I’ve always felt that your friends and families made the worst audience for your art but had a hard time explaining why. I think it’s partly because every context brings out different aspects of a person. In some ways, it can be said that art is a way to express aspects of yourself that are suppressed in your everyday life. If what you express in your art is naturally and continually expressed in your everyday life, there wouldn’t be much need for doing so using art forms. When you do express these different aspects of yourself, your friends have a hard time recontexualizing who you are.
Imagine a scenario where you had been a boss to someone at a large corporation for five years, and this person suddenly got promoted and became your boss. To successfully work under her, you would have to clean-slate the images of her in your mind. As becoming an effective leader requires a different set of skills and self-awareness, she would need to bring out different aspects of herself which were previously unknown to you. Such a transition may prove so difficult that she might be better off getting someone else to work for her, not because of competence or qualification, but purely because shifting the dynamics is not easy for most people.
Your friends and families will like or dislike your art for the wrong reasons. An extreme example would be parents loving the artworks of their own children. Parents commonly frame and hung such artworks on their walls, because they genuinely enjoy looking at them. But would they do such a thing for the work of a random child purely based on its artistic merits? Obviously no. That is, what they are enjoying has little or nothing to do with artistic substance.
I would also imagine that, after a sex-change operation, it would be easier for you to make new friends based on your new gender identity than to remove the awkwardness in your existing relationships.
The inverse of this happens when you get to know a famous artist personally. This is expressed in the common piece of advice, “Don’t meet your heroes.” What happens in such a situation is that the image you form of the artist as a person would begin to interfere with the image you have already formed of her as an artist.
I believe this is true even for writing, because when you write for the general audience, you write in a different tone and style. It brings out different aspects of yourself that your friends are not familiar with. The voice that comes through in your writing may feel strange to them. The images they have already formed of you will interfere with your art; they wouldn’t be able to objectively evaluate your artistic merits.
So, to grow as an artist, I think you have to step outside of your own circle of friends and build an audience of strangers. Getting feedback from your friends and families can lead you to a wrong path as an artist.