Hi Dan, and thanks for some awesome sharing!
Yes – I can relate. And in my own process of establishing comfortableness and fluency in writing, I have realized that this fear/constriction when it comes to writing, is usually what holds me back from me expressing myself naturally. For me, it has usually been because I wanted to share something that is 'good', that others can 'relate to' and like, and to achieve that, I would project/envision a finished project in my mind – how my text would look like, the words I would use, the feel of it, and the point it would convey. Then I would attempt to force myself into this small box that is my vision, which would be uncomfortable, because as I would begin to write, the point would change, something else would open up, my words would go in one direction, and my vision in another – hence – the resulting experience of constriction.
The solution I have applied for myself is to, as I sit down to write, take a deep breath, clear myself, bring myself into my body, and then look within myself for a topic/point that I would like to write about. Then, as I have decided upon one, I stop 'looking' and I instead begin to write, and instead of envisioning my blog, I create it then and there as it flows and moves in the moment. Hence, making the process of writing very simple. Thus, you could try that, let yourself go, be spontaneous and allow yourself to play with the words and see what comes through.