If I may, I think I have one piece of advice that might make it easier to evaluate your progress as both a writer and a thinker.
One thing I like to do from time to time is to argue in favor of an idea that I completely disagree with. I used to do this all the time with the death penalty. I oppose capital punishment myself, but on a purely emotional level, I’ve never been entirely comfortable with my position on that issue. When I saw a story on tv about a particularly gruesome murder, I often found myself instinctively thinking that the guilty party does indeed deserve to die. But at the same time, I knew that the only way to prevent the executions of innocent people is to ban capital punishment altogether.
I had difficulty reconciling my thoughts (against the death penalty) with my feelings (in favor of the death penalty). So basically, I started arguing with myself. I began writing articles in support of the death penalty even though I opposed it. I looked for all the holes I could find in my own logic and tried to expose them. Simply put, I tried to debunk my own arguments.
After that, I’d write a response to myself, refuting the points I had raised in favor of the death penalty. Then I’d write a response to my response. Then I’d write a response to the response to my response. And so on and so forth.
In other words, I kept arguing with myself until I finally figured out precisely why I believe what I believe and discovered how to argue in favor of that belief more effectively than I ever had before. Once I reached that point, I knew that I had genuinely matured as both a writer and a thinker. But the only way I could get there was by trying to beat myself at my own game.
So if you have the time to do it, you might want to consider doing something similar. Not every day, of course. But maybe once a week, or even just once a month. I think you might find it useful!