"Keep thy mind in hell, and despair not."

This revelation is very often misunderstood. What does it mean to keep your mind on hell and not to despair? "Keeping your mind in hell" is not keeping your mind on hell. It is not just thinking about hell or meditating on it. It is the actual living experiuence of being in hell, of being without God, of losing his grace yet still searching for it.

The following passage should shed some light on the matter

From the book "St. Silouan the Athonite" by Archimandrite Sophrony Sakharov, Essex, England 1991 pages 210-211

"Keep thy mind in hell, and despair not." What does it mean to "keep thy mind in hell"? Can it be that we are to use the imagination to conjure up circumstances for ourselves similar to those figures in some primitive painting? In this instance, no. Father Silouan, like certain great Fathers - St. Anthony, St.Sisoe, St. Makarios, St. Pimen - during his lifetime actually descended into the darkness and torments of hell. They did this not once but over and over again until their hearts were so permeated that they were able to repeat the movement at will. They took refuge in it when passion - especially the most subtle of passions, pride -reared its head. The struggle against pride is, in fact, the final stage in the battle against passions. To begin with, the ascetic must wrestle with the greater passions of the flesh, then with irritability, and finally, pride. This last combat is undoubtedly the most painful of all. Taught by long experience that pride leads to loss of grace, the ascetic consciously descends into hell where every passion is 'seared with a hot iron' The Starets observed that most people despair when they approach this state and give in. This is why the great Sisoe said, 'Who can bear St. Anthony's thought? By the way , I know a man' ( it was himself Sisoe) 'who can bear it' Here, as Staretz Silouan explained, Sisoe was thinking of what St Anthony learned from the shoemaker of Alexandria... " ....[story follows with other examples from the desert fathers ]
"Blessed Staretz Silouan said that many ascetics when they approached that state - which is vital if one would be cleansed of the passions - would fall into despair and be unable to continue. But the one who knows 'how greatly the Lord loveth us' escapes the pernicious effect of total despair and knows how to stand prudently on the verge so that the hellish fire burns away his every passion and does not fall victim to despair. 'And despair not.' If the Staretz' s account is a simple one - as simple as the shoemaker's at Alexandria - the power and mystery of the matter will remain incomprehensible for anyone who as not known a similar experience of hellish torment, on the one hand, and the great gifts of grace, on the other."