Interesting topic.
I too was having problems with self-image/esteem. I decided for one week I would not wear any makeup. I was getting tired of taking so long to get ready out, and how this was impacting my general life. At first it was nerve-wracking, but each day I thought about it less and less, and by the end of the week I felt quite liberated. Everyone still treated me well, and in the end no one else really cared.

I've always done things like this instinctively -- only recently did I learn that many of these ideas are actual techniques in some forms of therapy.

I say stick to your instincts. As long as you confront your fears in a safe way (and it sounds like you are), it can be a very powerful thing. It also tells me that you trust yourself enough to make that leap, which is an important part of the equation.

Trust yourself as you face this next challenge..I wish you well.