In Culture and Value Wittgenstein remarks: ‘Thoughts that are at peace. That's what someone who philosophizes yearns for’. The desire for such conceptual tranquillity is a recurrent theme in Wittgenstein's work, and especially in his later ‘grammatical-therapeutic’ philosophy. Some commentators (notably Rush Rhees and C. G. Luckhardt) have cautioned that emphasising this facet of Wittgenstein's work ‘trivialises’ philosophy – something which is at odds with Wittgenstein's own philosophical ‘seriousness’ (in particular his insistence that philosophy demands that one ‘Go the bloody hard way’). Drawing on a number of correlations between Wittgenstein's conception of philosophy and that of the Pyrrhonian Sceptics, in this paper I defend a strong ‘therapeutic’ reading of Wittgenstein, and show how this can be maintained without ‘trivialising’ philosophy.