Right when I went full-time.
It was a pretty seamless transition for my friends, but my family took a lot longer to get on board. These days most of my family has made the switch, but my dad now, even after 6 years of being full-time, still messes up. It really, really bothers me and is not something I can take too much longer. It really just shows me that he's clinging to the image of me before, and since that's not who I am it just increases the distance I put between him and myself.
There is a time when you've given people enough time to come to terms with it and either make the switch or get left behind, in my opinion.