This essay deals with the legacy left by Wilhelm Dilthey to contemporary philosophy. In particular, what is highlighted is that the legacy of this philosopher transcends the influence he exerted on several authors since his legacy is, above all, an experience of the limits and the crisis of philosophical knowledge. Dilthey’s desire to depart from the traditional metaphysical horizon and propose a philosophy of life able to decode modern times, socially complex and devoid of ethical considerations, is specifically evident in his Leben Schleiermachers. Shifting the emphasis from the traditional Schleiermacher- Dilthey-Heidegger-Gadamer genealogy, this essay provides a more articulate horizon to the comparison between Friedrich Schleiermacher and Dilthey. In the light of this horizon, it can be understood why we cannot speak of a homogenous "Diltheyan school" as heir to the restless mind of the master.