1. It just seems that some philosophy problems are created (ex nihilo as well) just for having something to be frustrated about. The naming problem in the philosophy of language seems to be one of them: this is the problem where philosophers fret about how do proper names ('Socrates', 'Obama') refer to the bearers of these names. "They just do" obviously isn't a good enough answer for philosophers. In cases such as this, a philosophy student has to sometimes try to care about how pressing the problem is. Perhaps it's not altogether a ridiculous question to ask, if you frame the question as a sub-question which will tell us more about the nature of our thoughts; but unless you bear in mind the ultimate purpose of the question, philosophy can get quite tiresome.
2. It seems that some philosophers are just missing the point. Take the vagueness problem as an example: this is the one where philosophers wonder whether 'Peter is tall' is a true or false statement when applied to Peter, whose height is just between what you would typically call 'tall' and 'short'. Some philosophers think it's a problem because if you answer that Peter is both 'tall' and 'short', you would end up with a contradiction (p ^ ¬p). In my view, this problem does not arise when you consider how language is used (e.g. you assume that 'tall' is used relative to a conventional standard of tallness) or reject the idea that sentences can only be either true or false; this is a problem for how logic can encounter difficulties in modelling reason, and not a genuine real problem inflicting the universe. I don't believe many philosophers actually conceive of the problem in the latter view, but there isn't a very strong impression on me that there is an acknowledgement in the discourse that the problem ought to be treated in such a way. There are many other examples, especially in the area of metaphysics, where often little attention is paid to how people use language, and the nature of the discipline itself.
3. Philosophers often use problematic concepts in arguments without coming up with an account first. I know it is is impractical to give a full account of all the fundamental concepts in presenting an argument, but this nonetheless does "grind gears". This includes the following: the correspondence theory of truth, the bivalent view of truth, the notion of knowledge (hardly it is clear what knowing means, especially in philosophy of mind and psychology), the thesis that there exists real moral truths and the notion of reference. Although one can foresee asking philosophers to be more elaborate means longer and duller philosophy texts, this seems to be a necessary evil that philosopher students have to bear with.
4. Very often it feels that no philosophical progress (if there's such a thing) can be made without hammering at the "pillars" of your belief. I suppose this is connected to the third point; you cannot make significantly more satisfying arguments without changing how you understand the very basic concepts. This is similar to what is achieved in the cognitive revolution, the movement in analytic philosophy and the movement in pragmatism. Perhaps this is the less frustrating of the five problems; if you are given enough space and support to think freely, this can actually be a very strong motivation for doing philosophy.
5. It's always difficult answering the question "what did you learn?" from a philosophy discourse. While you may learn as a by-product certain factual information (e.g. that Hesperus and Phosphorus are other names for the planet Venus), since most of philosophy is non-factual it seems hard to say that you've actually learnt anything. Soft skills, perhaps? But we do want to say that philosophy is good in itself, not just good for something else. But do we really want to say that "I haven't actually learnt anything from philosophy, but it's all good fun"?
6. When there's too much quoting and history going on. Maybe I'm wrong, but I find it unhelpful if there is a significant amount of quoting and history going on in an argumentative piece of philosophy text. It's certainly interesting to set the background, but it's not clear what has been stipulated necessarily has to re-appear in what you stipulate, especially when the historical context does not affect the soundness of your argument. This is partly why I didn't like how some political philosophy courses go about - why must you say that Edmund Burke argued that 'traditions are valuable' when you can give the same argument independently? This is the exceptional case when I find an additional meta-level of thinking less appropriate: arguing a case just seems more satisfying than examining how a case has been argued. Arguing a case is a job for philosophy, but examining how a case has been argued is a job for the history of philosophy.
Not that these problems will stop me from doing philosophy, but becoming aware of the source of these frustrations help me reinstate my motivations.
sometimes it does bug me that why philosophers don't deal with problems that are more essential and useful to our daily life, instead of figuring what the word "essential" really means, and how to differ "essential" and "less essential" just like what you've said abt the tall and short contradiction... cos philosophers usually have brilliant brains, but they seem to enjoy using their brains to mindfuck you instead of being productive. XD
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