My writing also has always been an extension of conversation with me– which I love– but I'm realizing that releasing things unedited also means I have an instinctive block because just as in conversation, some thought are best when edited, or even unsaid.

I am going to take this to heart and not lose completely some of that conversational writing, but focus on a different type of writing as well– writing that I know I will re-read and edit, and see if that helps open the floodgates a bit more.

Well put; though, I think it'll do you well to re-read what you've written. Not for the sake of clarity (though, that will improve as well) but for the sake of learning how you think through an argument.

When we think, it's our tendency to go from A -> B -> C -> D -> E… but, it's usually communicating D and E that are the salient points. Journalists say, “Don't bury the lead”, so go from A through E, but tell us where we're going so we have more incentive to get there; A roadmap, if you will.

After a while, you'll start doing it naturally, thinking from A to E, writing A to E, and then filling in B, C, and D afterwards as points of clarity.