Four Keys to Cultivating Character

children developing character

In his New York Times bestseller The Work: Searching for a Life That Matters, Wes Moore reflects on life-changing factors of the 21st century (robotics, globalization, information technology) and notes that this historical moment has “created a greater sense of urgency around the task of designing our own lives to tap into our own specific ideals, talents, and resources—to find ways of not just working to live, but finding the work of our lives.” Moore urges us to “embrace the possibility of living for more than ourselves.”

A transformative professional development experience came early for me. We teachers, a cohort from dozens of different schools, had gathered for a summer conference. Affinity groups were organized by the disciplines we were then teaching, and my group, teachers of English, was asked to imagine we were a department at a school. At our first meeting as a group, we walked into a classroom with three chalkboards. They were labeled “Skills,” “Habits,” and “Values.” Our first task? Fill up those boards. Identify expressly what we hoped our students might one day accomplish, at our school and with our support. My teaching, I realized, was about much more than my subject.

I think back often on that exercise. Indeed, as a school leader the framework has proven indispensable as we work to envision the totality of our boys’ school experience; as we work with them to master skills, internalize habits, and embody values; and as we strive, above all else, to help them become good men.

Moore’s attention to ideals, talents, and resources – and my group’s prioritizing skills, habits, and values at that conference years ago – speaks to the necessity of holistic education and the psychological, social, and emotional growth of each student.

“Seeking to understand character has been a human occupation for thousands of years,” British educator Tony Little states, “and upholding some ideal of character education is as old as education itself.” Age-old though the ideal might be, the need for good men living for more than themselves has never been greater.

Tony Little identifies four avenues toward the “ideal of character education”: trusting relationships, opportunities to lead, dealing with failure, and ambition. While Little’s is a boarding school background, these dimensions strike me as applicable to multiple settings – another helpful framework, then, in school, at home, or just about anywhere.


Trusting Relationships

Commissioned by the International Boys’ School Coalition, Richard Hawley and Michael Reichert conducted a worldwide study (across 35 schools in 6 countries) and concluded that boys are relational learners – that in school they very often connect with the teacher before they do the subject, reciprocating empathy with an adult from whom they not only believe they can learn but wish to learn. Their study is summed up, aptly, in their 2014 book I Can Learn From You.

Modeling empathy in trusting relationships begins at home. In his book How to Raise a Boy, Reichert stresses that “a boy’s experience of parental love lays the foundation for goodness” and identifies “making sure that boys are cared for, that their need for connection is not overshadowed by their performance, as the essential foundation of good men.”

I was recently reminded of this foundation of trust in conversation with a fellow teacher and administrator. In a struggling school receiving an F on the state report card, she described the challenge of working with so many students who fear themselves to be categorical Fs. Her success – and theirs – came only after resetting the conversation. Before talking about American history and government, she sought their input on a topic of interest to them. She demonstrated care for and interest in them. With empathy made evident, they could learn from her.


Opportunities to Lead

Leadership as accomplishment – whatever the setting, scale, or scope – is a cornerstone for character development. “Schools tend automatically to laud success or excellence, but the higher praise should go to the teenagers who take a lead and get things done,” writes Little. Getting things done is crucial to boys getting it right in the long run.

Boys’ own ideas about leadership take root early and run deep. Early notions often have to do with high-profile status and objective feats. The fastest. The biggest. The strongest. How one distinguishes himself from others is inarguable and can be rightly impressive. (“Children are naturally enchanted by extreme things,” notes Matthew LaPlante in Superlative: The Biology of Extremes; “if you doubt this, just try to wrestle a copy of The Guinness Book of World Records out of the hands of an elementary school student.”)

Boys’ ideas about leadership also evolve, however. In conversations with middle school-aged boys, I marvel at the many qualities they cite as indicative of good leadership, particularly among their own peers. They talk less about superlatives and more about qualities. They still recognize undisputed accomplishments, of course, but also point to care, kindness, dedication, and generosity. With maturity and sophistication, they recognize there are many kinds of leaders, and that, far better than statistics, characteristics reflect character.


Dealing with Failure

Leading and failing seem innately at odds for many boys, and we as the adults in boys’ lives must work to help them reconcile the two.

“Of course, we pay attention, advise when necessary, mitigate risk when we must, and never abandon our children,” educator and psychologist Madeline Levine writes – in keeping with the aforementioned relationships we hope to foster. “But we must allow them enough internal space, enough meaningful life experience to be able to develop the protective coping skills that are known to lead to the well-being and resilience that are the hallmarks of authentic success.”

Even the prospect of failure can be destabilizing for boys. Anthony Rao, author of The Way of Boys: Promoting the Social and Emotional Development of Young Boys, writes: “A boy is in competition all the time, with his siblings, his peers, and even himself. He doesn’t just want to learn a skill; he wants to wrestle it to the ground and own it.” Only intensifying the challenges are the social, emotional, and psychological challenges of growing up. They will fall short and they will get it wrong. Still, to a boy failure can seem nothing less than an existential threat.

None of us is perfect. We have crucial roles to play in helping boys to navigate missteps (just as other trusted partners in their lives will one day, as well). I remember receiving a call once from a recent graduate, a young man I had taught and coached across a number of years. He had made a mistake that he recognized had hurt people he respected. He knew he had to apologize even before he had picked up the phone; on that matter I just affirmed him and rehearsed some language with him. With next steps agreed upon and in place, however, he lingered on the line. It became clear that he was worried that my trust in him was shaken, that I might no longer believe him. I assured him that I did believe him. And more important, I still believed in him.



“Encouraging young people to have the ambition and confidence to try things and believe in the possible should be an essential tenet of every teacher’s mission,” Little writes. He stresses, though, that he speaks “of a true sense of self-worth, not the glib self-confidence that can tip into arrogance.” Ambition is appetite. The hunger to be, do, or accomplish more is to be encouraged in boys, even as their aspirations change. And ambition need not come at the expense of character.

Boys should wish always to be better human beings just as they wish to be better students, athletes, or artists. Scholars like Dolly Chugh, author of The Person You Mean to Be, connect this wish with growth mindset: Working at being a good person is a worthy ambition and a daily commitment.

Take the example of Mark. Mark was a talented athlete of extraordinary drive. At home, as a pre-adolescent his parents told him that they would drive him to every contest, provide him all the necessary equipment, and do whatever they could to help him achieve his lofty goals. They also told him that they would never wake him up for early-morning practices. That was up to him. At school, Mark forged a number of meaningful relationships with his teachers and coaches. He welcomed challenge and elected courses of interest to him, not simply those he thought might bolster a college application. By graduation, he was respected and recognized by peers and adults alike as an exemplary citizen and leader. And today he is availing himself and others of his experience. Thanks to the skills, habits, and values he learned as a boy, as a man Mark is living for more than himself.

My belief that parents and teachers can partner effectively in educating for character has only been confirmed and deepened over the course of my career. Thinking back to the provocative exercise of decades ago, to filling up those three chalkboards, I also think back on instructive moments in the developmental arcs of so many young people, and reflect with pride on the fine people they have become.


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Patrick T. Gallagher, Head of School at University School

Patrick T. Gallagher was named Head of School in 2018. Prior to that, Mr. Gallagher was the co-director of the Upper School and Hunting Valley campus for five years. He came to US to teach in 2005 from The Culver Academies, where he taught English and humanities. Mr. Gallagher received his master of arts degree from Columbia University, where he was a Klingenstein Scholar in Educational Leadership; and his bachelor of arts degree in English language and literature from Princeton University.