I know failure is a difficult topic to discuss with all of you as you got into the most selective school in the country and therefore probably have rarely encountered failure, but this year, I challenge you to be fearless and fail spectacularly. Whether in your academics, athletic, or carnal pursuits, I challenge you to be rejected.
This rejection would simply put you in the same position this very school found itself a century ago. Many of you may not know this, but Deerfield’s history while impressive and intriguing, is also full of boom and bust times. Our darkest hour was just before our greatest headmaster Frank Boyden was hired after leaving Amherst. With only 14 students, the school was near closure. However, within twenty years, Mr. Boyden and his wife had reestablished Deerfield as an academic institution in the standing it exists today.
While he was a master educator, Mr. Boyden failed miserably on one ground: managing the school finances. After the Great Depression hit, it looked like Mr. Boyden’s vision was doomed, as the schools debt and falling donations seemed like a fatal blow. However, long before TARP and Fed Rescues, Deerfield was rescued as the headmasters of Taft, Andover, and Exeter traveled with Mr. Boyden to their alumni around the country to bailout Deerfield in a move that, to this day, has no precedent or decedent.
So, fail spectacularly. The consequences are not nearly as dire as one might imagine, and I will personally assure you that you will be better off for it.