How best to support a friend going through gender reassignment (male to female)?

I have a very nice friend of mine who just told me he's going through gender reassignment. He's been taking hormones and plans to have the surgery eventually. Within the next few months he will start living as a woman but he's scared it may cost him his job and some friends and acquaintences. In all honesty I never expected this of him but of course hindsight is 20/20 :-) I am worried for him with all that he has in his future. With the strike in Hollywood, he's been out of work for a little while and with talks going on by the time he goes back to work the change in him physically will be evident. He hasn't met much resistance in fact most people have been supportive of his decision so far. Just wondering for any of you who have done this or helped a friend through it, what practical advice can you give to help get through making such a big change publicly? He's already gotten an amicable divorce and his grown children and ex all seem ok with it (mostly) but work scares him.