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When I left the classroom in 2015, I started my journey into doing independent contractor education work through hourly Home and Hospital tutoring with a public school district until I had to move to a more rural area.

Since then, I’ve worked multiple other nontraditional education jobs with multiple online teaching companies (VIPKid, GoGoKid, and Outschool) as an online ESL teacher and formal mentor, as well as independent tutoring in-person.

Over the years, I’ve gotten better at keeping track of my income, setting my own work hours, and finding other like-minded online teachers. I’ve also started branching out into new endeavors, such as creating this blog and a personal teacher brand.

Here are 5 of the biggest mistakes I’ve made so far as a “teacherpreneur” and what you can learn from these mistakes wherever you are in your journey!

Coming soon will be a new post of my experience with 8 teacherpreneur jobs & activities in 2020! Subscribe or join my online teacherpreneur Facebook group for notifications on future posts.

The 5 Biggest Mistakes I’ve Made in 5 Years of Working Nontraditional Education Jobs

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Putting All My Eggs in One (Or Two) Baskets

Although I was content and making steady income with the online education jobs that I held over the past few years, I was always at the mercy of a specific school district or company (except for a little bit of in-person independent tutoring I did locally before moving).

The problem with independent contractor work is that you’re bound to the conditions of the company. When someone else has control over your pay structure, access to clientele, and more, there’s always the looming possibility of drastic changes or losing your income completely.

While working as a Home and Hospital Teacher in 2016, I started also working for VIPKid in the mornings. Once I moved, I was able to make a steady income working only for VIPKid as an ESL teacher and a Mock Class Mentor.

However, changes in booking rates and pay slashed my income to 25% of what it was the past few years.

Money Now Vs. Later

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A huge issue I’ve experienced is not knowing the best way to balance making money now vs. doing activities that could potentially pay off later but aren’t guaranteed.

For the past 19 years (minus the 2 years I was a classroom teacher), I’ve worked hourly jobs, so it’s hard to break that mentality of needing to see the financial benefit of work sooner rather than later.

Diversify With Long-Term Goals in Mind

All of my education work the past 8 years has been live teaching, which I plan to continue doing in some capacity.

However, I’m not able to sustain the energy to be an engaging teacher for long periods of time.

I wish I had previously diversified and spent time on both active teaching and non-live/more passive income.

In education, there are lots of options that I’m trying out to varying degrees. Some examples include Teachers Pay Teachers products (so far I’ve only listed one freebie a year ago), Etsy products, blogging, and more.

Not Establishing an Online Presence Sooner

About 4 years ago, I started trying to create a personal website about my education and teaching experience but gave up.

I wish I hadn’t!

Now that I know I want to work in this field long-term, one of my biggest regrets is not creating some type of online teacher presence sooner.

Establish a “Brand” and/or Your Own Corner of the Internet

My first few posts on my online teacher Instagram 1.5 years ago!

Your online “brand” could be:

  • Your name
  • A “catchphrase”/brand related to yourself
  • A brand related to the work you do

Whatever you choose, it helps for it to be uniquely “you” and eventually not limited to any one company, social media platform, etc.

A few simple ways to start can include:

  • A complete LinkedIn Profile
  • Some virtual presence, such as:
    • A website
    • A blog/YouTube channel/Podcast/etc.
    • A social media account (I’ve met lots of great online teachers on Instagram)

I was extremely apprehensive initially about putting myself out there online, so I decided to make this “teacher brand” and started out not showing my face for almost a year. I posted pictures, quotes, etc. until I felt comfortable attaching it to me! I’m also mindful of what I do and don’t share to set healthy boundaries.

Keeping Track of your Experience

Whether or not you’re ready to put yourself out there online, it’s helpful to keep track of what you’ve done so far.

Beyond just an updated resume, some online teaching experience to have on hand includes:

    • The companies you’ve worked for, certifications you’ve earned, etc.
    • Your skills and other teacher-related experience
    • A few glowing parent reviews you’ve received
    • A sample of any lessons, materials, etc. you’ve created

In the field of nontraditional, online education jobs, opportunities come up quickly. It’s a lot easier to jump in and apply to something when you have a portfolio of sorts of your experience.

Being Disorganized

I’ve always been naturally cluttered and have to make a conscious effort to be organized.

One of my old online teaching setups – note the toilet paper roll to hold props!

As such, I’ve had to redo work and material that I’ve completed in the past (such as teaching materials, researching websites, etc.) because I can’t find them.

I’m learning that not devoting time to organization hurts my work in nontraditional education jobs. I’ve had to spend way more time creating materials, trying to find things, etc., which lowers my hourly rate for the work I do.

Dedicating Time and Resources to Organizing

I eventually prioritized at least getting a little bit better at organizing and creating systems.

To improve in this area and reduce stress due to clutter, I’ve started to use some physical and online organizational tools to improve my work efficiency, which allows me to devote more energy towards actually teaching and creating! 


Lack of Community/Professional Network

Once I started working nontraditional education jobs, I didn’t have any in-person coworkers.

It took me a while to make a conscious effort to find online teacher communities as I tend to work solo naturally.

Once I did, it added tons of value to my online education work and motivates me to keep growing and trying out new opportunities.

If you want to find other online teachers, keep an eye out for teacher groups on either Facebook, Instagram, Reddit, YouTube, or other platforms that motivate and inspire you – check out more details about how to find valuable online teacher communities!

No Long-Term Vision

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Up until recently, I didn’t exactly know what my work goals were in the long-term.

Do I want to keep doing online education work?

I know now that the answer is YES!

I enjoy online teaching and self-employed education work, so I’ve started to try to create more long-term oriented goals and habits.

Sometimes I feel overwhelmed by the number of options out there, but now is the time to try different opportunities out!

MY GOAL: To try to have a mix of live and non-live education work and be at least 50% independent from any one company.

Bonus: Trying To Do Everything Myself

This category is a bonus because…

Time will tell if this strategy is a mistake or not.

I created and manage this blog & website, my different social media accounts, and many of the pictures and graphics I use. I’m also working on TpT products without any outside help.

I know that trying to “do it all myself” slows down my progress and growth. However, I’m trying to reduce costs and see how much I can do on my own. I know I’ll probably have to outsource some work eventually!

Have you made any of these mistakes while working in nontraditional education jobs?

Related Resources

  • Subscribe here for online teaching tips, resources, and posts related to mindfulness!
  • Join my Facebook group for support and resources on your “teacherpreneur” journey.
  • Want to know more about teaching ESL online with VIPKid, Outschool, or other companies? Check out my FAQ on VIPKid and Outschool. If you’re not sure where to begin, email me at for free resources and guidance.
  • Connect with me on Instagram, Facebook, or over email for regular tips and updates.



The Introverted Online Teacher


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  1. I admire you for posting your clutter! Your bit about making time to organize is something that I have also learned over the years. I have become much more aware of the need to take time time to organize, especially when it comes to my computer files. I have also learned to develop better systems for my work flow. It’s still a constant work in progress, but I remind myself that the organization is also part of the job. I see it like doing the dishes after cooking! 🙂

    1. I completely agree about organization being part of the job, that’s something I refused to acknowledge for years because I didn’t want to spend the extra time (and usually some money) to make it happen. I’ve been working on my computer files now also – thank goodness for Google drive! 🙂

  2. I need to get better at staying organized with my experiences!! Such great actionable ideas all throughout the post- thank you.

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