Case Study: How Inktober Helped Shape My Creative Journey

It’s Fall—October, to be exact—one of the busiest and most exciting months for art challenges. I personally love art challenges because they help me create consistently. Through these challenges, I’ve learned a lot—whether it was identifying areas where I needed more practice, or discovering what I truly enjoy (and don’t enjoy) in my art.

The first drawing challenge I participated in was Inktober. I believe it was 2017 when I gave it a try for the first time, but it wasn’t until 2018 that I really dove in, focusing on pushing my skills, especially in portraiture.

As I began thinking about what type of portraits to draw next, I had an idea: why not revisit my old art? I could update or completely reimagine some of my past sketches. To my surprise, I found a treasure trove of portraits scattered across various sketchbooks, at different stages and skill levels. I realized I had plenty of material to work with and rework.

For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer.
— Ira Glass

Looking back, I can see the ideas I had back then, but I also recognize the frustrations and doubts that came with finishing each piece.

Roasted Portrait Illustration

Roasted 2024

So, I decided to start by revisiting three illustrations from my participation in Inktober. 2017 was my first attempt, and while I had a bit of a love/hate relationship with the challenge, I participated again in 2018 and 2019 (though a little less so). Ultimately, I learned that daily 30-day challenges are too much for me. Now, I prefer shorter commitments, like two-week challenges or prompts that allow for multiple days of work. But I have to give Inktober its due credit—it helped me build consistency, deepened my love for portraiture, and pushed me past my fear of drawing people “perfectly.”

You could say this is a case study of sorts. I took three ink illustrations from Inktober 2018—each depicting female portraits—and recreated them as digital illustrations in my current 2024 style. I fixed proportions, added extra details like patterns, and enjoyed the process immensely. Not only was it a trip down memory lane (six years ago!), but it also reinforced the fundamentals: proportions, balance, and composition—things I’m still refining today.

I plan to revisit more of my older work and share those updates, too. As I mentioned in Treasure Found: An Art Journey, Chapter 3: “Practice, Practice, Practice”—reimagining your work can be an integral part of your creative process. And for October 2024, it’s definitely a part of mine.


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