One of my earliest experience was to overcome the fear of technique or rather fear of lack of technique. If you are after something and can't get at it because of technical or stylistic problems, you are stuck. That's extremely bad. In fact that could be the end to just about everything. You ought to be at ease with your aims and your technical and stylistic abilities.
People often suppose realistic painting and here especially portraying to be most demanding.
I found out and later proved to my pupils in class that this is not a problem at all. Read the first issues of my Creative Journals , they start easy and arrive at drawing portraits. This is a life's question, of course, so no definitive answers can be expected. I think it can be seen very easily, once you are experienced, at which level of artistic expression a painting is. Technique and style alone is nothing.