Social stigma is going to be my most difficult hurdle in my early to mid-times prior to full transition.
I am a very social cat, both professionally and in my myriad outside interests and community activism. At 53, my standing and place in society is fairly cemented in concrete; this change will be highly difficult not only for myself and my nuclear families (work and home), but exceedingly difficult for my extended activities. I have excelled in male dominated, socially backwater, conventionally conservative places that I am accepted as liberal, but regarded highly accepted for successes. This particular change is going to be particularly awkward for the suspected people that are either unfamiliar or too narrow to understand.
This is a great topic in my discussions with my support professionals. For the most part, change will initially have to be bearded and sloughed off as a change in diet, or worse, perhaps, questioning my health. I will need to be stealth for as long as I feel I can realistically hide the changes from HRT. I don't want to live the life of lies, but we feel it may be necessary for a longer more sensible transition. Little things over time so people do not get shocked. It will be no different than us looking in the mirror and not seeing outward changes, because we look everyday. Those that only see me irregularly, will see the most change.
So, for strength in walking, dressing and talking/living the new exciting life on the streets as a new born woman; I cannot yet attest to this. I have my own demons and expected processes. As for social stigma for most, all I can really recommend search yourself to have a very strong self-esteem, and a slightly thicker skin to those that are so narrow as to treat you with hate. Indifference may be an ally. Walk tall ladies.