I am loving this thread. There are so many wonderful suggestions. My personal additions (though I know they are not obscure): Down and Out in Disneyland - Cory Doctorow (This was gifted by a friend and really inspired me to make some significant changes in my life. That includes the decision to learn to code and escape the user end of the spectrum.) Procrastination- Jane B. Burka , Lenora M. Yuen (This book has fundamentally altered my introspective conclusions. That is to say, I am now more aware of times when I am procrastinating and the impact it has on my life.) This year was a great year for reading and I hope to read even more next year.
Also recommended in this reply