"Don't think, but look!" This is one of Wittgenstein's main exhortations. It is a recurring theme in the Investigations, where Wittgenstein in case after case tries to highlight how often in philosophy what we tend to think reflects a picture we have become captive to rather than a reflection of how things actually are.
One way Wittgenstein himself failed to live up to this idea is his general ahistoricism. For someone who emphasized so much looking to the use of sentences, it is striking that he let himself make claims about the nature of philosophy without looking to see how philosophy actually functioned in the past. Or in different traditions. When Socrates in 5th century BC Greece asked, "What is justice?", in what ways was such a question used? When Shankara in 8th century India asserted that our ordinary experience of objects in an illusion, what was the use of that assertion? When Descartes in 17th century France asked himself if he was being deceived by a malicious demon, what was the use of that question?
Imagine Socrates asking, "What is justice?" Now imagine a contemporary philosophy professor raising in class the question "What is justice?" What are the differences in use between these two instances of the question? Are the two uses different? Wittgenstein seemed to assume they were the same, that he could dismiss in the same breath Russell, Descartes and Socrates altogether. As if there was some one bad thing all of them did. That philosophers throughout history have done. It is an amazing to see Wittgenstein essentialize philosophers, treating them as if there was some one thing they all have in common.
Wittgenstein's ahistoricism, together with his idea that much contemporary philosophy was confused, lead him to a dead end. It led him to the idea that all there was to do was to get rid of our confusions, and then move blissfully on. It led him to give up the idea of positive projects in philosophy. After all, if philosophers through out history have been making the same mistakes, then how can there be any positive philosophy?
If we distinguish the contemporary philosophy professor's use of, say, "What is justice?" from Socrates' use of that question, a different possibility for going on in philosophy starts to emerge. One where the trouble isn't philosophy as such, but the current institutional structures of the philosophy profession. It becomes possible to think that certain uses of philosophy which Socrates practiced have perhaps become lost in the institutional structures. That in order to recover those loses we don't have to give up on philosophy as such, but become more critical of our current philosophy institutions. That we might need to leave those institutional structures to rediscover other possible uses of philosophy, the kind of which Socrates and Descartes and Spinoza were able to do as non-academics.
Down this line of thought, positive projects in philosophy, which nonetheless are influenced by Wittgenstein, become possible. For what Wittgenstein helps with is how to weaken the grip of contemporary academic philosophy. Once that is weakened, there is still the positive project of recovering other modes of doing philosophy. Of being inspired by those uses of philosophy from the past which we have forgotten, and realizing them in our time, in new ways, in hitherto unimagined ways, in order to create new versions of them.
"To show the fly the way out of the fly bottle." That was Wittgensein's aim in philosophy. But Wittgenstein as a person tended to be a tortured soul because academic philosophy was his fly bottle, and he never figured out how to escape it. This doesn't mean academic philosophy as such is bad, or that every one needs to leave it. No. But it does mean that for some people academic philosophy cannot capture their own growth and trajectory in philosophy, and this has to be taken seriously, faced up to, without treating such people as if they are therefore no longer interested in philosophy as such. Wittgenstein was, I think, such a person. If he had been able to find the peace to be out of academia, and yet continue with philosophy as it is inspiring to him, then he could have been a much happier person. Instead, unable to leave academic philosophy, his life's work ended up being defined more by what he was against than by what he was for. As if there was nothing positive in philosophy for him to do. Or for anyone to do.
But if only he had changed his thinking around one axis, if he had become more open to using the history of philosophy to understand the multitude of uses to which philosophy has been put, he might have had an easier time having hope for the future of philosophy. He could have then seen how much there is still to do, how many positive projects in philosophy, how many new things to build and new forms of life to create. If he stopped equating contemporary academic philosophy with philosophy as such, he could have found a kinship with Socrates and Confucius and, yes, even Descartes. And building that kinship, rediscovering those forms of philosophy would have been not a burden to bear, or an illness to be exorcised, but a joyful calling to be happily embraced.