About Outschool, Building Business   June 1, 2022  ▪  8 min read
Build Your Teaching Business Your Way
Two educators share their Outschool journey and the strategies they’ve used to create the teaching life they want on Outschool.

On Outschool, you have the opportunity to teach not only what you want, when you want, and where you want but also to decide how many hours you want to teach. You decide how you will chart your success as an online educator entrepreneur!

Two Outschool educators, Nicole Dyson-Smith and Daniel Grissom, have leaned into the possibilities to create and shape teaching businesses that suit their needs.

We spoke to them about strategies they’ve employed to run their businesses and create the future they want on Outschool.

Develop sustainable practices

Both Daniel, who previously taught English in a brick-and-mortar school, and Nicole, whose background is in music, say that creating sustainable practices that work for you is key to retaining your energy and staying organized to build a successful online teaching business.

Developing repeatable class elements is a strategy that Daniel uses to reduce the amount of time he spends planning lessons. When he decided to teach full time on Outschool in fall of 2021, scaling his classes to grow his teaching business became a priority. One example he gives of a time-saving practice is using the same discussion protocol in his writing classes as he uses in his reading classes.

He also organizes his drawing classes so they follow the same structure every time. “So the technique will change, the content will change, but the structure is going to stay the same,” he says.

In addition, he focuses on the same lesson concepts throughout a family of classes. For instance, if he’s introducing a certain shading technique, he teaches that across many of his drawing classes, no matter whether learners are drawing scary monsters, silly monsters, or anime characters.

Nicole highlights the importance of regular planning time so that she feels organized and ready for her teaching week. She has begun to diversify her teaching business and has been working as an adjunct instructor at a community college in addition to teaching part time on Outschool. She has identified a couple days each week to plan for teaching in multiple settings.

“It’s literally written down that I’m going to spend this time planning. Then, I make sure it happens,” she says. That way, “I always feel on top of everything. That has been really helpful for me.”

Keep innovating until you gain traction

Nicole and Daniel know that adjusting their classes until they get the right content mix is part of succeeding as an online educator entrepreneur.

Daniel laughed as he shared a story about the first class he planned on Outschool where he combined many interests he had as a kid — salamanders, drawing, and Spanish. Tapping into his memories of what he enjoyed at age 10, he envisioned teaching Spanish while sharing information about salamanders and how to draw them.

Although he understood the interests that learners that age may have, “the niche was so tiny that I overshot the niche there,” he says.

Daniel recalls that he received feedback to break these topics into separate classes. Now he has grown his base classes into 14 active ones — drawing and cartooning with different focuses and philosophy for kids.

When Nicole started teaching on Outschool in spring of 2020, her most popular classes were escape rooms centered on music education. Eventually, she started noticing that learners taking these classes weren’t all that interested in learning about music. So she shifted to just incorporating music, and those classes really took off, to the point that she was leading the same escape room adventure 8 hours a day.

As someone who has created a variety of successful classes on Outschool, her advice for others looking to do the same is:

“I would recommend trying new ideas, not panicking when something doesn’t work out because sometimes it’s just not the right time for it, but you can still keep your ideas and try them at a different time.”

Stay with it, even with a few learners

Both educators shared that they have had periods in teaching ongoing classes where they just had a learner or two enrolled.

Daniel says that ongoing classes can take a long time to get started and recommends that educators give themselves time to build a following. “You need to teach to one learner, two learners, three learners, but two months later, three months later, it could be a sold-out class. It might be half a year later,” he says.

If you continue to have a small number of learners for a long time, you might need to make a change, Daniel says, “but teaching to a few learners for several weeks is worth it even for a month because they build steam. They build momentum over time.”

Encourage enrollments with marketing

Daniel has applied some marketing strategies to build his classes on Outschool and make virtual teaching his full-time work. He uses keywords in his class descriptions and has added his photo to all his class images to build a brand that families will recognize.

“A parent might not enroll the first time,” he says, “but when they’re searching for drawing classes later, or the10th time, or three months down the road, and they see your face again, then it builds awareness and then eventually they might.”

He also organizes his classes around the idea of a class funnel, where learners take a foundational class with him then have the opportunity to choose another class on a more specific but related topic.

Teach what you really love

Who isn’t inspired when you’re learning something you enjoy in the presence of someone who also is passionate about it — and has expertise in it! Both Daniel and Nicole model this approach of sharing what they love with learners. This has provided an ongoing connection with learners and keeps them coming back.

Although Daniel taught English before joining Outschool, his first Outchool classes in early 2021 were art classes, and they continue to be his core offering. He explains that art has been a lifetime hobby, and teaching it has come easily to him.

Nicole has taught different types of classes on Outschool, from music-based escape rooms to individual piano lessons. But one constant for her during most of her time on Outschool has been an ongoing music class called A Kaleidoscope of Music – Ongoing Classical Music Exploration Class. Learners study a different piece of classical music each week then create something in response to it, which they share with others in the class.

“Some of my students (in that class) have been with me since week three,” she says. “I will probably always do that one because I just love it.”

Keep adapting to create your future

When asked why he made the change from in-person to online teaching, Daniel points to the breaks he can now take with his family during the day. He mentions his ability to go places like the beach and teach from there. He continues to expand and refine his class repertoire and the way he presents them.

Nicole found creating new escape rooms (at least the way she did it, she says) to be very time consuming. So although she still teaches a few escape room classes, she has made a shift to something new on Outschool.

She discovered Outschool pods in fall of 2021 and now teaches on a team with two other educators. She provides music classes, and the other educators teach art and p.e. for the same group of learners each week for four weeks.

Nicole says she didn’t plan to team teach but decided to try it when the opportunity arose. She likes the ability to collaborate with other educators and to get to know a group of learners. “It’s been so awesome to work with some other teachers on Outschool, and we have the same students so we can kind of compare notes and come up with ideas,” she says.

Nicole estimates that she’s currently teaching less than 10 hours a week on Outschool and is considering adding a business offering in-person private piano lessons, something she used to do.

If she decides to teach full-time on Outschool in the future, she thinks it’ll be time to try some marketing practices. “If I do decide to try to push and go full-time again,” she says, “I’m going to have to do a different strategy (like marketing).”

She’s continuing to embrace change and adapt, just as she recommends to other educators. “Keep innovating and trying out new things,” she says, “and explore things that you wouldn’t have thought you would be interested in.”

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