Lessons from the Messy Middle

May 8, 2023

Whenever I start a new painting, I begin with anticipation and hope. I suspect that is true for anyone who creates. Yet as the work progresses, things get a bit more difficult. Hope and anticipation give way to frustration and chaos…the messy middle! 

When I contemplate this phase of work, I recall the term ‘Creative Battles’ from Steven Pressfield’s influential book, The Art of War.  I stare at the canvas, deep in struggle, filled with  doubt, sometimes angry, usually frustrated.

The painting is complex and muddled, the cacophony of the words and works of painters from whom I gain perspective offers little or no seeming direction. 

I can land in self-doubt – is the painting a puzzle that will go unsolved? Am I a fraud? To be honest, I have to paint, but I don’t always love to paint. It’s a passion and a compulsion. Creating is in my bones, I am not myself if I am not creating. 

Picture this: I have heaped loads of outlines, layers, colors and shapes onto the canvas. It’s not a painting, it’s a data dump of information. Many of the choices I make to add a color or shape, and outline or a layer seem very random. 

I’m responding to a simple thought, ‘this is a blank space, fill it with something.’ “This color doesn’t sing loudly enough, cover it up.” It seems at times as if I am heaping things on rather than making intentional creative decisions. Yet the goal is to create as much information as I can. And there is a lot to be said for the unconscious running the show. Choices are never fully random. 

The pitfall lies in having to create order out of the intentionally created chaos. As I stare at the canvas, I can feel adrift for days and sometimes, weeks.  If you’ve ever tried to get out of a corn maze at night, you’ll have a sense of the experience of the messy middle. 

Here’s an example of a problem I had to solve in this painting.The two circled areas were disruptive, they didn’t belong to any of their surrounding groupings. They stood out and distracted from the overall flow of the painting. 

Bit by bit, I begin to edit; to make choices. This is where the conversation with the painting takes on new importance and meaning. I ask the questions, What do you want? What do you need? And then, I watch and listen. 

I take comfort in the awareness that I am making choices to shape and consolidate the work. Sometimes I’ll add a color, a shape, a line that appears to be the wrong choice. Often, I leave it and return the next day, it now has a meaningful presence, it makes sense. It’s also possible that in a few days, it’ll be covered over by something else completely! This is the heart of the messy middle, and it’s not for the faint of heart!

The problem in this painting resolved through the addition of layers, colors  and transparencies to integrate the isolated areas and create a unified structure and flow. 

Sometimes I take a painting too far. I cross the finish line, and then…keep going. It’s incredibly frustrating! I then end up breaking the painting back open, returning to late stage messy middle, to find a new path to completion. 

True confession: I love complexities… I love things that contain possibilities. I love things that shift perspective as I look more deeply. Yet sometimes, I’ll step up to the canvas, having seen from a distance a change or addition to make, and by the time I arrive, the aspect to address is no longer a concern. I literally can’t find it! Did I imagine it? It’s the messy middle! 

It is this dance with chaos that ultimately will define what this work wants to be. Because it is a dialogue, the work has a voice and a will of its own. Together, the painting and I bring it to clarity, like a figure emerging from a block of stone.

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