12 Books That Destroyed and Rebuilt My Mind

“If the book we’re reading doesn’t wake us up with a blow to the head, what are we reading for? … A book must be the axe for the frozen sea within us. That is my belief.”

― Franz Kafka

Some books are not books at all.

They’re sticks of dynamite.

They blow things apart.

In your mind. In your world.

Often things you didn’t even know were there.

Things you didn’t think to consider.

Things you didn’t have the courage to look at.

And you’re not the same afterwards.

In fact you might be a mess, grappling to pick up the pieces of your shattered mind and put them back together.

You’re changed.

Stronger, broader, deeper, less certain.

And that’s the point.

Here are 12 life changing books that broke things in me and taught me more about the world than I can ever say.

1. The Undiscovered Self: The Dilemma of the Individual in Modern Society by Carl Jung

For such a slender book, this one packs a serious wallop. Jung doesn’t waste any time. In the first page or two he’s already digging straight into his profound case for why truly self-aware human beings are our only hope for resisting the all-engulfing forces of mass-scale extreme tribalism, dogma, and tyrannical government that threaten to destroy our world. Jung’s fundamental premise is that man does not know himself. Humankind is, by and large, enslaved to vast forces that the average person cannot see. Most will not even peer honestly into the depths of their own souls and acknowledge their dark side. But it is precisely this that we need to do, Jung argues: It is only through rigorous reflection, self-scrutiny, and an individual relationship to the Vast that we become capable of understanding and withstanding the forces that threaten to tear our world apart. Please read this life changing book.

“Ultimately everything depends on the quality of the individual, but our fatally short-sighted age thinks only in terms of large numbers and mass organizations…”

― Carl Jung, The Undiscovered Self

2. The Portable Nietzsche by Friedrich Nietzsche

“Whoever fights monsters should see to it that in the process he does not become a monster.”

— Friedrich Nietzsche, Beyond Good and Evil

If there’s one writer who has been “the axe for the frozen sea within” me, it’s Friedrich Nietzsche. Let’s just say I have one tattoo, and it’s Nietzsche’s maxim, “Become what you are.” When I first read him nearly five years ago, he hit me like a deep-space asteroid. Reading Nietzsche is like finding some dusty ancient scrolls in a mountain cave that were left by a demigod who once visited Earth—like reading something secret and forbidden that humans shouldn’t really have access to. No one’s words have leapt off the page and punched me in the face in the same way. I’m still not sure how such a person actually walked this planet.

“At bottom every man knows well enough that he is a unique being, only once on this earth; and by no extraordinary chance will such a marvelously picturesque piece of diversity in unity as he is, ever be put together a second time.”

— Friedrich Nietzsche, Schopenhauer as Educator

If you’re curious, there is no better book for you to get your hands on than The Portable Nietzsche. Walter Kaufman’s translation of Nietzsche is impeccable, and the volume includes four of Nietzsche’s major books, in full: Twilight of the Idols, The Antichrist, Nietzsche Contra Wagner, and Thus Spoke Zarathustra (I recommend starting with Zarathustra). Kaufman also brings together selections from Nietzsche’s other books, notes, and letters to give a full picture of the development of one of the most influential and controversial philosophers ever to breathe. One thing I love about this book—and about Nietzsche—is that you can simply flip open to any page, start reading, and get something precious. I haven’t read all of its 700+ pages, but Nietzsche’s incomparable spirit shines forth in all that I’ve absorbed. He’s an endless fountain of some of the most soul-stirring insights of all time—on individuality, art, death, morality, religion, and the human condition. For the love of Nature, read Friedrich Nietzsche.

“If we affirm one single moment, we thus affirm not only ourselves but all existence. For nothing is self-sufficient, neither in us ourselves nor in things; and if our soul has trembled with happiness and sounded like a harp string just once, all eternity was needed to produce this one event—and in this single moment of affirmation all eternity was called good, redeemed, justified, and affirmed.”

— Friedrich Nietzsche, The Will to Power

We created a 900-day self-mastery obstacle course based on Nietzsche’s idea of a “gymnastics of the will.” 

3. Cosmic Trigger, Volume I: Final Secrets of the Illuminati by Robert Anton Wilson

If you want to test whether your mind is truly open, this is one of the life changing books to read. Don’t let the semi-satirical title fool you: This is a book written by one of the most skeptical philosophers who ever lived—a genius who just so happened to undergo one of the most uproarious journeys into the realm of the Weird ever recorded. This is a record of his peculiar travels. Robert Anton Wilson, though unknown to many, had a major influence on iconic figures such as George Carlin, Philip K. Dick, and Vinay Gupta. Wilson considered himself akin to an astronaut exploring the inner space of conscious experience, experimenting with a variety of methods of “deliberately induced brain change.”

For Wilson, agnostic mysticism was a kind of internal science—a way of “studying the nervous system directly by varying the parameters on which your nervous system functions.” In this spirit, Wilson conducted extensive experiments, using psychedelics, rituals, forms of meditation, and other means, and in the process encountered events and synchronicities that were truly Stranger Than Fiction. All the while, though, he remained skeptical of his experiences, never elevating any finding to the status of Absolute Truth. His stated life goal was to get as many people as possible into a state of “generalized agnosticism”—not just agnosticism about God, but agnosticism about everything. I’m not quite finished with this book, but it’s everything I dreamed and more; I was already a huge fan of Wilson’s work via YouTube, and this just took things to the next level. Read it, read it, read it.

“Since we all create our habitual reality-tunnels, either consciously and intelligently or unconsciously and mechanically, I prefer to create for each hour the happiest, funniest, and most romantic reality-tunnel consistent with the signals my brain apprehends. I feel sorry for people who persistently organize experience into sad, dreary and hopeless reality tunnels, and try to show them how to break the bad habit, but I don’t feel any masochistic duty to share their misery.”

— Robert Anton Wilson, Cosmic Trigger

4. The Righteous Mind: Why Good People are Divided by Politics and Religion by Jon Haidt

In the depths of my soul I wish everyone in the world would read The Righteous Mind. Within it, psychology professor Jon Haidt drops a proverbial atom bomb on everything you thought you knew about morality, revealing a much more complex, fascinating, and empathy-inducing picture of things. Haidt explores the foundations of our moral psychology—why we see certain behaviors as “right” and “wrong,” and more importantly, why different people have totally different perspectives on what moral behavior looks like. After reading this book, everything in the world will make more sense, and you will possess much more compassion and understanding for those who disagree with you about politics, religion, and morality.

You can buy the book via Amazon. Also, Dr. Haidt is great on Twitter.

“Morality binds and blinds. It binds us into ideological teams that fight each other as though the fate of the world depended on our side winning each battle. It blinds us to the fact that each team is composed of good people who have something important to say.”

― Jonathan Haidt, The Righteous Mind

5. Letters to a Young Poet by Rainer Maria Rilke

For me, Letters to a Young Poet was one of those life changing books that seems to come to you at precisely the time you most need it. I read it when I had first moved to South Korea and was going through a period of loneliness and uncertainty. It offered me new ways of understanding my solitude and my questions, challenging me to embrace them as unavoidable aspects of life. Its author, Rainer Maria Rilke, was a renowned Bohemian-Austrian poet who passed away in 1926. Between 1903 and 1908, Rilke penned a series of responses to a would-be writer, offering advice on being an artist and a sensitive individual in an often cruel and unforgiving world.

Reading Letters to a Young Poet gives me the sense that Rilke was a man who was channeling the eternal wisdom of the cosmos into a language humans could understand. And that’s coming from someone who doesn’t really say things like “the eternal wisdom of the cosmos.” There are just so many passages in this book of the sort that make you stop reading, widen your eyes, and stare off into the distance as you soak in the impact of the words on your life. It’s like Rilke is talking to you. I really feel that everyone—especially anyone involved in a creative endeavor—would be enriched by this book. Read the following passage slowly, and really taste it. It’s one of the passages that I found exquisitely insightful and liberating during my “dark night of the soul” in South Korea:

“You are so young, so much before all beginning, and I would like to beg you, dear Sir, as well as I can, to have patience with everything unresolved in your heart and to try to love the questions themselves as if they were locked rooms or books written in a very foreign language. Don’t search for the answers, which could not be given to you now, because you would not be able to live them. And the point is, to live everything. Live the questions now. Perhaps then, someday far in the future, you will gradually, without even noticing it, live your way into the answer.”

6. Meaningness by David Chapman

David Chapman is a Buddhist and artificial intelligence specialist who has influenced my worldview more than perhaps anyone else in the last couple years. His perspectives on human development, ethics, politics, science, and the nature of meaning and existence have profoundly shaped the way I see the world. Meaningness (his main site) is an in-progress hyper-text book, one of the most life changing books I’ve ever explored, and an attempt to synthesize Dzogchen Buddhist thought and Robert Kegan’s model of adult development (among other things).

Admittedly, Chapman can be difficult to get into, as he’s invented his own lexicon in order to more precisely describe his views, but once you get a handle on his terminology and realize what he’s talking about, life will never be the same. Among other things, he’ll show you why almost everyone throughout history who has made claims about the ultimate meaning or meaninglessness of the universe has been wrong. Here are some great entry-points into his work: this chapter on the purpose of life in Meaningness | an interview with David on the ‘Deconstructing Yourself’ podcast | David’s essay on the American culture war | David’s summary of Robert Kegan’s model of adult development. I also heartily recommend his tweets and other blogs: Vividness, Buddhism for Vampires, and Approaching Aro.

“Various religions, philosophies, and systems claim to have answers. Some are complicated, and they all seem quite different. When you strip away the details, though, there are only a half dozen fundamental answers. Each is appealing in its own way, but also problematic. Understanding clearly what is right and wrong about each approach can resolve the underlying problem.”

— David Chapman, ‘An appetizer: purpose,’ Meaningness

7. A Guide to the Good Life: The Ancient Art of Stoic Joy by William B. Irvine

“He is a wise man who does not grieve for the things which he has not, but rejoices for those which he has.”

— Epictetus, Greek Stoic philosopher, 50AD – 135AD

Stoicism is probably not what you think it is. When we think of the Stoics, we tend to think of emotionless creatures trudging through life in a state of passive indifference, perhaps even pessimism. In this remarkable and highly readable introduction to Stoicism, William B. Irvine takes a hammer to this myth, illuminating an entirely unexpected portrait of Stoicism as a philosophy of tranquility, mental fortitude, joy, and appreciation in the face of life’s inevitable shit storms.

This is another book I’m currently reading, but I can already tell it’s one I’ll never forget. It’s already inspired me to begin simultaneously reading Marcus Aurelius’ famous Meditations, and to eagerly await the day I crack open Seneca’s Letters From a Stoic and Epictetus’ Enchiridion. It’s already abundantly clear to me that Stoicism is an approach to life that will have a lifelong impact on me. It’s so simple, yet so wise and pragmatic: its emphasis on self-mastery and discipline, rejoicing in our blessings, and focusing on what we can control resonates deeply with recent (re-)realizations of mine about the vital importance of healthy long-term habits of body and mind. I cannot recommend this book enough to anyone who wants to live a more serene and contented life.

(Purchase it via Amazon or take your learning even further for free at the Stairway to Wisdom.)

“And when asked what he had learned from philosophy, Diogenes replied, ‘To be prepared for every fortune.'”

— William B. Irvine, A Guide to the Good Life

8. The Most Good You Can Do: How Effective Altruism is Changing Ideas About Living Ethically by Peter Singer

“Effective altruism — efforts that actually help people rather than making you feel good or helping you show off — is one of the great new ideas of the 21st century.”

— Dr. Steven Pinker

The philosopher Peter Singer is renowned for his power to completely alter your understanding of what it means to be a good person. He’s perhaps most well-known for his book Animal Liberation, which convinced millions of people of the vital importance of treating animals with compassion. In The Most Good You Can Do, Singer outlines a blossoming ethical movement called effective altruism. In essence, effective altruists use evidence and reason to determine the most effective means of helping the world—of saving the most lives, human and non-human.

Astonishingly, effective altruists have demonstrated that the most effective charities are literally 1,000+ times more effective than the least effective—i.e. they save 1,000+ times more lives with the same amount of donations. This is an earth-shattering revelation that revolutionized my approach to charitable giving. And this is just the tip of the iceberg: effective altruism is an ethical phenomenon of superheroic proportions. I want so badly for more people to learn about it that I made a rap album about it.

9. Crime and Punishment by Fyodor Dostoyevsky

“’What I mean is that if you were successful in persuading a man that there was nothing for him to cry about, he’d stop crying, wouldn’t he? That’s obvious. You think he wouldn’t?’

‘Life would be much too easy then,’ replied Raskolnikov.”

— Fyodor Dostoevsky, Crime and Punishment

It’s difficult to explain the way in which I was so completely swept up in the torrent of psychological desolation that characterizes Crime and Punishment. Utterly torturous in its suffocating examination of the deterioration of the protagonist, demoralizingly tragic in its fearless portrayal of the suffering of righteous individuals, and unapologetically depressing in its vision of despair and hopelessness, the book is hardly for the faint of heart. Truthfully it haunted me. I couldn’t put it down, and I became so attached to the protagonist, Raskolnikov—a murderer suffering the terrible wrath of his own conscience—that I literally began to experience his confusion, anxiety, and guilt as if they were my own. This novel is the work of a master and possibly my favorite book of all time. I literally named my rap alter-ego after Dostoevsky after reading this book. If you’re feeling courageous, read it.

10. The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Timothy Ferriss

“The question you should be asking isn’t, “What do I want?” or “What are my goals?” but “What would excite me?”

― Timothy Ferriss, The 4-Hour Workweek

Don’t let the cheesy title and gaudy cover art fool you; this is one of the most paradigm-shifting, life changing books I’ve ever read. It’s the first book I recommend to aspiring world travelers, entrepreneurs, and digital nomads. In it, Tim Ferris systematically dismantles pretty much every myth you’ve ever heard about work, productivity, retirement, and world travel. He lays out a detailed, easy-to-follow map for stopping spending most of your time doing things you don’t want to do and building a life with plentiful time to do things that truly excite you. This is the absolute Bible of lifestyle design. If you have a single rebellious bone in your body, or the vaguest inkling that you want your life to be more than what it’s shaping up to be, read the fuck out of this book. Yesterday.

(You can also learn about additional high-velocity concepts at the Stairway to Wisdom.)

“For all of the most important things, the timing always sucks. Waiting for a good time to quit your job? The stars will never align and the traffic lights of life will never all be green at the same time. The universe doesn’t conspire against you, but it doesn’t go out of its way to line up the pins either. Conditions are never perfect. ‘Someday’ is a disease that will take your dreams to the grave with you.”

― Timothy Ferriss, The 4-Hour Workweek

11. Consider the Lobster and Other Essays by David Foster Wallace

David Foster Wallace was a literary wizard and you should read him, plain and simple. His writing style alone was a complete epiphany for me. His ability to map the micro-contours of the human condition and convert raw experiential data into zinging, singing, poetic prose never ceases to astound me. He is a wonder to behold and you should read him just to witness his literary genius, if nothing else.

Of course, Wallace offers much beyond his writing style to adore. Consider the Lobster and Other Essays is a rare sort of book—one which traverses boldly across numerous disciplines to dissect the dark underbelly of modern American culture, politics, and society with a razor-sharp scalpel. Published a little over 10 years ago, Wallace’s incisive, far-seeing commentary remains utterly poignant today, and its central theme—that we, as individuals, must take responsibility for becoming thoughtful and scrupulous cultural participants lest we be led as blind cattle to doom by the misguided or maligned agendas of those in power—is arguably timeless. Thus, a passionate recommendation to anyone with a pulse: purchase and read Consider the Lobster.

“Is it possible really to love other people? If I’m lonely and in pain, everyone outside me is potential relief—I need them. But can you really love what you need so badly? Isn’t a big part of love caring more about what the other person needs? How am I supposed to subordinate my own overwhelming need to somebody else’s needs that I can’t even feel directly? And yet if I can’t do this, I’m damned to loneliness, which I definitely don’t want … so I’m back at trying to overcome my selfishness for self-interested reasons.”

― David Foster Wallace, Consider the Lobster

12. Kafka on the Shore by Haruki Murakami

“She leaves behind a damp pillow, wet with her tears. You touch the warmth with your hand and watch the sky outside gradually lighten. Far away a crow caws. The Earth slowly keeps on turning. But beyond any of those details of the real, there are dreams. And everyone’s living in them.”

— Haruki Murakami, Kafka on the Shore

I had to include Haruki Murakami in this list. When I discovered him while living in Asia, I was blown away by a proverbial tornado. Entering his stories is honestly like entering a dream, and finishing them leaves you with the same sort of “What just happened?” feeling as when you awaken from a vivid sleep-space. I’ve never encountered another author who creates this effect in the same way—it feels akin to a consciousness-expanding magic trick. This novel is my favorite of Murakami’s and a beautiful example of the surrealistic, infinitely imaginative style and engrossing storytelling that had led to his acclaim. Murakami’s signature blend of magic realism and metaphysical mischief abound in these pages, and it will leave you a deeper, broader person with more questions and fewer answers. A novel I could never forget.

Bonus: Tao Te Ching by Lao Tzu

“Life is a series of natural and spontaneous changes. Don’t resist them; that only creates sorrow. Let reality be reality. Let things flow naturally forward in whatever way they like.”

― Lao Tzu, Tao Te Ching, 604BC – 531BC

This list would not be complete without turning the spotlight on Taoism for a moment. I discovered Taoism circa 2013 and took a deep dive into its ideas and principles during my time in Asia. Interestingly, one of my all-time favorite rappers, KOOL A.D., has been perhaps my greatest Taoist teacher and sage over the years. The Taoist attitude of playful non-resistance, which you can think of as more or less “going with the flow,” is abundantly present in KOOL A.D.’s music, and for this reason I find it deeply therapeutic to listen to—a poignant reminder to stop taking everything so seriously and trying to control the things that are not within my power to control. When I saw in an interview that KOOL A.D. periodically reads the Tao Te Ching, the ancient original Taoist text, I knew I needed to as well, and it was like a breath of fresh mountain air.

Having been taught as a child to always be thinking of the next goal and milestone and to perform unenjoyable labor in the present for some hypothetical future gratification, my discovery of Taoism was a truly profound paradigm shift for me. So much so that I think the pendulum of my mind swung a little too far in the Taoist direction, and for a while all I wanted in life was to be goalless, flowing, living purely in the moment. I’ve since realized that some amount of goal-setting and future planning are actually good ideas for me, but the Taoist attitude of flowing with whatever happens, approaching reality playfully, appreciating life in this moment, and not resisting what we cannot change, has sunken deep into my bones. It’s become so automatic for me to flow with the currents of life (not struggle against them) and to accept things immediately when I have no hope of changing them, that I barely notice this attitude anymore—it’s become part of me. Of course I’m no sage and my feathers can certainly be ruffled, but Taoism has been an invaluable medicine for me in this world. Lao Tzu’s Tao Te Ching (I recommend the Gia-Fu Feng and Jane English translation) is the book to read on Taoism, though if it resonates I highly recommend supplementing it with Alan Watts’ Tao: The Watercourse Way.

“Flow with whatever may happen and let your mind be free. Stay centered by accepting whatever you are doing. This is the ultimate.”

— Chuang Tzu, Taoist sage, 370BC – 287BC

If you’d like to learn to embrace the unchangeable and flow tranquilly with reality, consider taking 30 Challenges to Enlightenment.

Conclusion: Books are Sacred

And that, as they say, is all she wrote. Or all I wrote. Or something.

Ahem, so, uh, I feel kind of naked right now. I’ve just revealed to you the 13 books that have probably had the greatest impact on my lifeworld. I drilled deep into my being to discern this list. I feel like you’re staring into my mind-soul and I need to hastily cover up with a shower curtain or something.

Because I can, here are four final honorable-mention books that nearly made this list:

• Frankenstein by Mary Shelley: Another truly genius, haunting, mind-shattering novel that ranks among my favorite life changing books of all time. What does it truly mean to be human? What does it truly mean to be a monster?
• The Prophet by Kahlil Gibran: The book that’s become my go-to wedding gift when loved ones of mine get married. Timeless, soothing wisdom on love, death, morality, community, and other universal aspects of the human experience.
• In My Own Way: An Autobiography by Alan Watts: Watts needs little introduction around here. One of the most talented, eloquent orators of the 21st century, and perhaps the foremost Western articulator of Eastern thought, Alan Watts is That Dude. His autobiography is a stunning, captivating tale bursting with insight and sagacity.
• Zero to One: Notes on Startups, or How to Build the Future by Peter Thiel: One of the absolute best books to read on startups, entrepreneurship, and what it takes to innovate the future. I couldn’t put it down. Thiel’s clear thinking and no-bullshit, contrarian approach to existence are truly a joy to behold.

In conclusion, books are sacred gifts: time capsules of knowledge passed through the ages, allowing us to know what it was like inside an individual’s mind, long after they’ve left this world.

If you think about it, that’s pretty magical—almost psychic-transmission type of stuff. The written word was a technology that utterly transformed human civilizations, paving the way for the inventions that resulted in the world we see around us today.

Despite all our marvelous technological advancements, we have yet to come up with a better way to radically and rapidly expand a person’s understanding of the world than a good ol’ fashioned paperback.

Countless leaders, innovators, and visionaries throughout modern history have been voracious readers and sworn by the power of books. Books genuinely make you smarter, fuel creativity, and put you in a much better position to be effective in almost any undertaking. Plus there’s that whole thing about showing you entire mental galaxies you never knew existed. Books are adventures.

As you can tell, I treasure books with all my corazón. I absolutely would not be who I am without them, and I’m not sure I’d want to live in a world devoid of them. They’re my default gifts for all occasions (hint, hint: give books this holiday season; what other gift has the power to occasion an intellectual rebirth?). I l-o-v-e love them, man.

Anywho, I truly hope you’ve benefitted from this list and will take the time to read some of these remarkable tomes. If not these, find others. But make sure they’re good ones. And never forget these words from that most wily of scriveners, Mark Twain:

“The man who does not read good books has no advantage over the man who can’t read them.”

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