As someone who similarly writes to think, I found a lot of insight from this video [0] from the University of Chicago. Long story appropriately short, he recommends writing something twice: once for yourself and once for the reader.
1) If I am considering possible objections to my position, I have to be very clear which points I am raising only for the sake of argument, and which are the ones I am actually advocating for, or else it will appear confused or self-contradictory.
A related issue is to preempt possible objections to the point where the reader might lose track of the main issue.
2) After making several passes to hone my position, it can seem so obvious to me that what I write for the reader is too terse for anyone who is approaching the issue for the first time.