My initial plan was to play it by ear. I started laser and electrolysis immediately (January 2017), but was unable to see the doctor and start HRT (using informed consent) until late March. I planned to wait until I thought the changes were becoming noticeable before coming out, but the woman inside had other ideas!
I still present as male, but this will start changing soon. I have not had a haircut in nearly a year, but I keep it plastered down with mousse, no one has really said anything about it. For the last several months I have only been wearing women's jeans to work, and again no one has said a word. I bought some new glasses last week from the woman's section, I'll see if anyone notices next week. I am staring to look into a trachea shave, but that may be hard to hide.
I work in a company of over 30,000 that is very LGBT+ friendly. I came out to my manager (who works in another start) on Oct 11 (National Coming Out Day in the U.S.), and his response was overwhelming. I had to have someone at work to talk to, so I came out a coworker two days later -- her response made me cry tears of joy. HR also knows, and they have been very supportive. I plan to stay at this company until I retire.
I mentioned this in another post, but a year ago if someone suggested I was transgender I would have laughed at them. Six months ago I was scared to death about coming out. Today I look forward to the day I tell the world 'look out, here I come!'. I currently plan to do that March 23, my one-year HRT anniversary.
My wife is still trying to understand. I went to a therapist last week for the first time in my life, and she was awesome. I have another session next week, and then hopefully she will know me well enough to help my wife understand.
I have two daughters. 'E' is 21, she graduated college a few years ago and has a great job about 1000 miles away. 'K' is 19 and is a senior in college about 500 miles away. They will both be home during the Christmas holidays, and I plan to tell them a day or two after Christmas. Although I don't like the idea of associating my coming out with Christmas, I need to do this in person and that is the only time during the year when we will all be together.
Once I have come out to my daughters, I will come out to the rest of my family - probably in mid-February. Hopefully my name change will be nearly done by then. My parents and siblings all live near each other, but about 1000 miles away from me. I want to tell them all at the same time so my siblings may be able to help my parents understand. I may lose some of them, but I have accepted that the pain of staying 'him' outweighs the pain of losing contact with any members of my family.
I have felt some regret for 'him' occasionally, in a few months 'he' will be gone. 'He' served his purpose - got married, had children, and provided for and protected them until they could be on their own. Now it is time to let 'her' take over.
I am 6ft 1in tall. Will I be passable on the day I come out to the world? Probably not, but I will no longer let that stop me. I will 'own' it. I will hold my head high and be the woman I have always wanted to be.
This is a long process, but the sooner you start the sooner you will finish. It is an amazing journey, and I wish you the best of luck.