How can I learn and help others to learn to mean more precisely by saying, doing and making things? By attending to how Ludwig Wittgenstein and Robin Collingwood answered that question during the first half of the twentieth century. I show how the last of three answers given by Wittgenstein, and the journey that he undertook to arrive at it, exemplify the kind of answer that Collingwood had been advocating and exemplifying. I conclude by suggesting, however, that a fourth answer upon which they converged unwittingly points even further along the road to philosophical understanding than either of them was able to go, namely that if we are to answer such questions exactly, we must approach them not only historically but biographically.