Sip & Script · Instructor Development
Letter League
Build a creative side hustle teaching calligraphy
Letter League is Sip & Script's flagship instructor development program. Over the course of training, you'll master modern calligraphy, learn how to run a class, and join a national network of working instructors — the Script Squad.
Who is this for?
Four kinds of people
thrive in the program
Letter League draws creative thinkers from all corners. If you see yourself here, you belong.
Type
Doodler
A creative person that’s always crafting, doodling or journaling. (Do you have a gel pen collection?!?)
Type
Entrepreneur
You're ready to turn calligraphy into income — workshops, events, commissions.
Type
Performer
Love to command a room? You’d love the opportunity to share this passion with our students in a fun, laidback environment!
Type
Stay-at-Home Creative
A flexible craft that fits around the kids, the home, the life you've built.
What you'll learn
The Letter League curriculum
Six modules covering the craft, the business, and the teaching practice.
Modern Calligraphy Fundamentals
Strokes, alphabets, materials, and pen control.
Branded Lookbook
Your portfolio piece you'll teach from for years.
Class Design
Lesson plans, timing, and reading the room.
Hour-by-Hour Business Plan
Pricing, venues, marketing — the operational map.
Ongoing Email Support
A year of mentorship after you certify.
Script Squad Onboarding
Your introduction to the working instructor network.
More than a course
A cohort, an alumni network, and a year of mentorship — Letter League is the doorway into a working creative community.
Meet the CohortCohort
Learn alongside peers
Train with a small group of future instructors going through it with you.
Squad
Join the Script Squad
Graduates enter the national directory of working Sip & Script instructors.
Support
A year of mentorship
Email access to the team and quarterly community calls long after you certify.
From application to instructor
A clear four-step path. We move at your pace.
See the PathApply
Fill out the application form below — takes 5 minutes.
Discovery call
A 30-minute video chat to see if Letter League is right for you.
Train
Complete your chosen training path with our certified team.
Teach
Launch your first class as a Sip & Script instructor.
From the Script Squad
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FAQ
Common questions
Do I need calligraphy experience to apply? +
No — the program is designed for total beginners as well as established letterers. We meet you where you are.
How much does the program cost? +
Tuition is shared on your discovery call. It varies based on the training path you choose.
How long does training take? +
Most students complete training within a few months. Some paths are weekend-intensive; others are self-paced.
What's included after I graduate? +
You join the Script Squad directory, get a year of email mentorship, and participate in our quarterly instructor calls.
Can I do this while working full-time? +
Yes — most of our students do. Training is structured so it fits around a busy life.
Apply to Letter League
5-minute form. We reply within 1 business day with next steps.