Do you dream of hustling on the side, starting your own business, or going beyond teaching? Many teachers do. Some are even brave enough to actually embrace their entrepreneurial side and go for it—and they crush it.
We interviewed nine different teachers-turned-entrepreneurs that started their own successful small businesses online, some of them leaving the classroom entirely. Here are their thoughts on what it takes to grow a business from the ground up, lessons they learned from their mistakes, and what they want others to know about making it happen as an entrepreneur.
Tori: Self Motivate and Never Stop Learning
Tori (@ESLGems) has always had an entrepreneurial spirit, but that doesn’t mean starting her own business—an Etsy and online shop centered around ESL resources—was easy. She has had her fair share of struggles, from production delays caused by COVID-19 to issues with quality control when she partnered with a less-than-stellar fulfillment company.
But she wouldn’t trade it for the world. Like many successful entrepreneurs and every teacher, Tori is fueled by possibilities to learn and grow: “Learning about running a business and making progress on my goals keeps me going.” She’s honored to have customers that love the products she’s put so much time and effort into creating and knows that investing in herself and her future makes it all worth it.
Her advice? Stay hungry: “For me, the best thing I’ve learned to do is to self motivate and be proactive about learning new skills. Adapting as I’ve learned more is such a powerful learning tool that I’ll continue to use.” But she doesn’t recommend trying to do it all by yourself. “Don’t be afraid to ask others questions and reach out to like-minded people. … Most experts are happy to help because they were in your shoes at one point.”
Tina: Do What You Love, but Don’t Overdo It
Tina (@teacherkristinagarcia), a life coach and content creator, is the definition of a helper. She’s passionate about helping others unlock their potential, then supporting and encouraging them to reach it. Tina appreciates that coaching and encouraging others allows her to serve people on her own terms in precisely the ways that they need it.
As a former teacher, Tina was already well-versed in human psychology, but when she started her business, she found that diving more deeply into what makes people tick has empowered her to help them more effectively. For her, reading books by experts on how to engage with people has made all the difference in discovering what they want and need from her.
Tina has valuable advice for service-oriented people like her that want to start their own business: “Try not to overdo it. It’s easy—especially if you’re an empath like me—to ‘give, give, give’ and wind up feeling depleted. I encourage folks looking to start their own business to ensure that it’s something they truly care about, or else the passion will fizzle fast.”
She recommends that you identify what it is that motivates you and what value you offer before you ask for anything in return. Above all, she says, know your limits and don’t let work take over your life, no matter how much you love it.
Angela: Do One Thing Every Day for Your Future
Angie (@angelagrams) is also a coach and content creator, and she’s no stranger to taking risks. Inspired by her kids above all else, she’s grateful that her career provides her with the flexibility to be there for her family.
But being a family-oriented self-starter has had its challenges, and Angie learned the hard way to be confident in herself. When her family was struggling with money while her husband was in school, she considered scaling back her business in order to continue receiving financial support. Luckily for her, she knew then that she had what it takes to succeed as an entrepreneur, and the risk she took by continuing to push rather than backing down ultimately got her to where she is today.
As a mother and teacher, Angie has made nurturing a part of her business model. She works hard to engage with her followers and audience not only to show people that she genuinely cares about them but to build trust and grow her brand.
Her advice to those considering entrepreneurship is: “Do one thing every day that your future self will thank you for. Whether it’s posting on social media with your business in mind, buying a website domain, or listening to a marketing podcast—it’s the little things that build success.”
She also cautions against putting all your eggs in one basket or marrying yourself to a single product or project. If you instead pinpoint a movement or passion to be loyal to and then cast a wide net, you’re much likely to achieve success.
Angie: Start Small and Be Flexible
Etsy and Teachers Pay Teachers shop owner Angie (@crafty_teacher_angie) was inspired to start her small business when her husband was deployed and she needed to busy herself. Now, she’s blown away by what she’s been able to accomplish in just two years. What began as a small side hustle operating out of VIPKid Buy and Facebook Sell groups has bloomed into a full-time job for this busy entrepreneur, and Angie says that she is able to support her family financially and she loves what she does.
Most teachers have perfected the art of being flexible. Angie continues to exercise this skill as a small business owner. She does her best to stay on top of the market and apply new business strategies—such as social media involvement and partnerships with other brands—in order to continue growing. She advises that entrepreneurs should not be afraid to make adjustments and that she herself is always doing so.
Angie’s advice to you, if you’re considering opening your own business, is to start small: “Choose one or two items that you want to sell and list them!” Another word of advice? Find a way to support others in their journeys and share what you know, and they will return the favor.
Lisa: Don’t Wait Until You’re Ready
Lisa (@lisamarklesparkles) is an Etsy and Teachers Pay Teachers shop owner, a former preschool teacher, and an idea machine. Her store, which is five years old this year, allows her to capitalize on her strengths as a crafter and creator and incorporate her knowledge of what teachers need in their classrooms.
While Lisa says that she never struggles to come up with new product ideas, she has a hard time deciding which ideas to pursue. Over time, she has learned to go after what she’s best at and do that well rather than trying to appeal to more customers and do that so-so. This meant switching gears after getting started, but this approach was most conducive to her long-term growth.
Many of us have heard the Lemony Snicket quote: “If we wait until we’re ready, we’ll be waiting for the rest of our lives.” Angie definitely agrees, saying, “Grab a snack, research what you need to know, and DO IT!” She warns against spreading yourself too thin and trying to do too much and instead recommends focusing on one or two things that you’re great at and finding your niche and audience. Once you’ve done that, you’ll be able to more effectively reach potential customers through targeted media marketing.
Kaley: Use Your Network
Kaley (@kaleysclassroom) is an Instagram and Affiliate for VIPKid and Outschool, and an entrepreneur that every teacher on social media should follow. Though her work outside of teaching is technically a side hustle, she is an adept marketer and has many streams of income coming from affiliates including Amazon and other online shops.
Kaley taught herself, through trial and error, how to run a successful small business and learned that the key to this is storytelling. She found that her audience grabbed onto her personal stories and experiences. And because telling stories comes easily to her, Kaley shares what she has learned as a teacher and keeps her content engaging and relatable. She likes that she doesn’t have to overthink it and her followers respond best to her authenticity.
Most teachers are fortunate to have extensive, wide-reaching networks, and this is something that Kaley is constantly using to her advantage. She advises that you make friends and seek out networking opportunities whenever you can. You might just be surprised by who refers you or wants to partner with you. And, of course, don’t neglect the people already in your corner—nurture your relationships, especially with your followers, always.
Mechell: Have a Plan
A creative person by nature, Mechell (@mechellsclassroom) knew that she had teaching tools and products that other teachers want. So, she started her Etsy and Teachers Pay Teacher stores, and she’s been sharing her content ever since. She sells many of the same products that she herself uses when teaching.
She also often offers teaching tips to her followers. The customer service aspect of her business is her favorite part, and she enjoys being able to engage with her patrons and followers however she wants to. However, she admits that behind the scenes activities like this can quickly become exhausting and that running a business on the side often feels like a whole extra job.
This is why Mechell stresses the importance of having a plan for your business. This will not only help you to steadily carve out a place for yourself in a saturated market but also to achieve work-life balance, something that she still finds challenging at times. She encourages potential entrepreneurs to take calculated risks and leverage what makes them unique: “Your products need to be made with passion and stick to your own original ideas as that is what will set you apart and help you become successful!”
Nancy: Just Start and Everything Will Fall Into Place
For Nancy (@heynancytaylor)—content creator and store owner—, there is nothing more rewarding than helping other educators become successful content creators. She has been through many ups and downs and taken many risks to get where she is today, but they have all paid off immensely. Between overcoming brand obstacles to hiring $10K worth of coaching and marketing, Nancy has always given her business everything she’s got.
Nancy is also skilled at delegating tasks to her team and feels that hiring help was one of the best business decisions she ever made. Together, she and her sister-in-law effectively manage all the moving parts of their growing business. She still loves building YouTube content as much as ever and knows that starting her business was the right thing for her.
Nancy wants anyone thinking about starting a small business to just start growing something on the side now. “You have the gift of a paycheck with your teaching that gives you the ability to build something on the side, and if you are drawn toward doing more and going beyond teaching, there is no better time than now!”
Sam and Rachel: Don’t Get Discouraged
Together, Sam and Rachel started a subscription box called The Good Fortune Box (@thegoodfortunebox) designed especially for online teachers. As former online teachers themselves, they saw a need for community in the field of online teaching and now pack their subscription boxes with items to help inspire these teachers and connect them with each other.
These two entrepreneurs took a huge risk when they started their business—this box was the first of its kind, but they both agree that the risk was well worth it. They are setting their own path and their business is growing quickly because they pour so much of their time and effort into carefully curating boxes that they themselves would find beneficial.
Sam and Rachel also recommend starting small. “Once you find something you are passionate about and mix that together with an audience that will support your passion, you will be unstoppable. Start with a small attainable goal and build from there.” Finally, the two remind you that you can never make everyone happy and to learn to trust yourself to make great products and let the rest fall into place.
Former 3rd grade teacher now online ESL teacher and mother, Tori loves connecting with other teachers through her website and shop, ESL Gems. Here she shares resources, ideas, and tips for like-minded teachers to help them engage with their students online.