A lot of this is luck of the draw. I grew up in the 1960's when you would expect very little acceptance of all of this, and yet I was able to partially transition with my family and school supporting that... although in fairness they just thought that they were letting me express my feminine side... It doesnt matter - it was enough to prevent me growing up with self acceptance issues, and feelings of guilt.
So when I fully transitioned and had GCS which was early to mid 80's I had remarkably little trouble. There was one work colleague who tried to make things a bit awakward for a while, and I think there was the inevitable bit of negotiation about toilets, but on the whole everyone was very supportive and friendly. Since when I've never encountered any noticable prejudice and I've enjoyed a pretty high profile career in a number of senior roles. I'm still getting the lucky breaks too at the age of 55, and being allowed to retrain for another fairly demanding career, so I do think it is partly luck.
By the same token I've always had a very modern take on this, in that I'm a decidedly modern woman, who does not acknowledge the restrictions or pressures that earlier generations might have done. I make no attempt to conform to any ideals other than those that please me, and I reject the idea that my history should be shamefully covered up, so I adopt the attitude I am me - I've always been me, I chenged my appearance and physical form a 30 years back, but i'm still the same person, so everything else is someone elses issue!
In short I make them come to me for approval and acceptance, rather than the other way about. For me that works.