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The 5 Books Every Classical Educator Must Read

Starting a classical school––whether it be a public-charter, private, co-op, or homeschool––is an exciting undertaking that I encourage everyone to consider. The idea might sound daunting or even terrifying, but that’s only because most people are not aware of the many available resources. In my almost twenty years of “classical” work (first as a student, then as a teacher, and now as a school leader), I’ve picked up a few tricks of the trade that make starting your own classical school easier. I’d like to share some of these insights, particularly focusing on one question I am often asked: “What books should a person read to prepare to open a classical school?”

There are several books that teach classical pedagogy. However, not all of them are equal. Some lack clarity, others are so basic that they barely offer any insights. And a vast majority of books are so pretentious that most readers put the book down after a page or two (and rightly so, no one likes a pedant).

Considering all these things, I have put together a list that I consider to be the best when it comes to learning and understanding classical. I have arranged this list in order of difficulty – from the most accessible to most challenging (yet still very rewarding). In my humble opinion, if you are looking for a survey of the classical worldview and its underpinnings, these are by far the best sources available at the moment.

Now one quick caveat before we jump into the list: Many years ago when I was working towards my B.A. in philosophy, my professor introduced me to a life-altering truth that I now want to share with you. He would say, “There is no such thing as philosophical reading, only philosophical re-reading.” In other words, however accessible (or easy to follow) this list of books can be, I recommend you read them many times over––and over many years. With this, I begin with the first book on my list:

  1. Consider This: Charlotte Mason and the Classical Tradition by Karen Glass. Glass possesses a strong grasp of classical education – in particular, the Charlotte Mason style of classical. Charlotte Mason ranks as one of the most influential British educational reformers of the turn of the 20th century, re-envisioning classical pedagogy for the modern world. The Charlotte Mason “method” is particularly popular among homeschoolers. Glass does everyone a favor with her superb book, summarizing six large volumes of deep educational philosophy written by Mason into a single 129-page book. Moreover, her writing style is clear and concise, making it a top pick among educators seeking to gather a quick but robust understanding of the classical model. With the Mason model as her standard, Glass then works her way out towards classical education in general, offering the reader a bird’s eye view of classical thought. The two main takeaways from Consider This are Glass’ exposition of synthetic learning vs. analytic and how all the sciences are interconnected. This is why it should be first on your list, since it will give you a good foundation with which to absorb more challenging texts.

  2. Second on my list is not a book but an essay (hooray for a short reading!) and a free one at that: “The Lost Tools of Learning” by Dorothy Sayers. It’s ironic that I place Sayers after Karen Glass since Glass has a very good reason to be critical of Sayers’ way, or our modern way of interpreting Sayers, of organizing the classical model: as corresponding to “stages” of a child’s growth. Leaning on the educational theories of her day, Sayers seems to have accepted Piaget’s child developmental psychology wholesale. Nonetheless, Sayer’s essay is insightful to understanding how the classical movement understands its educational program not as teaching “subjects” but as teaching children “how to think” and “the love of learning.”

  3. Awakening Wonder: A Classical Guide to Truth, Goodness, and Beauty by Stephen R. Turley. Don't be deceived by the humble size of this text; it is going to require some effort on the part of the reader. So make sure you set aside some alone time, a cup of coffee, and that you are prepared for some mental cardio. Turley’s book is one of the most rewarding texts on the classical transcendentals of Truth, Goodness, and Beauty. Turley offers the reader what I have rarely found in good classical education books: the foundational and philosophical pillars of classical education. Drawing you back to the ancients and in particular Plato, the author guides you through a historical approach of the classical movement and its iterations over millennia. If you love history and prefer to approach a subject by studying its beginnings, this is the book for you!

  4. Although this next book is for the bold-of-heart, it is still one of the definitive texts on classical education, and for this reason, should be read by everyone wishing to grasp the purposes and ends of a classical education. Published in 1981, Norms and Nobility: A Treatise on Education by David V. Hicks sets a standard for writers on classical education that will be hard to surpass. Making his main thesis that an education is meant to shape character, he provides a scathing but enlightening critique of models that surreptitiously claim to only teach “facts” while also shaping a child’s moral outlook on life (whether this is done willfully or unwittingly). Hicks is quick to point out that all models stem from philosophical assumptions that ultimately impact the children under their care. More importantly, Hicks offers a deep dive into how a classical education provides a solution to our modern educational challenges.

  5. This last book is my personal favorite. I place it last not so much for difficulty (although it is still very challenging) but for “dryness.” Lacking the stylistic rhetoric that would make reading enjoyable, The Trivium: The Liberal Arts of Logic, Grammar and Rhetoric by Sister Miriam Joseph, reads more like a manual. Sister Miriam assumes her readers already possess a hefty background in classical education, hence I place it last on the list. Because Sister Miriam gives the best exposition on the trivium and liberal arts I have encountered, this is the kind of book I recommend not so much as a requirement, but as a reward for those that have devoted their lives to pursuing a deeper understanding of the classical world.

Lastly, you might ask why I have omitted C. S. Lewis’ seminal work on education, The Abolition of Man. Not only do I believe this text requires its own blog post, but I also place it in the category of “classical education apologetics.” If I had to place it on the list, I would place it next to Hick’s book in degree of challenging read. Unlike the books on this list, however, it is a classic itself. So it is required reading for all classical educators.

In the end, there are many books new and old that can prove useful. If I have missed your favorite, please share it with me via email here. Classical education is both a lifestyle and hence a lifetime pursuit, and as my professor so accurately pointed out: there is no such thing as philosophical reading; only philosophical re-reading.


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