A less analytic and more wholistic approach to philosophy, described as best overall fit or seeing how things all hang together, is defended in recent works by John Rawls and Richard Rorty and can usefully be applied to problems in philosophy of medicine. Looking at sickness and its impact upon the person as a central problem for philosophy of medicine, this approach discourages a search for necessary and sufficient conditions for being sick, and instead encourages a listing of true and interesting observations about sickness which reflect the convergence of a number of different viewpoints. Among the relevant viewpoints are other humanities disciplines besides philosophy and the social sciences. Literature, in particular, provides insights into the meaning and the uniqueness of episodes of sickness in a way that philosophers may otherwise fail to grasp.