The Wasted Years?

Photo from the
Jessie Hart Archives

 Many times when I am asked what my biggest regret in life is, my quick answer is I didn't transition quicker to my authentic feminine self.

However, after taking a deeper dive on the subject, sometimes I have to come up with a bit of a different answer. Most assuredly I miss not being able to have experienced all the facets of life a younger woman goes through but then I needed to realize not all early life feminine experiences were good, as hopefully she made her way to being a woman. Not every female can claim womanhood as it comes through a socialization process.

Also, saying I wasted nearly fifty years of my life living as a man would be wrong to say. I did have good times as well as experiences I am intensely proud of. Plus I think several of the experiences made me a better transgender woman when I transitioned. For example, even though the process had its ups and downs, there is no way I would have traded the experience I had when I served three years in the military. Or how could I ever give up the years when my only daughter was born and grew up. Obviously too, my second wife and I could not have made it twenty five years together if there were not some good times mixed in.

I guess you can say I became a survivor of all my male years. As I was surviving, it's important to note I was experimenting the entire time being feminine. I studied how the cis-women around me carried themselves and reacted to the public situations the best I could. And, although I could have never gone as far as I wanted to with my experimentations, the thoughts were always there in the back of my mind. Finally I made it to a point where I could develop a plan to see if I could in reality follow my dream of living as a fulltime transgender woman. Every time I was successful trying one adventure, I was able to move on to another. I learned one way or another I wasn't the only novice transvestite or cross dresser in the world as I began to successfully navigate clothing stores and malls where I lived. When I became bored, I started to go to more challenging venues such as restaurants and test the environments there to see if I would be accepted  When that worked I began to work on my overall communication skills and again concentrated on improving my presentation which was an ongoing process.

So, in reality, I wasn't wasting any time as I attempted to live a life between both of the main binary genders. Trying to do both nearly killed me before the doors opened wide and I again could pursue my life long gender dream. Could I ever really be brave enough to leave my male past behind, along with all the privilege I had earned and live as my authentic feminine self. 

The more I lived as a transgender woman, the more I felt I was doing the right thing and began to resent the fact I didn't try earlier. Throughout the whole process, it was easy to forget the evil days when I disliked all aspects of being male. But over the years I came to realize it was all a learning experience anyhow and helped me to realize how I could lead a more complete life.