Often times people will surprise you. When something is abstract, it is easier to mock it. Without personal experience, it is common for people to not really think of us as a real, living human being. But then, find out your best friend or favorite uncle is transgender, suddenly it becomes real, and attitudes can change.
But it's still so incredibly hard, it really is. I too am in a small area that isn't a great place to transition(southeast GA), and have yet to come out around here besides to family. And even believing my dad's reaction wouldn't be negative (I worried neutral to me, maybe turning it in on himself), I was still absolutely terrified telling him. So many what ifs went through my head... But I knew one thing. If I didn't tell him, I'd give up. I'd go back into the closet and shove it all back down again, and I just couldn't do that. I'd seen a glimpse of the other side, and there was no way I could turn back with sanity intact.
I'd say just be sure to take it one step at a time. Don't plan ahead to your coworkers when you haven't even mentioned anything to family or girlfriend yet. Focus on telling individuals as you are ready, and don't worry about it if the time frame keeps getting thrown off either. (I know my carefully laid plans for Christmas reunion coming outs didn't work out at all.) This is all a slow process, and there is no reason you have to come out all at once before even really getting going.
The good news though is that cliche about coming out getting easier each time? 100%, absolutely true. The first is the hardest. The second pretty bad. The third is still not great. But by the time you are to #6 it's just old hat.
