Leo Babauta of Zenhabits describes an interesting concept of pigeonholes in interpersonal communication. My personal experience with this suggests that there is always a hassle that stops people from changing for better. Changing for worse usually happens gradually and unconsciously; and when it is conscious (I can not imagine that, but still) you do not care how others perceive you anyway. Changing for better is in most cases a conscious action and involves a great deal of thinking. Here perception of you by others is important.

Unfortunately, often the first reaction to change in you (or in other words you trying to change a pigeonhole) is suspicion. Why would he wonna do that? Is he going to fool us? And you really need to get through this. One of the better options to do that is to get an alignment of a person you trust. With her belief in your new personality and her support it would be easier to convince rest of the world that it is not about them being fooled, but about you becoming better.

Beware that when you want to move something from one pigeonhole to another you need to pick it up first.