What Wittgenstein actually wrote is: "Ich arbeite ziemlich fleißig und wollte, ich wäre besser und gescheidter. Und diese beiden sind ein und dasselbe." This is translated as, "I am working reasonably hard and wish I were a better man and had a better mind. These two things are really one and the same." If we translate gescheidter as "wiser" then it might sound better. If we translate it as "cleverer" then it sounds wrong. Wittgenstein might sound closest to the truth if we take being 'smarter' to include both being wiser and being more prudent, i.e. good at knowing what our goals should be and at knowing how to achieve these goals. But, as Anscombe points out, there seems to be more to ethics, to being a good person, than this:
It will have become clear that the practical syllogism as such is not an ethical topic. It will be of interest to an ethicist, perhaps, if he takes the rather unconvincing line that a good man is by definition just one who aims wisely at good ends. I call this unconvincing because human goodness suggests virtues among other things, and one does not think of choosing means to ends as obviously the whole of courage, temperance, honesty, and so on. [Intention p. 78]
What more is there to courage, temperance, honesty, and so on? I don't think it's very easy to say, but something like dispositions seem to be at least part of it. A courageous person is likely to be disgusted by cowardice, to admire the brave deeds of others, and to behave courageously. This behavioral part of courage might seem to be a matter of "aiming wisely at good ends" (although this is controversial), but the disgust and admiration parts certainly don't seem to be. Could Wittgenstein have thought that becoming smarter would affect his affect?
It seems possible. After all, he did think that one could understand a musical theme, and that this can involve learning to have certain feelings. At least, I take this to be implied by Investigations 531-537:
531. We speak of understanding a sentence in the sense in which it can be replaced by another which says the same; but also in the sense in which it cannot be replaced by any other. (Any more than one musical theme can be replaced by another.)
In the one case, the thought in the sentence is what is common to different sentences; in the other, something that is expressed only by these words in these positions. (Understanding a poem.)
532. Then has "understanding" two different meanings here? -- I would rather say that these kinds of use of "understanding" make up its meaning, make up my concept of understanding.
For I want to apply the word "understanding" to all this.
533. But in the second case, how can one explain the expression, communicate what one understands? Ask yourself: How does one lead someone to understand a poem or a theme? The answer to this tells us how one explains the sense here.
535. What happens when we learn to feel the ending of a church mode as an ending?
The next two sections talk about seeing courage in a face, of being able to read such things in a face, but not in the sense of reading them into a place where they don't belong. Rather, it "is there, alive, in the features." Learning to read a face takes smarts. Learning to read a situation no doubt does too.
Wittgenstein recognizes that the same face might be seen as being timid or as courageous, but he doesn't say that everything might be seen as anything. The fear or courage has to be, in some sense, there to be seen. And, of course, the viewer has to have the concept of fear or courage, too, in order to be able to see it. Mastering such concepts might well involve coming to feel in certain ways, or at least being able to feel in those ways. It takes a certain kind of sensitivity.
And in this way, I think, becoming a more understanding person, a person who understands more and better, is very likely the same thing as becoming a better person. A properly sensitized person should be aware not only of what is there but also of what it calls for, as an artist knows, or feels, what is needed to complete a painting, say. At least that's what I want to think.
[By the way, I was reminded of PI 531 by reading Kelly Dean Jolley's The Concept 'Horse' Paradox and Wittgensteinian Conceptual Investigations. I would recommend this book except for the fear that someone might ask me a question about it that I couldn't answer. It is short but dense, and reminds me of some tea that a friend of mine brought from China. The tea comes in a kind of cake or puck, from which I would carve a wedge or lump to put in the pot. After the tea is made the leaves in the pot expand and come almost to life incredibly, looking a bit like seaweed. My sense is that Jolley's book is one with which it would be good to be infused.]