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I'm feeling a little sheepish because I spent a decade in higher education studying philosophy and have also spent a lot of time online over the years, and yet I had never heard of the philosophy game, or more aptly, the Wikipedia philosophy phenomenon. I'll let the Wiki page explain it:
"The Wikipedia philosophy phenomenon, sometimes called the 'Philosophy Game', is the tendency that English Wikipedia articles' first hyperlink, when clicked in a chain, will end in a loop at the article "Philosophy."
In other words, go to any Wikipedia article, click the first link, rinse and repeat, and you'll end up at the article for Philosophy. Of course, you can continue from there, but you'll just end up taking a detour through language, communication, meaning, and so on, and then—you guessed it—looping right back to the philosophy page.
In Wikipedia's recent YouTube video where Matthew Prebeg demonstrates the phenomenon, it's explained as being to do with abstraction and categorisation. There are all kinds of complications with categorising things. For instance, many things can be considered of the same type despite individual members of the category not sharing a single feature—they instead have overlapping similarities, or family resemblances, which Prebeg explains.
He also explains how our categorisations can be to do with abstraction. For instance, "this exact chair, right now" is "a wooden kitchen chair", which is a "chair", which is "seating", which is "furniture", which is an "object", which is "matter." But the problem with this, as he explains, is that there are different ways to categorise things, and different ladders of abstraction to climb. For instance, you might instead abstract to 'sitting' and then to 'bodily movement'.
What's interesting is that the Philosophy Game shows us how, at least in the context of an online encyclopedia, we tend to do this in practice. And most importantly, to my biased brain at least, it shows that no matter how we decide to embed our understanding of concepts, it's always philosophy that underlies it.
Somewhat ironically, one philosophical debate is on the nature of philosophy—what philosophy is—but my own favourite definitions always involve fundamentality: philosophy deals with what is most fundamental. Often it's split into three or four areas: epistemology (the study of knowledge), metaphysics (the study of reality), ethics (the study of morality), and logic (the study of correct, formal reasoning). These four areas essentially underlie all other areas of knowledge or study, meaning they are more fundamental.
I like to imagine philosophy as a very annoying child that asks 'why?' to every answer you give them. Eventually, you'll reach points where you don't immediately have a good answer—say, 'Why do you believe the external world really exists?'—and then you've entered the domain of philosophy. Ie, a level where most people are content assuming there are no answers and it's all far too abstract.
With this in mind, it's not too surprising that (almost) all roads (on Wikipedia) lead to philosophy. Just think of each first link as the annoying child asking 'why?', or more aptly, 'what's that?' Eventually, it will end up asking something very fundamental and philosophical, and you'll be on that philosophy page once again.
Another interesting thing about the Philosophy Game is that it could be considered a kind of experimental philosophy. This is a new and somewhat controversial philosophical methodology that looks to use empirical research and data to come to philosophical conclusions. Philosophy is usually informed by empirical research and data, but experimental philosophy looks to make this contribution more direct.
At any rate, play the Philosophy Game at your own peril. You might be left asking the perpetual 'why?' like me.
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