[Serious] Generally speaking, is philosophy a worthwhile subject of study?

[emjay]

So pretty much the only way I think I can make things more concise is either to find that elusive perfect sentence that covers all its bases in the shortest/simplest possible form, which granted is always very satisfying if you do find one, or just to be less anticipatory in the first place... which is difficult if you're one, like me, with a tendency to overthink/dwell on things.

That's an interesting observation. I do think the solution is to shift your thinking from an anticipatory position to a conversational one.

By anticipating a question you end up having a conversation alone instead of allowing others to be inserted into it. (Which really only happens in writing; it's harder to anticipate a face-to-face conversation.)

This also means you run the risk of biasing your questions, answering ones that serve your position, and avoiding ones that don't. So perhaps realizing that your best thinking can only emerge in response to other minds, can reduce the need for anticipation, and welcome objections more.

Hey there, just wanted to clarify something a little further if I may?, since reading this again I realised there may have been a slight misunderstanding regarding the 'scope' of what I meant by anticipating questions/objections. I meant it mainly at the level of sentence structure, as opposed to at the level of whole arguments/posts. Ie my posts usually contain very long run-on sentences, with a lot of commas, lot of clauses, lot of qualifiers etc... basically a lot like legalese, and it's that that I wish was more concise, but it gets like that because of neurotically anticipating grammar nazis, nitpicking, general definitional misunderstandings etc and wanting to pre-empt that.

So just trying to clarify here that it's not so much the case that I'm anticipating whole arguments/questions/objections at the post level, and thus essentially conversing alone as your post states, and with all the attendant bias that would/could imply, ...but instead that anticipation mainly operating at the level of sentences, (because like I said before, I have a tendency to obsess over little details, and that is one example of it) so it's not the case that with this I'm having a one way conversation... ie I don't think conversation is impeded here, nor am I averse to receiving questions or objections at that higher level, it's just that, at the very least, this aims at/results in reducing the back and forth of just clarifying my own position. In other words I'd rather my own position be as clear as possible from the outset, rather than wasting time down the line trying to clarify it with lots of back and forth. It works both ways; I also like it when other people are clear with their definitions, and I don't have to spend forever questioning them, to understand their position. Once positions are clear, then in theory at least, useful conversation can flow much more freely, with less talking past each other and/or misunderstandings.