Learning through Failure

Last month, I was invited to participate in a principal forum at the Upper Valley Educators Institute (UVEI) to offer thoughts and insights to future UVEI graduates as they begin to apply for teaching positions. In a small-group session, I shared a story from one of my first job interviews: when I was in my early 20s, the interviewer asked why I was interested in teaching at his school. I responded with a lengthy description of the virtues of working in a boarding school environment—only to later learn that I was interviewing for a position at a day school! Needless to say, I was not invited back for a second interview.

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Around the same time I shared this story with the UVEI students, Tim Herrera wrote a piece titled, “Do You Keep a Failure Résumé? Here's Why You Should Start” in The New York Times. Herrera described keeping a “failure résumé” as a way to learn from past disappointments. He reflected, “ . . . the path to success isn’t a straight line.” To increase one’s likelihood of success, Herrera suggested, “When you fail, write it down. But instead of focusing on how that failure makes you feel, take the time to step back and analyze the reasons that you failed. Did you wait until the last minute? Were you too casual? Were you simply out of your depth? There are countless things that can go wrong.” 

In my experience interviewing at the day school, I was overconfident and should have spent more time researching the school and learning about its core values. And though I never wrote it down, this failed interview remains etched in my memory three decades later. I’ve had dozens of job interviews since, but I’ve never made that mistake a second time. I learned an important lesson. And aHerrera correctly points out, keeping a private inventory of missteps is a good way to continue to learn. I also believe it helps to have a sense of humor about one’s mistakes. All these years later, this blunder makes for a good story, especially because over the last dozen years I’ve enjoyed a successful career serving as a head of day schools!  

“Because you learn much more from failure than success . . . honestly analyzing one’s failures can lead to the type of introspection that helps us grow,” Herrera observed. Ever since, when I interview for a school position, I approach the conversation with much more humility and make sure to do my homework before stepping through the door. And I am grateful for the past mistakes that helped me get there.

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