Observations from a Journey into Classical Education: The Art of Teaching 

Over the course of 25 years, I have stumbled into teaching in a variety of settings: homeschooling, traditional public schools, private schools, and charter schools. I am profoundly grateful for each of these experiences. Education is an incredibly formative thing. There is a very real sense in which we become what we behold; and whether we are the teacher or the student, the atmosphere, the content, and the missions that drive our educational settings play a powerful role in our own lives and, of course, in the lives of the students we teach. 

My earliest teaching experiences were in a public-school setting; in fact, my first job was at an alternative school in west Texas. Schools like this exist for students who have been expelled from their main school setting. Teaching in this context compelled me to wrestle deeply with the purpose of education and consider what my students needed most—did they need Shakespeare or help filling out job applications?  

This was the question that eventually led me into the pursuit of a classical education, first for myself, and then for my own children, and then in my teaching endeavors. And eventually it led me to a Barney Charter School and then to Hillsdale Academy. I share this brief glimpse into my story because the art of teaching is inexplicably tied to what we believe education is for and also inextricably tied to our view of man. We orient our craft around the question of the nature of a child, what it means to flourish as a human, and what it means to live that education out in the context of community.  


With that in mind, I want to share three broad but, I hope, practical thoughts on the art of teaching and the kinds of things that, as a school leader and teacher, I want to see manifest in the classrooms within my school. Each of these components are prioritized at Hillsdale affiliated schools because we believe they are central to every student, and because we believe this kind of education is an education for every student. 

1. The content we choose to teach within our classrooms, must be worthy of contemplation for a lifetime.

Consider the power of timeless works of children’s literature: there is a good, a kind of beauty and substance, within a true work of literature that, should our students dwell on such stories for a lifetime, those works of literature would, in a sense, become a part of them and ought to do so. Humans are imitators, and we become what we behold. What we teach within our classrooms must not merely be good or clever or cute or popular; it must be something we want our students to chew on for a lifetime. It is fair to describe the content of our classrooms as playing a similar role to the food we eat; what our students contemplate within our classrooms has the power to develop the mind and to nourish the soul. We want it to be the very best—content that has an enduring quality, not because it touches on the current cultural debate but because it provides a stream from which to drink that nourishes in the moment and for a lifetime. David Hicks, author of Norms and Nobility, describes such an education as one that “refreshes itself at cisterns of learning dug long ago, drawing from springs too deep for taint…” The bottom line is this: your curriculum matters. It shapes you as the teacher. And it shapes your students. It has to be worthy. 

2. Because we have a high view of man and a high view of the content within our classrooms, we believe that not only the knowledge but also the habits we cultivate within our students are essential for human flourishing.

We also know that students need us to come alongside them and lead them in the pursuit of those habits. Because of that, the teacher, not the student, is the leader in the classroom. Seemingly small things that require thoughtfulness on the part of the teacher cultivate a kind of atmosphere in the classroom–the tone of our voice, our physical presence, the seating chart, and the questions we ask all cultivate a certain disposition toward learning in our students. We do not settle for a few students engaging well and the rest of the class passively sitting by “doing time” in the classroom.  We cannot force students to learn, nor can we force them to love what we love, but we do not let our students opt out. Our pace of instruction, the structure of our classroom, the behavioral expectations we have, the modes of assessment we use…each of these create an environment that tells the students what the good is and what we believe they are capable of knowing and becoming. Like the content we teach, a teacher who intentionally leads his students has a powerful impact on the disposition of learning the student has for a lifetime. 

3. The most powerful skill a teacher can develop is the art of asking questions.

I would argue that no student is learning unless he is asking questions, either externally or internally. Humans take deep joy in learning. When we wrestle through a question and come to a moment of perceiving a truth, there is almost nothing more satisfying. This poses the question of what an education is for; do we learn so that we can succeed in a particular trade, or do we learn because we are created to discover, to perceive, to love, and to live the truth? One of the beauties of teaching in a K-12 school is that we see the educational life of a five-year-old and an eighteen-year-old taking place in the same building, and we know that if the curiosity and wonder of a six-year-old becomes lost as the child enters high school, it is a great tragedy.  

I taught sixth grade for several years. My students’ natural curiosity and drive to know and connect what they knew about one body of knowledge to another was both beautiful and exhausting! In fact, I had a policy called “Sticky Note Me.” If we could not get to a question a student had within the class period, the student wrote her question on a sticky note and left it on my desk so we could come back to it another day. One of the great responsibilities we have as a teacher is to continuously cultivate that curiosity while also teaching our students to refine their questions such that they learn the tools to discern what is good, and what is true, and what is beautiful.  


I want to reiterate that regardless of the setting we teach in and the areas of content we teach, humans are humans wherever we go. My students in the public alternative school, my own children, my sixth-grade Latin students at a Hillsdale affiliated charter school, our students at Hillsdale Academy, myself as a 50-year-old student of the liberal arts, we all need the same things to flourish. Fundamentally, we long to know the good and find fulfillment in becoming the kind of person who can discern the good and live accordingly.  

The art of teaching is about seeing what aspects of our content are essential for human flourishing, both privately and communally, and what kinds of habits are essential for human flourishing. We must orient our classrooms and steward our craft accordingly because we recognize that the brief time students are within our classrooms is preparation for a lifetime outside of our classrooms.  

This post is adapted from a speech given at a Hoogland Center for Teacher Excellence event. For more information on how Hillsdale reaches teachers across the nation, please visit k12.hillsdale.edu.