How Teaching Modern Calligraphy Inspired Peggy Dean To Change Careers

Peggy Dean has always been an artist, and has been making a living as a creative for a decade now. “I’ve been working as a hair and makeup artist, primarily for editorial and weddings for the last 10 years. I’ve had five separate publications, everything from more locally focused stories to publications with worldwide recognition. I’ve given it a good run and had a lot of fun, but while I was working I was always learning new things and playing with new techniques.  That’s why I started hand lettering – it seemed like a fun new thing to learn and experiment with creatively.”

It was this interest in hand lettering that led her to Skillshare. “I took a traditional calligraphy class back in high school, so I learned some of the basics then, but then I wanted to master the whimsical nature of modern calligraphy. I started teaching myself and that’s how I came across Skillshare. I found a hand lettering class with a cool project and started playing around with that. I have a hair and make-up Instagram, so I decided to start an Instagram for hand lettering as well, and post all of my projects. After a few months, Tombow selected me as a Brand Ambassador, which was very exciting.”

It was when Skillshare reached out to her that she decided she’d actually teach a class. “I’ve always flirted with the idea of being a teacher. I’ve heard that it’s rewarding but also that there’s lots of ‘buts.’ I’ve taught things in non-traditional formats before – I teach hair and makeup, and I taught fire dancing for five years, but I’d never thought about teaching hand lettering until I got an email from Skillshare offering a bonus to join the Teach Challenge. I said, “You know what? Why not!”

A still from Peggy Dean's Modern Calligraphy Class

A still from Peggy Dean's Modern Calligraphy Class

Peggy has been blown away by how much she’s been able to earn on Skillshare. “I published at the end of the month, so my very first paycheck was like $20-$30. I thought ‘Oh cool, some nice passive income,’ but that was about it. But when I got my first full paycheck the following month, I was shocked. I’m still shocked. The check was for about $2200, and I thought this must be some kind of fluke. But then the month after that came, and it was consistent, and I started to realize that I could really make a living here. I was just texting my other half this morning as I was finishing my newest class, and I said to her, ‘I love my new art job!’”

Peggy loves teaching because it allows her to do two things she loves – research and connecting with her students. “I feel really good about doing a lot of research and figuring out what’s missing online. I think there’s a lot of base fundamentals that are important that people understand, and I love finding those holes and filling that gap. Then being able to work with students, to give them feedback and help guide them through the learning process – it’s just the best. It’s a really encouraging way to keep people going. I had one person redo their project after I gave them some feedback, and she sent me the updated version and it was amazing, and I just thought it was so humbling that she did that.”

But the money’s not the only reason Skillshare’s been great for Peggy. Teaching classes online has helped her realize where her true passions lie. “I can honestly tell you Skillshare’s the reason why I enrolled in college for the first time, and I’ll be starting in the fall. I’m 30 years old, I’ve never been to college before, nobody in my family has ever been to college. I want to learn so I can be an educator. Realizing how much I love connecting with my students and designing these classes for them helped me find that I have this great passion for teaching and I’m ready to pursue it.”

Her advice for first-time Skillshare teachers? “Start with a very specific project. Don’t overwhelm yourself with needing to put in every piece of detail. Just break it down to the fundamentals and share that. Seeing that outcome of that work is so, so rewarding. Especially in the creative realm, we can learn so much from each other. Coming together creatively and being able to share, it’s just fantastic."

Join the Teach Challenge and find your passion today!