The Ultimate 14-Day Drawing Challenge for Creative Growth

Building a daily drawing habit doesn’t have to be overwhelming. In fact, just 10 minutes a day can be enough to spark creativity and make drawing feel effortless. This 14-day drawing challenge is designed to help you doodle freely, explore new ideas, and enjoy the process without overthinking. There’s no need for big, detailed artworks—just grab a pen or pencil and let your imagination take over. Whether you're an experienced artist or a complete beginner, this challenge will guide you through simple and fun prompts to boost creativity and build confidence in your drawing and doodling skills.
doodling challenge to improve your drawing skills

How This Drawing Challenge Works – in Just 10 Minutes a Day

Each day, you’ll have a simple prompt designed to get you started quickly while teaching you a special skill each. You can follow the prompts in order or pick one at random—there are no strict rules. The goal is to draw or doodle for 10 minutes a day, allowing creativity to unfold naturally.

To help you stay on track, I’ve created a checklist for you to download, so you can make sure that you complete all the prompts by the end of the 2 weeks. 

14-day drawing and doodling challenge printable checklist

The best part? If you’re having fun, you can keep going beyond 10 minutes, but there’s no pressure to create a masterpiece. The challenge is all about enjoying the act of drawing and developing a habit of creativity.

By completing this challenge, you’ll massively improve your drawing skills, strengthen your creative thinking, and build confidence in your artistic expression. Even in a short time, you’ll start noticing progress in how you see and translate ideas onto paper.

14-Day Drawing & Doodling Challenge

Day 1: Fill a Page with Random Doodles

Start with a single shape or line and let your pen wander. No plan, no pressure—just see where the doodles take you.
How this drawing challenge helps you: Loosens up your hand and gets you comfortable drawing without a plan.

Day 2: Repeating Patterns & Textures

Fill a section of your page with simple, repeating shapes like waves, circles, or cross-hatching.
What you improve with this challenge: Develops rhythm and consistency in your line work.

Day 3: Draw Black Spots and Areas, Then Connect Them

Start by filling different areas of the page with solid black shapes of various sizes. Then, use lines, patterns, or shading to connect them into an abstract doodle.
How this exercise benefits you: Teaches you the power of black areas, as they give your drawings much more depth. You learn to work with negative space.

Day 4: One-Word Prompt

Pick a random word (or use an online generator) and doodle the first thing that comes to mind.
What you gain from this challenge: Encourages free association and imaginative thinking.

Day 5: Scribble and Find Shapes

Make a random scribble on the page, then turn it into something recognizable by adding details.
How this helps your creativity: Strengthens your ability to see patterns and create something out of randomness.

Day 6: Draw an Object from Memory

Pick something familiar (like a bicycle, tree, or house) and draw it from memory. Then, compare it to a reference and notice what you remembered vs. what you missed.
How this drawing exercise improves your skills: Trains observational skills and recall.

Day 7: Hidden Object Doodles

Create a doodle full of tiny hidden objects—things like keys, animals, letters, or faces camouflaged into patterns.
What you develop with this challenge: Improves attention to detail and spatial awareness.

Day 8: Draw an Object from a Photo Reference and Interpret It as an Abstract Doodle

Choose a photo of an object (like a plant, shoe, or lamp) and simplify it into abstract shapes, textures, and patterns.
Why this is useful for artists: Strengthens interpretation skills and helps break objects into basic forms.

Day 9: Try Different Pen Thicknesses

Use different pen sizes to create contrast—thicker lines for bold areas, fine lines for intricate details.
What you learn from this: Improves control over line weight and makes your doodles more 3D.

Day 10: Doodle Architectural Elements

Draw tiny buildings, bridges, towers, or abstract cityscapes. Play with details like windows, staircases, and pipes to create an intricate urban feel. For more inspiration, check out my blog post on architectural drawings and doodles.
How this improves your drawing skills: Helps with structural drawing and perspective awareness.

Day 11: Create a Mini Doodle Scene

Combine a few small drawings into a single composition—maybe a tiny city, a collection of objects, or an abstract pattern.
What this challenge teaches you: Helps with composition and storytelling in small spaces.

Day 12: Create a Floating Island

Design a tiny world on a floating rock—a house, a city, a tree, or something more surreal.
How this helps your imagination: Builds creative thinking, a sense for gravity and spatial composition skills.

Day 13: Use Only Dots (Stippling)

Create shading and depth using only tiny dots. Experiment with different densities to see how they affect contrast.
Why this is a great exercise: Teaches patience and shading techniques and can be applied to draw smoke, clouds, or sand.

Day 14: Reinterpret One of Your Previous Doodles

Go back through your challenge drawings and choose one to refine, expand, or recreate in a new way.
What you gain from this challenge: It will help you with your self-evaluation and you will be pleased to see how much your skills have already improved! You’re doing great, keep it going 🙂

Why This Drawing Challenge Works

  • It’s quick. Just 10 minutes a day keeps creativity active without taking up too much time.
  • Great to reduce pressure. There’s no need for perfection—doodles and sketches are meant to be playful.
  • Builds creative confidence. Drawing daily helps ideas flow more easily over time.
  • Improves skills. The challenge introduces new ways to observe, experiment, and develop artistic techniques.
  • It’s fun! The prompts are designed to inspire creativity without feeling like “work.”

Keep the Creativity Going!

Once you finish this 14-day drawing challenge, keep the habit going!

For more inspiration, check out these blog posts:
👉 Doodle Drawings: How to Start in Easy Steps
👉 The Ultimate Guide to Drawing Ideas & Doodling Elements

At artmefree, the focus is on easy-going creativity and finding joy in spontaneous artistic expression. The doodle-based designs from artmefree embrace flow, experimentation, and freedom—just like this challenge!

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Feeling inspired? Share your doodles on social media and tag #artmefree so we can see your creative journey! 🚀

14-day drawing and doodling challenge printable checklist
doodling challenge to improve your drawing skills
doodling challenge to improve your drawing skills
doodling challenge to improve your drawing skills
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