12 Reasons Why I Started My Teacher Side-Hustle

12 reasons why I decided to finally pursue my teacher side-hustle, and why I was so eager to make it work.

Maybe it’s the millennial in me, or maybe it is the fact that there are probably 1000 jobs opportunities now that didn’t exist when I chose to become a teacher, but I felt stagnant. 

Attacking my teacher side-hustle helped me feel like I was moving forward.

I am a good teacher. My mom claims that I am a great teacher, but I have enough modesty to place myself honestly in the ‘good teacher’ range. 

As a teacher, I am willing to try new things. I am flexible and an eager learner, and I do what I’m told, join committees, run PLCs, am *mostly* on-time for meetings, and my students really enjoy the project-based learning approach that I swear by.

I am a good, maybe even great, teacher.

But just because you are good at something, doesn’t mean you love it.

I don’t love teaching anymore. 

I love

• learning about online business. 
• dreaming about my own businesses. 
• dreaming about what my life could look like if I ever left the classroom. 

I love this dream so much, that a year before starting my teacher side-hustle, I made a list of what I want most from my life. The list lived in the ‘Notes’ app on my phone, and I looked at it frequently.

12 Reasons I started my teacher side hustle

#1. I want freedom

I want to be able to move about my day freely. Teaching is very structured, which works well for a lot of people, but I am an adventurer (seriously, I took a personality test, and that was the result I got). The motto of the adventurer is “Don’t box me in.” 

#2. I want to take my kids to school and pick them up.

This one was big for me. My husband travels for work on occasion, and if I continued teaching, our life was going to get really complicated. 

We didn’t live in the same district as the one I taught in, and open enrollment was not an option, so my son would go to a school across town from mine. Our schedules would be similar, but not exactly the same, and we were going to have a lot of issues with getting him to and from school. Most likely,  he was going to have to switch daycares and go to a before and after school program. 

To make it all work, I was also going to have to give up my extracurricular programs to do two drop-offs and pick-ups each day as my younger children would be at a different preschool. Refer back to #1 on the list to understand why this would drive me nuts. 

The imminent date of my son entering kindergarten provided the deadline that I needed to move my business ahead much more quickly than I originally planned.

#3. I want to chaperone a field trip.

To chaperone anything with my son, I was going to have to take personal days. It’s not that I really want to chaperone a bunch of little kids, but I wanted the option to make that choice myself. Being a teacher limited that option. 

Even if I wanted to be gone, being absent as a teacher is really hard. We are in a profession where it literally takes another human being to cover for us if we are sick or on vacation. Most of the time, it is easier to go to school than to create a sub plan.

#4. I want to go to NYC at Christmas time.

Seriously. I live and dream by Hallmark movies, and I want to ice skate at Rockafeller Center, see the giant Christmas tree all lit up, walk the streets and see all the lights, and spend some time in Central Park. I don’t need much more than that,  but I don’t want to miss seeing my family to do it, and if I go during the holiday break, that is what I’m sacrificing. 

#5. I want to travel in the fall.

Teachers typically don’t travel in the fall for a couple of reasons. 

It is the beginning of the year, and being gone right away would do mad things to the delicate balance of our classrooms, and nobody wants to use up all their personal days at the beginning of the year. We have to save those in case our kids are sick a lot or we want to go to a special conference later in the year, or we are invited to do a long weekend with family in February.

I want to be able to go somewhere beautiful in the fall. Somewhere where the leaves are changing color, the air is cool, and the pumpkin spice fills the air. I mean, a girl can dream, right?!

#6. I want to live debt-free.

My husband and I have worked hard the last couple of years to pay off our debts. We want to have financial freedom and the security that goes with living without debt. We have worked really hard at this, and I know that if I work really hard in my business, that I can get us to the full debt-free life that we dream about much more quickly than my teaching income would allow.

#7. I want to have control over my potential.

I can’t believe I wrote this. Not because I’m ashamed or think it’s dumb. Rather, because it is crazy brilliant. 

Teaching was starting to feel limiting to me. The political nature of teaching felt like I was at the mercy of others constantly. Our teaching salary was decided by a board room, and literally laid out in a pretty little chart. If I wanted to make more money, I had to get more education, and then when I maxed out that line, I could continue to get my $1,000ish raise every year until retirement.

When we were trying to get out of debt, I struggled to figure out how to make it happen faster, but I got paid one time a month, and it was the same the entire year. 

Now, as a freelancer, if I need an extra $1,000, I go make an extra $1,000, or I pitch a new client, or I consider taking on a few more hours for current clients. I am in control. It’s my business and my choice of how much I work and how much I make. 

#8. I want to write a book.

#9. I want to publish no fewer than 10 plays.

I’m lumping these two together because they come from the same creative place in my heart.

I love to write. I like creating something that an audience can read. 

I’ve already published one play, written two others (but I haven’t pitched them yet). I love watching other people laugh and respond to my words as they are acted out by actors on stage, and I love to read clean teen fiction novels that are simple and sweet. That is what I hope to write someday. Clean, sweet, heart-warming stories that make people feel loved and happy. Maybe I’ll even write a Hallmark movie script…I’ve got a thing for all things Hallmark movies.

#10. I want to take at least two (hopefully more) trips a year with my husband.

My husband is my favorite person.

Fully aware that this may sound cheesy, I’m just going to state it here. My husband is my soulmate. We met on a theatre stage in college, but he took his theatre major and turned it into a job in agriculture…long story, and I became a theatre teacher who worked on 4 plays a year. Together we have 3 kids and very little time to ourselves. 

We joke that for about three years, we didn’t see any movies together. He went to movies by himself when it was his turn, and I went to movies by myself when it was mine, but we didn’t go together because one of us is always busy or watching the kids. 

I want very little more than spending more quality time with him. He is my favorite.

#11. I want to own our home outright.

By the age of 40. Not kidding. 

I am writing that here for all the world to see, but I want this so bad. 

We have dreams of building our dream home on an acreage nearby, and I am going to do everything I can to make that happen, AND pay the whole thing off by the time I am 40. 

I’m a farm girl, and I have a good work ethic. Hard work and confidence will make this happen. 

#12. I want to spend more time on my parent’s farm.

Speaking of being a farm girl…

Every fall I spend all of my weekends riding around in a tractor and harvesting grain. 

I do it because being in a tractor on the farm is truly my happy place. You city-folks out there may not understand this but looking over a field at sunset is magical. 

I built this business in the tractor. You know those hundreds of podcasts I listen to…I listened to most of them with the hum of the John Deere in the background. 

If I started a teacher side hustle in the online business world, I am able to make my own schedule, and I am completely location independent. I can work from anywhere. Our house, a hotel, or our family farm. 

My goal is to spend my days taking stress off my dad’s shoulders and helping him with his own entrepreneurial journey as a farmer.

I knew it was time to start my teacher side-hustle.

These are the things I want. Could I do these things while teaching? Maybe. I’d have to save up my personal days, and give up my extra-curricular theatre activities, but maybe.

I’m not okay with ‘maybe’ though.

I’m ready to make these things happen, so I dug in. About a year and a half after I made this list on my phone, I built a successful business as a virtual assistant.

Now I can check #7 off the list. I know now that I have complete control of my own potential.

If you, like most people, have no idea what a virtual assistant is, check out the posts in this series: What is a VA and why is a great side job for teachers.

The posts in this series include…

#1: What is a Virtual Assistant is and who is hiring one? (You’re on this post now)

#2: What tasks are virtual assistants hired to do?

#3: How can a VA specialize?

#4: Why do teachers make great virtual assistants?

#5: 10 ways to get started as a virtual assistant today!