Huckleberry Finn - Twain. I was 14 when I read it, and it inspired me to run away from home. I was back two days later, but it was a start.
Crime and Punishment - Dostoyevsky. I read this book in my early 20's when I was really messing things up but telling everyone that all was OK. I took the wisdom from the book, opened up to people, and they supported me as I got things taken care of.
Slaughterhouse Five - Vonnegut. This one just changed my perspective in general.
More pragmatic choices:
The Seven Habits of Highly Effective People- Stephne Covey
How to Win Friends and Influence People - Dale Carnagie
The Power of Positive Thinking - Vincent Peale
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