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His greatest personal strengths are exactly those things that make it most difficult to be his parent,” mom of a challenging boy.

Challenging boys have many great personal strengths. They are sensitive, empathic, energetic, driven, persistent, principled, and committed. These characteristics give challenging boys a strong moral compass. They have clear convictions about right and wrong and oppose injustice and unfairness wherever it occurs. Challenging boys see beyond their own narrow self-interest and are budding social activists. They defend the rights of underdogs and outsiders. In sum, challenging boys are advocators, they advocate for justice and for the rights of the weak.

Challenging boys also think outside of the box. They are creative and insightful and do not accept conventional explanations of things. Challenging boys often question why and come up with their own answers and their own way of doing things. In short, challenging boys are also innovators.

Civil rights activist and Supreme Court Justice Thurgood Marshall, inventors Wilbur and Orville Wright, and businessman Steve Jobs were all challenging boys. Our society needs advocators and innovators to challenge our conventions, our prejudices and our status quo. We are all better off because of the life’s work of these and other challenging boys.

The mothers and fathers of Justice Marshall, the Wright brothers, and Steven Jobs, however, may very well have struggled with similar issues to those you have with your son.  In reflecting on his boyhood, Steven Jobs reports, “I was pretty bored at school and turned into a little terror.” These creative, insightful, activist men would have been thought of as “challenging” boys.  As boys, they did not cow-tow to expectation or accept conventional explanations.

But knowing that we might be raising the next Marshall, Jobs, or Wright does little to solve the problem of day-to-day stand-offs with our children. As a parent, 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 for a parent, when you have so much to take care of, and your authority is being questioned at seemingly every turn.

After years of frustration, many parents understandably find it difficult to see their challenging boy’s personal qualities as strengths. Instead of sensitive and empathic, we experience our sons to be easily hurt and angry. Instead of energetic, driven, and persistent, he is stubborn or hyperactive. Instead of principled and committed, we find him rigid and inflexible. Instead of creative and insightful, he seems sneaky and manipulative. Finally, the challenging boy’s greatest asset – his advocating and innovating spirit – is experienced by us as his having an oppositional and contrarian nature.

How does it come about that a boy with such vast potential comes to be experienced as having such big problems? The answer lies in the fact that many well-intentioned parental instincts lead us to act in ways that bring out the worst from challenging boys rather than building on their many strengths. This is not the fault of the parents; rather, it reflects the culture we all live in. Our society unwittingly undermines our chances at helping our challenging sons.

Over the course of a boy’s development, a negative pattern is established in which our well-intentioned parental actions lead to negative responses from our sons: anger, opposition, and inflexibility. These negative responses, in turn, create a negative view of the boy in the parent’s mind: “he’s stubborn, manipulative, mistrustful.” This negative parental view then leads to parental actions that result in even more negative responses from the boy. The negative image of the boy in the parents’ mind is then further reinforced. The cycle continues and deepens with each negative interaction.  The likelihood of helping our sons channel their energy in creative, productive and healthy ways is further diminished.

This blog is about transformation. Transforming the way you relate to your son and transforming the way he connects to you and the important people in his world.  In subsequent blogs, I will discuss how to reverse this negative feedback loop and instead, create a positive cycle for you and your family.  By showing you how to establish the cooperation you need to manage your family, I will help relieve your understandable frustration, and increase your confidence and calm as you parent your spirited son.