Why I Am Grateful To My Worst Boss

Why I Am Grateful To My Worst Boss

It has now been four years since my very short excursion into the world of education. The wounds have skinned over enough for me to talk about it, and so I wanted to take today to talk about why I am grateful for the worst boss I ever had.

I’m going to call it a mid-life crisis. In 2014, I decided that I needed to give back, and so I enrolled in a teacher training course, secured my provisional teaching license in math and started interviewing. I ended up at a job with my local high school, the school where my daughter currently attends.

I lasted one year. Education is not for the faint of heart. The first week I dealt with bullying, cheating and teenage pregnancy. Throughout the rest of the year I dealt with hostile parents, violent students, lack of handicapped accessible rooms, and a bomb threat made in my class. I did this while working with inadequate supplies, a school that had teachers leaving in droves, and the boss from hell, my principal.

Rose Colored Glasses

When I started at the school, I knew I would have to pay my dues. Every job has it. But I knew I could teach, and my teaching course had prepared me. What they didn’t prepare me for was the administration. I had assumed that as long as I could demonstrate the students were learning, everything would be fine. I was sadly very wrong.

I will say that I wasn’t aware of the fact that the math department had an 85% turnover rate in each of the past four years when I got there. Or that other teachers were leaving in droves, some of whom had taught their entire careers at the school. Had I known that, and steered clear, I would probably still be teaching today. At the same time, if I was still teaching today, I wouldn’t be working on a cutting-edge project in data science.

Lesson learned: always investigate turnover rates when looking at a new job.

The Performance Plan

I’ve been in the business world a long time. I know how to play the game. But I was completely unprepared when 15 minutes (and I mean that literally) after the email went out about the math support person going on maternity leave, I was put on a performance improvement plan with the other new teacher in the school. And in spite of the fact that we were two individuals with two different class loads with two different backgrounds, those performance plans matched exactly…all 43 points of them.

I knew from my business experience that documentation is key. So I enlisted my teaching mentor to go with me to all meetings with the principal, and I recorded everything on my phone. I also sat down with each of those 43 points and came up with specific actions that would meet each of the points.

Lesson reinforced: document everything in a media that is exact, like recording, or by saving all emails.

Photo by Rubén Rodriguez on Unsplash

Being “Tough Enough”

The six weeks that followed were hell. I was working 80 hour weeks, trying to hit each of the points. The math specialist brought in to observe me from the district told me in a meeting with the principal that I was on the right track and there was no need for the performance improvement plan. This helped to keep me going when I was exhausted and dispirited.

At the end, I had hit every one of the agreed-upon actions, and presented a packet to the principal with documentation of each. It had been tough, but I knew that I had improved. My scores had increased. My classroom management was solid. My students were engaged. I felt like I had taken the typical first three years and learned everything in one.

At that last meeting, my phone was still recording as the principal stood and shook my hand, telling me he would recommend me for my permanent license. And then he uttered the words:

“I’m sorry I had to put you through that. I had to make sure you were tough enough to teach.”

Yes, I have that on a recording.

I resigned two days later. I knew that if I was to continue teaching in that district, I would have to teach under him for two more years before I could transfer.

Lesson reinforced: I do not have to be demeaned or prove anything to anyone.

Why I Am Grateful

There are many reasons I am grateful to this principal, who was the absolute worst boss I ever had:

  • I was reminded I can do anything I put my mind to. It may be hard, but I can manage. I can still take on incredibly hard tasks and flourish.
  • I was reminded that my years of business experience are valuable. Career switchers like me are often looked down upon by career educators. But my years in business are valuable, not just with the application of what I was teaching, but also in working with people.
  • I am now paid according to my experience and skills. What teachers get paid in the US is scandalous. In Virginia, it is even worse, because as state employees in a right-to-work state, teachers are not allowed to have a union. There is no collective bargaining. My job in IT pays almost three times what I made as a teacher, and I don’t have to work nights and weekends. Oh, and I also get to use the bathroom whenever I choose.
  • I was reminded that respect is important. Respect between individuals who are working together, regardless of age or job role. A job without respect is soul-killing. There are other options.
  • I was reminded I have choices. I don’t expect to ever have a boss from hell again. And should the worst happen and I’m laid off from my IT work and unable to find anything, I can still teach. There was a time when I felt trapped and without options. Having options is an important safety net for me.


The principal is now gone from the school. The new administration is positive and has the interests of both teachers and students at heart. The turnover rate is slowing. I’m grateful that all of this has happened, especially since my daughter is a student there. And I’m also very glad I had the experience, because it makes me appreciate my daughter’s teachers in a way I never could before. And in spite of a terrible year, I was reminded of a lot of very important lessons, for which I am truly grateful.

Photo by Rubén Rodriguez on Unsplash