Mobile Menu

  • Home
    • About Lindsay
  • Blog
    • English Language Arts
    • Effective Teaching Strategies
    • Technology in the Classroom
    • Self Care for Teachers
  • Free Grading Guide
  • Grading Reset Course
  • TpT Store
  • Menu
  • Skip to right header navigation
  • Skip to main content
  • Skip to primary sidebar

Before Header

  • Facebook
  • Instagram
  • Pinterest
  • YouTube

Lindsay Ann Learning English Teacher Blog

  • Home
    • About Lindsay
  • Blog
    • English Language Arts
    • Effective Teaching Strategies
    • Technology in the Classroom
    • Self Care for Teachers
  • Free Grading Guide
  • Grading Reset Course
  • TpT Store

Starting a Teacher Side Hustle Saved My Career

Home » Blog » Self Care for Teachers » Starting a Teacher Side Hustle Saved My Career
teacher-side-hustle

May 16, 2019 //  by Lindsay Ann//  5 Comments

Sharing is caring!

  • Share
  • Tweet

english-teacher-side-hustle

Before my teacher side hustle…

It was December of 2015, and starting a teacher side hustle was the last thing on my mind.

I was nine months pregnant with my second child.

I sat in my office crying, overwhelmed with expectations (administration, students,  colleagues, not to mention my own) and feeling like I could never fulfill them all. In other words, my teacher stress level was at an all-time-high.

teacher-side-hustle-benefits

I was completing paperwork, emailing parents, trying to grade the latest pile of essays, and gather resources for my upcoming maternity leave… This was all on my “lunch” break.

It’s no surprise that I wanted to quit teaching, or at least go part-time. Do not pass go, do not collect $200, hasta la vista muchachos.

This feeling wasn’t new. I’d had it every single year since I could remember.

But I was stuck. I held the family insurance, had put in 13 years already, had my national board certification. What else could I do? I knew that I wanted to keep my summers off to be with my kids, knew that I didn’t want to do multi-level marketing, knew I didn’t want to add-on VIP-kid tutoring in the wee morning hours.

So, I told myself to suck it up. There was no “get out of jail free” card.

Classic signs of teacher burnout

I now realize that I had classic signs of teacher burnout. Teacher stress is an epidemic (I hyperbole not!) that should be on the mind of every educator and administrator.

It’s not just “teacher tired” and it’s not just for first year teachers. Teacher stress is one of the major causes of teacher depression and anxiety. Incidentally, it’s important to recognize and talk about this growing trend.

starting-a-teacher-side-hustle

You shouldn’t have to tell yourself to just “suck it up” and “stick it out” as a teacher. Most certainly, just going through the motions means that you’ve lost your teaching joy.

13 Teacher Burnout Symptoms (in no particular order)

  1. Inability to see the big picture
  2. Lack of focus and goals
  3. Lack of self-care
  4. Always feeling “behind”
  5. Inability to enjoy day-to-day student interactions (or day-to-day interactions in general)
  6. Choosing to focus on negative vs. positive
  7. Updating your resume and LinkedIn profile with “transferable skills”
  8. Calculating the number of years until retirement with many wistful sighs
  9. Consuming waaay too many cookies
  10. Loss of intrinsic motivation
  11. Less flexibility and openness to change
  12. Losing your cool (with students, family members, even yourself)
  13. Feeling like there’s no “off” switch for “teacher brain”

Starting a teacher side hustle

In retrospect, I disliked teaching because it consumed my life. I met with students during my plan periods as well as before and after school. I volunteered for extracurricular activities like yearbook advising and the school newspaper. I did waaaaay too much grading outside of contractual hours.

Something had to change. I wanted a life beyond teaching.

teacher-side-hustle

Getting Un-Stuck as a Teacher

I continued to surf the web looking for my “out.” After reading stories of success and listening to an encouraging YouTube video by Kayse Morris, I decided to try my luck on Teachers Pay Teachers. 

This wasn’t change, exactly. But at least it was something. It was a step toward getting un-stuck. 

I dedicated myself to learning the ins and outs of being a teacher entrepreneur. And you know what? I discovered that my sparkle was coming back.

“So when the world knocks at your front doorClutch the knob tightly and open on upAnd run forward and far into its widespread, greeting armsWith your hands outstretched before youFingertips trembling, though they may be”

– Anis Mojgani –

“Shake the Dust“

5 benefits of my Teacher side hustle

teacher-side-hustle

After three years, I still haven’t quit my teaching job, although it’s nice to know that one day I may have that option. Right now, I am thriving as a veteran teacher by focusing on what brings me the most joy and working smarter, not harder during the school day.

Beginning my teacher side hustle changed my mindset, taught me new skills, and saved my teaching career.

To sum up my experiences, here are five unexpected benefits of beginning my teacher entrepreneur journey.

1

Embracing Creativity

When I began to create digital teaching resources beyond the classroom, I re-discovered my passion. I honed in on what makes me MOST excited about teaching: instructional design. To clarify, I love the creative process. Lesson planning and resource creation are my jam. I’m always asking how an activity or lesson can have real-world application. If I can engage students, I feel on top of the world. I feel excited when I try new teaching strategies and share them with other teachers. 

Having TpT as a teacher side hustle played into my strengths. In focusing on what brought me the most joy as a teacher, I found satisfaction. Most importantly, as I focused on “what worked” for me in the classroom, I grew into a better teacher.

2

Learning New Skills

Who knew there was so much to learn as a ​teacher-seller of online teaching resources​?! 

Learning a whole new set of skills allowed me to feel a sense of accomplishment and pride. And it was especially rewarding when those skills started paying off!

3

Supportive Community

I’ve been so blessed to find supportive community beyond my classroom walls. “Find your tribe” is good advice for stressed-out teachers. My best tribe was beyond the walls of my brick-and-mortar school. I joined Facebook communities dedicated to teaching. I connected with educators from across the country. Signing up for an awesome course, Transform Your Resources, helped me understand how to be successful as a teacherpreneur and connected me to other go-getter teachers.  

english-teacher-side-hustle4

Boundary-Setting

Feeling “stuck” was my number one reason for teacher stress and burnout. I also lacked clear boundaries. I let teaching dictate my life, not the other way around. 

My teacher side hustle forced me to learn organizational skills and budget my time.

Teaching is a job that will expand to fill as much time as you’ll allow it to fill. I’ve learned to set firm boundaries with my time. I’ve also discovered different ways to manage grading, the English teacher’s ever-present friend. Classroom time is my time with students, so I’ve learned to make the most of it. As a result, I have a much better work-life balance. I’m re-energized and better able to focus in all areas of my life.

5

Dreaming Big

I now have a larger purpose as a teacher beyond the four walls of my classroom. 

I’m helping thousands of students across the globe. How cool is that!? 

I’ve learned that I can set a vision and dream big which excites me and fills me with hope for the future. In starting my TpT store, and then the Lindsay Ann Learning blog, I wanted a distraction at first. Then, I wanted to pay for a few household expenses. 

My goals grew from there. 

If you want to succeed, success will come.

You can set boundaries and enjoy teaching again.  

Click here to download a free workbook that will help you get started selling your teaching resources online.

Like me, you’ve got nothing to lose and everything to gain!

english-teacher-side-hustle

Sharing is caring!

  • Share
  • Tweet

Category: Self Care for TeachersTag: Back-to-School, ELA Skills & Ideas, high school ELA, middle school ELA, Teacher Evaluation, Teaching Hacks, Teaching Life, TpT, Work Life

About Lindsay Ann

Lindsay has been teaching high school English in the burbs of Chicago for 19 years. She is passionate about helping English teachers find balance in their lives and teaching practice through practical feedback strategies and student-led learning strategies. She also geeks out about literary analysis, inquiry-based learning, and classroom technology integration. When Lindsay is not teaching, she enjoys playing with her two kids, running, and getting lost in a good book.

Related Posts

You may be interested in these posts from the same category.

teacher-planning

10 Simple Ways to Streamline Teacher Planning

trauma-informed-teaching

Trauma Informed Education that Doesn’t Inflict Trauma on Educators?

teacher-burnout

5 Strategies to Combat Teacher Burnout

teacher-memes

Analyzing Teacher Memes

podcasts-for-teachers

8 Brilliant Podcasts for Teachers

concurrent-teaching

Concurrent Teaching…WTF!

first-day-of-school

First Day of School: How to Plan for Success

teacher-work-life-balance

Teacher Work Life Balance A-Z Guide

teacher-collaboration

How to Turn Your Teacher Collaboration from Zero to Hero

teacher-self-care

12 Incredibly Useful Teacher Self Care Items That You Need Now

grading-papers

Wondering How to Save Time Grading Papers? Read This!

Classroom Seating Chart Ideas for Teachers

Classroom Seating Chart Ideas for Teachers

Previous Post: « 31 Engaging Poems for High School English Class
Next Post: 70 Rhetorical Analysis Essay Topics for Secondary ELA rhetorical-analysis-essay»

Reader Interactions

Comments

  1. Carrie

    May 20, 2019 at 4:51 pm

    Wow!! Your post described ME so well!! I have done some research lately about teacher and school counselor burnout for my grad school classes in counseling. I love how you suggested remedies that helped you and some that were specific to creating your own online resources. I think that your post will help and encourage many people.

    A Fellow Go-Getter,
    Carrie Jones
    The Think Aloud Cloud

    Reply
    • Learning

      June 5, 2019 at 10:25 am

      Carrie, I’m so glad that this post resonated with you, and I hope it will encourage others, as well! I’d be curious to know any additional strategies you’d suggest for fighting burnout that you found through your research.

      Reply

Trackbacks

  1. Make Money Online Easy as a Teacher · Kayse Morris says:
    May 21, 2019 at 7:56 am

    […] Starting s Teacher Side Hustle Saved My Career […]

    Reply
  2. Why Teachers are Their Own Worst Frenemies | Lindsay Ann Learning says:
    November 9, 2019 at 1:07 pm

    […] Starting a Teacher Side Hustle Saved My Career […]

    Reply
  3. Teacher Side Hustle Jobs You Might Not Have Considered Yet · Kayse Morris says:
    September 7, 2022 at 4:08 pm

    […] joy while they are in the classroom will help them better the lives of the children in their care. We really love helping our teachers get their foot in the door with a side hustle before they make the decision to leave the profession […]

    Reply

Leave a Reply Cancel reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Primary Sidebar

Join me in the pursuit of engaged, dynamic classroom learning!

I’ve created a FREE guide with 20 of my best strategies for streamlined grading to help English teachers like you have more time to do what you love.

Get the Guide!

Categories

Latest Products

  • Late Work Submission Google Form Late Work Submission Google Form $3.00
  • Rhetorical Devices Activities for Google Drive & Print Rhetorical Devices Activities for Google Drive & Print $4.00
  • Distance Learning Google Form Student Survey Distance Learning Google Form Student Survey $3.00
  • Creative Writing Prompts Choice Boards Creative Writing Prompts Choice Boards $3.00
  • Slam Poetry Condensed Unit for Distance Learning Slam Poetry Condensed Unit for Distance Learning $7.00

Site Footer

  • Facebook
  • Instagram
  • Pinterest
  • YouTube

Copyright © 2025 Lindsay Ann Learning English Teacher Blog · Privacy · All Rights Reserved

40 shares