A Brief Theology of Painting Over
Over the years, my painting methods have changed.
Early on, I worked with great precision. I relied on careful underdrawings, plotted measurements, and a clearly mapped plan, using the drawing almost like a blueprint to be filled in with paint.
There is nothing wrong with this approach. In fact, it’s ideal for illustration and commissioned work, where clarity, efficiency, and predictability matter. You solve the design problems upfront, ensuring the final image closely matches what was proposed to the client.
But in my fine art practice, I’ve gradually moved in a different direction.
Today, I often work more intuitively, drawing with the brush and moving paint directly from palette to canvas. Instead of following a fixed map, I adjust, revise, and respond as the painting unfolds. This approach can feel less controlled and more vulnerable to error, but as your skill develops, your eye becomes sharper and your decisions more accurate.
Still, if many of my paintings were placed under an X-ray, they would reveal layers of revision beneath the surface: shifted proportions, repainted passages, altered compositions, sometimes even an entirely different painting buried underneath.
And I'm not alone.
Technologies like infrared reflectography now allow us to see these hidden layers in historic works as well. They reveal hesitation and discovery, the life of a painting beneath its surface. Rembrandt’s Flora shows changes to the brim of a hat. Picasso’s The Old Guitarist famously contains the ghost-like image of another figure behind the guitarist’s head. Such traces even help authenticate the original, since copyists tend to imitate only the final layer.
Often, these earlier forms re-emerge naturally as the paint becomes transparent with age. In other cases, the artist intentionally allows them to remain visible. Degas allowed earlier lines to remain to suggest motion and the passage of time. Others permit underpaintings to faintly emerge to create veiled presences that add complexity, memory, and depth to the finished work.
Whether accidental or intentional, these visible remnants have a name.
Pentimento.
Repentance
The word pentimento comes from the Italian pentirsi: meaning “to repent.”
For many of us, repentance conjures an image of someone on a street corner wearing a sandwich-board sign, megaphone in hand, shouting about the apocalypse while pedestrians politely avoid making eye contact. Given how often the word has been weaponized in religious contexts, it’s understandable that we cringe when we hear it. Shame has too frequently been mistaken for transformation.
Yet, the Greek translation for "repentance" is often the word metanoia. Which means "to change one's mind" or "to go beyond the mind one currently has." It points less toward self-condemnation and more toward a transformation of perception.
Somewhere along the way, many of us inherited the idea that repentance means turning away from a certain behavior (which it may sometimes require) but metanoia is not primarily about guilt, punishment, or seeking moral perfection. It is about seeing differently. A reorientation of consciousness. A widening of awareness that allows us to encounter reality in a new way.
Many artists understand this process intuitively.
Every painting begins with a way of seeing. And as the work unfolds, that seeing changes. We notice relationships we missed. We recognize assumptions that no longer serve the painting. We revise not because we have failed, but because we have discovered something truer.
Pentimento is what metanoia looks like when it leaves a visible trace.
From the vantage point of the artist, repentance takes on a very different meaning.
In the studio, repentance is not condemnation. It is the humility to revise, to admit that what once seemed right now needs adjustment so the painting can move closer to its own truth. It is not the institutionalizing of shame, but the discipline of attention.
The earlier version of the painting was not wrong.
It was partial.
It represented the best seeing available at the time. Repentance, in this sense, is not scraping everything away and starting over. It is staying long enough for something deeper to emerge. What came before is not rejected, it is transcended and included. Sometimes we even allow those buried layers to shine faintly through our outer veneer.
Pentimento teaches us that growth does not come from discarding earlier stages, but from letting them become transparent in the light of greater coherence. What once insisted now yields. The painting becomes more honest precisely because it remembers where it has been.
Pentimento is not only the record of a painting in progress.
It is the record of an artist changing their mind.
The Risk of Painting Over
I once worked with a client who had abandoned a painting for years.
It was an unfinished portrait floating against a blank background, face partially formed, the space around her unresolved. Before we touched the canvas, I asked about its history. What was happening in her life when she began the piece? Why had she stopped midway?
Her story was honest. And as she spoke, it became clear that the painting was carrying more than pigment. The figure had become a kind of vessel, an image through which something unresolved in her life needed expression. Perhaps finishing the painting might even become part of the healing.
Our time together was brief, and I was careful not to overreach. I am not a therapist. I didn’t want to pathologize her or project my own conclusions onto her work. I wanted her to arrive at her own insight.
Still, I sensed hesitation when we discussed painting over what already existed.
So I named the fear before it took control.
I told her, When we start working again, you may feel a resistance to changing something you already like, even if you know the painting isn’t finished yet. Then I asked, Is there anything in the painting you’re afraid to let go of?
She paused.
“I just want her,” she said, referring to the figure she had begun years earlier. “If I paint over her, I'm afraid I'll lose her.”
“You won't lose her,” I replied. “She’ll always be here. But we may need to transform her into what she’s supposed to become.”
She nodded. “Okay. I’m ready for that.”
The struggle to paint over earlier marks is real. Sometimes it feels safer to leave a portrait incomplete than to risk losing the version we know. Subconsciously, it can feel safer to leave something unfinished than risk seeing its true potential revealed. Even pain can feel preferable when it explains where we are and gives us a familiar story to remain inside.
Painting over takes courage.
It requires us to change our mind, to paint over the past instead of remaining suspended within it. This can feel vulnerable or even like betrayal, but pentimento reminds us that nothing is truly lost.
What we paint over remains, absorbed into the structure beneath the surface, shaping what comes next. The earlier image does not vanish. It is transfigured.
What looks like death may contain another layer of light, already breaking through.
For You, the Artist
Do not repent for the sake of some eternal someday.
Repent because your seeing has widened.
Because the horizon has grown larger than the map you started with.
Revise not because the first version failed, but because you no longer see from the same place. The hand changes because the eye has changed. The composition shifts because the artist has shifted.
Do not condemn the earlier layers. Let them remain. Let them authenticate the work. A forgery imitates only the surface; an original bears the history of its making.
So stay with the canvas.
Risk the next stroke.
Allow your beliefs to make room for what is emerging.
Trust that what is deepest in you cannot be destroyed by change.
Sometimes the greatest act of courage, in both art and life, is not wiping away what came before,
but painting over.
Sometimes what keeps us stuck isn't a lack of ability. We simply need another set of eyes to help us see what the next layer could become.
That’s part of why I created The Painted Path Studio. One-on-one mentoring for artists who want to strengthen their work, develop their voice, and find the courage to revise when the painting asks for something more.
You don’t have to erase what came before. Sometimes you just need help seeing where to place the next stroke.
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