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My Win-Win Teacher Business Story

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Welcome back to Your Win-Win Teacher Business. In episode #2, I’m sharing the story of my own teacher business so we can continue getting to know each other. Running a business is a rollercoaster of highs and lows so I’ll share about seasons when it has been a win-win for me, and seasons when it wasn’t. 

Why Start A Teacher Business?

Teachers are busy – they certainly don’t need any extra tasks on their plate. But I got to a point in my teaching career where I was teaching the same curriculum over and over on repeat and I was feeling hungry for a new creative challenge.

It’s okay to have a hobby that’s just for your own enjoyment – that’s the beauty of a side hustle! And while I’ve heard that some people have hobbies that they aren’t also monetizing, there is something about how entrepreneurs are wired that always seems to lead to multiple income streams in the end.

Business Ideas for Teachers

There are so many options when it comes to online business for teachers. You might choose to sell on a marketplace such as Etsy like my friend Lisa, Amazon like my friend Kassaundra, or Teachers Pay Teachers like I do. You might try tutoring on a marketplace such as Outschool like my friend Tara or tutoring independently like my friend Molly.

My Teacher Businesses

I currently have a Teachers Pay Teachers store as well as a virtual support provider business where I serve clients. But I’ve had many other business adventures over the years and you’ll hear about all of them in episode 2 of Your Win-Win Teacher Business.


–> I’d love to support your business

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–> Do you have a win-win story to share with the teacher business community?

Apply to be a guest here

–> Let’s chat business on Instagram @teacherjaniceva

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Read the transcript:

Janice Cook 0:00 Welcome back to Your Win-Win Teacher Business. In episode number two, I’m sharing the story of my own teacher business so we can continue getting to know each other. Running a business is a roller coaster of highs and lows. So I’ll share about seasons when it has been a win-win for me, and seasons when it wasn’t.

Janice Cook 0:21 You’re listening to Your Win-Win Teacher Business, a podcast for teacher authors who want to make a big impact in the world for teachers and students, and have fun doing it. I’m your host, Janice Cook, here with a pep talk to start your week off strong. Some seasons of running a business feel hard and sticky, but it shouldn’t feel like that all the time. Let’s make your business a win-win together.

Janice Cook 0:46 Hey, hey, teacher business bestie, I’m so grateful to be having this cozy chat today. Teaching was fun until it wasn’t. Towards the end of my 12 years in public education I could feel in my bones that this was not a sustainable path that I would be able to follow for 25, 30, or 35 years, as some of my retired colleagues had. I was married with two small children, struggling to juggle pumping and daycare and present parenting. It’s a tale as old as time, feeling like I was never doing enough as a teacher or as a mom, yet being more tired than ever before. With every new initiative and new administrator came a new flavor of frustration. Teaching changed each year, but it never got any easier. I had already hopped the state line and changed schools, so I knew the grass wasn’t going to be greener if I kept searching for the perfect teaching job.

Janice Cook 1:49 So I got curious.

Janice Cook 1:52 The first inspiring story that I stumbled upon was Millennial Money Man. Bobby Hoyt. It was the first time I read about the community of online business owners who generate a full time income by blogging. And what a core memory reading his story was for me. Once you find one full time blogger story, other similar stories naturally unfold before your eyes. Since his blog was in the personal finance space, I started to also read about the F.I.R.E. movement, and that got my wheels turning. You see, I wasn’t ready to leave my stable full time teaching job and take a chance on full time blogging, but I was open to a side hustle that could possibly lead to early retirement. That idea was exciting to learn about at a time when my teaching assignment was feeling a bit rinse, wash, repeat. So I started to look for the perfect side hustle to fit my season of life.

Janice Cook 2:54 Raise your hand if you taught English online to students in China. VIPKID, GoGoKid, Magic Ears, Outschool and beyond – teaching online was something that I could try while teaching full time to make extra money. While the idea of solving the problem of teacher burnout by teaching more on the weekends was puzzling to many, let me explain why it worked well for me. I taught on Friday and Saturday nights. I taught on Saturday and Sunday mornings. I still had the core part of the day available for family time, but what I also had was something for me. I had community in Facebook groups and many new online friends to meet and learn about. How did they get here? Why did they start teaching online? What were their hopes and dreams? Teaching online also brought the blessing of boundaries. I could no longer put in endless unpaid hours for my W2 job as I had another time bound commitment that was paying me for my time.That side hustle brought in about $1,000 every month, and I stashed it away into a high yield savings account. I started to feel just a little bit less trapped, and that helped me step back into my classroom each Monday morning, knowing I was taking some actionable steps towards a better path, even if I didn’t know exactly what the next chapter would look like just yet. Teaching online was a win-win for me. Families and students looking for support, got access to my time as a teacher, and I unlocked this whole world of possibility, hope, and financial margin.

Janice Cook 4:42 While teaching online, I learned that some teachers created resources to use in their classrooms. They also sold these teaching resources on Teachers Pay Teachers, a marketplace like Etsy where teachers shopped for classroom materials. I had made a few purchases on Teachers Pay Teachers over the years, admittedly, not very many. There just wasn’t a lot for my niche at that time. My husband enjoyed digital art as a hobby, especially if it involved penguins in some way. So I talked to him about making some items that I needed for my classroom. I sketched out what they would look like, and he was able to create these printable resources. He was not aware of Teachers Pay Teachers, but I told him that these resources he was making for my classroom could be sold on that website if we added a few finishing touches. He was skeptical, but willing to give it a try. If I was willing to do the market research for what teachers wanted, and then share the finished resources with the world to make sure they sold, he was willing to make a few and see what happened. So when the school year wound down, we made a reward system in the theme of a neighborhood that aligned to a popular lesson filled with vocabulary words that were challenging for teachers to pair with props. We made the tool for my own classroom, posted a picture on social media, and the requests started rolling in about where I got it. That special July evening, after the kids were in bed, we posted our first product on Teachers Pay Teachers, and woke up 27 cents richer. But more importantly, with the validation that this idea could actually work.

Janice Cook 6:27 Let’s talk about community again. I had a community of online teachers with inspiring stories and other side hustles that I loved learning about. Now I also had a second community of Teachers Pay Teachers sellers who were a wealth of knowledge and inspiration. Any big feelings about colleagues in my brick and mortar teaching situation were a lot easier to weather as I built a circle of like minded online business owners to spend time with. Social media gets a bad rap some days, but my screen time in this season saved me. The relationships that I built helped me not stay stuck. They helped me stay curious and hopeful. The relationships I built online helped keep my teaching spark alive. Teachers Pay Teachers is all about trying new things. It’s about throwing spaghetti at the wall to see what works. This accidental entrepreneur era is so different from the college coursework path, but there were plenty of courses and books where I could learn and get curious about the next step in my own online business journey. How can I optimize my resources to be found and purchased through the TPT search bar? There are courses and mentors for that. How can I bring my own traffic to my resources? There are courses and mentors for that journey as well. Soon, I had a website built, I started and monetized a YouTube channel, I connected and collaborated with others on social media. I learned about how to build an email list. Brands started to reach out to me for paid collaboration opportunities. My authority grew, and soon I saw other teachers dropping links to my resources in Facebook groups. I was having a lot of fun on this wild ride. Dabbling on Teachers Pay Teachers was a win-win decision for me.

Janice Cook 8:19 Let’s revisit my schedule during this season. At first, I was making $1,000 a month teaching on weekends. Additional revenue streams were added over time. I had a monthly payout from Teachers Pay Teachers. I had a monthly payout from YouTube ad revenue. I also had laser focused efficiency when it came to my time. When a student was a no show in my online teaching schedule, I wasn’t wasting time scrolling. I was chipping away at editing a video or finalizing a new resource to be posted in my store. When we had a day off from school, a week off from school, or an early release day, I was able to pick up a few extra classes teaching online, and also tackle some tasks for the business. During the summer months and school vacations I taught for a few hours in the morning and then spent the rest of the day with my kids. The amount of money I made in the summer was now similar to the amount of money I was making monthly during the school year, except I was making that money without missing out on time with my kids and without stepping foot inside that school building.

Janice Cook 9:31 That’s when things got interesting. I started to wonder if it made sense for me to return to the classroom that fall. My husband had a stable W2 job that offered health insurance. We had the option to move to his health insurance instead of the plan offered by my school district. As long as the bills were paid, my husband said he didn’t mind if I worked as a freelancer or if I worked as a teacher.

Janice Cook 9:59 I met with my principal to talk about some concerns I had with the schedule and offer some ideas and solutions. He said that he agreed with those ideas, but was going to stick with the original plan. I passed him my keys, my badge, my school technology and a resume and cover letter for another local colleague who would be a great fit to take my job. I stepped away from teaching that day and walked to the parking lot feeling so much lighter. What a scary leap, but I was determined to make it work. I taught seven days a week for a few hours in the morning. When I finished teaching around 9 or 10AM, again, many others turned to chatting in Facebook groups, but I worked on new TPT products and YouTube videos to market them. I may have traded a five days a week, summers off job for a bit more of a 365 day school year, but I was my own boss. I was calling the shots and I was doing it from my pajamas.

Janice Cook 11:06 Why am I sharing this story today? There are times when teacher business has felt sticky, for sure. But it has so much more flexibility than what I had as a teacher in the traditional school system. So I’ve always considered it to be a win win, and couldn’t dream of returning to the classroom. That was a chapter that I enjoyed, until I didn’t. Once it stopped feeling like a win-win, I took action. I made a change. I did something about it.

Janice Cook 11:38 As you tune into this podcast every Monday, I want you to feel hope and options. I encourage you to get curious and trust in your ability to find a new path that helps life feel like a win-win again. My teacher business has evolved over time, and I now spend most of my time supporting other teacher business owners. In the next episode I’ll share about this chapter of my win-win teacher business story.

Janice Cook 12:06 Thanks for making this podcast a part of your day. I’d love to help you find clarity with your next step in business. Go to cookfamilyresources.com/hiring-guide. I’ll also leave that link in the show notes for you. This guide is packed with good news for those days when you feel like you can’t possibly do it all. It might be time for you to invest in paid support, but the truth is, there are a lot of free steps to explore first. After you dive into that guide, I’ll be in your inbox every Monday morning with more actionable tips to help you enjoy running your business again. See you in the next episode.

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