How your family will react can be very tricky to judge, especially if you are an only child. They may be ok w/ OTHER peoples kids transitioning, but not as much for one of their own. Its hard to say. Same w/ other family members and friends. The best you can do is to demonstrate how much happier you are as your authentic self as you move forward. But dont be surprised if some people withdraw from you further along. And some who may initially reject you, may eventually come around.

As for your job that can often be a serious mine field to navigate,. I previously worked many years for a nonprofit Media organization. I could not have ever asked for a better place to transition at. But then I had a new boss come in and that relationship ended a year ago. I suggest having an mergency exit plan in place just to be safe. Im now working in something Tech related, where they have known me solely as my female self from the start. Begin your transition slowly, dont expect overnite mirricals.