Thanks for all the insightful responses. Working through an outline is definitely something I've never really practiced, and may alleviate the feeling of grasping at aether in terms of getting my ideas out there. I think my main issue is having the mind of a goldfish. I have little confidence in my ability be clear and concise, most of my thoughts and ideas lack focus and I find myself trying to overload each sentence with as many ideas as I can fit. I think most of the responses are spot on in that I need to slow down and reflect on what my words are really trying to say.
Definitely coerce yourself into the habit of making an outline- I still dislike making one, but the quality of writing is noticeably more lucid, exact, and stronger logically. A suggestion from my favorite English teacher (Rene Wang) is that for an essay, get a blank sheet of paper and write down anything that comes to mind all over the page, then connect those that have a relationship and group those ideas into major points. It also beneficial for you to read novels; not only do you pick up some ways to structure your sentence, you also can 'borrow' some of their style and diction that make it easier to elucidate your idea. p.s I tried Dickens for vocabulary- on every page there'd be at least 5 words I didn't know, 3 I've never seen, and 1 that made me go 'there's a word that means that?'