Alexis de Tocqueville, subject of my grad school thesis at St. John's College.
Alexis de Tocqueville, whose Democracy in America, epitomizes the intellectual curiosity of St. John’s. I wrote my thesis about this book.

I recently read (and loved) Frank Bruni’s paean to my alma mater, St. John’s College. St. John’s is well-known for its “great books” program, in which students read many of the foundational texts of the western canon rather than summaries or critiques of them. The idea is that by encountering these works in the original you give students the chance to form their own opinion about the big ideas that have shaped our world.

I went to St. John’s for my graduate degree. They only offer two: a master’s of liberal studies (western) and a master’s of eastern studies. I did the former and spent two years tearing my way through Plato, Euclid, and Tocqueville. In many ways it was an intellectual boot camp bar none.

As Bruni notes in his piece, questioning is the key skill you learn at St. John’s. And, of all the questions you learn to ask the one that’s stayed with me the most is the critical question: What’s at stake? Johnnies (as St. John’s students sometimes call themselves) learn to ask this when the discussion starts drifting into the weeds, or maybe someone in the group—all classes are 12 or fewer students, sitting around a table a la the Harkness Method—is flirting with pedantry. Someone in the group would say, “but, wait a minute, what’s at stake here?” 

This simple phrase has the wondrous ability to pull everyone out to a higher level—a 10,000-foot view, if you’d like—and forces us think about why this text or idea matters. It reminds me of James Ryan’s fantastic commencement speech at Harvard a few years back where he extolled the virtue of pausing and asking good questions, especially why something matters—his gloss on what’s at stake? If you haven’t watched his speech I urge you to do it with alacrity.

When I applied to St. John’s in my prime earning years (20s) I remember a lot of people questioning my sanity. It was the 1990s, and Lani and I were living in early dot.com NYC. What a completely un-pragmatic decision. Yet, in retrospect, it remains one of the most best things I’ve ever done for myself. Not only did it engender a love for the classics that lead directly to the founding of Context, but it taught me how to back away from a problem and ask some really key questions. Currently, as I navigate through the minefield of homeschooling my kids afloat I find this an incredibly helpful technique, not only for them, but for myself.