Walter Benjamin is generally known as a thinker who was critical of the philosophy of life. But Benjamin's early writings from the 1910s to 20s reveal a number of interesting arguments about life's crisis and potential, and the uniqueness of the mental dimension of life. This article aims to reconstruct his philosophical considerations on life based on his early writings such as “Life of University Students” (1914), “On the Language” (1916), “Program of Philosophy” (1918), “The Task of the Translator” (1923) and “Cognition-critical Introduction” (1928). This paper has three main goals. First, Benjamin's philosophy, like that of other important modern philosophers, is rooted in a deep concern for life's crises and possibilities, freedom and expression of life. Second, Benjamin's observation and analysis of life is not merely subsidiary. On the contrary, it is closely related to the philosophy of language, philosophy of history and philosophy of art, which are the three central fields of his philosophical thinking. Third, Benjamin's philosophical reflection on life is worth appreciating itself. It has remarkable implications for modern philosophical anthropology as well as for aesthetic reflections on art and the sensitive dimensions of human beings. In particular, the mental essence of language, the dialectic of communicability and incommunicability, and the argument for the purposiveness of life need to be re-appropriated in connection with the philosophy of life.