What Drawing Thousands of Strangers Has Taught Me

When I first started offering live illustration at events, I thought the biggest challenge would be learning how to draw faster. And while that definitely became part of it, I’ve realised over the years that the job has taught me so much more than illustration.

I’ve now drawn thousands of people at luxury brand events, conferences, private dinners and celebrations. When you’re sitting across from people all day, sketchbook in hand, you end up noticing a few things. The first is that people rarely see themselves the way others see them. It’s something I witness almost every event.

A guest will sit down for their portrait, often saying they’re not photogenic or don’t know how to pose. Then they’ll come back later to collect their illustration and immediately point out something they love about it. Maybe it’s the dress they spent weeks choosing. Maybe it’s their smile. Maybe it’s a detail about themselves they hadn’t noticed before. I always find that moment interesting.

Another thing I’ve learned is that people value things differently when they see the process.

In a world where almost everything is instant, there’s something special about watching something being made in front of you. Guests often stop by multiple times to check on the progress of their illustration. They bring their friends over. They ask questions. They become invested in the outcome because they’ve witnessed the journey. The finished artwork matters, of course. But I think the experience of watching it come to life matters just as much.

I’ve also learned that some of the best opportunities come from unexpected conversations.

Many of the projects I’ve worked on over the years weren’t the result of pitching or networking events. They came from chatting with someone while drawing. A guest introduces me to a friend. A brand representative sees the activation in person. Someone keeps the artwork and remembers it months later. I’ve realised that showing up consistently and doing good work often opens doors in ways you can’t predict.

And perhaps my favourite lesson is this:

People don’t remember every detail of an event. But they do remember how they felt.

Years later, guests might not remember the presentation, the menu, the speeches or the run sheet. But they’ll remember receiving something personalised. They’ll remember feeling celebrated. They’ll remember a moment that was created just for them. That’s what makes live art so special to me.

Yes, I’m creating illustrations. But more than that, I’m helping create memories. And for a job that started because I simply loved drawing, that’s something I never expected.

Recent illustrations created during an event for Dior | Artwork by Cai (Soy Street)