Drawing Challenge #05: Introduce Yourself Through a Drawing

#W2DTogether Challenge #5

Original Run: Sunday, October 12, 2025 – Sunday, October 19, 2025

Hi everyone!

It’s time for our fifth #W2DTogether drawing challenge. This week’s theme runs a little deeper than usual and I bet it’s going to make you think.

If you’re new to the site, you can catch up on where we started by checking out our previous challenges here. For now, let’s get started on this week’s drawing challenge!

The Challenge

Challenge number 5: Introduce Yourself Through a Drawing

This is not a simple self-portrait challenge. Here’s the twist: it’s not just about drawing your face. The challenge is to create an artwork that tells us who you are without you having to say a single word.

If someone looked at this drawing, what would they learn about you? Your personality, your story, your dreams, or your struggles?

The Twist: Show, Don’t Just Tell I didn’t want to make this a predictable “draw your face” prompt. Instead, the idea is to introduce yourself through your art. Your drawing must contain a self-portrait somewhere, but the overall style can be:

Realistic
Abstract
Symbolic
Surreal

Imagine a family member who never met you, or even a random stranger, had to get to know you solely through this piece of art. What would it look like? That’s your challenge.

Need some ideas?

If you’re stuck, think about these perspectives:

Hobbies & Passions: Are you floating in water because you love swimming? Are you surrounded by books or plants?
Emotions: Are there patterns in the background representing your thoughts (like grey “overthinking” clouds)?
Style: Use a medium that represents you best, whether it’s bold markers or soft graphite.

The Rules

Must be YOUR drawing.
Medium: Drawings only (pencil, pen, colored pencils, markers, or digital). No paintings.
No AI art.
Required Element: Your drawing must contain a self-portrait.
All skill levels welcome: Beginners, intermediates, and experts.

Where It All Started

This challenge was originally posted on Reddit. You can check out the original thread to see the deeply personal and creative ways our community members introduced themselves: