I recently was asked to think about my biggest failure.
At first, I wanted to reject the premise of the question and just frame everything as an opportunity to learn. I have tried so many things that haven’t worked and all of them have helped me get to where I am today. Failure is a scope question. On a short time horizon something may look like a failure, but on a long time horizon everything looks like learning.
While there is insight in all of these thoughts, it avoids the hard work of identifying a concrete example. What happened that would typically be viewed as a failure to most people that I was able to use as a massive learning moment?
Then it struck me: Book in a Day. An event I co-hosted with a friend in the winter of 2018 at University of Delaware. The idea was to provide lessons and work time for people to start writing an outline of their book in just one day. It was exciting idea and people showed interest in the concept.
But when the day arrived, we had one attendee. A massive failure. A waste of a Saturday. What was I doing spending 10 hours teaching one person?
While the event wasn’t quite what we envisioned, it was an opportunity to make a deep, personal connection with that one person. He stayed for hours, enjoying every moment, making productive use of the time and left feeling optimistic about the next steps.
At the end of the day, we found joy in learning that far outweighed the disappointment.