A great many physical ailments are diagnosable by way of the doctor’s question, “Does this hurt?” The doctor applies pressure to the body, and a healthy body feels no pain. An unhealthy body suffers from pressure, though. The doctor applies pleasure not to harm the body, but to determine where harm has already been done.
Classical education aims toward the restoration of the soul, much like medicine aims toward the restoration of the body. For the reason, the good teacher will have to determine where harm has already been done to the soul. The soul has been harmed by sensuality, vice, lies of all kinds, bad theology. The teacher must first apply the pressure of the text to himself, and the text must extract winces and yelps of confession from the teacher. However, the teacher and the students will not suffer from all the same ailments in all the same ways. A book like GK Chesterton’s biography of St. Francis has the power to apply pressure all over the soul of the reader; Chesterton’s book is a trip to a very thorough physician.
In teaching books like Chesterton’s St. Francis of Assisi, the good teacher should be yelping often, but so should the students. This is the purpose of such a book. Boethius’s Consolation should have a similar effect, as should Frankl’s Man’s Search For Meaning, Job and Ecclesiastes. The good teacher will often ask students, “Does this hurt?” He will say, “Sell all you have and give it to the poor… Does this hurt? He who has two cloaks should give to him who has none… Does this hurt? If your right hand or your iPhone causes you to sin, throw it away… Does this hurt?” The bad patient will immediately begin making excuses for the pain.
Education must take place under conditions of freedom and leisure, but freedom and leisure are not the same thing as pleasure. A man must have the leisure to take a nice long time at the doctor’s office. No discipline seems pleasant at the time, but painful, and a good education is the discipline of the heart.