It is not uncommon to find people with very sensitive consciences and who seem to have a certain attraction, even aptitude, for the contemplative path, but who cannot come to terms with things that have happened in their past. Not only can they not accept divine forgiveness, they cannot forgive themselves. Consequently their self-esteem is too low to accept the fact that failure is part of the search for God. As Eckhart says of all the saints and sages down through history, “We rarely find people who achieve great things without first going astray.” But such wisdom is little comfort to these individuals. This preoccupation with sin can become a type of obsessive-compulsive disorder (in former times this was called scrupulosity), which increases the likelihood of sliding back into the same old problems. According to the author of The Cloud, if you are constantly obsessing on what you’ve done and frightened that it might happen again, it is more likely to happen again, than if you could simply come to terms with it and move on. In a similar context Meister Eckhart distinguishes two types of repentance. He says that there is a kind of repentance that “draws us downwards into yet greater suffering, plunging us into such distress that it is as if we were already in a state of despair. And so repentance can find no way out of suffering. Nothing comes of this.” Eckhart contrasts this kind of repentance with the repentance “which is of God” and says that it “brings spiritual joy that lifts the soul out of her suffering and distress and binds her to God.” It becomes a question of dealing with afflictive thoughts in the right way.
This was the key to Mary Magdalene’s success; she was able to break the cycle of obsessive thinking. How did she do this? He says “she hung her love and her longing desire on this cloud of unknowing.” By this he means she simply returned to her prayer word rather than to her obsessive thinking. In doing this she discovered perfect humility.
Martin Laird, Into the Silent Land: The Practice of Contemplation