Tapping into selected works of Erasmus of Rotterdam, this book offers a series of philosophical meditations designed to retrieve and deploy a distinctively Erasmian manner of thinking - one that is capacious in its perception, agile in its judgments, and unsettling in its irony. In purpose, it takes a philosophical route, addressing perennial questions of self-knowledge - what we can know and how best to communicate what we take to be true, what we ought to do or how we should live, and what we might hope for or what would offer us fulfilment. In method, however, this work taps into the various strategies of irony at play in the works of Erasmus, looking for guidance in handling these age-old questions. What readers will find in Erasmus is a knack for playfully reversing appearances and realities, a penchant for pushing disturbing questions relentlessly to the limit, and a skill for juxtaposing oddly matched opposites. Again and again, Erasmus presses readers to rethink these fundamental questions with dexterity and nuance, ever ready to appreciate the surprising and unsettling upshot of ironic insight.