On January 6—after surging COVID cases required a remote start to the winter term—Headmaster Kerry Brennan welcomed students and faculty back from winter break in person, ushering in the new year and the hope that it may represent. At the heart of Mr. Brennan’s remarks was the question Who am I?, and what that question means when a person wrestles with imposter syndrome in moments large and small throughout life.
Through personal stories—ranging from tales of little league tryouts to musical auditions, from college orientation through his early years of teaching English at Roxbury Latin—Mr. Brennan offered his own experiences and struggles with imposter syndrome. He ultimately implored boys to remember that they belong and are worthy, regardless of the setting, or challenge, or circumstance:
“You, in your particular gifts, in your limitations, in your experience, and especially in your desire and passion have the capacity to grow and change and improve. You have the capacity to fulfill your ambition to be excellent at something, or, perhaps, many things. You have the capacity to contribute, to make a difference.
“In our lives we are seeking authenticity. We want to be real. We want to be the same person regardless of whose company we are in. We want to feel competent, and contributing, and lovable. Virtually every day, we will ourselves to confront a novel situation or make the acquaintance of a person we did not know before. My parents had different but similarly instructive advice about how I ought to imagine the challenge of pursuing that which is new and daunting and strange. They suggested how I might see myself in the world. My mother admonished my brother and me that we were neither better than someone else nor were we lesser than someone else. Of course, in certain particular ways each of us is better or worse—with some skills, or in some subjects, or applying our knowledge to problem solving, or making friends even. Her point was more of an existential one: We, all of us, are children of God and therefore deserve respect and kindness and love. I am imperfect in the way I encounter and judge people, but I strive for her ideal. My father, on the other hand, advised that half the battle is won not just by showing up but by signaling that you belong there. Some of that, especially if someone feels out of place, or an imposter, requires projecting oneself as confident and committed and concerned. And that one does not betray that he may be, or at least feel, out of place. In those situations, I find myself striving to quickly imitate the patterns and protocols that most others already seem to know. My father’s point was that once an opportunity is offered and accepted that each of us has the chance to prove our legitimacy, or even our excellence in that realm.
“Today, as we all face the New Year, 2022, a year in which we hope that we can know normalcy and health and happiness in our lives, I wish us a few things. I wish that we grow to know and love ourselves in such a way that we can push forward at moments when we might feel most vulnerable, when we have the greatest doubt. I hope that we will know the confidence and ambition that will allow us to grow into the people we are capable of being. Every day we are challenged in significant ways. When we try out for a team; when we volunteer an answer in class; when we audition for a part; when we run for office; when we wonder at what table we will sit in the Refectory; when we first meet new classmates or teachers; when we are in a social situation in which we want the other people or a special other person to like us—usually the liking comes before the admiring and the respecting; when we worry that no one will want to spend time with us over the weekend or the break; when we apply for admission to a school or college; when we apply for a job; when we pursue a relationship with a particular person who might become our life partner; when we wade into any room, a meeting, a reception, a bar. In all these situations, I hope you feel the opposite of what the imposter feels. I hope that you humbly and confidently will imagine yourself anywhere, with any person or group of people, regardless of the circumstances or the prestige or fanciness or the consequences of the situation. For us to evolve, we have to take risks. We have to put ourselves forward. We have to believe that we are worthy.
“We have to summon courage even when we are most fearful. We have to have both the knowledge and courage to ask for help. Over time, we grow more confident not just in who each of us is—our one true, authentic self—but we become eager to project that persona, to risk rejection or ridicule even as we are also risking the possibility of making lifegiving, lifelong connections, of feeling challenged or affirmed, or even falling in love. I wish you all of that in the New Year, and will be especially glad to be part of a community in which no one feels himself or herself an imposter.”
