Finding Confidence Through The Practice of Daily Cartoons

Written by Steph Halligan of Art To Self


When I told my friends that I was starting a daily cartoon newsletter - that every single day I was going to write, draw and send out an inspirational cartoon email - they thought it was crazy.

In retrospect, it was crazy. And that’s exactly what I needed.

I needed something crazy to reignite a fire that had died in me a long time ago. I needed something crazy to hold me accountable to share my passion with the world. I needed something crazy to make up for the decade of my life that I’d stopped cartooning.

I’d grown up with a singular career in mind: to become a professional cartoonist. To follow in the great Chuck Jones and the brilliant Bill Waterson and their respective creations, Bugs Bunny and Calvin and Hobbes. But like the dreams of many artists, my early childhood dreams began to wither away as I grew older. As I headed off to college, I pursued more reasonable (i.e. money-making) career options. And as I settled into adult life after graduation, my once-fiery passion faded into a hobby which faded into nothingness. Ten years without drawing a single new cartoon.

Sure, adulthood got in the way. Time certainly played a factor in my commitment to my craft. But more than anything, I had lost confidence. And as I grew older, the more I believed that no one wanted to see my work. Not even myself.

Still, there was something in me that wanted creativity in my life. I looked around at my cartooning idols - like Chuck Jones - and even the folks drawing online - like The Oatmeal - and craved what they had. At the same time, I thought that it was impossible. That I could never get to that caliber and that I could never produce that consistently. The truth was, I couldn’t get to that caliber because I had no consistency. And I had no consistency because I didn’t believe my work was at a caliber worth sharing. It was a vicious cycle.

Which is why I needed something crazy. And which is why I came up with Art to Self.


I needed something to hold me accountable for not only practicing my art, but practicing it consistently. I needed something that would boost my confidence and hone my skills. I needed something that would let me experiment and grow while putting it out into the world. And I knew the only way I would get there was by showing up each and every day.

So I started drawing. Each day, I drew a cartoon, wrote a note, posted it online and emailed it to my list. Every day: lather, rinse, repeat. Soon I had 100, 200, 300 cartoons under my belt. Soon I had hundreds and then thousands of readers following my work. And little by little, as I practiced sharing my work with world and my skills grew, my confidence grew.

Now almost 450 daily cartoon notes later, I finally have the confidence to declare myself an honest-to-goodness cartoonist. A professional one. Like the kind I always wanted to be when I grew up.

Those small steps - that consistent practice - is what brought me here. And when I look back to those first cartoons, I realize just how far that consistency has taken me.

The other day, I was doodling “Cartoon Steph” (whom I draw a lot on Art to Self) and something about the scene I was sketching felt very familiar. Her posture, her stance… I felt like I’d drawn this before. So I started skimming through my past notes to find a similar doodle. That’s when I stumbled upon one of my first cartoons, a drawing of “Cartoon Steph” in a very similar position. But that’s where the similarities stopped, because this sketch looked so remarkably different from the one I drew today. And when I compared them side-by-side, I was stunned by the difference:

To me, the difference between these two cartoons is night and day: the quality, the energy, the personality. And the two years of practice and 450+ cartoons are baked into the lines, the detail and the nuance of my new drawing.

My cartooning is alive in a way that it wasn’t just a few years ago. But even though the second drawing is technically better, I’m actually a lot prouder of the first drawing.

That first drawing was the start of my practice. A daily practice that I stuck to longer than anything I’ve ever done before. Even though that first drawing wasn’t perfect, I put it out there. And even though I had minimal confidence in myself, I started anyways.

Those early cartoons did not feel comfortable. In the beginning, I second-guessed nearly every doodle that I put out into the world. Only practice made it easier. Only time boosted my morale and my ability. Time helped me develop a rhythm: a stroke of my pen, a pattern to my themes and a flow to my work. With that practiced rhythm, my mind quieted. With that quieted my, my creativity could flow without fear.

I knew that if I drew a cartoon every day, my drawing skills would naturally improve. And I knew as my skills grew, my confidence would naturally grow with them. But I had to start before I was entirely confident. I had to start before I had the skills locked down. And that meant starting where my skills were then - not where are today.

Like my idol Chuck Jones says: “You have a million bad drawings in you. You better get started.”

Thank goodness I did.