When September rolls around, it always feels like a fresh start for me. School is back in session, the air starts to cool, and I find myself craving a new creative rhythm. It's the perfect time to jump into a September drawing challenge.
Over the years, I've learned that committing to a month of daily drawing doesn't just improve my skills—it completely changes how I see the world around me. I approach it with an observational mindset: seeing the big shapes first, letting the imperfections show, and enjoying the expressiveness that naturally follows.
The first few times I attempted a full month of drawing, I made the classic mistakes: setting goals that were too complicated, getting frustrated when my drawings didn't look “good enough,” and feeling stuck halfway through. Now, after years of experimenting, I take a much more forgiving and grounded approach. If you're thinking about doing your own September drawing challenge, I'll walk you through some ideas that have worked for me, along with a few tips for making it sustainable and actually enjoyable.
Key Points Before You Start
- Focus on Big Shapes First: I always start by blocking in the big shapes. Whether I'm sketching a tree or a crowded coffee shop, focusing on the overall forms first saves me from getting overwhelmed.
- Embrace Imperfections: My favorite drawings often have weird proportions or wobbly lines. The more I accept the messiness, the more personality my sketches have.
- Have a Loose Plan: I find that knowing my themes ahead of time keeps me grounded. But I leave space to adjust. Some days I'll want to draw from a list, and some days I'll just grab whatever catches my eye.
September Drawing Challenge Themes to Try
If you're looking for structure, it helps to start with a clear theme for your September drawing project. Having a theme keeps you from overthinking each day's subject.
Nature Journaling Themes
September is a beautiful transition month in nature. I love weaving my sketching practice into the seasons by nature journaling. You can focus your daily drawings on things like:
- Changing leaves
- Mushrooms and fungi
- Early autumn flowers
- Bird migrations
- Clouds and changing skies
When I’m doing nature studies, I keep my setup simple. Sometimes it’s just a mechanical pencil and a small sketchbook tossed into my backpack. If you want to deepen your practice, I've found wildlife sketching to be a really inspiring companion to September nature journaling.
Urban Sketching Themes
If you’re more city-based, urban sketching offers endless material for a September drawing challenge:
- Street scenes
- Café corners
- Bikes parked against fences
- Lamp posts and streetlights
- Daily commuters
One trick I use when sketching in public is to draw quickly and focus on capturing the energy of the place rather than the details. You can check out how I approach sketching scenes if you want some extra tips on this.
Expressive Drawing Themes
Some days, you won't want to draw “things.” You'll want to draw feelings. That’s where expressive drawing shines.
- Draw the feeling of a windy day
- Capture the weight of a rainy afternoon
- Sketch the idea of “change” as September unfolds
These drawings usually end up being some of my personal favorites because they feel the most honest. They also really help when you're trying to find your drawing style.
September Drawing Prompt Ideas
Sometimes all you need is a simple prompt to kickstart your hand and brain. I’ve collected a few different sources I lean on when I need that nudge.
My personal method is to jot down 10–20 ideas at the beginning of the month and then let myself pick from them each day depending on my mood.
How I Personally Approach a September Drawing Challenge
Every time I do a month-long drawing project, I remind myself: it's about the process, not the product. I don’t aim for polished pieces. Instead, I approach it almost like illustrative journaling.
Here's my basic framework:
- Observation First: I start by quietly looking. Whether it's a crowded street or a single leaf, I look for the biggest shapes.
- Big to Small: I block in the big masses first, then carve into them with smaller details.
- Embrace the Mess: If my lines look wobbly, great. If my proportions are off, even better. I believe deeply that drawing is imperfect, and that's what makes it alive.
When I catch myself getting too precious about a sketch, I remind myself about messy drawings and how much more exciting they often are compared to “perfect” ones.
Tools and Materials I Recommend
You don't need a lot to start—and honestly, the simpler your kit, the better. Here's what I use for a September drawing challenge:
- A small portable sketchbook (like a Moleskine—but here's a real talk about are Moleskine sketchbooks worth it)
- A mechanical pencil or an ebony pencil
- A ballpoint pen (check out my tips for drawing with ballpoint pen techniques)
- Optional: a small watercolor kit if you want a splash of color
If you're feeling fancy, you can explore colored pencils on black paper.
For those curious about experimental materials, I've been playing with drawing on rice paper lately, and it's an amazing experience for textural sketches.
Ideas for a “Backup Plan” When You Feel Stuck
There are days you’ll miss. Days you’ll want to quit. Here's how I create a “backup plan” for those rough days:
- Draw your coffee mug
- Sketch your shoes
- Outline the view from your window (even if it's just rooftops)
- Copy a flower from a photo (I use my how to draw flowers tutorials when I need ideas)
Having a few go-to easy ideas for drawing can be a lifesaver.
If you’re still stuck, my giant list of 100 easy things to draw when you're bored can help you.
If You Want More Structure
If you want a little more community or lessons to keep you focused, consider checking out my online sketching courses. Sometimes having a little guidance can make a daily practice feel lighter and more fun.
Or if you're planning ahead for a future month, I also have some ideas for December drawing challenges. You might even want to build momentum through September and carry it into the holidays!
Drawing every day in September isn't about being perfect. It's about showing up. It's about finding beauty in the ordinary and letting your sketchbook become a record of a single month of your life.
If you’re interested in digging deeper into developing your style, check out my article on how to find your artistic style or even creative in drawing to spark new ideas.