When I was young and just starting out, I conceptualized self-development in the narrow sense of becoming more “successful” (whatever that meant).

As I’ve grown older, I’ve come to view self-development as the much broader process of learning how to navigate reality effectively.

In order to do this, there are three basic questions that must be addressed:

1. What is reality? In order to navigate reality, we must first understand the nature the reality we inhabit.

2. What kind of creatures are we? In order to navigate reality, we must understand the different aspects of the individual doing the navigating.

3. What kind of creatures should we aim to be? In order to navigate reality, we must have a sense of where we’re going and which values are worth pursuing and embodying.

The books I’ve chosen for this list are those that have helped me answer these questions most effectively and in the deepest sense. They are the books I’ve read and re-read time and again, revisiting each regularly for fresh insights and guidance.

I hope they enrich your mind and improve your life as much as they have mine.

Note: All books are linked to Amazon for easy ordering. I may receive a small commission from any sales made through the links provided below. If you’d like to help support my work, this is a great way to do so. Thank you.

The Happiness Hypothesis by Jonathan Haidt

This is one of my all-time favorite personal development books. It’s a modern self-help masterpiece—the perfect blend of ancient wisdom and modern science.

It’s less about happiness in the superficial sense and more about finding meaning and cultivating well-being in our lives in the eudaemonic sense.

Haidt, a social psychologist, considers 10 Great Ideas that emerged from his study of dozens of works of ancient wisdom including The Bhagavad Gita, the sayings of the Buddha, the Tao Te Ching, The Old and New Testaments, the Greek and Roman Philosophers, and more.

He argues that, although we are awash in wisdom every day, the problem is that we don’t take the time to savor it and apply it to our lives. In each chapter, he analyzes one Great Idea in light of modern research and shows how it applies to modern life, while also highlighting the relationship between these Great Ideas.

Haidt is an excellent teacher and a master at distilling an immense amount of information down to to its most essential and useful elements.

Inner Work by Robert A. Johnson

Robert A. Johnson was a psychotherapist and Jungian analyst.

Jungian psychology (and depth psychology in general) takes a much different approach to personal development than most modern self-help. Where most modern philosophies assume the conscious mind is the driving force of our behavior, Jungian psychology assumes it is our unconscious mind that is responsible for most of our actions, as well as our neuroses.

This book offers two very simple, step-by-step approaches for accessing the contents of our unconscious mind. One is through analyzing our dreams and the other is through engaging in an exercise called active imagination.

I’ve used both approaches on myself and with my clients and I can say this is some of the deepest personal development work you will ever do. If you’re unfamiliar with Jungian psychology, you likely haven’t tried anything like this.

Johnson does a fantastic job of making the sometimes esoteric concepts of Jungian psychology both practical and accessible. Highly recommend this.

Meeting the Shadow by various authors

This book is an excellent introduction to the shadow—what it is, how it operates, and how to deal with it. It opened up a whole new dimension in my psyche and was instrumental in helping me begin to confront my own darkness.

The shadow is that part of psyche of which we are unconscious. It’s the aspects of our personality we don’t want to admit to. It’s the parts ourselves we’ve repressed or ignored or disowned in one way or another in an effort to fit in or be accepted.

If self-development is the process of developing the underdeveloped and dysfunctional parts of ourselves, then I consider integrating our shadow to be the most essential work we can do as individuals.

One thing I love about this book is that it’s an anthology so it contains perspectives on the shadow from a diverse array of thinkers, including psychologists, mythologists, writers, poets, philosophers, and more.

The Righteous Mind by Jonathan Haidt

This book has been hugely influential in my understanding of human nature and morality. It helped me grasp the psychological, social, and biological reasons that people hold certain moral positions.

One of the main points social psychologist Jonathan Haidt makes is that, contrary to popular belief, when it comes to making moral judgments, we don’t think rationally, we think intuitively.

These moral intuitions have been shaped in response to the many adaptive challenges humans have faced over the course of our evolutionary history.

Consequently, liberalism, conservatism, and libertarianism are not arbitrary political positions but very real psychological dimensions.

A fantastic book if you want to better understand how others—and you—think about the world.

Sapiens by Yuval Noah Harari

This book is an interdisciplinary delight. If you want a crash course in history and prehistory that covers the past 2 million years, this is the book for you.

Unlike traditional history, the focus here is not so much on specific dates and historical figures but overarching patterns and trends. Harari is a brilliant, philosophically-minded historian who’s  interested in the big questions in life.

This book helped me make sense of the messiness of history by highlighting important through-lines. It also helped me think more clearly about personal development and well-being through the lens of evolution rather than merely through our modern perspective.

This is helpful because in order to shape ourselves into the kind of creatures we ought to be, we must first come to terms with the kinds of creatures we actually are. 

A Brief History of Everything by Ken Wilber

This is flat out one of the most enlightening and mind-altering books I’ve ever read. Wilber puts forth a grand theory of everything that attempts to unite all domains of knowledge. Like, everything.

For the past several years, my primary aim with reading has been to understand both myself and the world in as comprehensive of a manner as possible. I’m interested in the big picture. I want to know how the different pieces of reality fit together to form a unified whole. I’ve even made humble attempts to piece together my own “theory of everything.” That’s exactly what this book aims to do.

One of Wilber’s big ideas is that the stages of development an individual goes through over the course of one’s life are essentially the same stages of development that have characterized the evolution of humans and even consciousness itself.

Each stage of development has its own worldview, values, presuppositions, etc. Healthy development of individuals and cultures is the result of “transcending and including'“ previous stages of development. Dysfunction occurs when this process is disrupted, either by transcending and dissociating from a previous stage or by failing to transcend a stage altogether and becoming stuck there.

This model has major implications for how we should conceptualize everything from politics to business to spirituality to self-development.

One of the best things about this book—and Wilber’s work in general—is that he explains everything in language a high-schooler can understand.

Tao Te Ching by Lao Tzu

If Yoda wrote a book, this would be it. It’s the foundational text of Taoism, a Chinese philosophy that dates back to the 4th century BCE. The title (pronounced Dow De Jing) translates roughly to The Book of The Way.

If you grew up in the West, this book will offer a completely new way of looking at reality—not merely as a collection of separate parts but as a unified whole made up of a complex web of relationships.

Composed of just 81 short verses, this is a concise but wisdom-packed read. Even if you take nothing from it practically (which is hard to imagine) it stands on its own as a beautiful literary work.

There are a vast number of different translations of the Tao Te Ching (second only to The Bible). I recommend starting with the one by Stephen Mitchell, simply because it’s the easiest to read and digest. For a more literal (but still beautiful) translation, I highly recommend Jonathan Star’s translation.

My suggestion: Read slowly and thoughtfully to digest the deep—and sometimes cryptic—teachings of the Tao.

Self-Reliance by Ralph Waldo Emerson

In this brief essay, Emerson delivers a simple message in elegant and powerful prose: You have genius-level potential inside you that can only be expressed by being authentically yourself. So be who you are and don’t conform to what society expects.

I don’t know of a more inspirational or better articulated argument for embracing one’s individuality and authenticity than Self-Reliance. Emerson accomplishes in a dozen or so pages more than most modern self-help authors do in several hundred. As someone who tends to suppress my voice at times, reading this essay gave me the courage to start speaking my truth and owning my personal power more consistently.

The opening paragraph was so profound for me that I took a month to fully absorb it before reading the rest of the essay. I highly recommend this if you need a reminder of the potential you possess.

The War of Art by Steven Pressfield

This book is for the creatives, the artists, the entrepreneurs—anyone who has ever wanted to create something great but feels like something is holding them back.

Steven Pressfield identifies this negative force as Resistance and describes the many forms it takes. More importantly, he explains how to overcome it so you can let your creativity shine. 

Every time I read this book, I feel inspired, motivated and encouraged. Pressfield’s passion for encouraging people to express their unique gifts gives me Ralph Waldo Emerson vibes (see Self-Reliance above).

This book is short and can be consumed in an hour or two but the lessons will stay with you for a lifetime.

7 Habits of Highly Effective People by Stephen Covey

This book holds a special place in my heart because it was the very first self-development book I was introduced to. During my Junior year of high school, my psychology teacher, Mr. Corner, used it as the basis for an entire semester’s worth of curriculum. I was hooked.

The seven habits are an excellent foundation for creating a solid and well-rounded life. Steven Covey helped me understand the difference between principles and tactics or strategies: Tactics and strategies change but principles are timeless.

If we can learn to lead our lives by principles rather than tactics, we’ll be in a much better position when it comes to making decisions in our family or business life.

How to Get the Most From These Books

Unless you read purely for entertainment, the point is to integrate newly acquired knowledge into your life in a meaningful way. Otherwise, why do it?

I used to struggle with remembering what I read. So I spent years compiling and testing the very best methods for improving retention and becoming a better learner. What I found were 4 basic principles of effective learning.

If you’d like a more comprehensive and in-depth framework designed to save you the time and energy of figuring it all out for yourself, check out the learning system I created: The Total Recall Toolkit.