged to confess my sins only to God, and also to anyone I had wronged. I also remember a popular method of spontaneous prayer called ACTS: adoration, confession, thanksgiving, and supplication. It’s a good model for prayer, and I am thankful that personal confession of sins was presented in mostly a positive light, knowing that God would hear and receive us.

But there is a quality of the saints’ mindset and attitude that is new to me. Even among those who were miracle-workers and known as saints while they were still alive, the closer they drew to God, the more they considered themselves to be the greatest of sinners. This was not false humility; they looked at themselves with a clear-eyed honesty and saw failure, selfishness, and sinfulness. Yet this self-understanding did not lead to despair. They expressed great hope, great trust, great confidence in God’s love. They saw, as that anonymous Desert Father so beautifully expressed, “not what I have failed to be, but what by the grace of God I can become.”

To me, it’s a mystical paradox. Throughout history the saints have resided in this position of hope, of rest in God’s love within a life of continual repentance. This really resonates with me. I want to live like that. I’m not there yet, but by God’s grace, I hope that I too am traveling in that direction.

Saint Porphyrios stated,

I, too, think that I am sinful and that I am not living as I should. Nevertheless, I make whatever distresses me into prayer. I do not shut it up inside myself. I go to my spiritual father and confess it and it is finished and done with. Don’t let’s go back and recriminate and say what we didn’t do. What is important is what we will do now, from this moment onwards—as St Paul says, forgetting the things that are behind and stretching forth to the things that are before us (Phil. 3: 14).

A Different Kind of Resolution

Let’s resolve together to live a life of repentance, acknowledging both our sins and God’s great love and mercy. This is a resolution that is not dependent on the time of year; let’s not give repentance a try in January then give it up by February.

And, I encourage you to talk to your priest about your struggles with repentance and confession, whether it’s a negative religious background, shame, fear, pride, or any of the other things that are blocking your way back to God. We are living in a spiritual war zone, and Satan wins a great victory when he can keep us away from repentance and confession.

As St. John Chrysostom wrote so long ago, “Pay attention carefully. After the sin comes the shame; courage follows repentance. Did you pay attention to what I said? Satan upsets the order; he gives the courage to sin and the shame to repentance.” 

I will end with the words of St. Porphyrios, an Athonite heiromonk who reposed in 1991 and was known for his spiritual discernment:

We need to feel Christ as our friend. He is our friend. He confirms this Himself when He says: “You are my friends . . .” (John 15:14). We need to look at Him and approach Him as a friend. Do we fall? Do we sin? We should run to Him with feelings of familiarity, in love and trust; not in fear of punishment but in courage granted by the sense of friendship. And say to Him: “Lord, I did it; I fell; forgive me.” 


It’s good to be back after such a long break. I’m still deciding what to write about next time—I have about five different ideas in my head—but I hope you can join me.


  1. Congratulations and Welcome back! I missed your Posts while you were gone.
    I know I will reread this one over and over again. Thank you 🙏

  2. I think this also applies to parents and guardians as to making those under our care not to fear but to trust us! We want them to come to us, not be turned away by discomfort !

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