I think about "Outliers" by Malcolm Gladwell a lot directly. Over time I've appreciated it as a way to both motivate me to work towards success, and also to cope with feeling not successful enough. The fact reflecting on that book is helpful for both sides of that coin is part of its staying power for me, I think.
"The State" by Franz Oppenheimer was also impactful. It was the first kind of political theory that really gripped me. The idea that the State was something to analyze and scrutinize in the way that he did was exhilarating. Touched a nerve that resulted in significantly more questioning of authority and critical thinking about power, generally.
"why's (poignant) Guide to Ruby" made a difference, too. The book itself is great and it helped me to learn Ruby, and it also introduced me to _why. His work made me view programming as not just a craft, like building a chair, but also as an art form, like writing a book. It can be a way to express yourself and be creative, and programmers can, indeed, be creative, too!
Franz Oppenheimer (1908), "The State"
Please do not confuse the social and societal with the political, that's a fallacy.
Hope I'm not referencing Godwin's law so soon in the discussion, but this quote makes me think about the deference most of the German intellectuals had for "Der Staat", starting with Hegel. There are countless examples, but a quick search brought me to this (which is actually a book written from an "individualist" POV, as far as I can tell):
> Oppenheimer's view of the state is profoundly opposed to the then dominant characterisation propounded by G. W. F. Hegel of the state as an admirable achievement of modern civilisation.[1] Proponents of this view tend to accept the social contract view that the State came about as every larger groups of people agreed to subordinate their private interests for the common good. (http://en.wikipedia.org/wiki/The_State_%28book%29)
As an outsider, I always regarded the Anglo-Saxon system (meaning the United States and Britain) as an antidote to the views expressed by Continental Europe, seems things have changed.