Father Anthony Bloom makes a case in an essay in “God and Man” that our approach to God when we come in prayer can be part wonder and part despair. The despair he has in mind obviously isn’t what is often called ‘faintheartedness’ by the Church Fathers — that dissolution of our mind and spirit that makes us give up on everything. It’s something different, something best understood by reflecting on the story of Bartimaeus, the blind man who cried out “Son of David, have mercy on me!”

Prayer and holiness seem to me to be rooted in a twofold experience, not in two experiences but in a twofold, correlative one.

On the one hand, there is the amazement that we feel in the short — but real — moments when we perceive God, when we almost touch the hem of His garment; and they leave us in a contemplative state, in deepening prayer, meditation and interiority which are on the border of profound contemplation and life in God.

On the other hand, at the other pole of this twofold reality of prayer and holiness, we find despair and compassion: despair such as we see, for instance, at the end of the 10th chapter of St. Mark, the despair of blind Bartimaeus at the gate of Jericho, the despair of a man who has been blind and has suffered from it, who has fought for his sight for years and finally, crushed by misfortune, has settled into his blindness. And then suddenly he hears that there is a man living in Galilee in Judaea who has the power to give sight to a man born blind, to cure every sickness, to heal every infirmity. And this man is passing his way. And this moment when the last hope is passing by is a moment of reawakening of all the feelings of despair that he bears within him as well as all the hope of which he is capable.

We can pray at moments when we become aware of our blindness — and we can include in this term whatever makes us blind to God and to all that surrounds us — and when we sense that the One who can cure us is passing near. Prayer arises at moments when we become deeply aware of our separation and of the fact that our life is suspended over death, that nothingness is within us and lapping round us from all sides, ready to engulf us. And when we turn our gaze towards others, in place of that despair linked to an ultimate hope, which is the hope that Bartimaeus had, it is compassion which awakes in us, the capacity to suffer deeply, intensely, … and in a mysterious way, beyond all experience, participate within this unity of the Body of Christ, in the common suffering which is His.

– Fr. Anthony Bloom, “Holiness and Prayer” God and Man