Here are a couple of examples where not caring what others think may be taking it too far. This first example involves connection versus isolation. There is a difference between not caring what others think and not wanting to be part of the herd. If you want to be totally independent of others and want to sing out loud in public places and wear underwear on top of your head, that is great; however, you are trading human connection for it. People who are completely independent of the opinion of others are truly unique, this is true, but they also tend to get isolated. When we make ourselves intentionally different from everyone else, not caring at all about social norm, we are telling others that, “I do not want to be like you, and I am not going to connect with you.” This is a personal choice. I think it is good to follow social norms and still be able to express your uniqueness. Human connection is vital to happiness.
The second example involves relationships. If you are having tension with someone in your life and there has been communication left unsaid, then this is not the time to take the attitude of not caring what they think. This is the time to make sure you have fully understood where they were coming from and to make sure that they have fully understood where you were coming from. Once you have communicated with them and you are confident that they understood what your intent was, then it is time to let it go. If they still hold a grudge, there is nothing else you can do, and it is not about you anymore at that point. Depending on the closeness of the relationship, it then may be time to not care what they think and move on.