How To Get Into Philosophy Without Going Insane

I received two speaking invitations last year from two university philosophy societies, and the most frequently asked question during the QnA section seemed to be:

“So… Where do I start?”

I always struggled to answer this question on the spot. Asking this question is like asking: hey, how do I get into coffee drinking? or man, how do I get into cooking more? It seemed like these students didn’t want me to tell them the way into philosophy, but they wanted me to tell them precisely what to read, how to read them and how to think about them.

But philosophy, like coffee drinking and cooking, is a deeply personal pursuit. You’ll figure out your way by doing it a bunch, making mistakes and gradually getting a handle on it. No one has the same entry point into philosophy, and there are no universal titles everyone should read.

However, there are a few tips I’d like to share from my journey. The following points are not prescriptions, but pitfalls I fell into when I first entered the field.

0: Do you want to be a hobbyist or professional?

For most people, diving into the fine nitty-gritty of philosophy is a complete waste of time. Some of my friends get their food for thought from philosophy podcasts, blogs and video essays. There is nothing wrong with it at all. Whereas if you treat philosophy like a professional when you’re a hobbyist, you’ll get confused and resent it.

In reality, professional academia is all about sorting through the finer grains. Sometimes a philosopher would analyze the life out of a tiny paragraph from some obscure journal published in 1968. The pursuit prizes depth instead of breadth which could get overwhelming for untrained readers. On the other hand, if scholars forget to zoom out and see the larger context, their findings might be too obscure to do any good.  

Ideally, academics should use their talent in research to educate hobbyists in a down-to-earth way. We need thinkers who can pursue depth without sacrificing breadth. We also need creators who can link philosophy to a larger context without getting the finer details wrong. However, we’re still a long way away from this ideal. Scholars are either too obscure to understand, or they’re meddling in fields outside their expertise. With the cards we’ve been dealt with, here’s my best advice for you.

1: History, History, History.

Beginners like to treat a philosophy book as an isolated work, but they’ll soon tear the pages apart out of confusion. Besides a few fringe cases, philosophy is steeped in its history.

Hegel famously wrote:

“World history is a court of judgement.”

The history of philosophy tends to judge and shape the ideas of the present, hence contemporary authors tend to reference past thinkers. In short, philosophy is a historical conversation. Reading it without its history is like conversing with a table of people who speak a foreign language.

Aim for a broader understanding of the entire history through secondary sources (books) podcasts, YouTube videos and online courses. (I’ll list my favourites in the recommended readings section). View philosophy as a series of movements instead of isolated acts of genius, and this survey for context should be as broad as possible.

E.g.: What made Descartes’ cogito so significant during his time? What were people debating before Kant’s famous critiques? Why was Nietzsche so critical of the philosophical institutions of his time?

At this point, you don’t need to go too deep on one thinker. Imagine an empty timeline with philosophers scattered all over it. Your survey should find a broad relationship between their ideas. In short, identify an overall movement instead of getting lost in any single work. When you’ve done this, you’ll have enough context to tackle individual books from philosophers.

2: Should I start with Plato?

Logician Alfred Whitehead once wrote:

“The safest general characterization of the European philosophical tradition is that it consists in a series of footnotes to Plato”.

I debated this with my friends at a bar once. Though we all agreed that Plato is important after two rounds of drinks, none of us have read all of his works. We found our separate ways into philosophy thinking that we could ignore him forever, but as references to Plato started to pile up, we had to admit our defeat and return to him like good schoolchildren.

That being said, starting with Plato might not be the right choice. Reading philosophy chronologically could bore you to death because you have no reason or motivation to read Plato. Since philosophy is a grand historical conversation, sometimes it’s better to dive into a philosopher we love and let them guide us back to Plato. In this way, we can use ancient philosophy to supplement our understanding of recent thinkers, instead of drudging through them with dread.

We can apply the same rule to other cornerstone thinkers like Aristotle, Descartes, Spinoza, Freud, etc. Sometimes it’s better to let contemporary philosophers lead us back to the old ideas, instead of resting in paralysis because we haven’t read them.

3: Philosophical prose is a foreign language  

Before we discuss how to deal with dense philosophical prose, let’s reiterate point 0: do you want to be a professional or a hobbyist?

Again, for most people, reading a long and dense treatise is a complete waste of time. Philosophers tend to spend more time justifying their ideas instead of presenting them. So, if you just want interesting ideas or food for thought, diving into technicalities could do more harm than good.

Even in professional academia, it’s rare to find a philosopher who has read everything thoroughly. They’re usually experts in niche areas who have read a few works really well. So, to expect someone to read hundreds of books thoroughly is unrealistic even for professional scholars, let alone normal people who just want some interesting ideas to think about.

For a hobbyist, a really good podcast series, a nonfiction book, or an introductory online course is more than enough. But if you want to dive deeply, here’s an important pointer.

Learning how to read philosophy is like learning a foreign language. Words mean completely different things under a philosophical lens, and the early days of reading are all about hunting for the right definitions for seemingly ordinary words.  

For example, a simple noun like idealist carries two very different meanings. Ordinarily, it means:

a person who is guided more by ideals than by practical considerations

(Oxford Dictionary Definition)

But in philosophy, it means:

any philosophical view that stresses the central role of the ideal or the spiritual in the interpretation of experience.

(Britannica Definition)

And when enough of these specialized terms stack up in the same paragraph, philosophy writing could appear impenetrable. But if you take your time and build up your philosophical vocabulary, you’ll soon realize that these terms are usually shared among many philosophers. Though the learning curve is steep, you only need to do this once and it opens the door for you to read everything with your philosophical fluency.

Note that there are philosophers who break the mould and establish their own philosophical vocabulary. Heidegger’s Being and Time is a good example. He essentially invented a new language because ordinary philosophical writing was unfit for his subject. The same goes for Malebranche, Hegel, Wittgenstein and to some extent Lacan. But these are exceptions to the rule, and without learning the rules, it’s hard to understand these subversions.

Epilogue: start in ignorance, end in ignorance

Ethicist Elizabeth Anscombe once wrote:

“No second-rate philosophy is any good. One must start from scratch & it takes a very long time to reach scratch.”

Philosophy usually starts from ignorance. We want to be smarter than we were yesterday. But at some point, after years of learning, we’ll return to ignorance. Ideas we took for granted will self-deconstruct. Intellectual pride will morph into humility because our world just grew; there is still so much we don’t know. Once we’ve reached this point in our understanding, this is where we can philosophize from scratch.

In summary, pursuing philosophy isn’t about hoarding obscure concepts and definitions. It’s about cultivating a way of thinking that will expose our ignorance. We have to start in ignorance and end in ignorance. And when we take a step back, we’ll realize that ideas are only a means to an end, and that end is the pleasure of independent thinking.

Recommended Readings

  • History of Western Philosophy by Bertrand Russell

  • At The Existentialist Café by Sarah Bakewell Lovers of Philosophy by Warren Ward

  • Philosophize This Podcast by Stephen West

  • Philosophy Playlist by The School of Life

  • The Partially Examined Life Podcast

  • Modern Intellectual Tradition: From Descartes to Derrida, Online Course Taught by Lawrence Cahoone Ph.D.

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