Want to improve your lettering skills without overthinking or burning out?

In this 7-day lettering challenge, you’ll choose one meaningful word and re-letter it each day using a different creative prompt. Through simple constraints and playful exploration, you’ll strengthen your fundamentals, expand your stylistic range, and reconnect with the joy of lettering.

This class is designed to help you build confidence, consistency, and creative momentum—all in short, approachable daily lessons.

What You’ll Learn

Over the course of this challenge, you’ll practice lettering techniques that help you grow both technically and creatively, including:

Creating strong letterforms using monoline structure
Adding energy and dimension by playing with weight
Improving composition by learning how to fill the frame
Loosening up through texture and experimentation with unexpected tools
Exploring visual impact through scale, proportion, and exaggeration
Using color intentionally to communicate mood and emotion
Developing your personal style by remixing techniques into a final piece

By the end of the class, you’ll have seven unique lettering pieces and a clearer sense of what techniques feel most natural and exciting to you.

Why You Should Take This Class

Lettering can easily start to feel repetitive or intimidating—especially when perfectionism creeps in. This class removes that pressure by giving you one word, one prompt, and one clear focus per day.

Instead of chasing a “style,” you’ll discover it through experimentation. The challenge format keeps things light, focused, and motivating, while still pushing your skills forward in meaningful ways.

This is a great way to:

Break out of a creative rut
Build a consistent lettering habit
Generate new ideas and portfolio-worthy work
Reignite excitement for your creative practice

Who This Class Is For

This class is best suited for:

Letterers and illustrators with some experience who want to level up
Artists feeling stuck, bored, or creatively blocked
Designers who want to explore lettering more intentionally
Anyone who loves type and wants a fun, structured way to practice

You don’t need to be a beginner, and you don’t need fancy tools—just a willingness to experiment.

Materials & Resources

You can complete this class with simple supplies you likely already have:

Paper or a sketchbook or a digital canvas
Pens, markers, brushes, or an iPad + stylus
Optional color tools (markers, paint, digital brushes)

All prompts and project instructions are included in the Projects & Resources tab.

Class Project

Your class project is to choose one word and letter it seven different ways, following the daily prompts. You’ll upload your favorite versions (or the full set!) to the Skillshare Project Gallery and reflect on what you discovered along the way.

Extra Resources

Want to learn more about lettering?

Ready to better your lettering — one playful prompt at a time?
Grab your tools, pick your word, and let’s get started.

Estella Mai

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