2026.10.29

Lessons from a late start in drawing

JAY

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1. Learning to Trust Myself

When I was ten years old, an art teacher told me that I had no talent for art, after I had attended her drawing class for just a month.

I had started those classes with so much excitement, so you can imagine how disappointed I was. Her words stayed with me for much longer than I expected, shaping how I saw myself.

“I’m not good at drawing.”

And yet, my interest in art and design never really went away. For years, I found myself drawn to them, finding ways to stay close without actually creating art myself.

When I went backpacking through Europe, I somehow ended up planning much of my trip around art museums. Even in my career, I was happiest when I had opportunities to work with designers and illustrators.

Every few years, I would get the urge to draw again. I’d pick up a pencil, make a few attempts, decide that I really didn’t have any talent after all (though I managed to participate in a couple of exhibitions along the way).

After years of coming back to drawing and walking away from it, I finally started learning to draw seriously in my forties.

My first lines were terrible. I felt as though I was only confirming what the teacher had told me all those years ago.

But after a few years of drawing without giving up, I began to realize that what had held me back for so long wasn’t just her words. It was how I had taken them in and allowed myself to see my abilities through her eyes.

I believe that other people’s evaluations can be important. They can inspire us to take a step forward, help us recognize something we might have overlooked, or show us how our work is received by others.

But I also came to realize that what mattered most was how I felt about my own work.

Was I satisfied with what I had created? Had I done the best I could at that particular moment? Did it mean something to me?

No matter how much others liked my creation, a drawing never really felt finished until I could look at it myself and feel satisfied with what I had done.

Through drawing, I’ve learned to ask myself these questions first, rather than worrying so much about how others might judge my work.

2. Finding Wonder in the Ordinary

Once I started drawing, nothing I saw around me seemed quite as mundane or ordinary anymore.

The shapes of things, their colors, the way light reflected off their surfaces, and how movement changed their appearance – everything became something I wanted to observe more closely.

I found myself looking at things with intense curiosity, wondering how I might capture them in a drawing or recreate a particular color.

So much so that I sometimes feel a little embarrassed thinking about my thirties, when I spent so much time with my face buried in my smartphone.

I also began to notice how every season had its own colors and certain scenes that could only be found at particular times of the year. Even along streets I’d walked countless times without a second thought, I started discovering things I’d never noticed before.

The more I drew, the more I noticed. And the more I noticed, the more there seemed to be to enjoy in everyday life.

Even when my days seemed to repeat themselves like clockwork, I began to realize how much around me was constantly changing with time, and how nothing was ever quite the same.

Perhaps it wasn’t the world that was ordinary after all, but the way I had been looking at it.

And perhaps even the most ordinary things could become extraordinary, simply by learning to see them differently.

3. Finding Freedom in the Messy Middle

In trying to express exactly what I envision, experimenting with new materials or digital brushes has become almost second nature to me.

I’ve stopped spending so much time wondering whether I’ll be able to do something well. Instead, my curiosity takes over my fear. Whenever I come across something that intrigues me, I want to give it a try, and I often find myself reaching for it before I even know it.

Of course, things rarely go well from the beginning.

Unfamiliar materials feel awkward in my hands, the lines are shaky, and the results often look nothing like what I had imagined. But after going through this experience again and again, I’ve grown used to the idea that this is simply part of the process.

I’ve started to recognize what I call the ‘almost too ugly to look at’ stage.

It’s not just the middle of a single drawing, but also the middle of learning something new, when I’m still figuring out how to use a particular material or draw a particular subject.

At that stage, everything can look messy and disappointing. But I’ve learned that when I keep going and finish the drawing, the result often turns out better than I feared it would.

And after repeating this process enough times, I’ve come to trust that even when I’m not happy with the result, my next attempt will probably be better. That realizaiton has made it easier to begin something new.

And even when a drawing turns out terribly, I’ve learned a thing or two along the way – a new trick, a better way of handling the material, or something that helps me bridge the gap between what I imagined and what I can actually create with my hands.

With every attempt, that gap becomes a little smaller, and eventually, the effort begins to pay off. Gradually, I’ve stopped seeing awkward beginnings and failed attempts as something to be afraid of.

Not being good at something no longer feels like a problem. And when I try something and fail, I find myself thinking, ‘Well, that happens.’

In an age filled with AI generated content and images, many might wonder ‘why anyone would spend so much time learning to draw’ when images can be created in seconds.

So why do I still choose to spend hours drawing by hand?

By teaching my second brain (my hands) to draw, I’ve developed a habit of looking more closely at myself and paying greater attention to my inner world. Along the way, I’ve also become much freer from the things that used to hold me back.

I think that’s why I’ll keep drawing for as long as I can.