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How Teaching on Skillshare Became My Main Income Source

How Teaching on Skillshare Became My Main Income Source

Snippet from Skillshare: "With over 50 classes and over 400k students, Peggy Dean is one of Skillshare’s most successful teachers. Her success on Skillshare has led to appearances on the Today Show and The Wall Street Journal with monthly earnings of 6-8k in her first year alone!"


How to teach online


Prior to teaching on Skillshare, I worked as a hair and makeup artist. I enjoyed my career and while I was working I was always learning new things and playing with new techniques. That’s why I started brush lettering – it seemed like a fun new thing to learn and experiment with creatively.

It was this interest in hand lettering that led me 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 so I began teaching myself. I didn't actually find any lettering classes at that time (thankfully they're abundant now 🥳), but I did end up coming across Skillshare in my journey to learn creative techniques. I already had a hair and make-up Instagram, so I decided to start an Instagram for lettering as well so I could post all of my projects and connect with likeminded creatives. After only a few months, Tombow selected me as a Brand Ambassador, which was very exciting.

It was when Skillshare reached out to me that I decided I'd actually teach a class. I’ve always flirted with the idea of being a teacher…I’ve taught things in non-traditional formats before – I taught 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 [about teaching]. I said, “You know what? Why not!”

A still from Peggy Dean's  Modern Calligraphy Class
A [rather embarrassing] still from my very first Modern Calligraphy Class *NOTE: I was NOT an expert but at calligraphy, filming, editing, ANY of it. But it was the organic content and passion that mattered far more. My creative and filming skills would improve over time.

Y'all, I was blown away by how much I was 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, a little 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 (it actually grew!), and I started to realize that I could really make a living here. I remember texting my wife as finishing my flourishing class, just saying "I love my new art job!" At this point, I was regularly earning between $6-8k every month from Skillshare. 

I love teaching because it allows me to do two things I love – research and connecting with her students. I feel good about doing a lot of research and figuring out what’s missing online. I think there’s a lot of basic 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 still remember the first person that redid their project after I gave them some feedback, and they sent me the updated version and it was amazing, and I just thought it was so humbling.

And money’s not the only reason Skillshare’s been great for me. Teaching classes online has helped me realize where my true passions lie. 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 in so many forms. My eighth book has just been published, I've established a membership for creative entrepreneurs, I've launched Creative Course Lab - an extensive course creation school - and I support two actual humans who can rely on me for their full time income. It's an amazing blessing that I never saw coming.


How to create an online class


My advice for first-time Skillshare teachers: Start with a specific project. Don’t overwhelm yourself with needing to put in every piece of every detail. Just break it down to the fundamentals and share THAT. Seeing that outcome of that work is so, so rewarding. Remember: You don't need to be an expert; You only need to know more than the people you're teaching. 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.


Get a teaching referral from Peggy

I love being able to refer people to teaching on Skillshare, so if you're looking for a referral from a Top Teacher, I'm your gal. Fill out this form (or complete it below) and I'll see what I can do to put in a good word for ya. 


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