October's Opportunity
It makes sense that October would be the month that sneaks up on you—it’s the "Jump Scare" month after all.
The Outpost
Let’s dive right in! October is packed with drawing challenges, and a few of my favorites are Pouchtober, Disney Drawtober, and Inktober. Two of these were dreamed up by friends of mine, so I gotta shout them out. If you’re looking to spark some creativity this month, here’s a rundown of each one:
1. Pouchtober
When bad jokes and dad puns grow legs and take on a life of their own, you get Pouchtober. The mastermind behind this challenge is Rico Renzi. We were chatting over dinner recently about Pouchtober’s origins.
“It was a joke. It wasn’t supposed to take off like this. Now I’ve got to dig up more characters with pouches.”
Rico shared how his friends in the comic industry jumped on the idea. While they’ve all got ridiculous deadlines, somehow, they still find time for this. It’s either a burning desire for something fun or silly, or maybe ADHD takes the wheel. Either way, Pouchtober was born and lives on.
Grab a pencil and your favorite cargo pants, and head to the drawing board to whip up some characters with a serious love for pouches!
2. Disney Drawtober
For Disney fans who love Halloween, this challenge is a perfect match. The prompts are always thoughtful, and the team behind it—Andrew Sale and Mariana Koontz (LandandWorld), are joined this year by Christopher Michon (failedimagineer). They are bringing the magic.
They’ve been running Disney Drawtober for five years, and it gets better each year. Every week in October comes with a new theme, so it’s never stale. Even if you're not participating, it's worth following along to see all the creativity that comes from it.
3. Inktober
Inktober is the OG drawing prompt challenge, which has been going strong since 2016. The idea behind it is simple: to encourage artists to step away from the computer and improve their inking skills. While it's traditionally done on paper, plenty of people do it digitally now.
One of the coolest things I’ve seen is when artists take the daily prompts and weave them into a continuous story. Each drawing builds on the last, creating a narrative that spans the whole month. That’s a concept writers can use too! Imagine using Inktober prompts as inspiration for a serialized story, each building on the last. This is a new take on a Choose Your Own Adventure story.
But what’s happening in the design world?
One more thing that launches this week is a course from some of the most genuinly wonder women in the industry. Hoodzpah’s Visual Identity course is happening on Maven. Currently, it looks like the class is full, but I’d suggest joining the waitlist. I’ve not been able to take it yet, but I am looking forward to jumping in as more dates become available. I’m already hearing excellent things from previous participants in the FABAS Slack community.
What’s happening in The Woodshed?
I’m still gathering my thoughts on the Zine Fest from last weekend, but stay tuned for the next Woodshed update. I’ve got images and stories I’m excited to share.
In the meantime, if you’re looking for an October drawing challenge, it’s not too late to jump in! We’re only on October 2, so there’s still time to catch up. Let me know if you’re participating, and I’d love to see what you create!
I’m sure you all know of some prompts that I’ve not listed, please drop some links in the comments to any you are doing.
One thing I’ve learned throughout my career is the power of personal projects. Early on, gig posters were my first dive into self-driven work. They shaped the way I approach design and illustration—pushing me to think in ways that went beyond anything I learned in college. Over the years, these personal projects have continued to emerge, offering opportunities to explore and experiment.
Challenges like 36 Days of Type, The 100 Day Project, #DailyDoodle, Layer Tennis, Type Fight, Inktober, MerMay, March of Robots, and Smaugust are just a few examples of passion projects that creatives throw themselves into. There’s an undeniable element of escape and play that’s often missing in the structured confines of a day job. These projects aren’t just for fun; they’re opportunities to flex creative muscles and discover new ways of thinking.
They also keep you creating. Consistency is a huge part of growth. Whether you’re a writer, artist, or working in a trade, it’s just like working out at the gym. You have to continue to show up before you start seeing results. Sometimes, it takes years to get the results you’re looking for—all the more reason to start today and show up again tomorrow.
I believe play should inform the work you do at your day job too. More than once, I’ve solved complex problems at work while "playing" with personal projects. Stepping away from the grind and diving into something playful sparks fresh ideas, opens up possibilities, and often leads to solutions I wouldn't have found otherwise.
How to Apply This in Your Own Life
Find Your Escape Hatch: Pick a creative challenge or start your own. It doesn’t have to be grand, just something that excites you. Let it be an escape from daily pressures.
Make Room for Play: Whether it's doodling, writing, or experimenting with type, carve out time for playful work. This helps break the routine and keeps your creativity sharp.
Let Your Side Projects Influence Your Main Projects: Don't silo your passion work from your day-to-day responsibilities. You might be surprised by how the ideas and techniques you develop on the side can improve your performance on the job.
Stay Consistent: Just like working out, showing up consistently is key. Even if the results don’t show up right away, the act of doing the work builds creative muscle over time.
Don't Overthink It: Personal projects don’t need to be perfect or polished. The value is in the process, not just the product. Keep it loose, have fun, and let your creativity wander.
TTFN
I hope something here has sparked your curiosity and stoked the fire to try it out in your own adventures. Keep the embers of curiosity glowing—one idea at a time.
Doc
I love a good drawing challenge. Thanks for sharing these Doc! I did a 365 challenge years ago and it was so fun and rewarding... I think I need to set aside some time and jump into one of these.