How to Fail at Teaching: An Introduction

As an educator in and out of the classroom since I first got my substitute teaching credential in 2002, I have failed at teaching more times than I would like to admit. While I have also had plenty of success at teaching and made an uncountable number of connections with wonderful young people, it’s these failures that I am curious to explore in a series of essays. My most recent attempt at teaching ended abruptly two weeks before the end of the school year, when after a mostly pleasant year in the classroom in which I felt like my soul had been reawakened after five years of working from home as a marketing professional, I was fired for telling a parent and tutor that the tutor had rewritten the student’s perfectly acceptable work for their final and requested that the tutor refrain from doing the student’s work. As is always the case, the story started long before that, but that was the straw that broke the administration’s back. 

While I briefly interviewed for other positions, I realized that I’d lost the heart to fight for this career that I loved. First of all, teaching was too often for me, like chasing a man who would never love me back. Second, I am pretty stuck in my values and I’m not sure it’s possible to show up as my authentic self as a teacher, even though ironically the classroom is where I feel most like myself. Writing allows me to show up as my whole, fallible self, it lets me express my own truths that my teacher self struggled to find words for. 

Maybe this series of essays will help me merge teacher and writer to build a better version of myself. Maybe it resonates with other teachers or others who have attempted and failed at a career.