5 Books That Will Make You Less Stupid

There’s a famous quote that goes something like, “As the depth of my knowledge increases, so too does the breadth of my stupidity.” I can’t remember who said it. But I do know that dude/chick was onto something.

In fact, you may have heard of this idea before. It’s also known as the Dunning-Krueger effect. The graph looks something like this:

One look at your social media feed is all it takes to confirm this idea. When it comes to the latest trending topic, the dumbest opinions will invariably be the most prominent. Meanwhile, the people who do know a little something about it are silent — because they also realize how much they don’t know.

As such, becoming smart is simultaneously an act of discovering your own stupidity. It isn’t until you’ve crossed the border of competence that you begin to feel less stupid — only regaining an idiot’s swagger once you’ve become an expert.

The following five books are some of the best I have ever encountered for this reason. That is, the wisdom they distill stems from a breakdown of something you probably think you know a lot about. Paradoxically, this awareness of your own foolishness is what makes you wiser.

So without further ado, here are five books that will make you less stupid.

The Denial of Death by Earnest Becker


Take a second and think about what motivates you in life. Is it love? Is it money? Is it fame? Is it glory? Whatever you cite as a motivation, Earnest Becker’s book The Denial of Death will probably shit on it.

Indeed, the central thesis of Becker’s work is rather disturbing, because it asserts that everything we do stems from an avoidance of the inevitable.

Whether it’s the clothes we wear, the careers we choose, or the movies we watch, Becker proposes that all human activity is motivated by the desire to avoid what we will eventually become. On the surface, this idea seems intuitive. After all, if we wanted to die, what would be the point of farting around down here? Yet what’s striking about Becker’s claims is the extent to which death anxiety permeates our psyches.

Bouncing off the work of previous thinkers like Freud and Kierkegaard, Becker asserts that the central problem of existence is the knowledge we are Gods who shit. Unable to comprehend this duality, our minds reject their constant process of defecation and decay and instead seek an ‘Immortality Project’ that will survive their physical deaths.

With vibrant detail, Becker goes on to trace how the successful completion of this immortality project is what leads to mental well-being, while the collapse of one is the source of all pain and suffering.

Disturbing as this book may be, it helps make you less stupid in the following two ways: 1.) it exposes you to the futility of your daily struggles, and 2.) it helps you see what you have in common with your fellow woman and man — thus making you feel a little less alone.

Key passage:

“Each person thinks that he has the formula for triumphing over life’s limitations and knows with authority what it means to be a man, and he usually tries to win a following for his particular patent. Today we know that people try so hard to win converts for their point of view because it is more than merely an outlook on life: it is an immortality formula.”

The Varieties of Religious Experience by William James

If you’re like me, you’ve probably gone through a phase of militant atheism at some point. And why shouldn’t you? On top of being responsible for nearly every war, religions are rooted in some pretty absurd claims about the supernatural.

While William James’ The Varieties of Religious Experience does not prove the legitimacy of religion by any means, it does offer some profound insight into the nature of ‘God’ as it appears in consciousness.

By exploring the accounts of figures such as Francis of Assissi, Ralph Waldo Emerson, and the Oracle of Delphi, James proposes that religious experiences do correspond with a transformative power, regardless of their fundamental origins.

He accomplishes this feat through extensively detailing the trance one undergoes during a ‘conversion event.’ This trance is profound enough to make all previous suffering seem laughable — even inspiring crazy actions like self-flagellation, voluntary starvation, and complete withdrawal from society.

As such, he asserts that religious experiences speak to a very real, transformative part of our psyches. And this idea serves as the kernel around which religious psychology (and I would argue, psychology as a whole) has formed.

While this book might not turn you into a believer, it will offer a thorough understanding of the nature of religious phenomenon. In doing so, you will become less stupid about your own doubt/ belief in the Big Man in the Sky.

Key passage: 

“The perfect stillness of the night was thrilled by a more solemn silence. The darkness held a presence that was all the more felt because it was not seen. I could not any more have doubted that HE was there than that I was. Indeed, I felt myself to be, if possible, the less real of the two”

The World as Will and Representation by Arthur Schopenhauer

Arthur Schopenhaur’s The World as Will and Representation is often known as the book that inspired Friedrich Nietzsche. Yet personally, I think Schopenhauer’s work deserves much more acclaim than a simple footnote in the life of his predecessor.

Throughout this lengthy tome, Schopenhauer deftly guides the reader through his theory of existence. His central thesis is as follows:

Everything we experience in the world is the product of a metaphysical Will. This Will serves as the thing-in-itself, from which the fundamental universe springs. The material world is simply an offshoot the will-to-life, which is constantly striving against its counterpart — the will-to-death. Yet the two are a part of one whole, thus making our existence a constant battle against itself.

While this conclusion seems pretty shitty, Schopenhauer does offer some redemption in his conception of the aesthetic. Namely, he asserts that art offers of a momentary transcendence of the will. As such, asceticism is the highest form of existence – because it consists of a denial of one’s own self-destructive will.

With elegant prose (not to mention the hilarious jabs he keeps throwing at Hegel), Schopenhauer seamlessly weaves his thesis through the works of Kant, Hume, Plato and even the Upanishads.

Overall, The World as Will and Representation will make you less stupid by helping you conceptualize the ties that bind everything. It’s a brilliant complement to the previous two books, as one can see shadows of James’ God (i.e. the aesthetic) and Becker’s Immortality Project (i.e. the will-to-life).

Key passage:

“Therefore the man of genius requires imagination, in order to see in things not what nature has actually formed, but what she endeavoured to form, yet did not bring about, because of the conflict of her forms with one another”

Moby Dick by Herman Mellville

These next two books are your stereotypical Works of Literature. As such, telling you to read them might be like telling you to invest in a 401k or go the gym. You know you should do it — but do you really need this asshole to remind you?

Well, sorry gang. I don’t mind being that asshole today. Truth is, these books have earned their snobbish reputations for a reason. And I’ll do my best to briefly lay them out here.

The first, Moby Dick, has gained its widespread esteem because of the scale of its allegory. When you read about the White Whale, you know Melville is actually talking about something Big and Important. Its just hard to put your finger on it. The only certainties are that Moby Dick is an object of desire, and that Captain Ahab is willing to kill himself in the pursuit of it.

See what I did there? Okay, probably not. Let me explain: The theme behind Moby Dick can best be understood in terms of Schopenhauer’s Will.

Because Schopenhauer claims that material objects are subdivisions of a higher Will, things are constantly striving against themselves: a fight that results in eternal suffering, and eventually, failure.

When viewed in this light, Moby Dick is merely a metaphor for the tragedy of existence. Ahab, Starbuck, Ishmael — each are part of a single unit, as is Moby Dick.  The crew thinks they’re chasing the White Whale, but little do they know, the whale is also chasing them. We too are being pursued by this whale. You, me, and everyone are but sailors on the Pequod, forever awaiting the vengeance of the beast we seek to slay.

Key Passage

God help thee, old man, thy thoughts have created a creature in thee; and he whose intense thinking thus makes him a Prometheus; a vulture feeds upon that heart forever; that vulture the very creature he creates.

Don Quixote by Miguel de Cerventes


The second work of fiction, Don Quixote, can also be viewed as a metaphor for the Will. Yet while Moby Dick relates the tragedy of willing, Don Quixote speaks to its comedy.

The book outlines the story of Don Quixote de La Mancha, a self-described knight errant who has read too much and slept too little. He rambles around Spain in search of adventures, hoping to win the heart Lady Dulcinea Del Toboso — a woman whom he completely made up.

Indeed, the hilarity of the book stems from Señor Quixote’s madness. While he imagines he’s on some quest for love and glory, the only results his adventures seem to bring him are blood and bruises. Time and time again, he’s confronted by the incongruity between his desires and their fruits. Yet he blames his misfortunes on the wrath some enchanter — bound to discourage the noble quest of knight errants.

Don Quixote and his faithful squire, Sancho Panza, symbolize the quest that each of us are making for the sake of our wills. Though we know we’re led by a crazy master, for some reason we keep going, following our code of honor, hoping to find that lover who has already closed the door.

Key passage

“It excited fresh pity in those who had heard him to see a man of apparently sound sense, and with rational views on every subject he discussed, so hopelessly wanting in all, when his wretched, unlucky chivalry was in question.”