Two things have become a common practice for me. One: after a break from art making, I get back into the practice with some quick portrait sketches. Two: when I’m stumped for ideas, I turn the brush on myself and paint a self-portrait. Back in January, after a string of trips, I followed this pattern. I painted a series of head sketches. One of them was me – live model with a fresh hair cut, why not?

In a more serious attempt, I envisioned a flatter and more stylized approach. I picked warm tones close to my skin color for the background – partly for harmony, partly to pop against my blue hoodie. I used abstract shapes to balance the realistic face. To lean into the flat design, I outlined everything with a Sharpie first, and then filled in the colors, letting some of the black lines show through. The collage-like result is a step up from the sketch. I wanted the face to stay more stylized and almost blend into the fragmented background, but the more I worked on it the more it slid back into a standard realistic portrait. Eventually, I just stopped.

That got me thinking: Is aesthetic the only thing I could work on? What else could I do to make the painting a bit more meaningful? I recalled a self-portrait I did years ago in a class. The teacher told us to paint ourselves in a different role. I went with a witch – surrounded by classic witchy themes with my own spin: a frog brewing potions and a black cat reading the Malleus Maleficarum (often considered the first major anti-witchcraft document). While the painting was crude in execution, but dreaming it up and piecing it together was a blast.

So why not give it some character? Pick a costume I’d never wear in real life (I’m a muted-hoodie kind of person), or visualize some thoughts I usually keep under wraps? I went for a bolder color and more dynamic palette. I still wanted the face to feel like part of the design, but this time, I let it be drowned by the unsettling shapes, vibrant colors and swirling energy. I kept the ideas of black outlines but used the paint instead of Sharpie this time, allowing more varied and expressive marks. That hint of punk—is it just wild imagination, or a quiet piece of me sneaking out?

In retrospect, neither of my paintings addressed the likeness or posture issues that bothered me in the first place. In the process of further creation, they became irrelevant. Painting’s at its best when it’s a journey—when it’s messy, exploratory, and forces you to reckon with yourself.