A Pair of Annual Portraits

At least once a year, I draw these two people

“My drawings are compositions of recall. Remembering is a montage. To remember is an act of imagination, usually spontaneous and once the drawings are started they take a life of their own.” — Lee Baxter Davis

(My drawings are not acts of recall. But I do think that who we are and what we remember and what we think and feel in the moment bleeds into our drawings. Every drawing thus becomes something new and born of then and now. — Amy)

I’ve looked through photos this week, rummaged in boxes and bins, located hundreds of old journal files on my computer, and thought back to a very early sketchbook, a sketchbook I remember as an embodiment of creative want, a catalyst for the art that I’ve been tracking and practicing ever since.

I never filled that sketchbook. I think I was intimidated by it. But it was still a beginning. It was mystical and mythical and slightly medieval with its gold-fabric cover. It led me to mapping, and now excavating, my creative life in the margins.

We are never too old to start again, to pick up a thread whose music we hear and follow it, hand over hand until the destination and the journey blur and we are creating, not following, the path.

When I started drawing portraits a few years ago, it was in a humble composition book. There is often the greatest freedom in the simplest choices.

When in doubt, I always suggest a composition book as a place to start. I rather miss the spirit of that.

Thank you for reading.

Amy

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Year After Year

One of the things that I do each year, and I wish I had done this all along, is draw portraits of people I care about on their birthdays. I haven’t drawn every single person, but I have drawn my kids for the last several years.

People often look at my illustrated journals and are surprised by the fact that I include lots of portraits of people I don’t know. It may seem like an odd choice to include so many people that I have no connection with as part of my journal. People sometimes expect the contents of a journal, of a project rooted in the documentation of daily life, to have limited and clearly-defined contours based on the realities of an individual life.

I can argue against this and justify my approach in many ways, but the simple fact is that I love to draw portraits.

So I draw portraits.

Every week, I add portraits to my pages.

I weave my notes on life, quotes, book covers, TV shows, recipes, broken memories, loneliness, family, the state of the world, and mood tracking, around portraits.

I sometimes use the portraits I draw as a mouthpiece for something that I am thinking about or want to say for the week. Sometimes what is being said, what I am thinking as I ink the lines of the face, the shadows under the eyes, the rhythmic fall of hair, doesn’t make it onto the page in a concrete way, a string of words, but there is something about the attitude or the mood or the expression that resonates for me in the moment. Sometimes the connection is much more obvious and overt, words appearing in a thought balloon or a dialogue box.

Sometimes I stare at a portrait throughout the week (because I work on weekly spreads) trying to decide what I think it is trying to say.

They almost always look like they have something to say.

This is part of their appeal, the way they stare up at me from the page.

I draw lots of portraits of people I don’t know. They have nothing to do with my story, and yet they are part of a thread that runs throughout my journals.

But every February, I draw my kids. Drawing People

I started talking about art and creative life in 2006, but it wasn’t until late 2016 that I started drawing portraits. I had drawn selfies here and there, but, other than an early desire to draw my kids, I had never really been interested in drawing people… until suddenly I was.

It was a passion I didn’t predict, but it hasn’t waned.¹

The early portraits are crazy to look at. They have an odd but overarching angularity that always makes me think of science fiction, of characters from some dystopian world. There is something cyborgian about them.

I don't show those photos often, but when I stumble over them in my files (or go looking for them), I am always sort of delighted by them.²

I respond to their wonkiness, to their angles, to their hard edges. There is something in those early portraits that speaks to me, and I'm so glad I continued. I'll never be a really good portrait artist. But I can reasonably draw a picture of someone from a photo. You'll at least know it's a human in the end.

Drawing people we know can be harder because there is more pressure to draw someone that doesn’t simply look like a human, but looks like the person you know.

Little Boys

I always say that what brought me to drawing, as an adult, was my desire to draw and paint my boys. I did a terrible job at it for a really long time. I was determined to paint a little boy in a fishing hat and a vest, a toddler body that was equally legs and torso, reaching into the flower beds or the sandbox in the backyard. I was obsessed with trying to draw and paint the same little boy walking along the edge of a swimming pool in Maine in a hat and a little white terry coverup that hung to his knees, photos that always made me think of Holly Hobbie or the vintage silhouette of Sunbonnet Sue.

I know there are pages of bad and misshapen drawings from more than twenty years ago. Kids are hard. I still have trouble drawing kids.

I wish I had stuck with it when they were little, pushed through and accepted my learning curve, but it was many years later that I started drawing portraits.

Visual History

It sometimes takes some doing to get a photo, but I try to draw the boys during the week of their birthdays.

I started keeping my illustrated journal in the format I use now in 2019 as part of a yearlong Fifty Before Fifty project. Illustrate Your Week grew out of that year. The following boy portraits appear in weekly spreads over the last six years. (The earliest pair shown here are just a few months before I started the illustrated journal.)

Journal and illustrated journal pages with portraits of my sons during birthday weeks between 2019 and 2024. Viewed this way, these drawings capture the passage of time. ©️ A. Cowen

This Year

I still don’t have a stove, and Valentine’s Day didn’t even really cross my mind though I did vaguely wonder if I should buy the boys a token bag of candy or send a gift card. I guess in the past I would have. I would also have made brownies, their favorite, to mark the birthdays.

Those things didn’t happen, but I did draw their pictures. This doesn’t matter to them, but it does to me.

These pages aren’t done. I might end up filling in around the portraits. (The rest of my week is on the two pages before these.) I might turn the wonky ovals into frames of a sort. That is how I was thinking of those containers, but one portrait spilled outside the borders. I could do any number of things, but the core drawings are there.

This is a record of now.

A. Cowen 2025

These are just quick portraits. I draw while I watch TV at night after work. I didn’t spend hours and hours. I didn’t sit at a table or in a studio. The drawings are simple, a bit wonky, but there is something really nice and mindful about stopping and looking at a current photo of each kid, penciling in the lines, and then using the sketch as a map for inking.

Drawing people that matter to us personalizes drawing in a way that is really important, especially in an illustrated journal. I might be satisfied if I draw a really nice version of the salt and pepper shakers in the kitchen. I might be pleased if I draw the portrait that I picked for the weekly drawing group or a bird. But there is something extra special and meaningful when you draw someone you love, whether that is a friend or a family member.

This doesn’t mean that it’s not valid or meaningful to draw your keys, your chair, the house on the corner, or the jean jacket in the donation box. Those things might also be sentimental. Last week I drew a child’s doll. This week I drew a toy car, something random from the shelves that has survived the years.

It was satisfying, but not quite the same as drawing the boys.

Who might you draw? Snap a photo or find an old photo and add someone to your pages.

Weekly Bits and Pieces

• Prompts for Illustrate Your Week - Week 8 (2025)

Related (or timely) posts:

• Draw the People You Love

• 11 Steps to Choose a 100 Day Project

• Stone Lanterns and 100 Day Projects

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Made It?

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1. My focus on portraits fits in with my overall simplification of life in many ways because I know what I most enjoy drawing. I am not “restless” in my creativity. There are things I someday want to do, but right now, the journal offers infinite space and flexibility. I still branch out and explore, but I feel like I know what makes me me on the page. Portraits have a lot to do with that.

2. We often have a tendency to be embarrassed by our early art. We try to distance ourselves from our starting point, but we all start somewhere. We start with an inkling, an urge, a desire, and sometimes it grows in spite of its wonky or crooked roots. There are even earlier portraits that do make me cringe. A watercolor of the boys hangs on my mom’s wall, and I can’t stand to see it. But when I look back to 2016, I see the thread that became woven into my story and into my creative habit. I see my naïveté when I look at the early portraits, but I have a fondness for them. I am forever grateful that I embraced their wonkiness and continued drawing. I am grateful to have had a friend at the time who encouraged me, too.