The Buddhist version of the Dark Night of the Soul is little advertised (for obvious reasons) but universally experienced by advanced meditators. In Buddhist terminology the Dark Night is called the dukkha-nana (dukkha meaning suffering, and nana, pronounced "yah-nuh," meaning knowledge.)
In the tradition, there have been many formulations of this process found in both the Theravada and Mahayana. The experience of the Dark Night is a process where the mediator becomes inconsolable where nothing in life feels worthwhile, and everything seems pointless to an intensity that seems bottomless. It’s an experience of the fundamental suffering of duality causing a crisis of identity. The duration of this process varies from days to years and “some may get run over by it on one retreat, fall back, and then pass through it with no great difficulties sometime later. Others may struggle for years to learn its lessons” (Ingram, 2007). In the Zen tradition this stage is called 'rolling up the mat' because the yogin finds they can no longer meditate and wants to quit the whole process.
The Vimuttimagga (解脫道論) is an early meditation manual by the arahant Upatissa (Sayadaw, 1994) and describes the stage of ‘misery’ thus:
[T]he "knowledge of misery" will arise in him before long. [Then all] objects noticed, or ...states of consciousness engaged in noticing, or in any kind of life or existence ...will appear insipid, ...and unsatisfying. So he sees, at that time, only suffering, only unsatisfactoriness, only misery. Therefore this state is called "knowledge of misery."
Another stage is described as the knowledge of misery:
“Seeing thus the misery in conditioned things (formations), his mind finds no delight in those miserable things but is entirely disgusted with them. [H]is mind becomes, as it were, discontented and listless. [He] spends his time continuously engaging in it. He therefore should know that this state of mind is not dissatisfaction with meditation, but is precisely the "knowledge of disgust" that has the aspect of being disgusted with the formations. Even if he directs his thought to the happiest sort of life and existence, or to the most pleasant and desirable objects, his mind will not take delight in them, will find no satisfaction in them.”
When in this state it is pretty bad with pains, sickness and unbelievable suffering and it is impossible to even to meditate which is exactly what you need to keep doing. In the Zen tradition, this part of the path is called the “rolling up of the mat” for just that reason because there is a great desire to quit the whole process and for me I really did resign from the sangha, and quit being Buddhist for about one year only later to rejoin. Again from the Vimuttimagga:
“[T]here will usually arise in his body various kinds of pains which are severe, sharp, and of growing intensity. Hence his whole bodily and mental system will seem to him like an unbearable mass of sickness or a conglomeration of suffering. And a state of restlessness will usually manifest itself, making him incapable of keeping to one particular posture for any length of time. For then he will not be able to hold any one position long, but will soon want to change it.”
This can be considered “the entrance to the third vipassana jhana, or perhaps its the entrance to the fourth vipassana jhana” (Ingram, 2007). The worst thing is the Dark Night begins after a period of profound clarity, equanimity, bliss, focus and mystical style experiences.
For people practising in a monastic setting the dukkha-nana would be recognized and worked through but in a secular setting it is not always so easy and hence one reason why a teacher with knowledge and experience is so needed on the path answering common questions about mediation and the necessity of a teacher. Well, look at it like this: you can lift heavy weights by yourself and that works until the day that something goes wrong such as pulling a muscle and finding there’s no-one around who can help you up or call an ambulance. Well, there are dips in meditation and without a knowledgable teacher to help you though it it can be extremly difficult and it is not recommended.
Mahasi Sayadaw, 1994, The Progress of Insight (Visuddhiñana-katha), http://www.accesstoinsight.org/lib/authors/mahasi/progress.html, accessed 4/2/2017
Ingram, Daniel, 2007, THE CORE TEACHINGS OF THE BUDDHA: An Unusually Hardcore Dharma Book, www.interactivebuddha.com