I dwell on this topic quite a bit it seems. Perhaps it's because I get asked the question about what it's like to go "full time" as a transgender woman. All of a sudden, it wasn't which gender I was going to a party as, it became what I was going to find to wear. As a woman, I didn't want to embarrass myself. Didn't want to under-dress or over- dress for the evening.
In many ways, it's a tough question, yet easy to answer. First of all, it is different than anything I ever imagined. Back in my cross dressing days, I was obsessed with so called "passing." Now I'm obsessed with looking the best I can and letting the cards fall where they may.
Along the way, I have crossed so many frontiers, they are hard to remember. Communication barriers arose the more I lived as a woman. Both genders communicated with me different. For the most part I was ostracized by men and treated with curiosity by women. Along the way, I just came to expect it. I learned to be more of a listener and be on the outlook for passive aggressive behavior.

"Passing" was also replaced by comfort and blending. It became simply impossible for me to put together a complete "heels and hose" outfit for every occasion. Instead, I began to dress to blend...with other women. So, again, I was dressing for women and not men.
I think too, in many parts of the country, living as a transgender woman or trans man is becoming somewhat easier. In fact, I recently gave job advice to a new trans woman friend. I asked her if there was a Kroger Grocery Store near her. At least around here, Kroger makes it a point to be very diverse.
Not to say life is a piece of cake for a trans person, but in someways there is a glimmer of hope on the sunrise. Especially with the political situation beginning to change. Even in Alabama.
Finally, if you really are thinking about going "full-time", dress to blend and go to the hardest places you perceive to go. If you can make it there, you can make it anywhere!
Good luck...on your new gender skill.
I, like Paula, am a musician. I had long wondered how I would be accepted by an audience as a woman, and also by other musicians. I had been performing for mostly cross dressers for about a year, but that was more of a novelty, and not so affirming. I was in a blues/jazz band as my male self at the same time, and one day I secured a job for the band at a charity event called "Cross Dress for Success," raising money for "Dress for Success," helping low income women with business attire to help them find jobs. Using my cunning and decisiveness (honed so well over the years), I had a clause put in the contract that "at least one member of the band must be cross dressed." That opened the door for me to come out to my band, but what happened later was far beyond my expectations. Someone at the event wanted to hire us for another event (having nothing to do with trans), but insisted that I be just who I am. That led to a series of gigs for "Connie Dee and The Sciaticats (we all had bad backs, but were cool as cats), and I never appeared on stage as my old male self again. I went on to bill myself as "The Fabulous Connie Dee," adding the "fabulous" because there was already a "Connie Dee," hence the name you see here.
I'd have to say that love is what helps to make the decision to transition. Love who you are, love those who are important to you, and love what you do (or continue to do what you always loved)."