It’s trendy in educational circles to talk about “embracing the learning experience of failure” or “teaching students to not fear failure,” but at the end of the day, it’s the same old story: we’re afraid. When we do a cost-benefit analysis, we tend to overload the cost side and assume it is not worth the risk. When we consider our shareholders, our customers, and our employees, we decide to play it safe and minimize damage. Playing it safe can certainly be appealing—especially in the independent school arena. When the school board looks at enrollment numbers and makes a direct comparison to customer satisfaction in the classroom, it can be enticing to continue to rely on tested methods of the past. It can be enticing to avoid failure at all costs. It can be enticing to stay comfortable. But comfort is the enemy of progress. 

This kind of thinking is in line with self-made billionaire entrepreneur Sara Blakely who explains that true failure is “not trying in the first place.” 

The impacts of this style of thinking on education are endless. Redefining failure is a key attribute of what is referred to as the entrepreneurial mindset. In enabling our teachers, and our students, to think like entrepreneurs—to ask, “What if?” and “Why not?”—we are giving them a path to success. A bumpy and misshapen path, for sure, but a path nonetheless where the learning yields not only rewards but a life free of inconsolable regret. 

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