Doubt, Certainty and Confidence

Hackley School
Hackley Perspectives
8 min readJun 2, 2023

By Andy King, Director of the Upper School, Hackley School

Adapted from Andy King’s May 4, 2023 Chapel Talk to the Class of 2023

Director of the Upper School Andy King delivers the final Chapel Talk of the 2022–2023 school year.

Like most middle-aged people, I am prone to wild bouts of nostalgia. And what is the exercise of writing a Chapel Talk if not an exercise of turning nostalgia into a semi-cogent, hopefully articulate lesson? So, the nostalgia machine fired up for me as I thought back to this time in my life. For me, it was 1994–29 years ago. I was a senior at Chatham High School, a small New York public school where my graduating class had a whopping 90 students.

In early May 1994, I was feeling pretty darn good. I had just come back from a great trip. I had taken a huge chunk of the money that I earned working at a pharmacy to take a school trip to Europe with a teacher and a bunch of my friends. It was my first time on a plane. I had just decided that I was going to Colgate University. Early decision was very uncommon back in my day, so May 1 was a very exciting time for all of us who were seniors. I had a great group of friends, and we were scattering to a wide range of schools. My brother was in his second year of college. I visited him a few times at his school, and college seemed great to me. My parents were (and are) loving, supportive and proud. All in all, at that time in May 1994, I was rightfully feeling pretty darn good.

Graduation came and went in a blur. I remember a cap and gown and high humidity in the gym because it was storming that day. I remember lots of sweating, lots of laughter and some tears. And I remember a flurry of celebrations in the days following graduation. Then I was in the thick of “the summer before college.” As the calendar moved closer to August, I started to feel less than pretty darn good, and it was not hard for me to pinpoint why I was suddenly feeling this way. It was the onset of doubt and profound feelings of uncertainty. Was Colgate the right choice for me? What if my roommates are totally bizarre? Will I make friends anything like the cherished friends from home? Will I be able to do the schoolwork? If I can do it, will I be able to do as well as I had done in high school? Only a few months earlier, I was a very confident young man. In early August, a few weeks before I was supposed to leave for college, I was buried with feelings of doubt and grappling with the weight of uncertainty.

The doubts proved to be largely unfounded — uncertainty abated and confidence returned. Colgate proved to be the perfect fit for me. The doubts about my roommates washed away quickly. I was in a quad. One of my roommates proved to be a great friend and a four-year roommate. I made amazing friends while keeping close ties to my hometown friends. In fact, to this day, the group text with my college friends is a constant source of laughs and reminders of the powerful friendships forged in the crucible of college. I was able to do the schoolwork. I have told some of you about my rough start with my biology placement exam, but I rebounded from that and moved over into the realm of the humanities where I was at home. I found professors who inspired me and encouraged me to pursue teaching, thus changing the direction of my life and ultimately leading me to Hackley. And, best of all, I met my wife Magee at Colgate. You know her as Mrs. King. I know her as my great love and favorite Colgate alum.

Andy King addresses students on Class Day 2022.

So, is the moral of this Chapel Talk about how life is all about overcoming and erasing doubts? Not at all. Rather, I want you to recognize the significance of your doubts. Doubts can keep you safe (for instance, I doubt it’s a good idea to go to a frat party all alone), but don’t let doubts control you and limit you. Wrestle with the doubts as they have inherent value. You will often hear from people “Don’t doubt yourself. You can do it.” In this well-meaning advice, doubt is set up as the impediment to action and progress. I would tweak this to note that doubts can actually be a catalyst for action and progress.

As I encourage you to examine and embrace your doubts, I also encourage you to pause and think carefully about the emotional opposite of doubt — when you feel absolutely certain about something. In my estimation, certainty is far more problematic than doubt. I caution you about certainty since you are coming of age at a time where certainty is everywhere and yet nowhere. Consider our political climate. Politicians and pundits talk with a stunning abundance of certainty and a shattering lack of nuance about how their ideas will solve whatever problem they are addressing while their opponent’s counterproposal is a path to certain ruin. They are certain their approach is the only approach. Grandiose proclamations of certainty may win over followers, but they also risk stifling the opportunity for more thoughtful analysis, multiple perspectives, genuine debate and actual learning. And while people wielding platitudes of certitude are talking at us nonstop, we are also inundated with fake news and exposed to AI tools whose speed and seeming precision can trick us into thinking that there is nothing to doubt in what’s written and that this work bears the mark of accuracy and certainty.

How then do I suggest that you thread the needle between doubt and certainty? My advice is to aim to lead and live a life marked by confidence with perhaps a new way of thinking about confidence.

The pursuit of confidence is not the eradication of doubt nor the attainment of certainty. A confident person is someone who understands their doubts and manages them enough to move from doubting to doing and from questioning to acting. Consider the start of your senior year. The entire college application process is, in part, about balancing doubt and acting with confidence. With each college you researched and visited, you arrived with questions and doubts similar to those I expressed above. Through your own efforts, conversations with your families, and the support of your steadfast college counselors, you reached a point where you were confident that applying was a good idea. You were not eradicating doubt and there’s no such thing as certain admission, but you acted. The moment you pushed “submit” on a college application was a moment where confidence overtook doubt.

As you get older, you will experience this complicated dynamic among doubt, certainty and confidence. For me, I can tell you about two times — one personal and one professional — that illuminate the tension very well.

First, any of us in the room who are parents understand all too well the potential for doubt when it comes to raising kids. As Magee and I drove our son Henry home from the hospital 11 years ago, there were so many doubts in our heads about our readiness to be responsible for another person’s life and raise a child. Over time, we became more confident new parents, never shaking those doubts entirely and never feeling certain that we had everything right, but also knowing that Henry needed us to parent confidently.

This same dynamic was also evident for me professionally in summer of 2020. None of us want to go back in time to our memories of the pandemic summer, but that was an obvious time in recent memory when doubts ran roughshod over certainty. In the middle of that summer, Mr. Wirtz led a series of Zoom meetings with the leadership team of the school where we discussed our approach to the reopening of school that fall — the fall of your sophomore year. Would we try to reopen the campus or would we stay largely remote? At that time, most schools seemed to be heading in the direction of remote instruction because there were too many questions and doubts about how to safely reopen during a pandemic. After many conversations, and I am sure hours of reflection and consideration, Mr. Wirtz admirably and confidently directed us that he wanted Hackley open in the fall and we had to find a way to make this happen.

Michael C. Wirtz, Hackley’s 12th Head of School, and Andy King on Class Day 2022

Was he certain that it was the right call? No. Were there many doubts about if it could even work? Absolutely. But he wrestled with the doubts, not letting them overcome him, took in the information available to him, consulted with others, and then confidently concluded that the best option at the time was to open school. To me, his leadership in that moment and in the months that followed during the pandemic embody what you should bring to your adult life. Consider the doubts you are feeling. Ask the questions. Seek out credible information and multiple perspectives. Consult with others. And if your confident decision to act goes sideways, admit it and then try something else. Confidence is strength, not rigidity. In the end, remember that it is better to be confident, not certain.

In closing, having intoned against the perils and limits of certainty, I would be remiss if I did not tell you that there are some certainties facing you in this pivotal moment.

You can be certain that you are more than prepared to flourish in college and the post-Hackley adventures that await you.

You can be certain that the connections you forged here will endure. Though the friendships may change over time, be certain that your Hackley ties are strong.

You can be certain that your families love you very much and are enormously proud of you. And you can be certain that, at some point in the next few weeks, someone in your family will suffer a teary wave of nostalgia thinking about how time has flown. Let them have that moment.

You can be certain that the adults at Hackley who have taught you, advised you, coached you, checked you in each morning and hassled you about being late, taken care of you in the infirmary, fed you in the dining room, made your favorite chicken soup and, of course, the one who deaned you for the past four years, are proud of you and will always be cheering for you. Because, Class of 2023, you can be certain that your class of confident and joyful students will be dearly missed when Commencement takes place. Never doubt that.

Andy King has been a member of the Hackley faculty since 1998. Since 2008, he has served as Hackley’s Director of the Upper School. Prior to taking on this administrative role, Andy was an Upper School history teacher, advisor, dean, and coach. He is also the proud parent of Henry, a member of Hackley’s Class of 2030.

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