I disagree. I think we run into more problems when we coddle people and "protect" them when what they need is some tough love, or to be told that some fears/phobias/insecurities really are not worth worrying about. And the only way that someone can overcome insecurity is to face it and learn to deal with it.
If you have a fear of public speaking, the only way to overcome it is to expose yourself to it. If you have a phobia of heights, the only way to overcome it is to expose yourself to high places. If you have an insecurity about your dick size, you just have to deal with it and realize that it's not a vitally important part of life.
I've had insecurities. I have insecurities regularly, about things a lot more important than dick size (like my job, for instance), and the only way to get past them is to face them. They never, ever get better if you hide from them. They only get worse, and eventually your quality of life suffers.