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Oppositional, Rebellious, Difficult, Defiant, Explosive, Spirited, Challenging … What’s in a Name?


Who are Challenging Boys? They are kids who get tagged with many negative labels: oppositional, difficult, defiant, manipulative, willful, noncompliant, rigid, angry, temperamental, and rebellious and they tend to make life difficult for their parents and teachers. These negative labels, however, reflect a misunderstanding of who these boys are and why they behave the way that they do. These labels overlook the fact that Challenging Boys are full of important positive qualities. They are bright, curious, creative, passionate and sensitive kids who have a very strong commitment to justice and fairness. When we view them through the negative lens of these labels we set up negative expectations that make it even more likely that our challenging boys will act in difficult ways. The first step in more effectively parenting a challenging boy is to be careful to not use judgmental labels.


I have chosen the term “Challenging” to describe these boys because it captures their complex nature. Challenging first refers to the fact that it is often challenging to be the parent or the teacher of these boys. They seem to be almost constitutionally opposed to authority when it is arbitrarily administered. As a parent or a teacher there are decisions that have to be made, things that have to be done, places that have to be gotten to, and rules that have to be followed. It makes life pretty difficult to have your authority questioned at seemingly every turn.


“Challenging” also refers to the positive fact that Challenging Boys challenge us to grow as parents and as people. We have to develop a greater capacity for empathy as we search to understand what important principle our challenging boy is defending in an argument. If we don’t, we will be caught up in yet another power struggle before we know it. Challenging boys further challenge us to develop our skills at conflict resolution and collaboration. Because power struggles can be almost unavoidable, challenge boys also challenge us to learn how to be calm in the face of anger and conflict. Lastly, challenging boys challenge us to grow in that they challenge us to be honest with ourselves and with them. They are exquisitely sensitive truth detectors and they will call us on it if we try to BS them.


Finally, “challenging boys” means that we need to challenge our boys to learn how to pick their battles. They need to learn, as Aristotle said “to be angry with the right person, to the right degree, at the right time, for the right purpose, and in the right way.” We need to challenge our boys learn how to get along in addition to how to fight. We don’t want, however, to turn our boys in to “compliant boys.” Our culture needs these kids and their challenging natures to call into question the status quo and to make our society better and more just for us all. Many of the important revolutionaries in science, politics and business have been challenging boys. Wilbur and Orville Wright, Supreme Court Justice Thurgood Marshall, and Steven Jobs had been challenging boys just to name a few.

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