I have been practicing a number of years and recently began pivoting to a more insight based practice rather than concentration.

This has led me to question something which I have found i do not quite understand as fully as I thought i did. 

I would like if possible someone to confirm the following assumption is correct:

Assumption #1

During insight practice, the meditator observes the sense data. Feelings, Thoughts, vision, sounds etc

Through just observing this information (such as bodyscanning, noting)  - the 3 characteristics "just emerge"/or become noticable - leading to insight moments. The meditator does not need to do anything special to cause the 3 characteristics to be noticed, purely observe the sense data


This then leads me to the following curiosity: If the above is true, and merely through observing the sense data (feeling/sound/vision/thought..) insight occurs from "seeing the 3 charateristics" without the meditator doing anything special, Why then when the meditator does concentration practices, stilling the mind on a single object such as the breath, does insight not occur?

As surely the meditator when doing a concentration practice , stilling the mind on an object is still just observing the sensory data? should the 3 characteristics also not automatically be noticed?

Is this reason that for the 3 characteristics to noticed, the scope/field be wider than just a single area of attention?

Thank you for your time

The short answer is the "single object" aspect is fundamentally not consistent with the changing aspect of reality. It's a form of simplification that the mind finds restful, which means it comforts the mind but doesn't offer insights into the nature of experience.

The long answer is that all sorts of things can happen during all sorts of meditation practices and people define these things in all sorts of ways and concentration and insight happens in all sorts of ways so it's a big mess and there are no rules. There are just generalizations that generally apply, like noticing the not-self, imperminant, and not-fully-satisfying nature of experience tends to lead to insights, like noticing how the mind can be cultivated to hold a subset of experience with an unbroken continuity and this tends to cause jhana states. 

I think it depends somewhat on the person. Some people will pick up on it faster than others. Some people might notice things, but will they put it all together? If you know what to look for and look for it, you will see it faster. I am not really a big fan of the style of teaching where you tell the student to do a technique and wait for them to get it. I prefer to understand what I am doing, and why, what the technique is supposed to do and how it accomplishes it. Otherwise I won't have any faith in the technique or the teacher and if I don't trust either I won't feel justified in putting time and effort into it. This attitude is based on a lifetime of experience, but I don't mean that everyone should feel this way, it depends on the personality, character, and other qualities of the person.

There are many different practices that are considered concentration practice. Some of them really involve stilling the mind, to the point where there is nothing happening and nothing to observe. 

But for other types of "concentration", the way the average person would observe the breath - there is a lot of insight in that. Every time your mind wanders, you are reminded you don't control your mind (not self). Every unpleasant thought or emotion that arises and fades can teach you about the origin and cessation of suffering (dukkha). Every fleeting thought, emotion, impulse, body sensation, or noise in the environment tells you about impermanence, and they all barge into awareness seemingly from nowhere suggesting neither body nor mind is self. But you will get more out of it if you know what to look for and have the knolwedge to understand it in context.

There is also concentration in vipassana. When you are practicing vipassana you still have to keep the mind focused in order to do the technique. I do vipassana from within samatha, I get the mind quiet and tranquil and in a good mood, before doing vipassana, because vipassana can be unsettling if you look at your attachments and aversions and contemplate letting go or surrender, or if your worldview gets turned upside down by insights. Samatha and vipassana work better together.


This article explains that in the Pali canon samatha and vipassana are supposed to be developed together.

https://accesstoinsight.org/lib/authors/thanissaro/onetool.html.

Although I have done retreats in insight practices in the past such as bodyscanning, My daily practice for the last 10 years has mostly been observing the breath, developing calmness and relaxing. Due to strange almost psychokinetic effects when I meditated early on, i developed a lot of tension in my practice. I took me around 7-8 years to get past this. My object was usually the sensations of the breath entering and exiting. But I don't really feel that in this practice i ever had insights into the 3 characteristics, although I guess it is possible there were and it has been so gradual that i have no realised. 

     Meditation done within a system is defined by the system. The system will basically tell you what they expect you to experience or “see”.
They will tell you “our main experience is this, and we will get you to that experience”. Some even set a time frame dependent on a
definite way of practicing or try to push people through to the experience.
     As science is proving and a careful reading of contemplative literature in all traditions will show, the essence of meditation is the expansion of attention. Training has to begin where most people are, which is narrow attention. Single object concentration takes advantage of this. But by selecting an object other than the thought process, which is where the majority of people narrowly focus, the movement towards a more inclusive way of attending begins. The dance between the object of concentration and the mind processes vying for attention sets the stage for a growing field of observations. This preliminary way of practicing is not meant to be held on stubbornly or indefinitely. It is expected that it will be outgrown.
     This expansion of attention is what maps point to. They essentially ask, Have you noticed this while meditating?   But they are not cookbooks. Every person will have his own line of development and difficulties. A look at these maps is helpful as long as they are not fixated on. 
     There is one agreement in all traditions. In order to progress there is one main condition, that you remain calm and that you remain aware. It's the only way to move from observation to observation. What you realize you can try to explain or verbalize in the language of the tradition you prefer.  Experience will always be primordial.

"Although I have done retreats in insight practices in the past such as bodyscanning, My daily practice for the last 10 years has mostly been observing the breath, developing calmness and relaxing. Due to strange almost psychokinetic effects when I meditated early on, i developed a lot of tension in my practice. I took me around 7-8 years to get past this. My object was usually the sensations of the breath entering and exiting. But I don't really feel that in this practice i ever had insights into the 3 characteristics, although I guess it is possible there were and it has been so gradual that i have no realised. "

Use your breath as a anchor that you always can comeback while exploring the diferent phenomena that is arisign. 

But in the breath itself you have a lot to observe... 
Who is breathing? Am I breathing? 
What is breath exactly? What makes breath breath? How exactly feels breath? How exactly feels breath diferent from other sensations? 
Is breath generating desireable mind states and sensations? I see enjoying, clinning  these expirences? 
Is breath not flowing, getting stuck, generating not desirable mind states? I see rejection, try to control etc? 

There is plenty to observe and work with! 

I don't doubt there are these things to observe, or deny they are there, I just mean that in my personal experience and practice I don't recall any particular insights arising while engaging in stillness/concentration meditation. It was purely observing the raw sensation of the breath, and if something arose, attention was to be gently returned to the breath. 

I guess there must be something different occuring when the field of is expanded to allow in more data

This is a very good question. I think as long as the object of meditation is some part of reality that you are watching with indifference it is progress along the path of insight.  Breathe would be one of those objects.  Buddha used Anapasati himself and another arahant, Webu Sayadaw, used it as well.  It is straight out of the satipathana sutta, where you can also find allusions to Mahasi stye noting and Goenka style body meditation. That being said don't worry about jhana, it's unnecessary and often when people get far enough the jhanas happen on their own without any additional effort.

I think Shargrol is completely right, and so is Jim. There are a bunch of different techniques out there which get mixed and matched. It's a mess and some things were better than others for different people.

My style of sitting practice is similar to Jim's and my teacher recently asked me, when you switch from samatha to vipassana, what are you doing differently? I thought a lot about the question and, for me, at moment, it is mostly a matter of attitude. I switch from an attitude of willing absorption into the anchoring experience (the breath) or the resulting state (jhana) to an investigative attitude and, specifically, at any time, I am usually investigating one of the three characteristics. I usually get into absorption using either the breath on the upper lip or the breath throughout the body, but for vipassana, for example, I look just at the breath in the belly. I try to notice all (or in any case, many) of the very short sensations that it is made up of. The sensations produced by the belly's movements can appear as a network of flickering points of sensation, something like watching the flickering lights of a city from an airplane window. Impermanence. Alternatively, again, just as one example, I notice the difference in the movement of the belly between one breath and the next, look for a pattern, and see how good I am at guessing what is coming next. I suck at this game. And the fact that I suck shows me that I am not in charge of the breath. Sometimes the belly almost seems like some other animal that is just doing its own thing. Non- self. I'll spare you a description of suffering, but I use the same attitude. Basically, it is just observing, but it is not just observing in general non-specific way, it is observing a specific characteristic by looking at a specific subset of experience for a specific aspect of that experience.
 
As you are an experienced meditator, if you don't find that any of the three characteristics are jumping out for you when you sit then it might make sense to play around with different techniques. As you say, widening your attention may help (in fact, my teacher recommended it in this connection). One technique that was really helpful for me was the game Ingram describes in MTCBII, in which you put two fingertips together and watch to see which finger (right or left) is sending the signal indicating touch in that moment. The mind can only notice one sensation at a time, so the signalling finger that can be noticed tends to bounce back and forth. I used this as a warm-up exercise to set the pace at which I could notice sensations and it had the effect of accelerating my noting, which is good of getting a sense of impermanence. Then there is classic Mahasi style noting. If you play around with techniques and find one that leaves you saying, "Damn, that is some totally impermanent shit right there!" you've got a good one.

I know Jim already suggested Thanissaro, but I am going to suggest some more anyway. The short chapter titled Mindfulness Defined in this book (https://www.accesstoinsight.org/lib/authors/thanissaro/headandheartbook.pdf) (scroll down until you get to the chapter heading) does a great job of countering the notion that all we have to do is look and wait for the insight to come. This chapter doesn't describer a specific technique, but does set out a useful attitude toward looking.

Martin, can you enter jhana and then just do one of the common meditation techniques? Breathe meditation or Goenka style body meditation?

I know the other direction has happened to me frequently.  Meaning I do an insight techniques and naturally fall into a jhana without doing anything intentionally.

I am not sure how noting would work while in a Jhana though, maybe someone can clarify.

I have never achieved any Jhana states in daily practice, only on retreat. 

Though my question is more a theory based one rather than around my own personal practice. I was curious as to what exactly is occuring differently in the two practices such that the concentration practice doesn't produce insight to the same degree , given that both are essentially observing phenomena 

Kind of, but it brings the harder jhanas to an end. In the softer jhanas, focusing on the breath, for me, tends to have an impact of increasing the intensity of piti and sukha. And that pulls me away from the breath. So, I guess, for me, the answer would be: not so much. Mental phenomena, on the other hand, like thoughts, I can watch in a common mindfulness meditation style while still in a softer jhana, which I think is what people mean when they say "vipassana jhana."