The tradition of philosophical essayism beginning with Montaigne takes experience as its starting point, adopting a sceptical attitude towards grand philosophical systems and a priori truth. It was the favoured form of British empiricists, who looked to experience as the source of philosophical truth, and early analytic philosophers, who saw themselves as inheritors of the empiricist tradition and sought to avoid the perceived philosophical and rhetorical excesses of ‘continental’ idealism. Their adoption of the essay was accompanied by a view of writing, continued in present-day analytic philosophy, that stresses clarity, economy, and simplicity – virtues borrowed from the realm of mathematics and logic. But a tension, evident in Bertrand Russell’s work, emerges between fidelity to experience and fidelity to a mathematical model of clarity. This chapter argues that the notion of experience grounding the essay loses its philosophical richness in the analytic project.