I have not read a lot of self-improvement books but I had my fair share, enough to start hating them (at least some of them). I started to think like Nat Eliason as described in Level 3 Thinking: A Unified Theory of Self-Improvement:
When I started reading more energetically, I focused on practical, how-to style self-improvement books. The Power of Habit. I Will Teach You To Be Rich. The $100 Startup. Popular books that promised to teach me a “hack.”
Eventually, I grew bored of books that could be condensed to a blog post and pursued higher level books. Peak. Seeking Wisdom. The Monk and the Riddle. Books that provided a broader understanding, a richer context for their ideas.
Later I started exploring the category above that: books that take the leap to philosophy. Antifragile. Finite and Infinite Games. Godel Escher Bach. Books that do not promise to teach you how to do anything, but rather change how your mind works by the time you’re done with them.
Though not a book, Paul Bloom’s course on Introduction to Psychology (Yale) incorporates level 3 thinking. It teaches you how your brain, habits and conditioning works; how language, perception, learning happens; intricacies of emotions, social interactions, mental disorders; and finally ends with a holy-grail question What is a Happiness? Navigating through this course will give you pointers to the sources of a lot of self-help tips you know and their validity.
I also appreciate the new and cool animation style they attempted for this course. It is set up in a classroom where the camera keeps moving which helps me not loose attention.
As I am writing this I realize that Paul Bloom put up a new course on Coursera about Moralities of Everyday Life. I will check it out and let you know what I think about it.
Introduction to Psychology by Paul Bloom is a free and quick course which makes a lot of self-improvement books obsolete.