Not All of Us are Saints, by David Hilfiker. About a doc who switches from rural practice to running a shelter & clinic for homeless men in inner-city D.C, has to deal with depression & burnout, etc. I keep lending it out, not getting it back, and having to buy a new one (3x now), if that says anything for it. I highly recommend it for anyone interested in working with urban underserved folks.
How We Die - Reflections on Life's Final Chapter, by Sherwin Nuland. Death (in many different contexts - including doctor's own family, many different causes) from the perspective of a doctor. Sounds profoundly depressing, but somehow I didn't find it so.
On Doctoring, edited by Richard Reynolds et. al. A collection of stories, poems, essays, etc. about doctoring, being a patient, dying, etc. For those of literary bent.
I have the Nuland book too; didn't like it ALL that much, in part because I thought the guy had a staggering sense of self-importance.