Boys experience tremendous physical and emotional growth during their middle school years. Boys at this age are also more likely to explore new opportunities without fear of failure – byproducts of possessing a healthy confidence. Confidence is developed when the people around a boy have faith in his abilities and reinforce his effort.

How can parents help foster self-awareness, provide opportunities for exploration, and offer encouragement during these crucial years?


1. Tell stories.

When boys are given a prompt or an activity, rather than asked a “yes or no” question, they are more likely to engage and to share beyond the initial topic of the discussion. In class we often use “What if” questions to get boys thinking, questioning, and sharing. Improv games also provide opportunities for connection and confidence building (e.g., in the Question Game, you can only communicate in questions and the first to answer the question loses). These exercises help boys develop a more conversational way of speaking, which translates to other academic experiences. When they’re presenting a history paper or doing a reading in English, the rigid approach that is often typical in class melts away; they become more comfortable, more animated, and more relatable. 

2. Give him room to fail.

It takes small moments of uncertainty for a boy to figure out that he can do this. Parents and educators can support boys in taking positive risks by brainstorming possible solutions to deal with an uncomfortable situation. Help him come up with choices, give him space to process the alternatives, and support his decision. If we remove the obstacle, or if we force him to follow through in an uncomfortable situation, we aren’t providing opportunities for growth. We risk the boy shutting down when similar situations arise in the future. But if we coach the boy through, he builds confidence and is more likely to step outside his comfort zone in various areas of his life. 

3. Experience live theater.

As a member of the cast or stage crew, your son will create relationships with all different types of people, he will learn how to trust others and to trust himself, he will practice communication and collaboration, and he will gain empathy and perspective. If your son isn’t ready for the spotlight, take him to a community show. Whether it’s a performance at a local school where he can see people his age taking to the stage, or a full scale Broadway production that mesmerizes the senses, your son may walk away seeing more possibilities within himself. 

At The Haverford School, we believe that a well-rounded education in academics, the arts, and athletics builds character, confidence, and a lifelong passion for learning. Engaging in storytelling, taking positive risks, and experiencing live theater helps boys build connections, gain perspective, and practice 21st century skills that will impact him now and well into the future.