I read "...philosophers are no nearer to the meaning of 'Reality' than Plato got...". What a strange situation. How extraordinary that Plato could have got even as far as he did! Or that we could not get any further! Was it because Plato was so extremely clever?
(Ludwig Wittgenstein - Culture and Value p.15)
Wittgenstein of course talks explicitly about other philosophers very little. This brief nod in the direction of philosophy's founding father should therefore be treated with great care in order to understand what is really being said.
I can see two interrelated issues for Wittgenstein here. The first is a criticism of Plato's own project. The second is a criticism of our own understanding of 'progress' in thought.
When Wittgenstein exclaims, "How extraordinary that Plato could have got even as far as he did!", he is mocking the notion that by thought we can approach an understanding of the 'real' world distinct from the everyday world we live in. What is this reality that we are seeking? 'How extraordinary that someone should even begin to understand reality!' The question not asked often enough for Wittgenstein is, what is this 'reality' we are seeking to understand? Philosophers often use the term as if it were something different from the actual world we live and breathe in, the world we see before us now and forever.
Similarly to Nietzsche, Wittgenstein inverts the antiquated western metaphysical tradition which places the essential before the actual: the abstract is an abstract from the present material world. Thus the task of attempting to reach the real via a process of intellectual abstraction, or via an examination of linguistic forms, is doomed before it starts. The real is present before us - in analysing it and refining it into its (apparently) general essence we are not approaching the truth of the matter, the "real" which is concealed by the corruptible form of the actual, we are in fact becoming increasingly lost in the sterile imagination.
Wittgenstein has often been understood as standing counter to the Cartesian tradition which separates the mind (the essential self or soul) from the body (the corruptible material presence). His own picture, which we can glean from his various writings, is thoroughly integrated. The self is not an ethereal gaseous substance hidden from the world by this dumb robotic body through which it must attempt to make its presence and wishes felt...no, the self is that which is made manifest in and through one's actions. The self is not squeezed into expression via the body, the mouth, one's speech and actions but is given life, made real by these potencies. His comments such as "The face is the soul of the body" (CV23) and "The human being is the best picture of the human soul" (CV49) serve to make clear his own approach to 'essentialism'. The essence is that which is realised (literally, made real) by the contingent. If we want to see a person's soul we should look at their actions - then we will see where their heart lies. If we want to see a person's experience of pleasure or pain, we watch their face and words through which these are expressed. These are not some phantom noumena which struggle to find their representation via the maze of body, they are naturally expressed, acted out; in a Hegelian sense, the phenomena is the final stage of 'becoming real' of the object. In two separate metaphors, Wittgenstein says "the work of art does not convey something else, just itself" (CV58), meaning there is no feeling which is the meaning behind the work, which the work exists to transmit; and "A picture cannot...depict its pictorial form; it displays it" (TLP2.172), meaning that the form or essence of a picture does not exist behind it, represented by the picture but exists in the picture, it is displayed in the picture itself.
How does this relate to Plato? Plato's attempt to essentialise the world and perceive the 'real' behind the phenomena is, to Wittgenstein, fundamentally misguided. It is the phenomenal which is the real and if we desire to understand it we cannot subsume it under some abstract system. The abstract can only be an etiolated version of the real; it is the real, once we have nullified the differences, the vibrancy, the temporality of actual existence. What we consider essential in things is in fact a statement of human value, and should not be mistaken for a quality in things themselves. The attempt to do so confuses and denigrates both the nature of scientific enquiry and the role of human value in thought.
The actual use of the word 'reality', how we use it in our language, does not denote something outside experience, but merely something outside clear delusion or confusion. To seek a non-subjective reality seems like a meaningful quest, but as the concept is analysed it disintegrates before us. Reality is this very world we live in together.
Similarly to 'reality', Wittgenstein sees 'progress' as a term which requires justification before we run in pursuit of it. It is easy in this age of technological and scientific progress to believe that progress is inherently beneficial, that it moves us ever only forward and upwards. To Wittgenstein, this is not at all clear. Progress implies a steady march, but this may not be in a direction which is good to pursue. Indeed, when a civilization has lost its sense of direction, 'progress' can seem like an end in itself, and the effects of such an ideal can become masked by the unquestioned perception that we moving 'forward'. He says, "that the idea of great progress is a delusion along with the idea that the truth will ultimately be known...It is by no means obvious that this is not how things are." (CV56)
Wittgenstein's own aim in his philosophy is not for movement at all, but for the kind of clarity which can only be found in perfect stillness: "Where others go on ahead, I stay in one place." (CV66). Instead of blurring the world by dynamic movement, he seeks to bring everything into sharp focus so we can see what surrounds us. Instead of building giant houses of cards, he examines the ground beneath our feet.
In this sense, we can see Wittgenstein's exasperation at our constant need to improve and develop our thought, as if we were progressing toward an actual understanding of reality. We have always been here. True understanding is not something we strive towards, but something we should stop in order to appreciate. We will not soon break through into truth, into truly perceiving the world or ourselves as they are...we must instead learn to see carefully and without self-imposed delusion what is right here. Through thought we can lead ourselves astray, through winding paths further and further from the actual world which should be obvious to us.