From Teacher to Entrepreneur: 8 Questions with Sheila Jane

8 questions with sheila jane
8 QUESTIONS is a series of interviews with teachers who have effectively transitioned their classroom skills into new and exciting careers in the field of education. We at believe that teaching is a rigorous and diverse classroom in and of itself; the skills learned “in the trenches” can translate into an exciting portfolio of professional options. From education tech to consulting, the only “X factor” is where you want to go — our interviews hope to shine a light on the steps it takes to get there.


1. What’s your name, location and current profession?

Hi, I’m Sheila Jane, a teacher entrepreneur living in the California wine country north of San Francisco. Currently, I work out of my home office and manage essentially three businesses. A year ago, I launched my first business,, an online website to promote teacher wellness and to eliminate teacher burnout.

That's also where I run Teach Happy, where over 400+ teachers, from around the world, share their ideas, and support one another. Members receive access to motivational calendars, ebooks, the Teach Happy Magazine, teacher interviews, our monthly book club, and more.

I am also co-founder of Teacher Entrepreneur School, as six week online course to help teachers make their business dreams a reality. In October, 2015 I created the, a free teacher professional development live-streaming network on Periscope and Blab.

Sometimes you’ll also find me squeezing in some one-on-one coaching with teachers who reach out for that service.

2. Where did you earn your teaching certification and where did you go to school?

I earned my Bachelor of Science degree and teaching credential from Cal Poly, San Luis Obispo and an MA degree in Administration from Santa Clara University.

3. How long were you a teacher for?

I’ve been a teacher since I was 5 years old. Teaching my teddy bears counts right? I remember getting a chalkboard for Christmas and my lifelong journey as a teacher began. I OFFICIALLY taught kindergarten and second grade in Silicon Valley for 8 years. I’ve also taught 5th grade for two years.

4. What was the most rewarding part of being a classroom teacher? What about classroom teaching did you find most challenging?

Teaching pushed me to grow mentally, physically, emotionally and in so many other ways. Figuring out how to intrinsically motivate my students, differentiate curriculum, and positively shape the minds of future generations was a HUGE reward. Another reward was talking with my students one on one. Pulling up a chair and really taking the time to get to know them. Uncovering their talents and watching them grow more and more confident in all subjects.

5. Why did you decide to transition from classroom teaching to your current profession?

During the last several years in the classroom, I had an itch to impact teachers lives on a wider scale. It was my creative spirit that was hungry to be a strong voice for teachers. I had struggled with teacher burnout throughout my career and wanted to share with other teachers how I got my happy teacher groove back.

On the drive to school one day it hit me. What if I created an online oasis where teachers could come for support, camaraderie, and doses of happiness? What if I created a teaching website that I wished I had when I was going through the darkest struggles of my career? With financial backing from an angel investor, I took the leap from full time teacher to full time entrepreneur. I took some business courses along the way, but generally I’m self-taught. I launched Teach Happy Membership. I now have a map in my office with pins representing teachers from around the world who are saying NO to teacher burnout and choosing wellness, life balance, community support, and positivity instead.

The best part of my job is receiving messages from teachers. Messages of teachers who almost walked away. Teachers who found me in this online space and finally felt like someone understood them.

6. What is the best part of being an instructional designer?

The best part of my job is receiving messages from teachers. Messages of teachers who almost walked away. Teachers who found me in this online space and finally felt like someone understood them. Teachers craving a space where they belong. Teachers who want their needs, feelings, and wants validated. Teachers who tell me that because of Teach Happy Membership their entire outlook on teaching has flipped from negative to positive. It moves me to tears. We need teachers. We need happy teachers. I pinch myself every day that I have created a job for myself where I can motivate and bring happiness to teachers. And then, in turn, a happy teacher will impact the lives of so many students.

7. What skills did you gain from classroom teaching that have allowed you to excel in your current profession?

I’ve discovered over the course of this past year that my teacher skill set prepared me well for my life as an entrepreneur. I understand the heart and soul of what it means to be a teacher who needs positivity. I have walked in the shoes of the depleted teacher, so I’m passionate about teacher wellness. I felt the loneliness of teaching in a school that offered little collaboration, so bringing teachers together in membership to support one another made so much sense to me. The content that I provide teachers comes from my experience in the classroom for ten years. Also, I had NO CLUE that managing a classroom day to day would parallel being a small business owner as much as it does. I tell the teachers who take my course, Teacher Entrepreneur School, that teachers have entrepreneurial DNA locked inside of them; they just don’t know it. Managing a classroom and managing a business have many similarities.

8. What advice would you offer a current teacher who is looking to make a career change to outside of the classroom?

To take the leap from classroom teacher into the entrepreneurial world is exciting and also daunting at the same time. My advice is to find out as much as you can about starting a business before quitting your teaching job. If you can manage to teach and work on the business, that puts less financial stress on you. Consider taking the six week online course I co-created called Teacher Entrepreneur School. If you are leaving teaching to pursue money this can be a risky proposition. I became a teacher to impact students. My purpose was clear. I knew that anything that would take me out of the classroom would need an even bigger purpose. A purpose that would impact society on an even larger scale. Check in with your motives and purpose before you leave the classroom.

After teaching for 10 years, Sheila launched Teach Happy Membership in January, 2015. Teach Happy Membership is an online community of teachers from around the world. The core mission of membership is to equip teachers with strategies to fight burnout. Teach Happy Membership offers positivity, support, classroom success strategies, and daily motivation. In October of 2015, Sheila also founded iteachtvnetwork, the first live streaming Periscope network of teacher professional development, and in January, 2016, Sheila cofounded Teacher Entrepreneur School, a 6 week course geared towards teachers who want to launch a business. You can find Sheila on her website, or on these social media channels:

Instagram: @sheilajaneteaching
Facebook Group: Teach Happy Friends
Business Facebook: Sheila Jane Teaching
Periscope: @sheilajteaching


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