There are two ways that philosophy could transform a philosopher’s life to make it substantially more meaningful: On the one hand, philosophical inquiry might reveal other activities beyond it that would make the life meaningful, enabling a philosopher to live meaningfully as a result of the inquiry, while, on the other hand, it might be that doing philosophy is in itself one way to make the philosopher’s life notably meaningful. In this chapter, I explore the latter path. I argue against views of meaning in life entailing that philosophy could not itself be particularly meaningful or only rarely could be, after which I critically reflect on respects in which philosophical reflection might enhance the meaning in the philosopher’s life. In particular, I critically discuss views of Bertrand Russell, W. D. Ross, Joseph Mintoff, and Robert Nozick that purport to explain how philosophy itself confers meaningfulness in terms of the extensiveness of its object, contending that their explanations are not as comprehensive and explanatorily deep as the new one I provide.