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Notes -
What’s depressing about it, exactly? Might help tailor the recommendations.
Well I don’t want to spoil his whole schtick, but the basic idea is that if you truly want spiritual enlightenment you have to give up pretty much everything. The price is extremely high.
In retrospect it’s pretty obvious, but now that I’m having to stare this truth in the face I’m shook. Starting to question what I actually want in the first place.
I can't imagine what sort of enlightenment that would be. Some things can only be had with great sacrifice, yes, but is "enlightenment" one of those things?
The founding assertion of the European philosophical tradition is that, if we can speak of such a thing as "enlightenment" at all, then it is not to be found in any particular piece of knowledge or state of being, but rather it is to be found in a habit of mind. It's the process, not the content. Typically at the origin of a religion or a philosophy you will find a wise man who claims to have found the truth and is eager to share it with others. Socrates, in contrast, claimed to only know that he knew nothing. He had no wisdom to share; his only mission was to deflate the pretensions of those who pretended to wisdom. Such pretenders were in no short supply, since any mortal man who claims to be wise will ultimately falter when examined by the light of reason. Wisdom is for the gods; what mortals must be content with in its stead is the love of wisdom.
Of course Socrates and all of his students (Plato chiefly among them) immediately contradicted themselves. They didn't just give up and revel in ignorance. They had protracted debates about all sorts of ideas about all sorts of things - beauty, virtue, truth, reality. It looks like there were quite a few claims to knowledge in there as well. But that needn't distract us from the thrust of the fundamental lesson. Even as you do (try to) learn things, and you do make arguments and assent to propositions, that fundamental attitude of humility and wonder will always be lurking in the background - the understanding that wisdom is a process that never reaches completion, rather than a final state of "enlightenment" that you're hoping to attain (please for the love of God never listen to anyone who unironically calls themselves "enlightened", I mean dear Lord that's just about the dumbest thing you could ever say about yourself).
When you put this sort of distance between yourself and the ideas you entertain, it lessens their emotional impact and it makes philosophical reflection into less of a rollercoaster ride. Yes, perhaps there's no free will, and no "self", and everything is meaningless, and that's a bit depressing - but at the same time, perhaps all that is exactly wrong. You never know what sorts of new things could happen to you or what sorts of things you could learn that will reveal that all the "wisdom" you had accumulated up until that point was really nothing but so many sandcastles in the air. You're here for the journey, you're not here to Learn The Truth. And of course these habits of mind can be cultivated without any great sacrifice. It only requires time and patience.
You might enjoy reading Plato's Apology. It's very short.
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