His moniker comes from his most famous work, The Ladder of Divine Ascent. Even though it is intended as an instruction manual for monastics, it is still one of the most popular books among Orthodox Christians, especially now during Lent (our Easter, more properly called Pascha, isn’t celebrated until May this year).
The book posits thirty steps toward reaching the Heavenly Kingdom. This work, as well as St. John, is also commemorated on the Fourth Sunday of Great Lent. Associated with both the work and the Fourth Sunday is one of my favorite icons:
Note the people being pulled off the ladder by demons — some of them are wearing the vestments of priests and bishops. It is a reminder that we are all merely human, especially those who have been ordained. We all sin, but this sin only speaks to our human frailty not to the Christian faith or Christ Himself. Hypocrites we may all be, but Christ went to the Cross for us all anyway. As St. John more aptly puts it:
God belongs to all free beings. He is the life of all, the salvation of all—faithful and unfaithful, just and unjust, pious and impious, passionate and dispassionate, monks and seculars, wise and simple, healthy and sick, young and old—just as the diffusion of light, the sight of the sun, and the changes of the weather are for all alikeI have often seen the monastic life as a metaphor by which Christianity can speak to D&D. Player Characters are invariably those members of society that exist on the edges of Civilization doing things which allow Civilization to continue to exist, but which are not normally acceptable within Civilization itself.
I, therefore, find it interesting that the first step that St. John describes in The Ladder is the renunciation of the world — monks leave Civilization behind to wander into the Wilderness to fight the demons where they live. This is not far from what a normal D&D PC does in context of delving into the Mythic Underground to fight Evil and Chaos where it lives.
St. John notes that there are three types of people who renounce the world:
All who have willingly left the things of the world, have certainly done so either for the sake of the future Kingdom, or because of the multitude of their sins, or for love of God. If they were not moved by any of these reasons their withdrawal from the world was unreasonable.Of these three, the second most accurately describes the typical D&D PC — sinners who no longer totally belong to Civilization. I also find St. John’s advice for the sinner quite interesting:
The man who has withdrawn from the world in order to shake off his own burden of sins, should imitate those who sit outside the city amongst the tombsThe tomb, of course, being one of the classic D&D adventure tropes.
Finally, I would be remiss if I didn’t note that the metaphor of the ladder quite aptly describes the experience level system used in D&D (although I have never even approached getting to the 30th level either in life or as a player).