As always, it depends!
It is a lonely path because you will do things that will seem weird and maybe even immature to some people, and they will not understand without a proper explanation. But if you are in the middle of the journey, still learning, you haven't figured things out yet and are not capable of explaining it. In order to explain something you need to understand it yourself first. Today I can easily explain everything to people and make them not only understand, but even nod in agreement to what I say.
About family... It depends on your family, obviously. And on you. Maybe they won't understand the process, maybe they will. My parents did. And it will probably take time for them to see you as the new person you have become, and you need to "help" them by not falling back to you old role, and own whatever you are and do. For instance, my parents think I became more masculin. They accepted my new self.