Get better at drawing people, starting with the one you see most.

Drawing yourself, for yourself.

A guest post written by the one-and-only

Jason Chatfield

of

New York Cartoons

!

---

There's something deliciously voyeuristic about drawing people who don't know they're being drawn. I've spent the better part of two decades doing exactly that, and I've coined a term for it: Eavesdrawing. It's the bastard child of eavesdropping and sketching, and it's one of my favourite creative exercises.

A few years back, the New Yorker sent its cartoonists out into the city with a simple mission: lurk in popular spots, draw the locals, and write down whatever fascinating snippets of conversation floated our way. No context, no explanations – just raw, unfiltered New York dialogue paired with sketches of unsuspecting subjects. These people never knew they were being drawn, though some might have stumbled across their likenesses later in print. (If you're reading this and suspect you might have been one of my subjects, I apologise for nothing.)

---

RELATED:

Spilling Ink at the Hotel Chelsea

---

However, my experience with live drawing goes far beyond covert sketching operations. For the past 21 years, I've made a living drawing people live at events – everything from quick caricatures to detailed portraits, reportage, and, yes, even dogs. There's something uniquely challenging about capturing someone's essence while they're right there in front of you, fidgeting, chatting, or trying their best to hold perfectly still (which, ironically, often makes for a worse drawing).

Drawing from life versus photos is like the difference between fresh pasta and cup noodles. Sure, they're both pasta, but one has a vitality that the other just can't match. When you're drawing someone live, you're not just capturing their features – you're recording their energy, their movements, their little unconscious habits and micro-expressions. It's terrifying and exhilarating in equal measure, but still, something that can’t be captured from a photo or a video still. (If you want to dive deeper into the mechanics of sketching people in public, Beth has an excellent guide here.)

Of course, there's always that moment of truth when you show someone their portrait.

I've learned that people's reactions say more about their self-image than your drawing skills. Some people beam with delight at seeing themselves through another's eyes, while others... well, let's just say I've developed a pretty thick skin over the years.

As prolific caricaturist and illustrator, Tom Richmond shared in a recent substack post about drawing people:

There are times when you read your subjects wrong, and they are unhappy with your drawing. Unless you go the innocuous, generic route with everyone, this will sometimes happen. It’s the price you pay for trying to stay true to doing real caricature. You have to let those go and move on to the next one.

Here's the thing: if you want to get better at drawing people without the pressure of potential confrontation, start with yourself.

I have a New Year's Day tradition of doing a self-portrait, and I always choose a different tool or style based on my mood. Some years, it's loose and expressive with ink splashes everywhere; other years, it's tight and controlled with precise pencil lines. Looking back at these portraits, I'm amazed at how often they seem to capture the essence of what that year would bring.

The mirror is your most honest critic and your most patient model. It won't complain about its nose looking too big or demand a refund. Be bold with your choices – try that weird pen you've been avoiding, and experiment with a style that scares you.

The goal isn't to make a masterpiece; it's to understand how you see things and how you translate that vision onto paper.

The best part? You don’t have to show anybody. Ever. You can even throw it in the trash. Or burn it. You do you.

Drawing Exercise #2: The Dreaded Self-Portrait

I want to thank Beth Spencer for inviting me to share these thoughts on The Introvert's Drawing Club. There's something perfectly fitting about introverts being drawn to the quiet observation of others, isn't there? Now, if you'll excuse me, I think I spot someone interesting across the bar who needs to be eavesdrawn...

---

*@Jason Chatfield is a New York-based cartoonist, illustrator, and professional people-watcher. You can find more of his musings on the creative process at Process Junkie.*

Preorder Jason’s book, You’re Not a Real Dog Owner Until…!"

---