Mirabai Starr… writes of the dark night as one who has gone through it herself, like John of the Cross:
The dark night descends on a soul only when everything else has failed. When you are no longer the best meditator in the class because your meditation produces absolutely nothing. When prayer evaporates on your tongue and you have nothing left to say to God. When you are not even tempted to return to a life of worldly pleasures because the world has proven empty and yet taking another step through the void of the spiritual life feels futile because you are no good at it and it seems that God has given up on you, anyway.
This, says John, is the beginning of blessedness! This is the choiceless choice when the soul can do nothing but surrender. Because even if you cannot sense a shred of the Beloved’s love for you, even if you can scarcely conjure up your old passion for him, it has become perfectly clear that you are incapable of doing anything on your own to remedy your spiritual brokenness. All efforts to purge your unspiritual inclinations have only honed the laser of attention on the false self. Unwilling to keep struggling, the soul finds itself surrendering to its deepest inner wound and breathing in the stillness there.
The only action left to the soul, ultimately, is to put down its self-importance and cultivate a simple loving attention toward the Beloved. That’s when the Beloved takes over and all our holy intentions vaporize. That’s when the soul, says John, is infused passively with his love. Though his radiance is imperceptible to the faculty of the senses and invisible to the faculty of the intellect, the soul that has allowed itself to be empty can at last be filled and overflow with him.”…
From Mirbai Starr’s introduction to her translation of Dark Night of the Soul by John of the Cross.
You might also appreciate this Sounds True 2012 conversation with Mirbai Starr.