From: Ingram, D. M. (2018). Mastering the Core Teachings of the Buddha: An Unusually Hardcore Dharma Book, Second Edition Revised and Expanded. Newburyport. AEON Books.

Part IV: Insights

30.10 Re-observation, pg. 226-239

You can find this section online here, and here is the whole 2nd edition of the book for free online (buy physical copy &/or see all other versions of the book).

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Re-observation may not sound like much of a problem, as it has such a sanitized and boring name. However, friends have suggested renaming it with various four-letter Anglo-Saxon vernacular terms, usually in some grammatically problematic but emotionally cathartic string. This stage is often, though not always, like a brick wall, particularly the first few times we collide with it. It can be as if all the worst aspects of the Dark Night stages converge for one last important lesson, that of Re-observation.

We must perceive the true nature of the sensations that make up our ideas of perfection, all the ideals we cling to, all images of how the world should and should not be, all desire for anything to be other than exactly the way it is, as well as all desire for awakening to be anything other than this. It may seem impossible to sit for even a minute, as the levels of restlessness and aversion to meditation and all experience can get high. The sudden complete inability to sit on the cushion for even a few minutes is a classic mark of this stage. As a physician, I speculate that at some point they will find some physiologic commonality between this stage and the pathways of restless leg syndrome, but the whole-body version.

This stage, and part of the stage of Three Characteristics share some features. In other words, be warned, particularly those of you who are prone to being overly certain about “where you are” on these maps. I get a reasonable number of emails and calls from people who claim they are certain they are in Re-observation, and shortly thereafter they are describing A&P territory, meaning that they had just been in Three Characteristics territory, not Re-observation. Continuing to investigate the true nature of these sorts of sensations and our map theories is often difficult, and this is a common cause of failure to progress.

Now, I am about to describe all sorts of emotional or psychological manifestations that can sometimes happen in Re-observation. The more extreme the description of a possible side effect of this stage, the rarer that side effect is likely to be, particularly those that sound like descriptions of severe mental illness. For someone who is staying at the level of bare sensate experience, as I strongly recommend, the only difficult manifestations that seem to be quite common at this stage are a strong sense of aversion and resistance to formal meditation and experience, and a deep sense of primal frustration, though these tend to fade quickly in the face of good practice. If our concentration is strong enough and our other factors are in balance, we may move through this stage with no problem at all at the level of vibrations or even pure, abstract patterns of light and/or sound, bypassing all the potential complexity I am about to describe.

For those using more ordinary objects, aversion to meditation and experience can arise as we react to the vibrations in this stage, which can be fast, chaotic, and harsh. The noise in our repetitive minds can be quite irritating. By repetitive, I mean that this stage can involve repeating thoughts, songs, and stories, like we have a horrible case of the evil earworms (in the metaphorical sense of annoying songs that get stuck playing in our heads). Ever had a fever and had some irritating thought circling again and again in your head? This stage can produce similar experiences.

Some of my own descriptions of this stage while on retreat have included such phrases as “the mind-storm” and “a bracing work in D minor for six sense doors, hailstorm, and stuttering banshee”. If we are very powerful meditators who yet lack enough equanimity and tranquility (remember the seven factors?), it can literally feel as if we will be torn apart by harsh vibrations. At some illusory level of the sense of continuity and stability, this is exactly what we are trying to accomplish.

However, even if very difficult manifestations arise, if we are practicing well, they should not last long at all, at best minutes, at worst, hours or days. Once I began to get what this stage was about and what it was useful for, a perspective that had a hard learning curve, I would intentionally amplify the sense of being torn apart, directing this stage’s sharp and cutting ability to shred reality at anything that appeared even the slightest bit stable or continuous anywhere in the body, mind, or experience in general. That is a skillful use of the perspective that this stage allows us.

In a similar vein, and as mentioned before, those few who are crossing this territory with world-class concentration abilities and using a very rarefied object, such as a complex visualization on sacred geometry, may, if they are very good at it, pass through this stage with little or no difficulty. It can be fascinating and subtly rapturous, as this is the peak of the third vipassana jhana. Strong practitioners fusing insight and concentration practices may notice that the proportion of the visualized field that is organized into clear images gets broader and broader. The patterns may become more complex. The phase problems get more and more bizarre. The visual field may take on more spherical dimensions, with curving images beginning to encircle (or “ensphere”) you. The images may appear to have manifold symmetries and repetitions, and these generated images and sounds may come around to encompass basically the whole field of experience.

This can be like watching an IMAX movie of a moving technicolor spirograph in the front row. As mentioned earlier, I have also seen gigantic fields of hyper-detailed, repeating, shifting patterns of things like spiders, mushrooms, snakes, skulls, fingers with claws, and other creepy and disconcerting things but, on careful inspection, they were beautiful, vibrant, and amazing in their intricacy. I use this example partly due to my own experiments and partly to illustrate general points.

Different objects and practitioners will most definitely produce different specifics, such as colors, images, etc., while some aspects of what happens at this stage will remain the same, and are therefore universal. It goes to illustrate a basic point: Re-observation need not be a problem if you have very solid meditation skills. Even if you don’t, it still need not be a big deal if you know what to look for, what to expect, how to handle it, and that it too shall pass. Dry insight workers get through this stage all the time just fine with good practice. Further, if you are reading this book, you probably already crossed the A&P as mentioned already, and so you have probably already handled it at least once and may not have even known it, and even if you haven’t yet, you still may do just fine. We’ve all been through hard times, and this is just one more phase that might be potentially challenging.

You see, Re-observation is all fluff and no substance but, if you confuse fluff for substance, the effect will be the same as if it actually had substance. Bodily sensations of creepy revulsion, disgust, or profound existential angst may arise, and yet, those with wisdom will notice they are like confetti, like sparkles of light, like raindrops, albeit seemingly acid raindrops. Still, they are not harmful. In fact, they apparently do something great to the mind, since Re-observation leads to the next stage, Equanimity. This normalizing knowledge is power.

Re-observation is like a toothless dog with a ferocious bark. If you run screaming or faint from fear when the dog barks, then it needed no teeth to prevent your progress. It is like a hologram of a snarling demon that you can just walk right through and it can’t touch or harm you at all. There is a curious freedom when you deeply realize that you are safe in Re-observation, that you can go deep into the pit, and the pit is just fine. In Review stages, a period when it can be easy to call up specific stages and stay in them to get a better sense of them, I have again and again called up Re-observation just to check it out and learn its secrets.

On a somewhat different note, however bad Re-observation is, we can’t always blame it for everything. The primary sign that the negative side effects that may occur in the Dark Night are not associated with insight stages (but instead are due to other, ordinary, real-world processes) is that they do not change much in the face of strong and accepting investigation or when we stop practice entirely. Remember, you have two sets of effects going on: insight-related, and other circumstances and psychological aspects of your life. If good insight practice, done well and bravely, with strong investigation and good technique, is not fixing your life situation, then you may instead have standard, ordinary problems to be dealt with by ordinary, real-world methods.

As you can likely already tell, the Dark Night tends to get practitioners strategizing, trying to figure out the best way to crack it and get to Equanimity. This has led to various teachers and practitioners developing their own distinct schools of thought that may deem some techniques and approaches the most optimal, typically the techniques that have worked best for them. However, those who have gone through the Dark Night enough times and with a range of approaches, techniques, attitudes, and practice conditions will eventually realize that there are many, many ways to skin this cat, to use an un-Buddhist metaphor. Exercise often helps. Loving-kindness practices get recommended often for good reason. Strict vipassana and ultra-rapid noting work well for those with a high tolerance for pain. Slower noting might work for those with a bit more time and less interest in shattering themselves.

Some teachers highly recommend physical practices, such as yoga with a high degree of bodily awareness, as that can ground people in something other than their psychological stuff. Others might highly recommend plunging hard into their psychological issues and healing, with a high degree of sensate mindfulness of that process to ensure it keeps producing insights. Others with mighty concentration skills might go for more abstract objects, such as sacred geometry, as mentioned above. The “concentrate your ass off” strategy in the Dark Night has much to recommend it. Loving-kindness practices and other brahma viharas (covered in Part Six) are commonly reported to be helpful. Yet others might recommend more shamanic and psychonautic techniques to cause the sort of radical unsticking that can happen with those methods, and reality testing shows that those do sometimes work for some people but cause problems for others, and predicting which will result is not easy. Each of these strategies has risks and benefits to be considered.

In contrast to what most people might expect me to advocate here, it is true that much more gentle approaches can also work in Re-observation and the Dark Night in general. Some find that softening, opening, and accepting generate much better results than more aggressive approaches such as rapid noting or surfing fine vibrations. Sometimes just carefully investigating and gently relaxing what is often called “body armor”, those physical tensions that correspond to psychological blocks and tensions, can be quite effective in this territory.

Others among us will notice that just carefully investigating other aspects of our lives, like physical tensions related to roles and identities, will help facilitate progress here. Some do well with intellectual reflection coupled with some sensate investigation, and repeated questions such as, “Where am I contracted?” or, “What am I clinging to?”, asked well and often enough, will actually yield good results. Some with more spacious tendencies may notice that just feeling into the subtle moving warps in our sense of attention or space that are the hallmarks of the third vipassana jhana will be all they need, and doing this with the eyes open rather than closed can help us keep from getting lost. Many of these methods just require doing them well enough for long enough to get them to cause progress.

Even stranger measures can be oddly facilitating here although they may superficially seem to have little to nothing to do with insight practice. Some practitioners may just need to change locations, resolve a single conflict with one person, cry about one issue they need to grieve over properly, make some other simple change, or go through some other simple process, and then suddenly everything opens. Just giving yourself permission to care for yourself might make a difference. I recommend When Things Fall Apart and Start Where You Are, by Ani Pema Chödrön, as the yin energy of these books will help counterbalance the energy of this book, which can be too yang sometimes. Nurturing strategies often help a lot in the Dark Night.

I remember one cycle through this territory where what cracked it was just dancing wildly for hours until I was totally exhausted. A few will do oddly well by stopping practice entirely, forgetting entirely about progress and the maps and all of that, and just surrendering, but this last one generally only works when the meditator is in the correct place and has done enough work and growth already for that strategy to make sense.

This is a small subset of the various strategies that might work and that teachers advocate. You will have to assess your own capabilities, inclinations, intuition, resources, and what you have available to find what works best for you. Experimentation and a willingness to regroup and retry if you fail with one approach are key, as failure and frustration are common experiences the first few times we try to crack the nut of the Dark Night. If you are on retreat, it typically only takes about ten days to two weeks of struggling in the Dark Night to fall back to earlier stages and have another shot at it, so you can try a new strategy on the next pass if the first pass strategy didn’t work. I still generally feel that very simple practice: six sense doors, three characteristics, is the best practice for all insight stages. One day, I hope that scientific methods and controlled experiments are applied to find how best to navigate this territory. Until then, take your best guess and, if it doesn’t work, try again.

Due to the sorts of frustrations and failures that are common in this territory, this stage is sometimes called the “rolling up the mat stage”, when many who joined monasteries in the stage of the Arising and Passing Away now give up and disrobe. People on retreats tend to need much reassurance but often leave right then even with good support, guidance, and encouragement. Are you suddenly needing to leave a retreat that you had planned to stay in much longer? You are likely in this stage.

There can be the distinct feeling that there is no way to go forward, and it is useless to go back, which is exactly the lesson we should learn. Acceptance of exactly this, right here and right now, is required, even if it seems that this mind and this body are completely unacceptable and unworthy objects of investigation. Remember: no sensations are unworthy of investigation!

One of the hallmarks of the early part of this stage is that we may begin to clearly see exactly what our minds do all day long, see with great clarity how the illusion of a dualistic split is created in the first place, sensation by sensation, moment to moment, but there is not yet enough of a meta-perspective and equanimity to make good use of this information. This can be very frustrating, as we wonder how many times we must learn these lessons before they stick. The interesting thing is that this stage, when gone through at the level of emotions and vibrations, rather than in the realms of light produced by strong concentration, will nearly always come with a sense that it lasted just a bit longer than we could take it, and yet somehow, we can take it, and it does end.

Intense feelings of frustration and disenchantment with life, relationships, sex, jobs, moral codes, the world, and worldly responsibilities may emerge at this stage in ways that can cause enormous disorientation, disruption, and angst. Re-observation can take whatever issues and reactions arose in the earlier stages of Fear, Misery, Disgust, and Desire for Deliverance, combine them in fiendish ways, and then crank that intensity to the next level, a level that can seem overwhelming. These aspects of our life can temporarily seem bland and pointless at this stage, though it may seem that this will always be the way we feel about them.

This stage can mimic or perhaps manifest as some degree of clinical depression. Beware of making radical life changes that cannot be easily undone, such as a divorce or firing off angry emails to your boss, based upon the temporary feelings that may arise during this stage. For those who recognize that they are in this stage, some form of active mental compensation for these potential effects can be helpful to facilitate maintaining our relationships, jobs, studies, etc., at a functional level. This can be very skillful if it is also combined with practice that allows the experiences of this stage to be acknowledged and understood as well.

I should be careful here in that, while I generally advocate for maintaining jobs, relationships, studies and the like, if possible, in the face of Dark Night stuff, there is obviously no way for me to know for certain that this is the right course of action for you or anyone else, as the future is unknown and unpredictable. This is obviously not helpful, as we might wish for concrete, reliable guidelines as to how to proceed, and yet, unfortunately, there are none. Maybe shaving your head and joining a monastery really is the best thing you could possibly do. On the other hand, maybe preserving your marriage and job is.

There are obviously many other options that might suddenly seem like good ideas in this stage, and whether, in retrospect, they will have been as good an idea as they seemed at the time is anyone’s guess. I wish I could definitively tell you what to do, but I can’t. Still, there is something to be said for optionality, even if, in the Dark Night, all options can seem like bad options. Not trashing possibly valuable relationships helps preserve optionality and generally lessens later regrets. There are ways to gain some space in which to let this disorienting and often disruptive process mature that are more skillful and less damaging than others, and I wish you well finding those.

Layers of unhelpful and previously hidden expectation, pressure, and anxiety can reveal their true uselessness, though this beneficial process can feel very confusing and difficult. We may get the sense that we have never had such a strong emotional life, and until we get used to this new awareness of our previously subtle or unacknowledged feelings, this stage can seem overwhelming.

Occasionally, people at this stage can also have what appears to be a full psychotic break, or what is often called a nervous breakdown, though if these are truly a side effect of insight practices, they should pass quickly. The main key here is to continue to acknowledge and accept the content but also to see the true nature of the sensations that make up these natural phenomena. This can be extremely hard to do, especially if people have chanced upon this stage without the benefit of the support and guidance of a well-developed insight tradition and qualified teachers who can easily recognize and navigate this territory.

Even for those who do get into this in a well-developed tradition, unrealistic spiritual ideals can really screw up practice. In your idealized spiritual world, you imagine you aren’t supposed to be insanely frustrated, on edge, shuddering from some strange wrongness you can’t figure out, because you are a meditator, you are practicing something good, and so you shouldn’t feel this way, or at least so the traditions might seem to tell us. However, this is exactly where your practice led you at some point, where it took you, what is really going on, because you have entered aspects of the human psyche you wished would just go away and you wouldn’t have to deal with. Go into them, but with wisdom, with clear morality, with some sense that you can go there and be okay, with some control of what you think, say, and do.

The classic arc of the hero’s journey, where at some point they must enter the underworld, mirrors this part of the path. Part of the flip side of the next stage involves going there, being honest, dealing with an utterly “un-spiritual” way of being that might not fit your ideals at all. Keep a lid on the bleed-through, but internally be willing to be emotionally honest, and keep investigating. This is an acquired taste and getting comfortable doing this is not easy for most people. Still, it is a great skill to learn.

Those who do not know what to do with this stage or who are overwhelmed by the mind states can get so swept away in the content that they begin to lose it. This is the far extreme of what can happen in this stage. Fear is frightening, Misery is miserable, and seemingly psychotic episodes are confusing and destabilizing. In the face of such miserable experiences, we may swing to the opposite extreme, clinging desperately to grandiose or narcissistic images of ourselves. These reactions can easily perpetuate themselves, and this can become a blatantly destructive mental habit if people persist in wallowing in these dark emotions and their deep and unresolved issues for too long. It can be like cognitive restructuring from hell. Do not do this to yourself.

I should mention the problem with developing concentration, which you must have succeeded at to at least some degree at some point to get into this territory. Strong concentration is a generic force that may be used for good or ill. If you use strong concentration to write positive qualities on the mind, they will be written more strongly than if you didn’t have strong concentration. Likewise, if you have strong concentration and end up writing negative qualities on the mind, those will also be written more strongly than if you lacked strong concentration. That is the danger in this stage. Thus, the essential point is, if you ever develop strong concentration, you must be extremely careful with what you do with it. Part Six, specifically chapters fifty-eight to sixty-one, will go into more about this, but the basic lesson is straightforward.

Specifically, if you continue to be strongly identified with content, without perceiving its true nature, and your strongly concentrated mind dives down that pathway of focusing entirely on the story, particularly negative interpretations of the story without seeing those thoughts as thoughts, then the mind can spiral down and down into madness and despair, and more madness and despair can lead to a horrid feedback loop. I call this “dark jhana”: like the exact reverse of jhana. In skillful jhana, we skillfully use positive qualities to attract and stabilize attention, which then reinforces those positive qualities in a positive feedback loop. In dark jhana, we unskillfully reinforce horrible mind states by obsessing about horrible mind states from within horrible mind states while being freaked out by horrible mind states.

If you recognize dark jhana is happening, put the brakes on it right then with everything you have. Seize control. Refuse to lose that control. Find a way to get a grip on yourself. Splash cold water on your face. Eat grounding food. Exercise or take a walk in nature. Take a warm bath. Listen to soothing music. Sing. Dance. Play a video game. Watch a funny movie or funny cat videos on YouTube. Read the section in Part One where the Buddha talked about the removal of distracting thoughts and apply those instructions with full force: this is when they really come in handy. Stand with your legs planted firmly on the ground, your hands gripping something like a sink, countertop, or the back of a chair, and figure out where the actual problem is in your body and the space in which you stand. Note physical sensations of restlessness and irritation with precision and bravery.

Dark jhana sucks and should be avoided at all costs. Wire your brain in a positive way, not a negative way, and you will do much better. Go into that territory at a bare sensate level that remembers there is space and you will do much better. Go into it divorced from the senses and lost in the content, and badness will likely result.

When people mention “touching their own madness” on the spiritual path, they are often talking about this stage. This stage can make people feel claustrophobic and tight. If they push to make progress, they can feel that they are just getting more and more tightly wound and are about to snap. If they do nothing, they continue to suffer anyway.

The advice here: stick with the process but don’t force it. Pay attention to balancing effort and gentle acceptance. Remember that discretion is the better part of valor. Practicing in moderation as well as maintaining a long-term view can be helpful. Think of practice as a lifelong endeavor, but do just what you can each day. Stay present-oriented. Walks in nature or places with open, expansive views can help, as can exercise. Re-observation has the power to profoundly purify us, given sufficient commitment to just being willing to sit with it. Be clear, precise and accept all this despite the pain and anguish, both physical and mental, that it can bring.

If you are on retreat, let the teachers know what is going on immediately. Sit and walk according to the schedule. Apply the technique as prescribed every second, if humanly possible, and do not leave the retreat early! Remember: applying the technique means seeing everything arise naturally, without anything having to happen at all. This can really take the pressure off, a pressure that really doesn’t help in this stage. There is a way to keep practicing well that nevertheless drops the unskillful aspects of striving which are pulling you away from each moment. Other than just sticking to the schedule, not a lot needs to happen beyond what is already happening. Thus, and very critically, you can’t power this stage, but you can try to accept and synchronize with what is going on at a direct experiential level.

Again, if on retreat, try walking outside as opposed to inside if logistically possible. Reclining sometimes rather than sitting might help, but some will find the restless energy too much, in which case walking may help. It can seem counterintuitive to keep practicing when things feel so unproductive, unspiritual, unpleasant, and unbearable, but keeping at it in skillful ways builds the wiring that leads to the good stuff that comes in the next stage even if it feels like it is doing nothing good at all.

This stage is a profound opportunity to see clearly the pain of the dualistic aspect of our attachments, aversions, desires, hopes, fears, and ideals, as our awareness of all this has been amplified to an unprecedented level. At its best, it is very humanizing and very emotionally honest. This is the stage that makes possible the path of heroic effort, the diligent investigation of this moment based upon the powerful wish for awakening, because at this stage all the unskillful aspects of this wish are beaten out of the meditator with a force equal to the suffering caused by them. You can get very far on highly imbalanced and goal-oriented practice, and it can provide sufficient momentum and meditation skills so that, should you get your ass kicked at this stage, you continue making quick progress anyway, even when you drop off the imbalanced striving power and let the insight machine you have built coast somewhat on its own momentum.

Again, if meditators stop practicing entirely at this stage, they can get stuck and haunted for the rest of their lives until they complete this first progress of insight. Not moving forward with practice at this stage will deprive meditators of its primary benefits, such as the increased perceptual abilities that allowed them to get this much insight in the first place. They teeter on the brink of meditative greatness. Remembering this will help increase faith, and it can take a lot of that to get through this stage. Good teachers will help students develop faith in their own abilities to handle these stages, and to balance this with backing off if it truly gets to be too much.

To get through the Dark Night on your own power and to get to Equanimity is true meditative greatness. The next stage is fantastic and what comes after it is even more so. Thus, those who quit in these stages reduce their chances of ever getting beyond this stage, and the whole range of consequences, both physical and emotional, can remain long after the meditation skills have faded. Finding that balance, knowing what you can take and what you can’t, is as much art as science, with no perfectly clear guidelines that can be given. However, we strongly need to consider that quitting in these difficult stages increases the chances of doing it again the next time it happens, as the way we practice creates pathways in the brain that will be stronger next time. This pattern of bailing on practice in the tough stages can create “chronic Dark Nighters”, meditators who just don’t figure out how to move through this stage for a long time.

You would be surprised how many of these people are out there. Their failure to unstick themselves may be due to their own psychological makeup, poor instruction, belief that the spiritual life is all about bliss and wonderful emotions, belief in unrealistic and absurd models of spirituality that do not allow for the full range of the emotional and mental life, or chancing upon this stage outside the context of a well-developed insight tradition.

I was a chronic Dark Nighter for over ten years without having any idea what the hell was happening to me, so I can speak on this topic with some authority. Further, I have gone through numerous other Dark Nights at the higher stages of awakening and have come across the same issues again and again. Being stuck in the Dark Night can manifest as anything from chronic mild depression and free-floating anxiety to serious delusional paranoia and other classic mental illnesses, such as narcissism and delusions of grandeur (which I am sure you recognize at points in this book, parts that were likely written in this phase). Dark Nighters may act with a disarming mixture of dedicated spirituality, social conscience, compassion, and reactive darkness.

I mentioned that the A&P could impart a bit of the inspirational, radical religious leader quality to those with such tendencies. For these same individuals, Re-observation can sometimes lend a bit of a paranoid, apocalyptic cult leader quality to them, a confused whirlwind of powerful inspiration and frantic desperation. Just because someone has borderline or antisocial personality disorder doesn’t mean they can’t make progress in insight, and when they hit these stages it can get wild. In fact, this basic pattern of the A&P happening to a psychopath leading to a cult-following and then mass-suicidal crash when they inevitably hit Re-observation is seen again and again in history and is perfectly explanatory of this otherwise perplexing phenomenon. Same goes for suicide bombers and militant recent converts in general.

We may all have our own neurotic tendencies that come out when we are under stress, but if you feel that you are really losing it, get help, particularly from those who know this territory firsthand and are willing to talk honestly about it. Don’t be a macho meditator, go it alone, or get stuck; and don’t imagine that spiritual practice can’t cause some wild and sometimes extremely unpleasant side effects. One of the best things about working with thoroughly qualified and realized insight meditation teachers before we get into trouble is that they will have some idea of our baseline level of sanity and balance and thus know what our capacity is and what we can manage.

That said, I suspect that both the mushroom factor and the dharma culture of jet-set teachers popping in and out of our lives with little chance for students to have meaningful contact with them off-retreat contributes to the significant number of Dark Nighters out there. I suspect that there are fewer problems with chronic Dark Nighters in traditions in which the maps outlining what can happen are well-known and in which there are teachers who are accessible and honest about their humanity and the varied landscapes of the spiritual terrain. Naming and normalizing these stages can be profoundly empowering to those going through them in order to find and master their own meditative power.

On the other hand, genuine mental illness or unrelated emotional or psychological difficulties can show up in people’s lives. Blaming it all on the Dark Night may not always be accurate or helpful, though if you have recently crossed the A&P but have not completed an insight cycle or gotten into the next stage (Equanimity), there is going to be some Dark Night component mixed in with whatever else is going on.

Meditation traditions tend to attract what can seem like more than their fair share of the spiritual, emotional, and psychological equivalents of the walking wounded. Sorting out what’s what can sometimes get murky and may require the help of both those who know this insight territory and those who deal with ordinary mental illness and the emotional and psychological difficulties unique to the culture in which practitioners were raised. The best guide would be familiar with both realms. I have an awakened friend who has found it very useful to take medication to treat his very real bipolar disorder. There is something very down-to-earth and realistic about that. These practices won’t save us from our biology. They merely reveal something in the relationship to it.

On the other hand, there are those of us who are so deeply indoctrinated by the models of “working through” our “dark stuff” that whenever it comes up we turn to psychotherapy or a whole host of other ways of getting our issues to “resolve” or go away. This view implies false solidity and an exaggerated importance being given to these things, making it very hard to see the true nature of the sensations that make them up. The trap here is that we turn a basic crisis of fundamental identity into a witch hunt for the specific parts of our lives we imagine are to blame for our feeling such dissatisfaction with our basic experience. If someone has gotten to this level of practice, no amount of tinkering with the circumstances or issues in their life will ever solve the core perceptual issue.

That doesn’t mean that some of the dissatisfaction with specific aspects of our lives are not valid—quite often it is. However, these relative issues get conflated with a far deeper issue, that of what we really are and are not, and until this cycle of insight has been completed, this conflation tends to cause us to greatly exaggerate our criticisms of those things in our lives that could actually stand improvement and work. Learning this lesson can be very hard for some people, and the dark irony is that we may wreck our relationships, careers, and finances, as well as emotional and physical health, trying to get away from our own high level of insight into the true nature of reality.

It can also make us have strong reactions to our meditation teachers and dharma friends, either being very dissatisfied with them, or demanding that they somehow save us, or more likely, both. Until we are willing to work on a more direct, sensate level, there is no limit to the amount of angst and negativity we can project onto our world. I have seen this play out again and again in myself and in the lives of my dharma companions—the strange volatility that can be created by Dark Night–amplified reactive attachment disorders. It can be a very ugly business.

My advice: if careful analysis of your insight practice leads you to the conclusion that you are in Re-observation, resolve that you will not wreck your life through excessive negativity. Resolve this repeatedly and intensely. Follow your heart as best you can, but try to spare yourself and the world from as much needless pain as possible. Through sheer force of will, and with the assistance of whatever skillful supports you can connect with, keep it together until you are willing to face your sensate world directly and without anesthesia or armor. I have seen what happens when people do otherwise, and have concluded that, in general, things go badly when people do not follow this advice, though some unexpected good, in the form of learning the hard way, can and does come from such situations.

The framework of the three trainings and the three types of suffering that are found within each of their scopes can be helpful here as well. Since most of us are generally not used to facing fundamental identity crises, which is the basic issue in Re-observation, we are not familiar with the misery of fundamental suffering. Being unfamiliar with that misery, we are likely to conclude that it is produced by the specifics of our ordinary world and personal circumstances. However, if we have gotten to Re-observation, that is, if we have found these techniques to be effective, we need to have faith that the remaining advice may be of value to fulfill this part of the experiment. If we are in Re-observation, the task that confronts us is to tease out the fundamental suffering we now know all too well from the specific problems of our lives in an ordinary sense. Remember the five spiritual faculties? Remember balancing faith and wisdom? This is one phase of practice when you get to see what that truly means, as it will test both.

This advice to at least partially decouple our felt sense of suffering from our ordinary circumstances may sound dangerous, heartless, or bizarre to some people. It is a valid criticism. In an ideal world, we would not have to go around second-guessing ourselves and the sources of our misery in the specific way that I advocate here. In an ideal world, we would really have our psychological trip together, be able to stay with the practice during these stages, and thus cross quickly through the Dark Night and finish this practice cycle. It can be done.

We are not always ideal practitioners, and thus the Dark Night often causes the problems mentioned previously that need to be addressed. My solutions to what happens when we cannot or will not do insight practices in the face of the Dark Night are also not ideal. However, the outcomes are likely to be much healthier in the short and long term than those that come from simply allowing unrestrained Dark Night bleed-through, which often occurs in the absence of solid and sufficient training in morality. Strangely, I have concluded that simply practicing is often much easier than trying to stop Dark Night bleed-through if we are willing to just try it, though it can often seem otherwise. The old kindergarten evaluation, “Follows instructions, plays well with others,” is still a valuable standard in the Dark Night.

While in the Dark Night, not restraining negativity and reactivity that issue from our thoughts, speech, and physical actions is a bit like getting stinking drunk and then driving in heavy traffic rather than just sitting down and waiting to sober up. Not continuing to do insight practices in this stage is like going into surgery, getting an incision, getting the surgery, and then having the surgeon leave you with a large, open incision. Until you get that wound closed you are basically screwed, no matter how anyone might try to comfort you. In this case, you are both the surgeon and the patient. Face the wound and close it up! You have the necessary skills, as you have gotten this far. Use them. The procedure is almost done.

There are also those who try to investigate the true nature of their psychological demons and life issues but get so fixated on using insight to make them go away that they fail to hold these things in perspective. This subtle but common corruption of insight practices turns practice into another form of aversion, escape, or denial rather than a path to awakening. Drawing from the agendas of mostly psychology and confused morality, in which there is concern for the specific thoughts and feelings that make up our experience, we fail to make progress in insight, whose agenda is simply to see the true nature of all sensations as they are. Both are important, but it is a question of timing.

I have concluded that, with very rare and fleeting exceptions, ninety-five percent of the sensations that make up our experience are really no problem at all, even in the difficult stages, but seeing this clearly is not always easy. When we fixate on very painful or very pleasant sensations, we can easily miss the fact that most of our reality is likely made up of sensations that are no big deal, and thus we miss many great opportunities for easy insights. Further, the Dark Night can bring up all sorts of unfamiliar feelings that we have experienced rarely if ever with such clarity or intensity. This has the effect of busting attempts at spiritual bypassing, as the Dark Night is basically the exact opposite of spiritual bypassing. We are in it, deep into it, facing our darkest and most challenging stuff. However, until we get used to these feelings, they can frighten us and make us reactive because of our lack of familiarity with them, even if they are not actually that strongly unpleasant at a sensate level. 

What compounds our misery is the mental content we tend to kick up in response to sensations. Often the stories we make up and then tell ourselves, about why these difficulties are happening and what it all means, exacerbate the problem they were intended to solve. There are multiple ways to reframe the meaning of these occurrences that might make them more bearable and point to solutions that are more likely to work, particularly learning to reframe them in terms of these insight maps (and the three characteristics), which is why they can be so valuable. It is not that the insight maps are the be-all and end-all of meaning, as they obviously aren’t. However, focusing entirely on the psychological end of our work without also focusing on the underlying insight process is a common trap that typically doesn’t go as well as the dual approach that keeps making progress on the insight front also. [Man’s Search for Meaning, by Viktor E. Frankl, may shed light on some of the skillful and therapeutic uses of meaning as we confront these challenging insight stages.]

I highly recommend using physical sensations as the objects of inquiry during the Dark Night whenever possible, such as those of the breath, with particular attention to the fact that these sensations occur in space. Diving into emotional content, even with the intention of investigating it, can sometimes be a very hard way to go. Remember, whether we gain insight through investigating physical or mental objects is completely irrelevant. Insight is insight. Whenever possible choose objects for investigation by which you won’t easily get caught. The best thing about reality, particularly in the Dark Night, is that you only have to deal with one little flickering sensation in space at a time. Staying on that level when doing insight practices is an unusually good idea. Pay attention to what is right in front of you, but keep your attention open.

Using physical object allows you to investigate how much physical pain you are actually in. Does reality seem totally horrible? Notice how much of it is actually excruciatingly painful. If it is not that painful, why do you think it’s horrible? Investigate that carefully in your body, so as to notice exactly where the pain is and also exactly where it is not. Open your eyes and notice the space you are sitting in. Are you in a safe place? No gunfire nearby? Have enough to eat? Decent water? Immediate threat to life or limb? If not, is that much fussiness, reactivity, and drama really necessary? Probably not. Sink into that down-to-earth, common-sense understanding, and basic, practical wisdom. Do some solid reality testing. Notice exactly what volume of space is really a problem and exactly how much of it is not. You will very likely find that the majority is not, and somehow your mind had forgotten that much if not most of it is okay and perhaps even pretty good or interesting. Then get back to a detailed but open, wide, all-embracing, moment-to-moment sensate investigation.

Scary stuff said, there are people who breeze straight from the Arising and Passing Away through the whole of the Dark Night in as little as a few easy minutes or hours and hardly notice it at all, so don’t let my descriptions of what can happen script you into imagining that the Dark Night has to be a major suffering event. It absolutely does not. These descriptions of what can occur are merely there to help those who do encounter these sorts of problems to realize that these things do occur, and can be skillfully addressed. There is no medal awarded for having a tough time in the Dark Night or for staying in it for longer than necessary, much to my dismay.

At my best and on retreat, I have gotten through Dark Night territory in as little as about a day and a half. Bill Hamilton said one Dark Night took him about seven minutes, which is really fast, but it means it can be done. I have had Dark Night phases that were no worse than the general stress I encounter in daily life in ordinary situations. That said, off-retreat I have had Dark Night phases hit hard for months, those being before I knew anything about what they were or how to deal with them. Contextualization, explanation, normalization, and the empowerment that comes with knowledge and well-applied time-tested techniques make a huge difference, as I have noticed by doing the experiment myself many, many times, and as many others have reported.

One of the more bizarre potholes we can fall into in the Dark Night is to become fascinated by and identified with the role of The Great Spiritual Basket Case. “I am so spiritual that my life is a nonstop catastrophe of uncontrollable insights, disabling and freakish raptures, and constant emotional crises of the most histrionic nature. My spiritual abilities are proven and verified by what a consummate mess I am making of my life. How brave and dedicated I must be to screw up my life in this way. Oh, what a glorious, holy, special, and saintly wreck I am!” Both my sympathy and intolerance for those caught in this trap are directly related to the amount of time I have spent in that trap being just like them. While we should not try to pretend that the Dark Night hasn’t made us a basket case, if it has done so, neither should we revel in or wallow in being a basket case, nor use the Dark Night as an excuse for not being as kind and optimally functional members of society as we can possibly be.

Try to navigate the Dark Night with panache, dignity, self-respect, decency, gentleness, poise, and if possible, a sense of humor, which often seems to be the first thing to be sacrificed at its bloody altar. Even a cutting, cynical, and dark sense of humor about your current experience would be better than none at all, but avoid hurting people with it. Feel free to use humor on yourself as much as you wish. Remember to balance all that with some honest humanity. It is actually possible to have fun with the Dark Night, just like it can be fun to go on a scary roller coaster or see a scary movie, like the alleviating feeling of a really good cry, like the weird thrill that comes from primal scream therapy. Remember that. 

Additionally, the practice of remembering the good, true, and beautiful aspects of the world, and the myriad kindnesses shown you and others by you and others—to literally stop and smell the roses—can help a lot to regain perspective. My roses are actually blooming nicely as I write this, with their beautiful fragrance wafting through the open window. This advice is likely to ring cheesy to one in the Dark Night, but remember this and you will do better.

Speaking of doing better, and getting away from the crazy and back to the vipassana, I should mention something about the micro-phenomenology that I really care about, that makes insight practice more than just psychology. The patterns happening from a sensate point of view in Re-observation are the pinnacle of the third vipassana jhana and, because of this, have the following qualities: first, they are very broad—very around the “back”, very on the periphery of attention. That is where attention is naturally very strong in this phase, so go with that first, as it is easier. Allowing attention to be its natural fluxing shape will make this work a lot better than trying to go narrow and forcing things—that would be using a first vipassana jhana coping strategy at a stage in which it isn’t likely to work well.

Second, the frequencies of pulses are chaotic and fast. We are getting into more sophisticated forms of more inclusive attention that are starting to broaden enough to include many diverse, irregular, erratic, intricate aspects of reality. Go for that attention-wise, meaning go into frequencies of the oscillation of the sensations that appear to be subject and object that are really fast and harmonically irritating, instead of regular and predictable. We are talking at least ten to eighteen pulses of sensations per second, if not a lot more. While noting can help if we are getting run over in this stage, if we can get it together to go into the broad vibrational complexity directly, we can learn to draw on the remarkable discerning power of our minds. We can notice how fast reality is arising, and, as reality and comprehension are the same thing in their essence, we can notice that comprehension, and thus contemplation, can go this fast. It takes an elegant letting go of control and an embracing of that to get what Re-observation is trying to teach you.

Do not try to power through this: that’s first vipassana jhana. Do not try to go for really tight, narrow, fine, tingly frequencies that are all about a center of attention and not about background: that is second vipassana jhana. Re-observation comes at the peak of the third vipassana jhana: it is broad, rich, chaotic, and about the “background” and issues of synchrony and asychrony. “Background” here means those things we typically think of as on “this side”, as well as those sensations that tend to frame objects in the center of attention, as well as just those sensations that are more in the direction of “us”.

The fourth jhana will put it all together later, so here, you just need to learn the third jhana piece well. The first jhana’s linear, controlling, effortful attention paradigm can’t go that fast, but reality can, and reality is attention itself, so just embrace that. You need to let reality start learning to recognize that it is already recognizing itself. That’s the only way the mind can realize the massive processing power it already actually has and embrace a vast and complex world of sensate experience that the limited, linear mind cannot possibly track in all its richness and intricacy.

This is vipassana. Notice that every little background sensation already is its own comprehension, where it is, as it arose and vanished, and that trying to pretend to be a little point in space observing and controlling all that sensate complexity is absurd and just causes suffering: that is the lesson here. That is the three characteristics, and the three characteristics are the key in this stage, as with all the others. Do not get all caught up in my psychological descriptions, they are there to help only if you get thrown totally off your vipassana game. As soon as you get back on your game even a little bit, get back to noticing all this come and go on its own, naturally, effortlessly, at a basic, fast, sensate level. This is the most important paragraph of this whole section.

One way or another, when we finally give up and rest in what is happening without trying to alter it or stabilize it, when we can accept our actual humanity as well as be clear about the three characteristics of naturally flowing mental and physical phenomena, there arises … [Equanimity]

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