Overheard on a commuter train: “You say you’re in a rut? A rut is just a grave with the ends kicked out.” This chapter explores the meaning of a phrase by the twentieth-century philosophic essayist, Michael Oakeshott, and its implications for the status of “labor” (physical and mental) in a human life. Oakeshott used the phrase “the deadliness of doing” on two occasions to denote the centrality and finality of practical human life, and suggest “escapes” from its attempted dominion in activities such as poetic imagining, philosophy, religious experience, friendship, and others. This chapter advances the view that the common denominator in all these “escapes” is the idea and practice of activity done for its own sake, rather than for some subsequent outcome or utility. It attempts to place Oakeshott in a large narrative running from Aristotle to Montaigne (one of Oakeshott’s heroes) concerning which human activities can be meaningfully done for their own sakes, and how these all escape, to greater and lesser degrees, the deadliness and endless Sisyphusian finality of practical human conduct, to include, saliently, labor, and its place in a human life. A related theme will be the idea of participating in salutary, established rituals done for their own sake, yet capable of providing in addition to psychic satisfaction, residual by-products of some utility as well.