The Aviator Archives
Volume 1.1
Greetings fellow Aviators,

I hope this email finds you well.

Today I share the first edition of a new newsletter we are launching at Archway Roosevelt. The Roosevelt Review, which will still continue every Friday, curates all of the important announcements, dates, and links you need to stay up to date on academy life. This is not going anywhere, and it will remain our key method of communication. In the past, especially in my previous years in the role of Headmaster, I would add additional thoughts and reflections to the weekly newsletter, which admittedly, could add some length to an already robust email! Moving forward, The Aviator Archives has been developed for the expressed purpose of sharing reflections on matters relating to school culture, our vision and purpose, and encouragement and exhortation as we continue to grow together as a community. The Aviator Archives will not necessarily be shared at a set interval, but rather, will be sent periodically to bolster and unify us throughout the remainder of the year (and beyond!) My hope is that you are reminded of our key purpose, that you are equipped with greater knowledge of classical education and the ideas that undergird our work at Great Hearts Roosevelt, and finally, that you are inspired and encouraged as fellow Aviators!

Last Wednesday, we met as a faculty to discuss two key works by one of the most influential people in world history – Plato. For those unfamiliar with his work, Plato, a student of Socrates, wrote many dialogues using Socrates as his central figure. Through Socrates’ many conversations with a variety of interlocuters, matters relating to the whole of life are thoroughly and robustly explored and discussed. So comprehensively, in fact, that A.W. Whitehead once said that the whole of western philosophy “consists of a series of footnotes to Plato.” The central theme reigning throughout all his work is the pursuit of the good. What does it truly mean to live a good life? How do we know we are actually living a good life, rather than merely thinking we are pursuing goodness? There are an abundance of questions tied into this central one – but the key driver behind Socrates many philosophical inquiries was not knowledge merely for the sake of gaining information, but true knowledge of reality that allows one to live an authentically good and meaningful life.

One of the dialogues we discussed was Plato’s Apology. In this dramatic and inspiring work, based on actual events, Socrates is literally on trial for his life because his incessant pursuit of the truth has made Athens quite uncomfortable. Many who hold positions of authority were threatened by his unwavering commitment to truth and his willingness to challenge the status quo and narratives of the day. Despite the fact that his life was at stake, he boldly claims that he cannot cease his inquiry, that his integrity and his commitment to goodness requires that he continue to ask questions and challenge his beloved city to join him in this pursuit. In the end, the often praised democracy of Athens sentences him to death by a majority rule. He closes with an impassioned exhortation, warning the city that others will follow in his stead, and taking comfort that “a good man cannot be harmed either in life or in death.”

In the early 1900’s, over two millennia after the events of The Apology, G.K. Chesterton wrote this concerning tradition: “Tradition means giving votes to the most obscure of all classes, our ancestors. It is the democracy of the dead. Tradition refuses to submit to the small and arrogant oligarchy of those who merely happen to be walking about.”

In Socrates’ day, the democracy of Athens saw his challenge to the status quo as a threat to the ideas of the state and a corrupting influence upon the youth. After reading the Apology, we look back at those sitting in the assembly and wish we could cast our vote alongside them in Socrates’ favor. We wish those Athenians could see that moment through the lens of the 25 centuries of history that followed his fateful death sentence. If only they had perspective, as we do!

In Chesterton’s quote, he wisely warns us of the unsuspecting arrogance that comes from paying attention only to those who “happen to be walking about.” We too, like the Athenians, may cast our votes in err. Through tradition, we are able to replicate, in a sense, that which we wish we could do for the Athenians. Though we cannot look into the future, we can look into the past. What if, in addition to the perspective found within the diversity of worldviews and people of today, we can see ourselves through the lens of the most profound wisdom, the most catastrophic failures, and the most wonderful accomplishments of our predecessors? What if we can invite everyone who has walked the earth into our democracy and join us in dialogue - especially while we make such consequential choices about the good life for ourselves and for our children? How can we ensure we are not a part of the “small and arrogant oligarchy” that Chesterton warned us about, the same oligarchy that killed Socrates?

This is what a classical education does. Through a dialogue with those across not only geography, but time, we are able to hold a mirror to ourselves and examine our own blind spots and paradigms. We are able to temporarily take off the glasses through which we see the world, and examine the assumptions that we hold so dear, but often uncritically. We too are made a bit uncomfortable by Socrates’ questioning. And we do this not so that we can remain in uncertainty, but so we can more firmly commit ourselves to the pursuit of truth!

A look into the past is humbling. Yes, we see many atrocities and great ignorance in our history, and we are often grateful for the newfound perspectives we have today. But the reverse is also true. The perspective of the past can shed light on the ignorance that can blind us so often today. It is eerie how contemporary the great books of the past feel – how ever-present the questions and problems of humanity are! It is quite sobering to know that we are still all-too-human. A relentless pursuit of the good requires that we give heed to the tradition that we have inherited and that has shaped the world as we know it, and that we allow those who have walked before us to cast a vote alongside us.

I end with two calls to action:

First, I would love to invite anyone interested in joining me for a Socratic conversation on Plato’s Apology to sign up at this link. If the spots are filled and you are still interested, or if you are interested in a session at another date or time, please send me an email and I am happy to open up another session. I will be sure to send more details and a copy of the text before the conversation.

Second, even without the context of the whole text, I think you will find solace in Socrates’ exhortation that “a good man cannot be harmed either in life or in death.” I encourage you to ask your children (and yourselves) this question at the dinner table. What do you think this means? Is it true? If you have any insights to share, feel free to respond our post on Facebook - you should see it come out sometime tomorrow. I’d be encouraged to hear from you! Often, our children have the most remarkable insights. I believe all children are born philosophers, and it is our job to cultivate this within them and make sure that the many competing distractions in our world do not rob them of this wonder and honest pursuit of the good.
I wish you a wonderful week ahead, fellow Aviators!

Stephen Philabaum,
Headmaster, Archway Roosevelt
Great Hearts Roosevelt Main Office: (623) 344-8003
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