My wife and I intentionally chose this picture (see below) for the wall in our living room where it hangs adjacent to pictures of our family experiences—a reminder that a prerequisite to flight is leaving the nest.

The full line of poetry from Erin Hanson in which this sentiment is taken is as follows: “There is freedom waiting for you / On the breezes of the sky / And you ask What if I fall? / But oh, my darling, What if you fly?”

Truthfully, I get chills every time I read those words because I am reminded that one of the core attributes of the entrepreneurial mindset is “redefining failure.” If we teach our students (and our own children) to fear failure, it has a paralyzing effect on our willingness to try. Often this teaching comes by way of example in our own lives—if we are spending too much time living in the space of comfort and not taking risks, we are demonstrating, whether we are aware of it or not, a fear of failure.

Nothing is more detrimental to growth than the paralyzing effects of fearing failure. If we never try, then we end up with the potential for lifelong regret and the lack of knowledge of “what could have been.” A poem by Dante Rossetti captures this when his speaker states, “Look in my face, my name is Might-have-been; I am also call’d No-more, Too-late, Farewell.” For me, I’d rather avoid this regret-fueled line of thought.

We encourage students who come through our entrepreneurship programming to ask two key questions on a regular basis: the first is “what if.” This question can be one of fear or curiosity—"what if fall?” could just as easily be “what if I fly?” and we must encourage the asking of both. The next question, however, is the impetus of action: “why not?” Why not take the leap, why not try out for the play, why not ask someone out, why not apply for the job? When we ask “why not” on the heels of “what if” we are teaching ourselves, and by extension those who look up to us, that the only fear is not trying in the first place. 

As a simple classroom experiment, consider posting these two questions side by side on your whiteboard—“what if?” and “why not?” and allow your students to begin exploring the various sides of this line of thought. If nothing else, it may lead to some interesting ideas…

After all, how else will we experience the feeling of flying if we are not first willing to experience falling?

Listen In on the Latest

I recently had the opportunity to be a guest on Steven Miletto’s podcast “Teaching, Learning, Leading K12” and am pleased to share the link for you here. In addition to discussing the key components of the entrepreneurial mindset, we talked about everything from innovative approaches to education to scaling revenue generating models and much more. Check it out!