I saw my mom for the first time this summer. Sitting alone in the busy Toronto Pearson Airport, I waited for my flight to Edmonton to join my family on a trip. I was armed with a couple of pencil crayons, a sharpener, and an Above Ground sketchbook bought from their tiny store next to OCAD University. 

I had been working at a children’s art camp where I spent my breaks outside sketching strangers from my Pinterest boards or friends from university. The kids would clamour around, ask me questions about the people I was drawing, and then enthusiastically confirm that my 15-minute scribbles did, in fact, look like their reference photos. Sometimes, perhaps unnecessarily, they would be brutally honest and tell me that I was way off. 

It’s hardest to draw people you know personally; when you know someone’s face so casually from seeing them every day, you take the minute details of their facial features for granted. However, you also know what makes these people who they are, so when they don’t fully resemble themselves, you can tell. Perhaps you drew a friend’s face perfectly, but it still wouldn’t be right unless you managed to capture their boundless whimsy you could only know from years shared together and a particular glint in their eyes. 

So, when I was stuck waiting in the airport, I felt like I was seeing my mom properly for the first time in this rough sketch of the woman who raised me. It was still imperfect, because the reference photo I used was a couple of years old—her smile lines and the creases in her eyes were softer than what greets me nowadays—but these are things I would only know from loving her.

I find that drawing people you’re close with makes you confront how much you actually don’t know about their faces. My mom’s face is one I’ve seen my entire life, but as I was drawing her, I forgot which side her mole is on. I realized I did not know that the right corner of her mouth tilts down at the very end. I do know, however, how loving her smile is, and how we have the same nose.

My favourite thing to draw has always been faces. I love drawing a portrait, starting with the same proportions and guidelines I learned from an Instagram tutorial when I was 11, then moving on to the eyes, nose, and mouth. Faces of people I know, faces of people online, faces of movie characters, and characters I made up. Landscapes and still-lifes bore me—I wish to understand people.

And, as much as I enjoy drawing portraits, others are even more delighted to have their portraits drawn. They like being seen, being recognized, and being known to others. Not only seeing themselves in a picture, but also knowing that someone took great care to translate their face into a piece of art. 

 The guidelines don’t change: A circle split by a horizontal line to indicate where each facial feature goes, and a vertical one for symmetry. You have to be careful, though, because if you mess up the roundness of their cheeks or the angle of their nose, the face distorts into a new stranger. It’s the same process each time, but I always get to learn something new. What does it look like when a person with monolids furrows their brow, or when an old man laughs? 

When the Sports section of The Tribune writes a “Know Your Athlete” piece, I sign up to do the illustration. Should you search through issues, you will find I have done several portraits for various sections. Some are scientists, rugby players, television characters, or filmmakers. 

It is an intimate and quiet waltz between my subject and me. Who has loved this face, I wonder? What features are they proud of? Which would they change if they could? These are strangers I will never meet, people who will never know someone spent hours staring at their faces, searching for their most recognizable features to ensure that they are represented as accurately as possible. Yet I know how their eyes crease at the corners, I gather how shy they may be to smile in front of a camera, and I see the way they style their makeup for a professional headshot. Maybe I even fall in love with them, my dance partner, while my pen etches lines and shadows. Though don’t tell them, of course.

I still struggle to draw myself. My eyes always turn out too wide or my nose too small, and please don’t get me started on the shape of my jaw. But I’ll keep trying; whether it’s the narcissistic impulse of a 20-year-old, or an effort to know myself as well as these strangers whose portraits fill my sketchbooks’ pages. Each time, I am a little more faithful to my image, slowly improving until the day I will recognize the face as my own. I wish to see myself as I saw my mother on the pages of my sketchbook, with her sweet but stern look etched in turquoise and dark blue pencil crayons.

My mom, Penny Lee 

– August 2025