My response is a whole load of excerpts from Jiddu Krishnamurti's book Freedom from the Known. I know I've pasted quite a lot, but I think it really touches on your observations (if I'm not off the mark). It even uses the examples of watching or painting a tree.
Have you ever noticed that when you are in a state of complete attention the observer, the thinker, the centre, the 'me', comes to an end? In that state of attention thought begins to wither away. If one wants to see a thing very clearly, one's mind must be very quiet, without all the prejudices, the chattering, the dialogue, the images, the pictures - all that must be put aside to look...
...But how can we be free to look and learn when our minds, from the moment we are born to the moment we die, are shaped by a particular culture in the narrow pattern of the 'me'? For centuries we have been conditioned by nationality, caste, class, tradition, religion, language, education, literature, art, custom, convention, propaganda of all kinds, economic pressure, the food we eat, the climate we live in, our family, our friends, our experiences - every influence you can think of - and therefore our responses to every problem are conditioned.
Are you aware that you are conditioned? That is the first thing to ask yourself, not how to be free of your conditioning. You may never be free of it, and if you say, 'I must be free of it', you may fall into another trap of another form of conditioning. So are you aware that you are conditioned? Do you know that even when you look at a tree and say, 'That is an oak tree', or 'that is a banyan tree', the naming of the tree, which is botanical knowledge, has so conditioned your mind that the word comes between you and actually seeing the tree? To come in contact with the tree you have to put your hand on it and the word will not help you to touch it.
It seems to me that one of our greatest difficulties is to see for ourselves really clearly, not only outward things, but inward life. When we say we see a tree or a flower or a person, do we actually see them? Or do we merely see the image that the word has created? That is, when you look at a tree or at a cloud of an evening full of light and delight, do you actually see it, not only with your eyes and intellectually, but totally, completely?
Have you ever experimented with looking at an objective thing like a tree without any of the associations, any of the knowledge you have acquired about it, without any prejudice, any judgement, any words forming a screen between you and the tree and preventing you from seeing it as it actually is? Try it and see what actually takes place when you observe the tree with all your being, with the totality of your energy. In that intensity you will find that there is no observer at all; there is only attention. It is when there is inattention that there is the observer and the observed. When you are looking at something with complete attention there is no space for a conception, a formula or a memory. This is important to understand because we are going into something which requires very careful investigation.
Now, when I build an image about you or about anything, I am able to watch that image, so there is the image and the observer of the image. I see someone, say, with a red shirt on and my immediate reaction is that I like it or that I don't like it. The like or dislike is the result of my culture, my training, my associations, my inclinations, my acquired and inherited characteristics. It is from that centre that I observe and make my judgement, and thus the observer is separate from the thing he observes.
But the observer is aware of more than one image; he creates thousands of images. But is the observer different from these images? Isn't he just another image? He is always adding to and subtracting from what he is; he is a living thing all the time weighing, comparing, judging, modifying and changing as a result of pressures from outside and within - living in the field of consciousness which is his own knowledge, influence and innumerable calculations. At the same time when you look at the observer, who is yourself, you see that he is made up of memories, experiences, accidents, influences, traditions and infinite varieties of suffering, all of which are the past. So the observer is both the past and the present, and tomorrow is waiting and that is also a part of him...
...One image, as the observer, observes dozens of other images around himself and inside himself, and he says, 'I like this image, I'm going to keep it' or 'I don't like that image so I'll get rid of it', but the observer himself has been put together by the various images which have come into being through reaction to various other images. So we come to a point where we can say, 'The observer is also the image, only he has separated himself and observes. This observer who has come into being through various other images thinks himself permanent and between himself and the images he has created there is a division, a time interval.
Awareness of all this, which is real meditation, has revealed that there is a central image put together by all the other images, and the central image, the observer, is the censor, the experiencer, the evaluator, the judge who wants to conquer or subjugate the other images or destroy them altogether. The other images are the result of judgements, opinions and conclusions by the observer, and the observer is the result of all the other images - therefore the observer is the observed...
...This awareness that the observer is the observed is not a process of identification with the observed. To identify ourselves with something is fairly easy. Most of us identify ourselves with something - with our family, our husband or wife, our nation - and that leads to great misery and great wars. We are considering something entirely different and we must understand it not verbally but in our core, right at the root of our being. In ancient China before an artist began to paint anything - a tree, for instance - he would sit down in front of it for days, months, years, it didn't matter how long, until he was the tree. He did not identify himself with the tree but he was the tree. This means that there was no space between him and the tree, no space between the observer and the observed, no experiencer experiencing the beauty, the movement, the shadow, the depth of a leaf, the quality of colour. He was totally the tree, and in that state only could he paint.
Any movement on the part of the observer, if he has not realized that the observer is the observed, creates only another series of images and again he is caught in them. But what takes place when the observer is aware that the observer is the observed? Go slowly, go very slowly, because it is a very complex thing we are going into now. What takes place? The observer does not act at all. The observer has always said, 'I must do something about these images, I must suppress them or give them a different shape; he is always active in regard to the observed, acting and reacting passionately or casually, and this action of like and dislike on the part of the observer is called positive action - 'I like, therefore I must hold. I dislike therefore I must get rid of.' But when the observer realizes that the thing about which he is acting is himself, then there is no conflict between himself and the image. He is that. He is not separate from that. When he was separate, he did, or tried to do, something about it, but when the observer realizes that he is that, then there is no like or dislike and conflict ceases.
For what is he to do? If something is you, what can you do? You cannot rebel against it or run away from it or even accept it. It is there. So all action that is the outcome of reaction to like-and dislike has come to an end.
Then you will find that there is an awareness that has become tremendously alive. It is not bound to any central issue or to any image - and from that intensity of awareness there is a different quality of attention and therefore the mind - because the mind is this awareness - has become extraordinarily sensitive and highly intelligent.