“To win true freedom, you must be a slave to philosophy.”—Epicurus

The great philosopher Ludwig Wittgenstein was once sitting in a park having a philosophical discussion with a friend when his friend, quite animated, stood up and said loudly, “That is a tree! I know for a fact that that is a tree!” An awkward pause ensued as the two men realized that passersby had stopped and were now staring at them. Wittgenstein, thinking quickly, turned to the people and said, “Do not worry, this fellow is not insane… we are merely doing philosophy.”

When most people think of philosophy, they likely imagine indecipherable books that stretch on for a thousand pages, saying and solving nothing. They envision stuffy old men in misbuttoned shirts, untied shoelaces with mismatched socks, shuffling about hallways of some archaic university, mumbling to themselves, completely unaware of the humanity around them.

As an undergraduate in university, when I told people that I was considering choosing philosophy as a major, they often looked at me with some mixture of horror and confusion, as though I had just told them I was considering shoving a stick of butter up my ass. One friend even went as far as to say, “Dude, why would you do that to yourself?”

Philosophy has been a favorite punching bag for centuries. The criticisms are worn and weathered: philosophy doesn’t actually solve anything; philosophers simply argue about arguing; science tells us all we need to know, therefore philosophy is no longer relevant, and so on.

These criticisms are hardly new. And they haven’t been limited to whinging college students or skeptical parents either. In fact, the critics have been many of the famous philosophers themselves. Albert Camus vehemently insisted that he was not a philosopher and would correct journalists if they referred to him as one. Schopenhauer considered most of the philosophers of his day—stalwarts such as Hegel, Fichte, and Schelling—to be navel-gazing hucksters and frauds. Karl Marx even went so far as to write, “Philosophy stands in the same relation to the study of the actual world as masturbation to sexual love.”¹

Ouch…

But it was those intellectual titans of our age—Monty Python—who perhaps captured these criticisms best with their classic satirical bit, “Philosophy Football:”

Caption: “Hegel is arguing that reality is merely an a priori adjunct of non-naturalistic ethics, Kant via the categorical imperative is holding that ontologically it exists only in the imagination, and Marx is claiming it was offside.”

All of this is to say that from the outset, I realize that I’m marching into an uphill battle here. Philosophy isn’t for the cool kids. Philosophy is seemingly lots of mental effort for little reward. Philosophy is not practical nor does it solve any relevant questions anymore. We have science. We have big data and artificial intelligence. Who cares if we can ever actually know if a tree is a tree, right?

Needless to say, I disagree with the haters. Philosophy is useful. It’s also important. In fact, I will go as far as to argue that philosophy is likely more useful and important to the average person in the 21st century than any other time in human history.

So buckle up—shit’s about to get real… just as soon as we figure out what exactly the word “real” means.

What is Philosophy?

“Science is what you know. Philosophy is what you don’t know.” — Bertrand Russell

Here’s a funny little quirk about those criticisms of philosophy: in order to criticize philosophy, you must engage in philosophy.

Philosophy is the inquiry into our understanding of reality, knowledge, and how we should live. When you string thoughts together into a coherent belief system, you are weaving together a philosophy. When you make value judgments to determine what is good and what is bad, you are relying upon a philosophy. When you are laughing at the ridiculousness of a book that has statements such as, “Being is the being of a being,”—well, hate to break it to you, but you are engaging in philosophy.²

Philosophy is, therefore, undismissable for the simple reason that it encompasses all of conscious experience. To criticize philosophy, you must rely on some degree of philosophy. To shit on systematic frameworks of understanding, you must generate a systematic framework of understanding.

This little logical conundrum is known as the “performative contradiction.” And where does it come from? That’s right, motherfuckers: it comes from philosophy.

Philosophy boils down to three major questions:³

1. What is true about existence? (Metaphysics)
2. How can we know that it is true? (Epistemology)
3. What actions should we take as a result of this knowledge? (Ethics)

I would say, “That’s it,” but all three of these questions have resulted in thousands of years of inquiry and debate with little consensus emerging on any of them.

That may sound ridiculous but that doesn’t mean that huge progress has not been made in philosophy. Much has. Over millennia, epistemology has given us science, logic/reason, economics, psychology, and many of the theories of knowledge that underpin our political systems and societies today.

Similarly, over the millennia, our understanding of ethics has progressed to the point where we no longer enslave vast portions of the population, systematically burn people alive for their beliefs, or watch people get eaten alive by angry lions in an arena for weekend entertainment.

Today, concepts such as democracy and human rights have generally been accepted the world over. In fact, the “expanding circle” of empathy has grown so much in recent centuries that we now not only concern ourselves with human welfare, but we see the treatment of animals and the environment as ethical issues as well.⁴

And in terms of metaphysics… well, in the past four hundred years we’ve gone from, “I think; therefore, I am,”⁵ to “Maybe you’re living in a giant computer simulation?”⁶

So, uh, I guess that’s progress?

Why does philosophy matter?

“The unexamined life is not worth living.” – Socrates

Philosophy matters because at some point in our lives we must all ask and answer these questions for ourselves.

1. What is true?
2. Why do I believe it to be true?
3. How should I live based on what I believe?

A failure to answer one or more of these questions will quickly result in what we generally label as a mental or emotional crisis—we fall into depression, succumb to anxiety, struggle to find any sense of meaning or purpose.

Philosophy, therefore, has an immediate and profound impact on our well-being and daily lives. A man knows he’s a brilliant salesman. His entire identity is wrapped up in his ability to accomplish his job, to do his work, and to impress his colleagues.

Then, one day, he gets fired. And not only is he shown that what he believed to be true was wrong, but it now calls into question his actions and motivations for the past twenty years. He doesn’t know what’s true. He doesn’t trust himself to figure out what’s true. He no longer knows what to do. He’s a mental and emotional wreck.

These sorts of events happen to us all. They may be triggered by the loss of a loved one, a dramatic health scare, or just straight up getting our ass kicked at work. But our mental structure for how we see and understand the world collapses and we find ourselves lost, unable to determine what is true about ourselves, about our lives, or about the world.

In fact, you may have heard of these sorts of experiences referred to as an “existential crisis”—as in, “Jane’s husband fucked the mailman and now she’s having an existential crisis.” It’s a term that was originally borrowed from existential philosophers such as Søren Kierkegaard and Jean-Paul Sartre and has since become a mainstay in psychology and psychiatry.

The existentialist philosophers said that to regain our composure and mental strength, we need to reconstruct a mental scaffold—we must redefine what we know to be true, how we know it to be true, and how it should dictate our actions. We must find new sources of meaning, more fundamental definitions of identity and purpose, more useful principles for relating to the world.

In many ways, this sort of philosophical reinvention is what therapy is designed to help us do. Practices such as meditation or journaling can be useful, as well. Using these tools, we can slowly re-evaluate our values, shift our beliefs, and take new actions to create a better life for ourselves…

…that is, we can do philosophy.

Philosophy teaches us the fundamental techniques for finding meaning and purpose in a world where there is no given meaning, no cosmic purpose. Philosophy gives us tools to determine what is likely to be important and true and what is likely frivolous and made-up. Philosophy shows us principles to help direct our actions, to determine our worth and values, to generate a magnetic field to direct our internal compass, so that we may never feel lost again.

Philosophy in the 21st Century

“Beware that, when fighting monsters, you yourself do not become a monster. For when you gaze long into the abyss, the abyss gazes also into you.” – Friedrich Nietzsche

If we all need to answer the three fundamental questions for ourselves to remain emotionally and mentally healthy, then I would argue that 21st-century life disrupted our ability to answer these questions unlike ever before.

• What do I know to be true? The flood of information has paradoxically not made us more confident of what is true and untrue, but less. Between fake news, bad science, social media rumors, and manipulative marketing and propaganda, it is harder to know if you can trust the information you come across than any time before.
• How do I know that it’s true? What’s more, our traditional methods of ascertaining what we know about the world have come under fire. Science is facing a widespread replication crisis.⁷ Scandals of corruption are being unearthed in almost every major institution. Authorities are distrusted. And to throw even more gasoline on the fire, we are more aware of our own proclivities for irrational biases, prejudices, and false assumptions. Not only do we not know what’s true, but we don’t even know how to figure out what’s true much of the time.
• How should I live based on what I believe? Without knowing what is true nor how to go about finding truth, it is less clear than ever before how we should live. What is good? What is useful? What is important? We all think we know, but there’s a general uncertainty that I think pervades most of our culture and generates a constant sense of existential anxiety and insecurity.

Philosophy is more important than ever before because it has been deeply contemplating these questions for thousands of years. It has been aware of the traps and failings of the human mind, of the inconclusiveness of all knowledge, of the almost impossible task of deciphering the moral good and acting upon it. When it comes to these existential questions, there are more than a few giants’ shoulders on which we may stand upon.

Below, I’ve written about three distinct ways philosophy can improve your life. It helps you better question what you know. It helps you choose how to live. And it helps you have an impact on the world.

I’ll go over each topic and then at the end of the article, I will give some book recommendations as well as pointers on how to start learning about philosophical ideas on your own.

Philosophy Helps You Question What You Know

“The only thing that I know is that I know nothing.”—Socrates

The beautiful thing about philosophy is that it is in a permanent state of questioning. There is no form of knowledge so assured that philosophy hasn’t grabbed it by the neck and had its way with it a few times.

Take, for example, René Descartes. In 1641, Descartes decided to tackle the first of the primary philosophical questions: “What do I know is true?”

Within about ten pages of writing, Descartes quickly realized that there was almost nothing that you could come up with that you couldn’t imagine a way that it wasn’t true. The room you are sitting in—it could be a hallucination. Your memories could be invented or made up. The news you read or hear about, an elaborate lie.

Descartes went so far as to posit what we today know as “The Matrix” scenario: that we could be asleep and this entire life a dream. In fact, even our choices and decisions could be controlled by some evil, manipulative force. Our self-control could merely be an illusion. He created a thought experiment of an evil demon who could be tricking you into believing that you are alive and free and enjoying this fine afternoon drinking a milkshake. Yet, none of it is real.

Therefore, when it came down to it, Descartes realized that the only thing he could say with absolute certainty was that he existed. Maybe the room was fake. Maybe the world was a dream. Maybe his friends and family never existed. But by the given fact that he could even ask these questions in the first place—the fact that something was conscious and aware—he must exist in some form. He then wrote one of the most famous lines ever: cogito, ergo sum.⁸

“I think; therefore I am.”

Descartes’ deconstruction of knowledge cleaned the slate and made way for a burst of intellectual creativity in Europe, which has since become known as The Enlightenment. Descartes believed that his insight would provide a fresh beginning for metaphysics (or, the “What can we know that is true?” question) and would lay the foundation for a new form of understanding—an understanding based on logic, reason, and evidence.

And indeed, it would. Descartes would be hugely influential on a new methodology of understanding that would later come to be known as natural philosophy, or what we today refer to as “science.”

But the mindfuckery didn’t end there. Roughly a hundred years after Descartes, the Scottish philosopher David Hume, at the tender age of 29, published A Treatise on Human Nature, where he demolished the idea of cause/effect and or the assumption that we can predict anything at all.

Bear with me here, as this might sound insane. Hume said, logically speaking, that it is impossible to prove that anything will occur in the future, no matter how often or how regularly it has occurred in the past. If the sun has risen in the east every day for millions of years, that still doesn’t prove it will rise again in the east tomorrow. It simply makes it insanely probable that it will rise in the east.

We can never be certain something will happen, no matter how many times it’s happened before. The best we can do is come to extremely probable approximations. Just as Descartes showed that we can never be certain that our perceptions are true, Hume showed that we can never be certain that our understanding of cause/effect is true either.

This blew the minds of just about everyone who was paying attention at the time… which was like maybe a few dozen wealthy white dudes.⁹

But still… As the 18th century proceeded, Hume’s influence grew, and soon his arguments became impossible to ignore. Not much later, a young man in Prussia named Immanuel Kant read Hume’s ideas and said it jolted him awake from a “dogmatic slumber.” It ignited a desire to pick up the mantle of understanding human knowledge and push further, to discover how we can know anything at all. Hume’s writing inspired Kant to become a philosopher.¹⁰

Kant took Descartes’ and Hume’s ideas and went even further. He said that there is a difference between our perception of something and the “thing-in-itself.” I can see the tree outside my office window—I am experiencing the light reflecting off of the surface of the tree and interacting with my retinas to stimulate the nervous system in such a way that the appearance of a tree is generated in my mind. I can theoretically reach out and “touch” the tree—that is, I can experience the nerve impulses that trace up my arm from the atoms in my fingers coming close enough to the tree’s atoms that the subatomic forces push them apart and signal to my nervous system that I am “touching” the tree.

But I can never know the tree. I can never experience life as the tree experiences life. No matter how much sensory data I gather about the tree, I can never experience the tree… I can only experience the data. I am limited by my biological equipment to only interpret the tree with the means I have—sight, touch, sense, taste, etc.

Therefore, one could say that I do not know that there is a tree. All I know is that there are cognitive reflections occurring in my mind of a tree. The tree’s true existence, its fundamental treeness, is forever unavailable to me.

Now, I know what you’re saying… “Yeah, Mark, but seriously. That is a tree. I know that that is a tree!”

And now who’s the crazy man standing in the park?

Okay, okay—so why the fuck am I bothering going through all of this? This is just mental masturbation, right? What does this have to do with anything?

These inquiries into human understanding raise many important points. But here are two:

1. In the past century, psychologists have caught up to what these philosophers were saying: that we are limited and confined by our biological and neurological hardware. Any notion of objective truth will always be bent and twisted by the need to fit our limited sensory faculties.
    
   Our perceptions are flawed, our memories often imagined, our ability to reason often impaired. Much of what we believe to be “true” at face value is inaccurate, at best, and completely delusional, at worst.¹¹ This has real-world implications as we struggle to ascertain what is really going on around us—what is real and what is fiction, what is propaganda and what is legitimate inquiry. It is a call for us to be vigilant, critical, and humble of our own beliefs.
    
   As George Orwell said, “To see what is in front of one’s nose requires constant struggle.”
    
2. Because human understanding is limited, we must be careful about what we choose to accept as true. Generally, philosophy has concluded that science is the best method of ascertaining and acting on knowledge, but it also admits that in most situations, solid scientific evidence is not going to be available or possible.
    
   Philosophy reminds us that many of our most closely cherished beliefs—beliefs about freedom, morality, and (especially) God—are not fundamentally provable by any sort of epistemological method. Everything, to a certain extent, must be taken with some degree of faith. Therefore, we need to be smart about what belief systems we buy into and which belief systems we ignore.

All of this is a very roundabout way of saying that not only is it more accurate to remain uncertain of most issues and circumstances, but it’s also more beneficial to you and the people around you.

Unfounded certainty breeds tyrannical, narcissistic behavior. Unfounded certainty alienates you from the perspectives and beliefs of others. Unfounded certainty prevents you from learning and growing from your failures.

It’s on this point that Buddhism was perhaps 2,000 years ahead of the west when it explicitly pushed a philosophy of “not knowing” and detachment from any tangible desire in the real world.

Whatever you believe you know to be true—you don’t. None of us do. We’re all floundering around in a metaphysical abyss. And we must each construct some form of understanding out of nothing to keep us afloat. If it is impossible to definitively answer the question, “What is true?” Then the next best question is, “What is worth believing?”

Philosophy Helps You Choose How to Live

“If you shape your life according to nature, you will never be poor. If you shape your life according to people’s opinions, you will never be rich.” – Epicurus

Once you begin to question the significance and veracity of everything that happens in your life, you will begin to realize that much of what you believe and value was not determined by you—it was determined by the people and culture around you.

You didn’t decide you liked dogs—you just grew up with a dog. You didn’t choose to value propriety—your community did. You didn’t think about wanting to be a doctor—your parents threatened to disown you if you didn’t go to medical school.

At some point in our lives, we must all step back and question the values that we were raised with and ask ourselves if those values are serving us. In many cases, we grew up with good values, especially if we had parents who were present and functional and didn’t vomit on our birthday cake.

But every family has its dysfunction. Every culture has its obsessions. And inevitably, as adults, we start to uncover places where the values and beliefs we grew up assuming to be true are not helping us, but rather hurting us.

The German philosopher Friedrich Nietzsche called this questioning of what we grew up believing, “the reevaluation of values,” and said that if one has the mental and emotional courage to question these inherited values and beliefs, they would become what he referred to as the Ubermensch, or “Superman.”

The Ubermensch, according to Nietzsche, was not limited by traditional or conventional beliefs of his/her time period. Even concepts of good and evil should be called into question, he said. Thus, the Ubermensch is not only willing to face social rejection or ridicule but in many cases, he welcomes it because it is merely further evidence of his willingness to define values for himself.¹²

Nietzsche believed that in the future, with the rapid acceleration of science and technology and the outsized social influence they wrought, only the Ubermensch would be able to remain thoughtful, independent, and mentally sound. Everyone else would be too easily corralled into this social movement or that religious doctrine. He argued that the Ubermensch would enter a realm “beyond good and evil,” a place where traditional morality was questioned and cast aside in favor of something deeper and more transformative.¹³

Nietzsche didn’t live long enough to explain what that “something deeper” would look like, but his work did prophesize much of what has occurred in the past 100 years:

• He believed that with the waning influence of religion, people would be attracted to political and social movements with religious fervor.
• He believed this zealotry would unleash wars and violence on a scale the world had never seen before.
• He wrote that much of the population, with their lives made so easy and comfortable by modern conveniences, would experience a pervading nihilism and listlessness.

Nietzsche went insane in 1890. It would take another fifty years for a group of French philosophers known as “existentialists” to finally pick up where Nietzsche left off.

Whereas Nietzsche wrote of the coming age of nihilism, philosophers such as Jean-Paul Sartre, Simone de Beauvoir, and Jean Merleau-Ponty wrote from within the thick of it. All of them were victims and survivors of World War II, confronting the inherent meaninglessness of life head-on.

Nietzsche wrote of the courage to choose one’s own values in heroic and lofty terms. He saw it as a daunting task only taken up by the chosen few. But the existentialists wrote of this task as an inherent responsibility for each individual. For Sartre, those who failed to consciously choose what they valued in their lives lived an inherently inauthentic life.¹⁴

Much of my work over the years has been in line with this—an attempt to help people “reevaluate their values” and to define what matters for themselves among a flood of useless information.¹⁵

This conscious choosing of one’s beliefs and values not only has repercussions for one’s own mental and emotional well-being, but it also determines the kind of footprint you leave in the world. In fact, as we’ll see, the people who make the greatest footprints tend to have clearly defined philosophical belief systems for themselves.

Philosophy Helps You Make an Impact on the World

“The object of life is not to be on the side of the majority, but to escape finding oneself in the ranks of the insane.” – Marcus Aurelius

In 1949, Simone de Beauvoir published The Second Sex. The book starts out tame enough—the first seventy pages explain, in scientific detail, the biological differences between men and women.

But upon arriving at Part II, the book quickly takes a revolutionary turn. Beauvoir announces boldly that, “One is not born but rather becomes a woman,” and the reevaluation of gender norms and the social definitions of sex began.

The Second Sex makes a simple observation: there are two definitions of “woman”—the biological definition and the social definition. The biological definition is solid and physical, and (mostly) fixed.

But the social definition is fluid. It evolves and changes shape based on the time and location of the culture. This social definition of womanhood is not a moral truth but rather a reflection of the economic and social realities of each society. Beauvoir then argues convincingly that the reality of most women’s lives in the western world did not live up to the values espoused by the Enlightenment. And because the definition of “woman” is flexible and can be molded, she aimed to recast the definition in a way that precipitated positive change.

It’s a dense philosophical work, numbering over 800 pages, with long prodigious passages attacking the notion of womanhood from every angle imaginable. There are over 100 pages dedicated to Freud and the psychoanalytic definitions of femininity and another 100 pages looking at the developmental effects of cultural pressures on girls beginning in early childhood.

In contrast to today where way too much “activism” happens on Twitter with the caps lock key on, Beauvoir put together a towering intellectual work, cast in hard science and bolted together with airtight reason.

The book was a scandal upon release. The Vatican quickly added it to its list of banned books. Women began to create networks to smuggle the book throughout Europe. Once translated to English, hundreds of pages were cut due to fear of public revolt. It took almost ten years for any publisher in the United States to agree to publish it at all.

But eventually, it was published. And while it didn’t tear up the bestseller lists, it quietly infiltrated the culture via the vast networks of bored, college-educated housewives—smart, ambitious young women who had gone to college, aced their studies, and then sat around their empty kitchens for the next ten years.

One of these housewives was a woman named Betty Friedan. After reading The Second Sex, Friedan attended her fifteen-year college reunion where she couldn’t help but notice all of her girlfriends from years before seemed to be suffering the same affliction as her: lonely, bored, depressed.

Friedan decided to write a book about the experiences of the American housewife. She wrote about them in moral terms. She called the book, The Feminine Mystique. In it, she explained the dehumanizing effects of the traditional gender roles of women’s lives.

She lambasted everything from the editors of women’s magazines being male, to the loss of agency due to women being expected to give up their careers to raise children, to the stultifying boredom of repetitive housework. Friedan took the heady and abstract arguments of Beauvoir’s reevaluation of gendered values and crystallized them into daily life of the American woman.

The result set off a firestorm. The modern feminist movement in the US was born.

In my opinion, Beauvoir will one day be considered the most influential thinker of the 20th century. Regardless of how you feel about the state of feminist activism, The Second Sex perfectly illustrates the outsized influence philosophical thoughts can have on the world.

This is why nothing appears to ever “get solved” with philosophy: its ideas move so slow over such a staggering amount of time that it’s only possible to properly gauge their influence hundreds of years after the fact. We could trace similar genealogies of socialist and communist thought back to Marx (1840s), capitalism and free commerce back to Adam Smith (1770s), the political philosophy of liberalism, democracy, and human rights back to John Locke (1680s), or the classification of the sciences all the way back to Aristotle (circa 330s BC).

Because philosophy deals with concepts that are so abstract and universal, the effort that goes into redefining our definitions of ideas such as justice, equality, freedom, and gender require not only monumental intellectual effort to redefine (Marx’s Das Kapital clocks in at nearly 2,000 pages long—and was still unfinished when he died), but it takes generations for the ideas to properly disseminate across populations and be translated down into day-to-day applications.

For every Beauvoir, you need dozens of Friedans. And for every Friedan, you need thousands of activists and adherents for any tangible change to actually take place.

But I believe that if you look at all of the people with the greatest impact on the planet right now, they are all driven by some form of personal philosophy—they too, have been forced to go through the work of “reevaluating all values” and defining good and evil for themselves. They have taken on the responsibility for choosing their own meaning and giving it to the world.

For example, much of the ethos of Silicon Valley (“move fast and break things”) is built off a philosophy that is part techno-utopian (derived from science fiction) and part libertarian (faith that market-driven innovations produce better outcomes for all). Mark Zuckerberg, perhaps the most visible of all Silicon Valley tycoons, built his credibility by espousing a personal philosophy of “connecting the world” and “bringing humanity closer together.”

(Note: This was back in the mid-2000s before we all discovered how fucking awful people were—it sounded like a great idea at the time.)

Another example: Alan Greenspan has quietly been one of the most influential figures in the world over the past 50 years. Greenspan, who in his younger years was a close friend and follower of Ayn Rand, became the Chairman of the Federal Reserve in 1987 and presided over one of the biggest economic booms in history.

During this period, he adopted a more activist approach to managing the economy via interest rates and debt. His policies remain influential and controversial, even to this day. Critics have argued that everything from the 2008 collapse to the growing inequality across the developed world can be attributed to the banking practices Greenspan pioneered during his tenure.

Another: Xi Jinping has reshaped the political economy of China, making it more aggressive and less democratic.¹⁶Xi has done this by going against his predecessors, reviving millennia of Chinese thought. He has then combined these traditional ideas with Maoism to justify clamping down on dissent, committing atrocities, and becoming more antagonistic towards the rest of the world.

Another: Most recently, a set of ideas loosely identified as “critical race theory” (CRT), with the help of famous authors such as Ibram X. Kendi and activist reporters at the New York Times, have become prevalent in schools, universities, activists communities, and news media in the United States. CRT teaches that not only is racism prevalent, it’s ubiquitous. Everyone and everything is either racist or anti-racist. And squashing racism should take precedence over all other concerns.¹⁷

The examples are endless. Philosophies emerge from the abstract clouds of ideas and gradually trickle down to ground-level activists and politicians who, over the course of generations, materialize these ideas into the world. Once made real, these philosophical principles are then put into action and reshape our lives.

And unless you are aware of them, unless you are aware of the intellectual forces molding and dictating the discourse underpinning your day-to-day life choices, you are helpless but to be influenced by them.

Where to Start with Reading Philosophy

Okay, so hopefully your nipples are all hard for philosophy now.

Good. Let’s talk books. If you’re a complete newbie to philosophy and are intimidated by the length and density of most philosophical works, that’s fine. We can break you in slowly. I’ve included a list of “entry point” books below that discuss major philosophical ideas of the western canon so you can have a little familiarity before diving in yourself.

There are also philosophical novels and memoirs. Many philosophers preferred this format rather than the classic essay. They are certainly easier to read, but sometimes their arguments and points aren’t as clear.

Finally, I included both easier philosophy books and more difficult and serious books. Obviously, none of these lists are exhaustive. These are mostly biased by my own taste and stuff that I have read and enjoyed. If you’d like more recommendations, you can check out the book recommendations section of the website.

I’d advise using study aids as you’re reading, as well, especially for the harder books. I highly recommend the Stanford Encyclopedia of Philosophy. It’s an incredible resource for summaries of major works and simpler explanations of difficult concepts. It’s also free.

Also, surprisingly, Wikipedia entries for major philosophers and their works are often very good. Don’t be afraid to hop on and read a summary of a book you just finished if you aren’t confident you understood all of it.

Happy reading. And happy mindfuckery.

Entry Points to Philosophical Ideas

• Sophie’s World by Jostein Gaarder – An easy-to-read novel that also serves as an introduction to the entire western canon.
• A Guide to the Good Life: The Ancient Art of Stoic Joy by William Irvine – an introduction to Stoicism.
• The Happiness Hypothesis by Jonathan Haidt – A summary of ancient wisdom on happiness combined with modern psychology research on happiness.
• The Denial of Death by Ernest Becker – Becker relies on the work of Freud, Kierkegaard and Otto Rank to put together an existential framework for how fear of death inspires us to create meaning.
• The Obstacle is the Way by Ryan Holiday – A great entrypoint to Stoic philosophy but also ancient philosophy, in general.
• Everything is F*cked: A Book About Hope by Mark Manson – Plugging my own shit here, but needless to say, if you got through this article and enjoyed it, you will love the book.

Philosophical Novels and Memoirs

• The Stranger and The Plague by Albert Camus
• Nausea by Jean-Paul Sartre
• Crime and Punishment and Brothers Karamazov by Fyodor Dostoevsky
• Candide by Voltaire
• Meditations by Marcus Aurelius
• Thus Spoke Zarathustra by Friedrich Nietzsche
• Man’s Search for Meaning by Viktor Frankl

Easier Philosophy Books

• The Republic by Plato
• Meditations on First Philosophy by Rene Descartes
• Ethics by Benedict Spinoza
• Letters from a Stoic by Seneca
• Nature and Other Essays by Emerson
• Beyond Good and Evil by Friedrich Nietzsche
• Fear and Trembling by Soren Kierkegaard

Serious Philosophy

• A Treatise on Human Nature by David Hume
• Critique of Pure Reason by Immanuel Kant
• Phenomenology of Spirit by G.W.F. Hegel
• The World as Will and Representation by Arthur Schopenhauer
• Being and Nothingness by Jean-Paul Sartre
• Reasons and Persons by Derek Parfit