Update:
After digesting the advice from Sly members, I decided to take a phase-in approach to my transition, with a #1 on the sides and #3 on top. I have to say, I'm loving the freedom of just putting it out there for the world to see - I no longer worry about trying to cover up the obvious! For the most part, everyone has been very supportive and I've even had a few "badass" comments, along with having a colleague tell me I look like "a German assassin. Anyhow, thanks to everyone who chimed in - your advice was right on the mark and just the push I needed to take the leap.