"Final Lessons" by Head of School Bob Henderson '76

Sometimes younger teachers or administrators, when thinking about their own career trajectory, come to my office to talk to me about why I wanted to be a school head. It doesn’t happen often, but when it does, I tell this story.

Thirty-six years ago, I was a young teacher at a boarding school in Pebble Beach, California. In those days, I was teaching five classes, living in a dormitory with 42 students, coaching soccer and lacrosse, and rarely sleeping. I was paid $9,800 that year, plus room and board. I loved it, threw myself into it, and found that I had reasonably good intuition about adolescents. My mother always said that was because I had been such a difficult adolescent myself. Indeed, my mother has long argued that my entire career is penance for being such a jerk as a teenager.

The school I was working at was struggling at that time. That is no longer true today, but in the early 1980’s the place was racking up massive deficits and spending down its meager endowment on the payroll and basic maintenance. It was headed for closure within a matter of a couple of years. I didn’t know any of this at the time and just put my head down and dealt with kids all day long, and sometimes all night long. I did notice, however, that admissions standards were quite generous and a number of the students were seriously struggling in both personal and academic ways. They needed lots of attention and care, and somehow, at the age of 23, I was cast into the role of their parent. The school had no counselors and no learning specialists, and I had to grow up fast.

After a couple of years, the old headmaster retired and a new young head came to the school. This is how I know how bad things were, because the new head met with the faculty and told them that the school was going into crisis mode in order to turn things around. He told the faculty to resign then or get on board to work extra hard for no more reward until the ship was righted. I was young, liked California life very much, and signed up to stay. I immersed myself even more deeply in the place, and the new head soon gave me the opportunity to take leadership roles. I suppose he did that mostly out of necessity because I seemed to be hanging around and was acceptably capable at the job.

Three years later he appointed me as the Dean of Students at the ripe old age of 27. I did that job for five years. I liked the responsibility. I liked being on the inside of things. I was good at it. And I was getting even less sleep.

My lesson from this experience is pretty clear. I believe that had I not been at a struggling school, and had I not been at a place with high faculty turnover and thus huge opportunity for a “young Turk,” I would never have been afforded the opportunity to join a senior administrative team at that early juncture. I still was not earning much, but I loved my career and I could hear my father saying to me, as he often did when I was younger, “do your best, invest yourself deeply in your job, and the money will come. Never,” he said, “trap yourself in something for which you have no passion because you won’t be able to summon the energy or offer the leadership to live the way you want to.” I have never forgotten that.

I come from a family of businesspeople. They are rife on both sides of my family. My father inspired three of my brothers to pursue business careers. Masters degrees in business administration are everywhere in my gene pool. For me to enter and remain in a career in education took some determined independence. Even though my parents always encouraged me to do what I wanted, the truth is that I had a narrow subconscious view of what success looked like, and it is probably the case that I wanted to please my father more than I could consciously articulate those decades ago.

So there was a psychological need that also accompanied my path to school headship. I admit I was in a hurry. Along the way I got married, fortunately, and started a family. I also continued to teach history. My marriage and my classroom kept me sane. Between work and young children, however, I got even less sleep.

I got to live on Maui in Hawaii as my career progressed, and then in the beautiful town of Yarmouth, Maine, where, appointed at the age of 35, I undertook my first headship. I thought I was ready, in my drive and ambition, but I was not. I thought I was self-aware and prepared to lead, and that I understood my proclivities and effect on others, but I was still hazy about all of that. The isolation of realizing that I had no true peers in the institution – I could be friendly but not truly tight with anyone – induced stultifying loneliness that I had not anticipated. I also reeled from crisis to crisis through my first couple of years there, of almost every imaginable type. I slept very little. Fortunately, a couple of great, wise and worldly trustees took me under their wings and made me into a good school head, forcing me to see myself and the role with greater clarity and inspiring me to become better at it. In my first headship, then, I was simply lucky to stumble on such guidance and support. Moreover, that the school passed through those crises was again an opportunity for me both to hone my skills and grasp the true dimensions of the role.

Then Nobles called me, at the age of 40, to consider coming back to my alma mater. It has been the greatest gift of my life, after my wife, Ross, and three boys, Paul, Patrick and David, to be back in this village. I have no doubt that had I not been challenged so deeply at so many junctures of my career, I would have had neither the opportunities nor the joys of my experience here. So today, in my last graduation talk, I get to offer you some final lessons from my own experience that I hope you will take with you on the path ahead in your lives.

First, much of what happens in your life is serendipity. You land in the right place at the right time. Your challenge is simply to recognize it and take advantage of it. Your glass is always half full and never half empty. Optimists succeed and bring other people with them.

Second, even bad situations, failures and near disasters can be opportunities. I never would have moved to that school in California had I known how bad the situation was there. And yet it opened amazing doors for me, connected me with great mentors, and provided me with experiences that would have taken me many more years to accumulate in a more promising environment.

Third, understanding yourself, and being able both to hear feedback and act upon it is critical. That is sometimes a tough process, and there are inescapable bumps along that road. Managing yourself, however, is the first key to successfully leading other people.

Fourth, knowing yourself may also involve coming to grips with some of your subconscious motivations. This need not take years of therapy. Rather, most of the time it simply requires us to acknowledge what is obvious from our upbringing and past, and then to own it.

Fifth, never stop learning. You may achieve mastery at something, but part of true mastery, in my view, is acknowledging that there is also so much more to learn.

Sixth, you can’t do it alone. Your need mirrors in your life, or rather people who can safely hold up those mirrors and help you to see what is really there, with hope and without judgment. Recognizing those people in your life, your truth tellers and genuine supporters, can get you through every problem.

Seventh, don’t embark on a career just for the money. There is nothing wrong with having ambitious financial goals for yourself, and you may have financial burdens that narrow your choices, but you can’t find happiness and fulfillment solely on that path. Find what you love, do it well, invest yourself in that life and the people you are with, and you will find a definition for success that transcends material reward.

Eighth, take risks. I’m not leaving Nobles because I no longer love the school. I am leaving because I have played a good hand here and I can depart on my own terms. I will miss it terribly, especially kids and advisees and classrooms and morning assemblies. But staying here just because I will miss it is too safe. I want to do other things, travel, write and try other professions while I am still healthy and able. You are about to do the same thing, jumping out of this safe little pond and into the ocean. Embrace this moment of passage.

The Lord had only Ten Commandments, so this is my ninth and last piece of wisdom: sleep more. I was really dumb to worry and push myself through so many long nights awake early in my career. The world looks brighter and the art of the possible is much greater when you have had a solid eight hours!

And with that I bid adieu to the Class of 2017 and the entire school. This is a special place. I hope you keep Nobles, both its beauty and the power of the relationships you engendered here, close to your heart and mind. I hope that the school has set you on the path to the life well led; and that both now and over the course of your life, Nobles will have provided you with the sense of hope, the good will, the drive and the character to make a difference for the better in the world.

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"Final Lessons" by Head of School Bob Henderson '76