I am a big blabber mouth... It seems like there is always a reason to share it with this person and that person... I am telling the people who would be supporting me if I G-d forbid, have a miscarriage or other complication...
I've told my DH, my dad and step-mom, one of my clients (because she was requesting my due date for an event, and because she knew we've been trying), and I told my cousin who is trying with IVF for her partner and we have been 2WW buddies.
My friends, I will probably tell them as I see them, which isn't often because I am working a lot. My mom, I am not sure when I will tell her, because I don't want a negative reaction (she wants the best for me, and I had a rough time with DD).
We thought of a funny way to tell my brother. We have a website for DD with pictures for the out-of-country grandparents and friends... It is DD'sname.com. He teased us a while back saying that by the time we have another we will be like, oh well, old news and just post pictures on DD'sname.com/sibling. So I was think of setting up a page like that and sending him a link... I will see him in two months so I may tell do it when he comes home for the holidays.
I will have to tell my professional community sooner than later because I will need to plan maternity leave (I am a newly-elected president of a non-profit board... It may not go over well... I also have clients that will be difficult to juggle because I am self-employed... So that will take some planning...)