Head of School’s Notebook | Riddles

March 24, 2017

There’s a riddle I was told when I was a kid that has stayed with me. You reach a fork in the road. One trail leads to everlasting happiness and the other leads to your doom. There are two brothers – twins – standing at the fork in the road. One brother always tells the truth. The other brother always lies. And there is no way to tell one from the other. You may ask only one question to one of the brothers. What question do you ask to assure that you will take the right path?

I still share the riddle from time to time – like when I am in the backcountry with students and we are marching for hours on the trail. It’s a great way to pass the time, and there is nothing like the intellectual challenge of a good brainteaser.

Most of us who are confronted with a riddle of this sort focus primarily on an answer, or more particularly “the answer,” because there’s only one. On the trail, students shout out possible answers, mostly because they are trying to eliminate options. It’s one of the few places, in fact, where students and adults don’t seem to worry too much about being wrong. The idea isn’t to get to a solution quickly. We’re on the trail, after all.  Eventually will do.

Strangely, though, at least for me – perhaps because I know how to solve the riddle – I see it more as a cultural artifact than an exercise in intellectual discernment. Within the puzzle are a series of rather telling assumptions: that our choices have consequences, that we can’t make them without input from others, and ironically that we can’t always trust the guidance we are given.

It’s a fascinating conundrum – not just the puzzle – but the assumptions themselves. Essentially, we have much at stake and we need help… but we can’t rely on any potential assistance being helpful unless we know the right question to ask. Only our intelligence (or perhaps our cunning) saves us from the wrong, perhaps disastrous, path.

It is probably best not to read too much into a riddle. It’s just a game, right? I remember becoming very frustrated my sophomore year of high school when my English teacher, Mrs. Howard, kept asking me to look beyond the story to find the meaning. Isn’t the story enough? Apparently not for Mrs. Howard.

This riddle tells a story too. It’s about twin brothers, a fork in the road, and a well-constructed question. It’s about consequences, choices, self-reliance, and strategy. It’s about habits of mind, inquiry, and bias.

But it’s also preparation for dynamics we’ll face in the world, for protecting or furthering our own interests, and for cultivating our minds. It’s about choices, not simply the ones we make at a fork in the road, but every day in the manner we cultivate our minds, interact with our peers, construct our futures.

Is that what the author of this riddle intended all along? Who knows. But I imagine there was a reason the author conceived it, and it wasn’t simply to occupy the minds of high school students on the trail. Frustrating as it might be, there is always more to the riddle… than the riddle. Mrs. Howard was right.