What if I fail?

New environments and experiences pull you out of your comfort zone, but also offer time and space to reflect on events more realistically. Summertime is a change from the pace of the school year and spending the summer in Ireland has offered a new setting for reflection. I have been contemplating the events of the previous year and the changes waiting ahead. For teachers and administrators alike, it is the summer break that sets the tone for the coming year. Looking toward the year ahead, I know that the staff culture I help establish in orientation will set the prevailing tone for the rest of the school year. I want to step out on the right foot, but it is daunting to step forward into known problems in addition to uncertainties.

The role of an administrator is to handle the quick decisions that are needed outside the classroom every day with others relying on you for answers to everyday problems and to lead in challenging situations. Even in the summer, problems role in like the tide and I found myself wondering if I was making the wrong decision by pursuing this role. Was I setting up others to fail because of my inexperience? What if I don’t have the right training or stamina to give parents, teachers, and students the correct answers? I found myself confident in only one thing- that I was going to fail. Two options were emerging: fail now or fail later.

Fail Now
Photo by Jens Lelie on Unsplash

In the last chapter of A More Beautiful Question by Warren Berger (2014), he quotes Robert Schuller’s question “What would you attempt to do if you knew you could not fail?” Berger adds that “this question is about giving yourself permission to think big.” After a few weeks mentally focused on failure as the inevitable outcome, I let myself put that question aside and ask a new one- What would it look like if I succeeded in my new role?

  • I would be asking questions rather than trying to have all the answers.
  • I would be learning to spark curiosity in others by asking questions which help teachers reflect on their own decisions, consider other options, and independently grow as educators rather than checking off a list of requirements.
  • My Chinese fluency would increase.
  • Teachers would see their colleagues as resources and experts.
  • Parents would see evidence of their child’s learning every day.
  • All children would feel safe in school.

Berger’s final question in this section is from Chris Guillebeau, who asks, What’s truly worth doing, whether you fail or succeed? All of these. Failure is a possibility in every task, but that does not mean that we should give up before we start. Failure simply offers another opportunity to try again. Standing here at the end of my summer break, I can see that failure is an option, but the pursuit is worthy even if I fail.


Berger, W. (2014). A more beautiful question: The power of inquiry to spark breakthrough ideas. New York, NY: Bloomsbury.

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