This blog series is meant to shed light to the world of edupreneurship and show an honest, behind the scenes look at trying to make it in this space. If you are just starting out, or on the verge of starting, I hope my experiences help you navigate this space with confidence and clarity.

I knew early on that I wanted to do work in education outside of my own classroom. My first years of teaching were stifled by rules, mandated curriculum, and endless test prep. I needed an outlet for my creativity and an opportunity for autonomy. Along with that, debts were rising and teaching salary was not. I needed something more!

Part time jobs and side gigs were not fulfilling me in any way. I was still not making the money I needed, but even worse, I was doing things I did not enjoy. Having obtained a masters and (at that time) pursuing a PhD in education, I did not want to wait tables or stock stores. I wanted to be in the education field, working with students and other educators.

After many conversations with my incredibly supportive wife, I decided to make my living entirely in the education space. Teaching in Florida, it was clear that this challenge would be enormous. Salary scales were disappearing, student loan debt was looming, and there seemed to be little opportunity for growth. No matter, I was going to make it!

My side-hustling career was officially started. But how to make money in education? How would I increase my earnings in my area of expertise? I began by taking every opportunity I could in my own school. I began coaching, teaching extra classes, and signing up for any paid clubs or organizations to sponsor. This was it. Work harder. Work longer. I’ll make it!

It didn’t take long to realize this was not the answer. A year of paid coaching showed that the extra money I gained went mostly to extra food and coffee, since I was at the school from dark to dark (6:30 am to 7 pm+ most days). The menial salary increase was destroying my health and the time I had to spend with family and friends. (pro tip – do not sacrifice your health & life)

Meanwhile, clubs and organizations weren’t paying off at all. The only opportunities my school hosted were being given to faculty with seniority. Try as I did, there seemed to be no way to crack this code. The result was a year spent overworking myself while continuing to fall behind financially. I was at the verge of giving up on my career in search of livable pay.

My breaking point led to the path to edupreneurship. Since there were no answers to be found in my school, I had to be creative. It was time to search outside of my school for opportunities. With my wife’s blessing, I spent a year seeking out opportunity anywhere within the education space.

Here (in order) were my first set of failures.

1. Creating reading passages and quiz Q&A’s for a new test prep company. I made around 15 cents per hour when all was said and done. The work was completely disorganized and unstructured. The company did not make it and my time there was short lived. I left as soon as I realized how little my earning potential actually was.
2. Online Tutoring for a tutoring company. I was all set to earn lots of money tutoring students. However, I failed to find any clients or understand how to market myself in that space within the company. I started and finished with a $0 profit.
3. Posting Curriculum on Teachers Pay Teachers. I took my best worksheets and most creative unit plans and started posting them on the TPT store. Again, I did not understanding the marketing or branding aspect to it. Somehow I thought that I could post excellent content and it would get recognized. I started and ended my store (or at least I think I closed it, it might still be there) with another $0 profit.
4. Creating Q&A’s for a reading comprehension program. I thought that I would give Q&A’s another shot. It was easy work in terms of making higher order questions. Again, I found that my work was worth very little financially. While I cranked out plenty of Q&A’s, my paychecks were coming out to the $15-$30 monthly range. I knew this could not be a long term answer.

I start this blog series here, because I want you all to know the series of failures I had from the beginning. That will be a consistent aspect of these posts. My failures have continually led me to amazing experiences and larger opportunities. I look back with gratitude for all of these moments that pushed me outside of my comfort zone. Those first four attempts at side hustling taught me so much of what I didn’t know. That path would lead me to a much bigger opportunity…

Which I will tell you all about in part 2 of the series! Stay tuned my friends.

I would love to hear from you! Tag me on social media (@kevinleichtman) and let me know what your first side hustle was in education. If you haven’t started yet, tell me what you think your first side hustle will be. Every journey starts somewhere and I would be honored to hear yours!