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Jane Morris Shares Her Teacher Misery Journey

Written by:

Howard Tillerman is the Chief Marketing Officer for Step By Step Business and an award-winning marketing professional.

Jane Morris Shares Her Teacher Misery Journey

Jane Morris is the mastermind behind Teacher Misery, a platform that has become a beacon of solidarity and humor for teachers worldwide. Teacher Misery, crafted by a team of current and former educators, is dedicated to making the teaching experience a bit more bearable. It’s a space for teachers to share their challenges and find camaraderie in the often-overlooked realities of the profession.

Jane’s journey began in 2007 as a high school English teacher, filled with aspirations to inspire and change lives through literature. However, the stark realities of the profession quickly emerged, revealing a path far more daunting and exhausting than anticipated. In search of solace and understanding, Jane turned to social media, using her wit and sarcasm to voice the unspoken frustrations of teaching. To her surprise, she discovered a vast community of educators sharing in her sentiment, all seeking a haven to express their own teaching trials and tribulations.

This interview delves into the genesis of Teacher Misery, exploring how what started as a personal coping mechanism evolved into a robust community with over 450,000 followers and four comedic teaching memoirs. We’ll uncover the insights and strategies Jane employed to cultivate this platform, offering invaluable advice for aspiring bloggers and those wishing to create impactful online communities. Her story is not just about the challenges of teaching but also about finding humor in adversity, building support networks, and giving a voice to the often-unheard narratives of educators.

Jane Morris

Introduction to Jane Morris and Teacher Misery

I grew up on Long Island, New York. I probably should have been a comedian, but I was raised by a practical single mother who always told me that teaching was a great job with great benefits. I did standup comedy in college while I pursued my teaching and English degree from the State University of New York at New Paltz. After that, I moved to the D.C. metro area to start my teaching career. 

The Genesis of Teacher Misery

I always had a knack for relating to teen angst more than most people could, but as soon as I started teaching, I knew there was no way I could do it long-term without becoming sick or crazy, or both. I needed an outlet for all the nonsense I experienced daily, so I started venting on social media under the pen name Jane Morris. 

Success in Self-Publishing and Growing an Audience

My following grew very quickly because it became a place where teachers could feel relief that someone was telling it as it really is and connect with others who were experiencing the same misery. Along the way, I got my Master’s Degree in writing from Johns Hopkins University and started to write about my teaching experiences. I self-published three books: Teacher Misery, More Teacher Misery, and What It’s Really Like, and they are all bestsellers. I have sold around 100,000 books, which is virtually unheard of in self-publishing.

Jane Morris
Jane Morris

Authenticity and Organic Growth

My ideas are completely organic, and that is what draws people in. I have always been completely authentic about how my day went, what I was feeling, what I found funny or crazy or awful, etc. If I sat in my car in tears at the end of the day, wondering if I could be a teacher for even one more day, I posted about it. The support I received and encouragement for truth telling was huge for me.

It allowed me to continue teaching for 17 years, whereas if I didn’t have the outlet and supportive community I created, I probably would have quit in my first five years like most teachers do. Currently, I get so many messages from teachers around the world that I always have something to post about, though it’s harder to find the comedy in it these days. 

Diversifying Income Streams and Online Presence

I have multiple income streams, and most of them are only as successful as the amount of energy I pour into them per month or year. The more I talk about my books on social media, the more they sell. The more I focus on getting web traffic, the more money I make from that. I also have a few major ad campaigns on my social media that pay well, but I’m very picky about what I advertise for and will only take on campaigns for things I actually like myself.

I have an average of 100,000 visits to my site per month. I get a lot more action on my social media. On Instagram, my posts have a reach of around 2 million. I also recently started a podcast which has excellent stats already. 

Marketing Strategies and Building Relationships

My #1 marketing strategy is you have to generally care about what you are talking about, feel passionate about it, and be extremely consistent and relentless about posting. Also, don’t underestimate the power of relationships with those you might see as competitors. Contact them instead of trying to beat them and see if you can help each other grow. Being kind and following through on your word, even if it doesn’t get you anything in the meantime, goes a long way toward success. People will want to help you in the future. 

SEO Strategies and Content Creation

I’m only now starting to take SEO more seriously, and I’ve hired an SEO expert I have an excellent rapport with. He gets what I’m trying to do and cares about it as well, so for both of us, it isn’t just about making money but helping teachers as well. I think what I’ve done has worked so far — writing genuinely engaging content. The number one search term from which I get the most organic traffic is the name of my site, so I must be doing something right. 

The SEO person I work with gave me a big list of keywords as possible topics. If I can work one into what I’m writing about or if it sparks my interest, then I write about it. When I have to write about something I don’t care about, it becomes painful to create and isn’t great content. I have SurferAI to help me with keywords, too.

Navigating Career Transitions and Business Strategy

Having left my career just a few months ago, I’m a little over the place regarding strategy and process. Up until now, I have just written and created whatever I felt inspired by at the moment. Now, I am inspired so much and often overwhelmed by the amount of things I could be working on that I get confused. Usually, working on whatever excites me the most at the moment leads me in the right direction. I am most excited by the gift shop I recently opened called teachermiseryshop.com. It is full of small, snarky goodies that any sarcastic person would appreciate.

I have a large email list, and I grow it by offering good freebies. I give away things I could easily make money on, like full digital planners that I sell in print for $30, but I feel it is a good exchange for a good contact. 

Personal Insights and Work-Life Balance

I turned 40 this past January, and just a few weeks before that, both of my beloved schnauzers, Rosie and Pearl, had to be put to sleep. Then, a week after my birthday, I had to leave my teaching career of 17 years due to a PTSD diagnosis and related health problems. I was so scared of not having a reliable paycheck that I jumped into working with someone I didn’t know full-time while ignoring my instincts that I shouldn’t trust her. Things weren’t what they seemed, and I was ignoring my usual ways of making money. I turned out to be right about this person and learned a big life lesson, so the first half of my 40th year of life had quite a few sucker punches, but I absolutely feel that it toughened me up for the second act of who I am meant to be, which will but much more interesting and lucrative!

It’s constant. I’m writing and researching for about six hours when my kids are at school or camp. Then I work for a few hours after they go to bed and whenever possible on the weekends. I’m not doing it because I have to but because it allows me to be creative and work through my issues in a healthy way, and I love it.

I am not a big fan of taking the advice of others as far as how you live your life or run your business. When I read articles or books about that stuff, it just gives me anxiety about how I should be doing things differently or that I’m not doing enough. What I find the most helpful are writers and speakers who encourage you to be yourself, follow your instincts, stop caring about what others think, and forge your own path to success by doing what you love. Authors in this arena would be Jen Sincero, Case Kenny, Russell Brand, and Damien Echols.

Essential Tools for Content Creation

I use Canva multiple times per day to create posts, memes, newsletter images, etc. I try not to stray too far from their template design and trust them in that way because I can get too creative, and it looks pretty amateurish. I always have Grammarly turned on, and even though I’m an English teacher, I often need suggestions that help me be more concise. Kindle Direct Publishing has helped me self-publish my books easily and for free.

Challenges and Learning Experiences

I think a challenge for me is taking on too many projects, having too many ideas, and not knowing what to focus on. You can’t work on too many things at once and do them well, and I think I tend to take on a bit too many things and overwhelm myself. 

When I first left teaching, I tried to write a new article every day, optimize it, start a podcast, start a support group that meets multiple times per week, publish two new books, work on a live show, and open an online store. In the morning, I would jump from one project to another, not doing any solid work on anything. I’ve scrapped some of those and put others on the back burner so I can concentrate on creating strong content for my site right now.

Community Building and Dealing with Competition

My most important accomplishment is growing my online following organically and creating a community of people who are genuinely there for each other through humor. 

I wish I had been willing to push through the negative feelings a competitor gave me and not let them get to me. As a writer and creator, I don’t even like viewing anyone else as a competitor, but there is one “brand” that was adversarial from the start. They were the only ones in the “edu-influencer space” (insert eye roll) who wouldn’t play nice with everyone else. Instead of making partnerships, they consistently stole ideas and climbed to the top by stepping on the faces of true creators and real classroom teachers. I have let this get to me sometimes, and, as you can see, it still bothers me a lot. I used to let it hold me back from building out anything they were also working on because I didn’t want to be around it or be seen as copying them. I have to do a lot of catch-ups now, and it feels silly. Karma is a thing, and how that will be played out for others is not my business. 

Financial Management and Key Mistakes

My biggest mistake has been not being a good bookkeeper because that stuff causes me anxiety. The irony is that the more you keep up with your financial records and taxes, the less your anxiety will be about it!

Final Advice for Aspiring Content Creators

Two words of advice, and they’re as simple as can be: keep going. If you love what you are doing and believe in it completely, then don’t worry about what anyone thinks or how much financial success you are having at the moment. Just keep going. 


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Jane Morris Shares Her Teacher Misery Journey