Coming out at Pitt actually turned out to be fairly easy -- we have a new associate vice-chancellor who coördinated the timing and delivery of the message to the various people I work with. It took a while to get the message right, but it is good to know that those who will come after me will have a better experience than those behind me.
The family was more...interesting. My parents were initially OK, then not-OK, then reluctantly accepting. It is still hard for them to understand, but they have never stopped loving me, and I will not stop loving them. My sister, however, was not-at-all surprised, and has been by-and-large wonderful.
Along with the above message at Pitt, I announced publicly my correct name and gender on 8 January 2016 -- along with that picture on the left. I was overwhelmed by the positivity and support that everyone gave me. It turned out to be the best day of my life.
After over 20 years of denial, secrecy, and anticipation, I am finally happy (mostly) with who I am and where I am going in life. A lot of detractors of transgender people point to some supposed sense of regret about transitioning...my only regret is that it took so long to start.