Punished By Rewards by Alfie Kohn. Explains the subtle detrimental effects of positive reinforcement in school and at work. He's written other books opposing standardized testing and other common classroom practices as well.
The Education of Hyman Kaplan and The Return of Hyman Kaplan by Leo Rosten (aka Leonard Q. Ross when he was moonlighting on the first and wanted his real name to remain respectably literary). Draws on his experiences teaching English to European immigrants in the 1930s to bring each class to life, with various accents and ethnic pride alliterated in the spelling of the dialogue. The star is an extremely thoughtful, outgoing, philosophical student who nonetheless struggles with the language more than most. (Oh Kaplan, My Kaplan! is a later abridged combination of these two he compiled later in life when his humour was more bitter; stick with the originals.)
Personality Type: An Owner's Manual by Lenore Thomson. A detailed Jungian approach to Myers-Briggs theory, explaining how each type is affected by its strongest and weakest characteristics. Contains numerous examples from pop culture, particularly Star Trek.
Please Understand Me II by David Keirsey. This Myers-Briggs sequel is less mythologically oriented than the original and much more thorough in comparing the four temperaments (SP, SJ, NT and NF).
Four Arguments For The Elimination of Television by Jerry Mander. A bold indictment of modern life in general, this book explains how TV is inherently limited in the kind of information it can convey and how it therefore shapes, or selects, the kind of content portrayed. (In a later book, he acknowledged the coming of HDTV and concluded that its resolution was not sufficient to offset its limitations.) Also explains to us moderns some of the nuances of Native American life by contrast, making me wonder if casinos are the benefit they really wanted...
The Gifted Adult by Mary-Elaine Jacobsen. A more inspiring explanation--and justification--of originality, cockiness and different-drummerhood I've never seen.
The Real AA by Ken Ragge. While I wouldn't personally confront known AA members with this scathing indictment (unless I had reason to believe they'd welcome it), I think it's healthy for people who've had reservations about the program to hear they're not alone--especially given the strong consensus in favour of it. In fact, awareness of anything disagreeing with conventional wisdom could only help our most intractable social problems (and is certainly worthy of discussion), although this book may be more suitable for people who know others in AA (as was my experience). There are far, far too many gems for me to quote here under "fair use," but essentially the book, in addition to exposing flaws in alcoholism studies, alleges that:
If such a confrontational book--or any guilty pleasure you fear it would impart--is not for you, How Alcoholic Anonymous Failed Me: My Personal Journey to Sobriety Through Self-Empowerment by Marianne Gilliam takes a gentler approach. Those wishing to research alternatives may want to consider Rational Recovery (which especially appeals to more independent, intellectual types), Moderation Management (which emphasizes insight, has flexible goals, and may feel more natural than AA to those who have trouble identifying with more severe addicts), and Women For Sobriety.
Unconditional Life by Deepak Chopra. Cites numerous unusual medical cases, both miraculous and tragic, as a basis for grounding an exploration of metaphysical ideas.
The Imponderables® series by David Feldman. Answers obscure questions about nature, social practices, and popular culture and products.
The Circle and the Practical Intuition™ series by Laura Day. Both contain focused exercises for tapping inner knowing and making choices (i.e., how do you feel when...).