'Female' versus' Woman'

I am a female because I have ovaries and a fair amount of estrogen coursing through my veins shaping and feminizing my body and my mind.  I am a woman because one day, though it was probably over the course of many days and far from a conscious decision, I decided that I wanted to identify as a woman and participate in social interactions with others categorizing me as a woman.  Others are male because they have testes and a fair amount of testosterone that determines which gonads the developing child will have and it masculinizes everything from their physical body to their mental processes, however, others may be a man because they made a multitude of subtle changes over a period of time allowing them to be portrayed by others as a man.  With only two distinct categories, it is oversimplified to say that this person is solely either a woman or a man.  But what about the people that do not fit so easily into these social categories, these socially constructed boxes?  What about the people that belong in the grey area within a black and white system?  I try to imagine how my life would be different if my sex and my gender were not aligned with one social category.  If I had the female sex and all the biological and physiological processes that correspond with that but I wanted to identify as a man, I would probably dress very different.  I wouldn't be wearing fitted jeans rolled up, ballet flats, a fitted t-shirt with a lace undershirt, and my hair would most likely be much shorter.  My day to day interactions would also be very different.  I would not sit up so straight, walk with my hips as much, use the women's restroom, worry about glass ceilings, care about my body weight, talk with as much musicality in my voice or high tones, take ballet classes, aspire for feminine careers (nursing, hair stylist, maids, childcare), or go home to my husband (depending on my sexual orientation).  These are obviously just guesses since I am in fact a woman, but the point is very obvious that my life would be completely different from my thoughts, my clothes, my desires or fears, and my activities.  I mentioned that I couldn't use a woman's restroom because it is a very basic change and it is a very simple way to enable others to make judgements about which gender you possess.  It is probably a little easier for a female (transman) to use a man's restroom - imagine the difficulty a male (transwoman) would face entering a woman's restroom even if this person identified as a woman.  Restrooms are just one artifact of the socialization of gender but it provides a clear example of how black and white our society is when it comes to gender.  There is a woman's restroom and a man's - that's it!  What do the people who transition do?  How do they learn which boundaries to push and when?  It seems that people who transition earlier in life have an easier time, however, the popularized stories of people transition are those who go identify with one gender (that is different than their biological sex) and decide one day to act on it.  The 'news worthy' stories are those of people who are married and they decide to transition or they choose to raise a family in the other gender.  So, I find myself asking, what would you do if you woke up tomorrow and realized that you wanted to identify as a man instead of a woman?  How would you alter the black and white male/female dichotomy to encompass your identity as you transition?