I think the first book I read like this, i.e., in the genre of "self help" on the edge of psychology, spirituality, and, heh, rhetoric was my dad's copy of Dale Carnegie's How to Win Friends and Influence People when I was about 11.
I half-heartedly borrowed a copy of Stephen Covey's most famous book, The 7 Habits of Highly Effective People, from my mother last time I visited. I guess I pick up something like this every once in a while out of malaise or boredom, as many people do. It covers a lot of the usual territory, but is unusually well done for its sort (which in my experience can often be nauseatingly sweet or brainlessly fluffy). One aspect of why it's good might be that Covey is grounded in the humanist, classical and post-classical tradition of success through character rather than personality. He makes a big point of that fact. It's not about changing your attitude (though that's part of it), but about recognizing and choosing good principles to live by and ingraining them into your character through the establishment of good habits (very classic, Aristotelian and Ciceronean virtue ethics).
An interesting aside mentioned in the book is that Covey did an "in-depth" study of all the motivational/self-help/success literature published in the U.S. since 1776. Covey admits openly in the first chapter that none of the principles taught in the book are original, and they sure aren't (except in the naming and numbering of them). But he's really done a good job of bringing these classic, fundamental principles to light in a modern, secular book. For me it's not only the habits but the anecdotes, quotes, exercies and arguments that make the book enjoyable and engaging.
Geez, I sound like a commercial. Anyway, good book. I'm trying to apply its principles to my own life as I see fit. Definitely worth a look if you're in the mood for that sort of thing.