I’m undertaking a 1000-day reinvention project, blogging here daily to track my progress. In Thursday Thinker, I share a smart idea or theory.
Existentialist psychotherapist Rollo May explored creativity as a deeply human, courageous act of self-actualization in his book The Courage to Create (1975). In it, he proposes that to create is to risk. In creating you must confront the unknown rather than clinging to the familiar. You must express something original that may be rejected. You must push through anxietiy as you resist conformity. To May, creativity is a willful engagement with life’s uncertainties.
I’ve been experiencing this as I complete the Christmas gifts I hand-crafted this year. I painted portraits of the pets in my family: five dogs and four cats. Because I’m not that great at drawing, I traced photos and then used painterly brushstrokes with color schemes selected for excitement and interest rather than using strictly naturalistic, representational schemes. I photographed the paintings and ordered notecards. I’m also framing each original with a thrifted frame and will be gifting them to the respective owners.
It feels a little scary to do this. I ask myself, “Who am I to suggest that my artwork should hang on someone’s walls, even my sisters’ or my parents’?” I listed myself as artist on the back of the notecards and, after submitting the print order, began to feel self-conscious about having done that. I’m working through the anxiety. I’m claiming authorship.
May describes creativity as emerging from a tension between what is and what could be. He views the creative act as a confrontation with the void, the anxiety of non-being. Creation, he suggests, is an act of affirmation in the face of that threat. The creative must embrace periods of incubation and emptiness. She must sit with and work through anxiety and ambiguity. And she must trust the unconscious.
May proposes that the creative deeply engages with her medium (the canvas, the idea, the material world) in the encounter. In this encounter, she is fully present and absorbed. There is a dialogue between the medium and the artist — the medium pushes back. Through this dialectical tension, authentic insight can emerge.

I found that in my pet portrait encounters the more I left natural colors and pure representation behind, the more energy I tapped into with the art. I discovered I could capture the essence of a pet even without capturing the exact way a pet looks.
My favorite is “Premium Melon,” capturing my daughter’s cat Kesha. She sometimes sits in a box from Costco labeled Premium Melon. I chose the color scheme of green and pink based on a suggestion from ChatGPT, not realizing it would make her look like a watermeon-cat hybrid.
The creative life is one way of finding meaning in a seemingly meaningless world. May writes:
Creative people, as I see them, are distinguished by the fact that they can live with anxiety, even though a high price may be paid in terms of insecurity, sensitivity, and defenselessness for the gift of the “divine madness,” to borrow the term used by the classical Greeks. They do not run away from non-being, but by encountering and wrestling with it, force it to produce being. They knock on silence for an answering music; they pursue meaninglessness until they can force it to mean.
With art, you go from the void of non-being to the realm of meaning, and the way you do it is by choosing courage rather than conformity, and suffering through anxiety as you encounter possibilities and limitations.
Am I seeing my pet portrait project as more ambitious and more important than it is? Am I really going from the void of non-being to the realm of meaning? Maybe so: I find it a useful antidote to the typical consumerist Christmas spirit. I chose to reject mass production. I instead committed to hand-creation, imperfection, second-hand goods (the frames, the paper I used which was gifted to me by my hair stylist — she found it at a yard sale). I refused to let the anxiety and self-consciousness of making my own objects stop me.
I have more work to do before Christmas to fully realize my anti-consumerist, anti-representational, pro-pet project. I have many frames from Goodwill in various states of disassembly waiting for use with just the right painting. I’m awaiting the printed notecards, worried at whether they’ll look amateurish (if they do — isn’t that all the better for promoting the meaning I’m after?) I am still working on other paintings, not pet paintings, not representational, intended as gifts.
It’s an artist’s Christmas, and I couldn’t be happier.