It gets easier every time.
I went from too nervous to go out my front door to take out the trash in January to almost full time in March, decided to make it permanent and came out to the world in April. Admittedly I had antianxiety and antidepressants working for me at first, but I'm off of those now.
The first couple of times I left the house I just drove around town and I don't think I ever got out of the car. Then I went to therapy a couple of times fully dressed as my therapist had double-dog dared me to do. Then I spent a weekend in San Diego in girl mode and got clocked bigtime by a real a*hole who was drunk and umm, quite vocal. I survived and worked on acting less nervous. I then started going out to dinner locally fully dressed and running errands in andro mode during the day. I kept going out more and more femme. By this time the lasers had done enough that there was no beard shadow and E was softening things up. So a month after San Diego, I went to Las Vegas for a weekend and left the guy clothes at home. Apparently I was passing pretty well at this time, had a great time being treated like any other woman and decided that I'd make it permanent. Since the growing breasts were about to out me anyway, I just stopped wearing guy clothes and did all of my business in girl mode from then on.
Confidence will snowball with only subtle physical changes and fewer double-takes. I still have to sport some bust enhancement to make it all work, but ditching the male facade this early in transition was worth it.