Conveying ourselves as characters on the page is tricky business, like expecting a butterfly to pin its own wings. As James Hall explains in The Self-Portrait: A Cultural History, when Montaigne put pen to paper, he referenced those who had put brush to canvas, citing King René of Anjou: “I saw…King Francis II being presented with a self-portrait by King René as a souvenir of him. Why is it not equally permissible to portray yourself with your pen as he did with his brush?”

But a slimly pen-stroked “I” isn’t a portrait: We need to convey detail, texture, shadow. And in this, visual artists have much to teach us.

Look Me in the Eye

When American street photographer Vivian Maier’s work was discovered after her death, her self-portraits proved especially compelling. “…[A] self-portrait is a unique confession by an artist. It tells us both how they view themselves, as well as how they perceive the world around them,” wrote John Maloof in the foreword to Vivian Maier Self-Portraits. Maier’s portraits ranged from the head-on mirror shot to the outlined shadow to a combination of the two. In some shots, her shadow seemed almost a mistake or coincidence, as did her reflection, though the sly smile in one hints that perhaps the reflections and shadows are precisely the point of these images.

What does Maier show us? The details of her face, her haircut, her clothing and her photographic gear all come into focus in her most direct shots. But to me, more intriguing are those that “show” her more obliquely: the contents of the handbag next to her shadow, the blurred larger image with the distant in-focus one reflected near her heart, the angles from which she chooses to observe others and those she allows into the frame with her. How she looks is interesting; what she looks at is compelling.

Head-on: Photograph yourself in a mirror. Write a description of yourself as if you were describing someone unknown to you.

What catches your eye? Throughout a day or a weekend, snap images of where your gaze settles: the irritating scuff on the white-painted stair riser heading up to your bedroom; the dog’s wagging tale as its dream delights it; the way the water pools on the barbecue lid in the rain. Print out the images. What insights might a stranger discovering your collection draw from these photos?

I Didn’t Mean to Show You That—Did I?

Eggs in an Egg Crate was the first work Canadian painter Mary Pratt completed after miscarrying twins. Pratt later wrote that the image was inspired as she made a birthday cake, placing the spent shells back in the carton as she used them. But it wasn’t until the painting was finished and she shared it with a friend that she fully realized what she’d captured: “[S]he pointed out to me that the eggs were empty.”

Sometimes an artist is more direct in revealing her subconscious. Frida Kahlo’s painting What I Saw in the Water (also sometimes referred to as What the Water Gave Me) is, for Kahlo, uncharacteristically surreal: an image of memories from her life floating in the water, her feet poking above them at the tub’s top end.

What draws you? What do you collect? Treasure? Find difficult to let go of? Whether it’s your collection of Pez dispensers or the penny you keep in your pocket for good luck, choose an object that you are drawn to, and describe it deeply, closely. As you observe it, what do you see, feel, smell, taste, hear? Put the writing aside for a week. When you return to the description, what does what you’ve captured on the page reveal about you?

What haunts you? What memories repeat themselves for you? What dreams—or nightmares—return again and again? What song lyrics linger? What smells transport you? Find a place in your daily environment that allows you to stare into the distance or some not-quite-reflective surface—a deck chair overlooking the water, the subway window, or, like Kahlo, the bathtub. Describe the setting first. Then, call up your ghosts and describe them as they inhabit the air around you or the surface before you.

Is That You, Leonardo?

It’s said to be a Renaissance maxim: “Every painter paints himself.” There are those who would have us believe Mona Lisa’s smile hides Leonardo’s self-portrait, and many artists have inserted themselves into a painted scene, as Julia Fiore writes on Artsy: from Raphael peeking from behind an arch in his Vatican fresco, to Caravaggio as the decapitated Goliath, to Dutch artist Clara Peters cleverly hidden in the reflection of a goblet’s pewter lid. Caravaggio was a repeat offender: In The Taking of Christ, he appears at the frame’s edge, holding up a lantern, in what The Self-Portrait author James Hall categorizes as a “bystander self-portrait”—distinct from the “group self-portrait” where the artist appears as themself with “family, associates or even the Virgin Mary.” 

Who’s in your group? If you were to paint a group self-portrait of you at 17, who else would be in the frame? Describe them—both the real people and the influential figures who loomed large (your Virgin Marys). Now step back and describe yourself as each of them sees you. Try it at 27. 57. 77.

Wish I’d been there: What moment in history would you most like to have witnessed? Research the scene—and then place yourself in it, but at its fringes. Are you Caravaggio holding the lantern? The short-order cook at the Greensboro Sit-In? The kid behind the kid who caught a World Series home run baseball? Be as true to you as you can be: What do you see of yourself in this imagined scene that you might miss revealing in a more factual moment?

One Final Art Lesson

In Likeness: Fathers, Sons, A Portrait, author David Macfarlane spends months contemplating a portrait of himself painted by John Hartman. “I’m not sure how much the painting looks like me,” writes Macfarlane. “I can tell you that it feels like one of those candid shots that surprise you, not always pleasantly. It’s not at all how you picture yourself. But you sense somehow that a certain truth has been captured. …It looks like it has the same memories I do.”

I’ve used the exercises here to reveal my self to myself, then gone back to an essay I’m working on to weave in an insight here or a glimpse of my character there—and in doing so, tried to ensure there isn’t a blank spot on the canvas where I should be.

And that, perhaps, is what as memoirists, as essayists, we might strive for: not a perfect portrait of a flawless subject, but an image that captures a moment of truth, of who we were and what we’ve lived through.

Kim Pittaway is the executive director of the MFA in Creative Nonfiction program at the University of King’s College in Halifax, Nova Scotia, Canada. She is the co-author, with Toufah Jallow, of Toufah: The Woman Who Inspired an African #MeToo Movement, due out from Steerforth Press in October 2021. She is at work on a memoir with the working title Grudge: My Ten-Year Fight with Forgiveness. Her e-newsletter on writing craft, I Have Thoughts, is available at