Taylor Stockdale - Head of Schools Welcome Letter

FROM THE HEAD OF SCHOOLS

I’m Glad...

You lost.

In the summer of 1980 I was on top of the world. I was heading into my senior year of prep school.

I had an interesting summer job working at a gas station on Cape Cod. And I was getting into shape

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for my final year of football, a sport that I loved.

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We had been through a few “building years,” and the team was finally poised for a strong season. I had a little success as a quarterback, but a rising star was emerging, and I was built more for my favorite position—that of full back.

As promising as the team was, I had my sights set on being the team captain. I had long dreamed of this role, being the guy to lead the locker room talks, the calisthenics, to go out for the coin toss before each game. Being captain would be the perfect ending to my high school sports career, and I thought about it pretty much every waking hour during that summer on the Cape.

When I arrived back to campus in the early fall for the dreaded two-a-days, I seized every opportunity to take the lead. I wanted to prove to my teammates that I was their

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leader, knowing that in two short weeks they’d be voting on their captain. I had no doubt I had it in the bag.

But to my complete dismay, when that day finally came, I lost. In fact, I didn’t even come in second on the team vote, but third. The two guys who won the vote were so close in the count that they became co-captains. I was stunned, hurt, and utterly confused.

Not long after the vote, as we started preparing for the first game, I finally was able to talk to the head football coach. Coach Farr wasn’t just my coach, but my advisor, my physics teacher, and I had known him since my first day as a freshman. I was expecting him to tell me how sorry he was that I didn’t emerge as the captain—that I

had deserved it and that the team had made a mistake. To my surprise, it was the complete opposite. As he started to tell me what he really felt, I only heard four words. Four words that changed my life forever; “I’m glad you lost.”

18-year-old brain. I agonized over it. I would go through phases of cursing him in my mind for being so hurtful.

And yet, deep down, I knew he was right, which made it even harder.

I was shocked when he said it and even more confused than before. I was deeply angry at him, the team, and thought that the whole situation was unfair. How could he hold such ill-will towards me? How could he be glad that I had such a harsh setback? In fact, to say I was confused would be a gross understatement. I moped around campus for the better part of a week. I felt that I was a victim of a terrible situation and betrayed by those who I thought cared for me.

Later that year, I came to a better place with it. We got close again, and I graduated from high school a far better person for having gone through that agonizing and embarrassing situation.

Several more weeks went by, and I did everything in my power to ignore him. Where I would usually hang out after class and talk x’s and o’s about the upcoming game, I would leave abruptly. Where I would usually come to practice early and play catch with him and some other players, I’d come a little late, and leave immediately after the last whistle. I pretended I wanted no part of him, and yet what I wanted more than anything was to ask him why.

Why was he glad I lost?

After letting me stew in my own stuff for long enough, Mr. Farr found the moment to circle back with me. Though it started as an awkward conversation, he was able to tell me that he was glad I lost because he didn’t want me to be rewarded for making the team captain position all about me. As all great teachers do, inasmuch as you can do for a teenager, he held a mirror up to me and made me realize that the entire way I had approached being team captain was all about me, and not about the team. I was focused on this leadership role for all the wrong reasons, and that as much as he appreciated my spirit and work ethic, he (and the entire team) knew there were other guys who were more focused on the team than themselves.

Sometimes, life lessons, the ones that stick, are brutal. They hit you deep in your soul.

They challenge you, or even jar you, into

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looking at your role differently—as a person and as a leader.

This was one of those moments. Like Mr. Farr, the greatest educators I know deliver these powerful life-changing moments with love and with wisdom. They know how formative the teenage years are and how important these lessons are in forging people who lead in all the right ways.

And once again, I go back to Thompson Webb, Ray Alf, Ann Longley, and the long list of educators at Webb who made it their legacy to deliver these same types of experiences to generations of Webb students, and more to the point, to our current faculty who carry on with this tradition of life-long lessons for a good and noble life.

Thank you Mr. Farr. I’m now able to say, I’m glad I lost, too.

Taylor B. Stockdale Head of Schools

As I departed from our talk, I knew in my gut he was right.

But I didn’t fully accept it for several months, if not years.

I had to let it sit there. I had to make sense of it with my

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