As has been previously said the Dark Night of the Soul is a period of disillussionment and despair. I've found it involves a cherished belief that has been crushed or a tragic event.
This sort of Dark Night of the Soul can occur many times throughout our lives and as dECLAN said can precede an awakening or change in attitude. Usually this results in a bit more integration and moving on.
However, I'm no expert but my reading suggests the DNotS is in fact an occult event. I'm not 100% on this but my general understanding is that preceding a total awakening to cosmic conciousness there is an intense period of doubt and disillussionment, the final test, much like Prince Siddhartha went through just before achieveing Buddahood. So there are many DNotS throughout our lives part an parcel of being human, then there is The Dark Night of the Soul before the final illumination.
Now having not yet achieved said illumination it's just speculation from me...
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