Practicing the Art of Discernment

When we drop judgment in favor of curiosity, only then are we able to discern what we need to do next.

Close up from an oil painting I made

“It’s not working.” 

“I don’t know what I’m doing…” 

“I’ve messed it all up.” 

“I’m not happy with it!”

These are some of the things fellow students say repeatedly in my art classes, no matter the session or setting. These classes are comprised of adults, many in their later years, and several quite talented and serious painters. They don’t depend on art for their income. Many are retired. Yet sulking, striving, and self-deprecation often show up; group art sessions can often feel like therapy sessions.

I used to lament my inadequate artistic skills in the same way. After training as a coach, I have learned to bring a lens of curiosity, rather than judgment, to the lives of my clients. For example, when a client reports that they have not done what they said they would do between sessions or have not done it well, they’re not being a “bad” client. That judgment does not serve them. Instead, they present an opportunity to ask what got in the way of doing the assignment and/or explore how they could improve on it the next time.

This approach is kinder—and more effective—in fomenting change. Looking at things with curiosity is a bit like turning over a rock in the garden to see the bugs and worms squirming underneath but not judging them because they live under a rock.

Curiosity is also a handy lens to bring to painting. As in coaching, it creates a space for discernment.

“If judging is a process of labeling, discernment is a process of learning,” says Amy Whitaker in her insightful book, Art Thinking.

So, now I catch myself out, too. I stop saying things like “I’m unhappy with my painting” and instead become curious about why it’s not working. 

Now, what makes a painting “work” is a lifelong study, and entire tomes could be written on the subject. We won’t go into that other than to say that the instructor and artist can together determine how well a painting works without it having to be a judgment of the artist. 

As Whitaker notes, art students are asked to stand back from their work to see what is happening. You cannot discern with your face up in the canvas and a brush in your hand. Sometimes, I will take my painting to the hallway and stand 20 feet away from it. How does it look from this distance? Next, I will turn the canvas upside down to determine how form holds in space. And when you look at a painting in the mirror, a technique handed down by da Vinci himself, it miraculously becomes a different beast altogether. The parts of the painting that need attention almost seem to pop out, while those that work well seem to take on even more resonance. 

All these tactics engender a shift in perspective through distance or an unexpected reversal. They challenge any preconceived mental images we have of what the completed painting “should” look like and instead focus on what’s actually here and unfolding now. 

These tactics help to separate our creation from ourselves. Once we stop looking at some paint that we slapped on a canvas as a measure of our inherent worth as creative human beings, we are liberated to discern what needs improving. Working on this edge of our present ability, of struggling, reaching, and falling short, takes us into the sweet spot of “deliberate practice,” extolled by Daniel Coyle in his revelatory book, The Talent Code. 

The vase in this painting (see photo above) epitomized this struggle because I just couldn’t get it to work with the rest of the painting, neither the shape nor capturing its curvature. It also did not sit and hold its place, as da Vinci’s mirror technique revealed. I returned to it at each session, never quite satisfied, trying not to blame the vase for being of a somewhat odd shape and color, to begin with, nor myself for being unable to render it as perceived. In the third and last session, it finally came together.

Making mistakes is inherent in this process. If anything, the painting usually gets worse before it gets better. When I first started oil painting, I was much more attached to the outcome. Under the cryptic Zen-like guidance of one of my instructors, I learned to let go. 

Invariably, in class, at some point, someone would knock a painting off an easel by accident, and everyone would gasp with horror. I learned to laugh when this happened to my paintings and joked that the now-smeared canvas looked better!

Gradually, as I became more detached from the imagined masterwork I would create, I found the process itself to be the primary source of enrichment. 

This metaphor of creating a painting can be applied to our own lives. Navigating our lives with discernment (via curiosity) rather than judgment allows space for deliberate practice to begin.

We have deemed ourselves inherently worthy and can now focus on the challenges of getting better at our craft or whatever else it is we turn our attention to.

We will know that it is at the edge of our ability, where we need to stretch—and struggle—a bit. We will grow and astonish ourselves and others if we do this consistently. We are essentially nurturing the crucial skill-building myelin sheaths of new neural pathways rather than merely traversing the old, worn ones that lead to judgment and dead ends. 

All of my fellow artists are committed to creating better art. Many are painting several times a week, and we’re often in a collective flow state in which the three-hour session evaporates in what seems like minutes. But when we switch to judgment, we’re headed down a slippery slope where our self-worth becomes entangled with the work we are creating.

At any stage in the process of art and life, we can pause and take a step back. We can disentangle, turn things upside down, and take a good, hard look in the mirror. We can drop judgment in favor of curiosity. Only then can we learn what needs to be learned and discern what we need to do next.