In the introductory “Intellectual Autobiography” of the Georg Henrik von Wright volume of the Library of Living Philosophers series, von Wright mentions the discrepancy he always felt between his narrow logical-analytical professional work and a drive to make philosophy relevant to his life, calling it a rift in his philosophical personality. This article examines the nature of the rift and the various stages the problem went through during von Wright’s career. It is argued that the initial impression that his books (...) The Varieties of Goodness and Explanation and Understanding had contributed to healing the rift, was subdued by a gradual shift in existential focus from individualistic ethics towards a critical concern for destructive ways of thinking inherent in the Western culture, connected with von Wright’s “political awakening” at the end of the 1960s. The most urgent questions of our times called for novel, non-analytical, ways of doing philosophy, employed in von Wright’s later works on science and reason, and the myth of progress. Eventually von Wright’s earlier methodological concerns were also alleviated by his belief that logical-analytical philosophy was inherently unsuitable for exposing the cultural structures it was very much a part of. (shrink)